May 21, 2025 • 38 mins
This Week's Episode: In this week's episode, Kevin and Matt sit down with industry leader, Janet Jaiswal, CMO and Global VP of Marketing at Blueshift, to explore the evolving landscape of software sales and marketing. They discuss the importance of storytelling, empathy, and understanding customer pain points to differentiate in a crowded market. Janet emphasizes the need for collaboration between marketing and sales, the significance of win-loss analysis, and the value of building trust with customers. The conversation also touches on the challenges faced by newcomers in the industry and the importance of mentorship and continuous learning.
About Our Guest - Janet Jaiswal:
Janet Jaiswal Janet Jaiswal has spent 20+ years in senior marketing roles at private and public companies such as eBay, Paypal, and IBM Tealeaf. She is currently the CMO / Global VP of Marketing at Blueshift, a San Francisco-based company that helps brands automate and personalize engagement across every marketing channel.
Janet is an advisor with Peakspan Capital and has been recognized as a Top 101 B2B Marketing Influencer by CMO Huddles, a FINITE Top 30 SaaS marketer, and one of the Top 14 Marketers to Watch by Drift. Janet earned a bachelor's degree from UC Berkeley and an MBA at the Tepper School of Business at Carnegie Mellon University.
How to Find out More About Janet Jaiswal:
You can find Janet's profile on LinkedIn:
https://www.linkedin.com/in/janetjaiswal/
Chapters
00:00 Introduction to Software Sales Simplified
01:16 Meet Janet Jaiswal: Insights from a Marketing Leader
02:50 Standing Out in a Crowded Market
05:21 The Evolution of Marketing Messaging
07:39 The Role of Marketing in Sales Enablement
08:47 Testing and Adapting Sales Strategies
11:29 The Art of Storytelling in Sales
13:39 Building Trust and Empathy with Customers
16:27 Rethinking Demo Strategies
18:45 Addressing Customer Skepticism
20:33 Balancing Aspirations with Reality
22:10 Navigating Early-Stage Development Challenges
23:53 The Importance of Post-Mortem Analysis
25:26 Learning from Losses
28:16 Validating Value Propositions
31:15 Advice for Aspiring Marketers
38:08 Farewell - Like, Follow, Subscribe and Comment!
About Software Sales Simplified:
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Send us your questions at - Sales@stratsalesllc.com
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Why Listen to Software Sales Simplified?
Make Software Sales Simplified: MOVE to Success, your go-to podcast for mastering enterprise software sales through authentic customer engagement and actionable consulting insights. Join us for each episode as we break down proven strategies and real-world experiences to help you build trust, close deals, and drive long-term success along your Enterprise Software Sales or Consulting journey.
Copyrighted Broadcast:
Thank you for tuning in to Software Sales Simplified: MOVE to Success. This podcast is produced by and is the sole property of Strategic Sales Optimization LLC, copyright 2025. Reproduction or use of this broadcast in whole or in part without express written permission from Strategic Sales Optimization LLC is strictly prohibited. All rights reserved.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:10):
To Software Sales simplified Move to success, your weekly
podcast for software sales professionals who want to sell
better. Whether you're a seasoned
professional or just getting started, make Software Sales
simplified your first stop for the latest and greatest in
insights, developments and news from the world of software
sales. I'm Kevin Donville.
I'll be your Co host today and I'm joined by my good friend and
(00:32):
partner in crime, Matt Long. Matt, how you doing today?
I'm doing great. How is everyone doing?
Doing fantastic together, Matt and I have over over 50 years of
experience in software sales, implementation and services
teams, and we're going to bring that together to you here inside
of our podcast. Today we've been joined by a
wonderful guest, a person that both Matt and I have had the
(00:54):
pleasure of working with in the past, Janet Joswal.
She is going to be joining us and sharing some of her
experiences and perspectives on what it means to be a software
sales professional these days. But before we go ahead and get
into the meat of our session today, just want to remind
everybody, if you like what you hear on our show, please take a
moment to like, subscribe, follow, and comment on the
(01:15):
podcast on whatever platform it is that you're listening to us
here today. That having been said, Janet,
thank you so much for joining us.
It was a real treat to see that you're going to be able to join
us on the call today. How are you doing?
Good. Good to see both you and Matt.
Thanks for having me. Well, we're really glad to have
you and I know you have very busy schedule your CMO and
(01:36):
Global VP of Marketing over a blue shift and we've walked a
few miles together with some of the past organizations that
we've worked with. Take a moment, take the floor,
tell everybody a little bit about your background and where
you are presently. So I'm Janet Chaswell.
I'm currently leading the marketing function at Blue
Shift. And Blue Shift helps brands to
intelligently engage with their customers using AI and real time
(01:59):
data. It turns the background.
I've spent my career helping B to B&B to C companies connect
with customers more effectively.It's so that could be launching
new categories, building AI solutions, telling better
stories. And so I'm excited to share how
marketing and sales intersect, right, especially around
storytelling, empathy, and positioning.
Yeah, that's a area that both Matt and I are very, very close
(02:22):
to. We're big on the concepts of
messaging and storytelling and being able to communicate with
the prospects about not just what the value of the software
is and what it can do, but how that relates to them.
So that whole thing about storytelling to make it
relatable and empathy so they understand that you get where
they're coming from. Now, when we were kind of
(02:43):
talking about how we were going to prep for today, you were
mentioning a few topics along those lines that you thought
were particularly interesting. And one of them really stood out
to me because it's something a lot of people ask us about when
we're talking with them, which is with respect to those types
of skills and emphasis. You were just talking about how
(03:03):
can software companies, companies like Blue Ship that
you're working with now, How canthey stand out?
What makes them different in these almost overcrowded market
that we're finding ourselves in these days?
Yeah, that's a tough one and every company wrestles with
that. Some are more effective than
others. But you know, what I've seen
time and time again is that great companies, they don't
(03:26):
leave with features. They lead with Impact, right?
Impact to their prospects, whoever they're targeting,
right? And the best preparation is
really aligning your differentiation to real customer
pain points, which means you really have to understand your
customers and the buyer personas, right?
But when they align those differentiations, they support
(03:47):
it also with proof points that show measurable outcomes, don't
just make claims, but show that,hey, you can measure it.
And here's here's what comes outof it.
So at Blue Shed, for example, weposition ourselves around
enabling smarter customer engagement through AI.
So not just faster, but more autonomous, more predictive,
more effective. And so that helps us to stand
out from all the other customer engagement platforms, which you
(04:10):
know they all have some form of data management, whether that's
ACDP and then you know orchestration and activation
through a cross channel marketing platform.
So our customer AI is what differentiates us.
That's that's a key thing. I mean, AI is very much
obviously a major buzzword today.
Security and AI are like the topics you're constantly hearing
everybody talking about. And those two industry areas,
(04:32):
those verticals are moving extremely fast, right.
So when you talk about how do you communicate the value you
want to, you want to come in andhave those conversations with
the customer early? When you're talking about market
fit, solution fit, are you sometimes like literally
throwing track in front of the train with respect to how you
put together that message? Because it's got to be a
(04:54):
constantly evolving thing. Yes, yeah.
And so we do test to see what resonates.
We're constantly testing whetherthat's sales conversations where
maybe we'll try a different pitch and that could be a
different pitch deck. It could be the messaging that
we provide on the website, right?
Because often times it's not what you and I think are are
right. Let the people who are targeting
(05:15):
make that determination. It it takes kind of the not the
ambiguity, but it takes a guesswork out of it.
Let the target audience decide what works.
Yeah. I have a question.
So, you know, we worked with a lot of different marketing
organizations at the companies I'm at, right?
And it seemed a while ago there was a shift towards just very
general statements to the point that you go on three competitors
(05:38):
websites and they're all saying the exact same thing, right?
And I think things have turned alittle bit since then, you know,
because it's always like we're going to improve your ROI by
maximizing your efficiencies across your sales team to
improve revenue. It's like something like that,
just like, yes, everyone does that.
I have, I have no idea what you do, right.
So can you talk a little bit howmaybe messaging from the
(05:58):
marketing side has changed? So it's not like these blanket
broad statements about strategy and stuff, but very pinpoint in
terms of what value we're going to deliver to you.
Yeah. And so allow me to expand what I
said earlier where we differentiate ourselves through
AI. We don't just say AI because
every company says AI, right? Like it's so overused.
We go into the details, right? We talk about the components of
(06:22):
it. It's predictive AI, it's
generative AI, it's agentic. But more importantly, we make
sure that the outcomes are prominent, right?
Outcomes make the message believable, right?
So when we talk about enabling a300% increase in revenue per
campaign or reducing time to campaigns by 80%, we're not
selling software, selling success and what that success
(06:44):
feels like to our customers who are marketers who are running
campaigns. And we backed that up with proof
points, right? So we show them real outcomes
from customers and how their situation is similar such that
they could also relate to and say, Oh yeah, I'm in that same
situation and they did XY and Z and they got to this.
(07:06):
I can get to that, right? And so while our software
provides a lot of other benefits, we only highlight the
ones that are relevant for that customer and not the 1200 things
that the software does. Like we're all excited about
what we, you know, what we market, what we sell, but that
doesn't mean the customer is excited about it or is even
cares about it, right? Stick to what's relevant.
(07:26):
So from the perspective of people like Matt and I who you
know primarily let on the pre sell side and one of the major
proof points I would imagine then in that strategy that you
have is going to be how you present something like the
solution demo to folks. Is that correct?
Yes, you know, and and somethingimportant when you're in that
(07:47):
pre sales processes, you know it's it's trust, right?
It's when you've gained that person's trust, meaning you
understand their world, you understand their pain points and
you can relate to it. That's the moment where that
trust happens. If your answer sounds like
everyone else's, you've kind of lost the right to a deeper
conversation. So it's not just about standing
out, it's, it's about being relevant to their priorities.
(08:09):
And that really does start way in the beginning, way before
they even contact you, right? And it continues when they
contact you and you're building up that that relationship over
time such that it comes to hopefully a happy outcome.
How engaged then do you feel that marketing should be, even
in today's day and age with how fast everything's moving?
How involved does marketing needto be in the collection of data,
(08:32):
preparation of data and then servicing of that data to the
sales team as an enabling feature?
Yeah. I think it's that partnership is
very important and both parties,the left and the right hand, if
you will have access to different data and it's
important to be able to collect that data and look at it
objectively, right? And not just, I've been doing
(08:54):
this for 20 years, I know what it is.
And it's like, yes, but not it doesn't mean that that
experience is going to be 100% relevant to that situation,
right? Of course we all have experience
that we rely on, but let the data do the talking.
So on the marketing side, we, you know, we try to test
everything at every step of the way.
(09:14):
It's kind of, it's like the adage trust but verify, right?
Like, yeah, I think I got it, but let's just make sure that
the customers have that. So, you know, we run surveys, we
run test, we tried different messaging.
And our partnership with sales is such that they are willing to
also trial some different thingssuch that then we're able to
say, OK, yeah, this work, this didn't, then maybe it wasn't the
(09:35):
message, maybe it was a delivery.
So like, you know, you look at all those different things and
they're all important. Yeah.
And how do you kind of convey this kind of approach to the
sales team? Because I there's some sellers
that innately will do this and make sure that they're
connecting and there's a sense of empathy pre salespeople as
well in the demo. But, you know, are there
messaging that you helped conveyso that they can actually lead
(09:57):
these things in a much more personal level?
Yeah. So you're right.
Not everybody will agree to doing that testing.
So you start small, you start a pilot, like most things, right?
Like get a few people that are excited about it, get them to
try things out. They'll share the results.
And if it comes, you know, if you're talking to sales, another
seller is more credible than someone in marketing, right?
(10:18):
So it's like, that's cool, that's all right.
But have them pilot it, have them share.
And soon you'll start to see that adoption because everybody
wants to improve. Everybody wants to up their game
and do better. And so start small, do a pilot
and then take your learnings andthen expand.
You don't need to involve everybody right away.
Yeah. Do you leverage a lot of like
just, you know, video recording or meeting recording technology
(10:39):
and things to help with the messaging and cross pollination
and and things like that? Absolutely, yeah.
And nowadays it's so much easierto do that, right.
There's about 1001 different tools that'll do recording.
They'll show share the transcript.
You can, you know, dump that into an LLM and be able to
analyze it. So it's become much easier than
it used to be even 10 years ago,heck, two years ago.
(11:02):
So yeah, that makes things a loteasier.
It helps us to go faster. One of the things that you know,
we've had several people on on the show talking about
strategies around those kinds ofrecordings and I'm curious as to
your thoughts on this. Do you guys over at your
organization utilize calls with not just the sales and marketing
teams, but also the customer success teams who are doing the
(11:23):
actual service delivery to the customers?
And if if you are, what would your advice be with to somebody
who is maybe considering or on the fence about whether or not
to to, to incorporate those kinds of elements in their
analysis? Yeah, definitely right.
It's not just sales, it's the post sales process and there's a
lot of cross sell upsell happening with our CSM.
(11:45):
So they get the same sort of enablement that we do.
If your question is how do we gain adoption, I think everybody
wants to improve or at least I'mmaking that assumption.
Everybody wants to be more effective.
Not everybody will adopt it because maybe their perspective
is they've had a bad experience or maybe it's something didn't
work. So we allow that flexibility as
(12:07):
well, which is we're going to recommend it, but we're not
going to force feed it. Now for folks that have
something else that's cool. We're going to show you
something that we as a company are going to adopt, but
ultimately the results show for themselves.
So they're not seeing the results.
There might be more open to it if they're seeing the results
because they have some other method that's OK as well.
No, I think it's really important to have that
flexibility for sure and to be able to adapt.
(12:29):
You know, it's, and this is the,I think this is the thing that
we can do now because there are data points that are easily
consumable where we can take those and then pivot quickly as
necessary. So I think that's definitely
something that's come about morerecently.
It would circle back a little bit.
You mentioned as a marketer a lot of Times Now you're trying
to tell a good story. You know, it's about telling
(12:50):
stories conveying that. Could you talk a little bit
about what makes up a good storyyou know, and what your approach
is there? I think it's really around
demonstrating understanding of the customers unique needs and
really empathy. And empathy starts, you know,
way before the demo, right? It's, it's the research, it's
asking what's frustrating your team today.
(13:11):
And then it involves tailoring that walkthrough to show, not
tell, but to show how you're solving their struggles, right.
Great demos rarely go through the features and functionality
of a product. They're not going to remember
here's, you know, all buttons. It's like they're not going to
remember. It's the first time they've seen
it. They're overwhelmed.
But what they will remember is how that demo that you did, how
(13:35):
quickly and easily that customeris able to solve the problem
using your product, right? After all, people don't remember
the product features and functionality, but they will
remember how easy it was, how intuitive it was and how they
were able to get to that end state that will they will
remember for sure and how it made them feel right.
(13:57):
If you can get them to a point where they're like, Oh my God,
that was easier, then you know, you've got a good opening right
for for that next stage, if you will.
Yeah, it's kind of like the the old adage, like people remember
how you made them feel, not whatyou said, right?
And that's really what lasts because I got to admit being on
the receiving end of demos and vendors coming in, I gotta
(14:19):
admit, sometimes after you're done, you're talking about a
vendor and it's the opposite vendor.
You're talking about the features like you, you can't
even keep them straight ahead, right?
You do remember not the featureslike that team just really
seemed on it. They seemed like they were
answering your questions and really going down the right
paths. And that's that's what really
resonates, I think. That's absolutely fair.
(14:39):
So, so Janet, to kind of extend on that, so for anybody who's
listening into the show today and are wondering, well, what
should I be considering about how our demo strategy might,
might be rethought? I really think you struck the
nail on the head when you said the whole whole thing about
establishing empathy with the customer starts before the demo
even happens, with doing your research and understanding who
(15:02):
they are and what they do. What do you think is the biggest
challenge then about taking whatyou learned ahead of time and
packaging that as messaging thatcan be reused with other sellers
inside the organization, like Matt and I would do that
instinctively as part of our prep, but you're in a different
(15:23):
role and you're packaging that in a broader sense.
What are some of the things thatyou would do in order to be able
to make that an effective bit ofkit for the rest of the team?
Yeah. So it definitely involves
acknowledging the customer's struggle during the demo because
it it's, you know, it's back to relating to them, right?
(15:44):
You get their trust when you acknowledge and you say it out
loud. OK, here's what you might be
struggling with because if you don't, you're just another
vendor pitching features. Everybody does that.
So acknowledging that struggle humanizes the conversation.
It shows that you understand their world.
It shows that you understand their struggle.
It builds rapport, right? And it makes them feel seen.
And when people feel seen, they're more likely to listen.
(16:07):
So then you've earned the right to continue that conversation,
right? And you know, in terms of just,
you know, what's the difference between showing features versus
creating confidence? Confidence is when it is built,
when you connect features to outcomes, right?
You know, the features very welltie it to tangible outcomes that
they care about, right. So instead of here's our
(16:29):
campaign builder, it's here's how a retail marketer like you
use this to reduce card abandonment rate by 40% or
whatever that is, right? So that then the retail marketer
is like, oh, I do care about card abandonment and yes, you
can help me reduce it. OK, I'm listening, right?
So then all of a sudden you've got their attention and.
(16:52):
Yeah, in some of our prep conversation, we talked a little
bit about, you know, the customer is the hero.
I mean, I have certainly my thoughts around that just in
terms of basic storytelling structure, right.
But what? What?
Could you elaborate a little bitof what you mean by that?
Yeah, the story has to, you know, it has to mirror a buyer's
reality, right? It's the using the before and
(17:14):
after storyline arc, if you will, right.
So first you talk about the challenge.
What is the challenge that the prospect is facing?
Then you talk about the shift, what caused them to look into a
specific solution or a differentway of doing things, hopefully
your solution. And then you talk about the
results, right? What was the result of adopting
the new solution? Basic stuff, but how you
(17:35):
delivered is what's hard, right?So you want to keep it specific,
you want to keep it short, you want to keep it relatable, and
you want to reference industry peers in the story.
You want to show the KPIs that are involved.
Hopefully those are the KPIs that your customer cares about
and examples of real impact, right?
So if you can pull all of that in there and make it seeing like
(17:57):
a conversation instead of something that's rehearsed, then
I think you have you built that credibility and you show that
they are the hero because guess what?
They solve this using your or people like them solve this
using your solution. And so they.
Feel good, obviously. I mean wholeheartedly agree with
that idea. Storytelling, such a much more
(18:17):
commutative and effective way ofbeing able to have a
conversation with another person, especially in a sales
situation. Sadly, a lot of organizations
struggle with that and as they're putting their material
together, it becomes this feature function dump.
Especially with folks that are early in their development
stages, what advice would you give them on how to look at what
(18:39):
they're really doing critically and how to course correct if
they're off the mark with respect to that?
That's a tough one. I would encourage them to shift
from a product first mindset to a customer first mindset.
Ask them to put themselves in the customer's seat and remind
them, hey, they are looking at 2-3 other of your peers or
(19:00):
competitors, right? So, so don't just jump to we do
this and this is really neat andit's a differentiator.
Forget about that. Forget the product stuff, right?
Ask them what does success look like for your prospect?
Start with that and then show how your product enables that
success, right? Use phrases like here's what our
(19:21):
customers achieved instead of here's what our product does.
Like, don't do that, right? And then, you know, a big
mistake, especially for folks that are maybe newer to this is
they try to fit too much into that demo, right?
And it's very tempting to communicate all of your unique
features and how much better your product might be.
(19:41):
But the value gets lost, right? They, they lose their power when
they're bloated with too much jargons, logos, or every
feature. It's just, it's overwhelming.
And you have to remember it's the first time they're seeing
your product or the second time and they've just come from
another meeting. They don't remember, right?
So keep it, keep it simple and keep it to just the most germane
(20:02):
points. And then resist, you know,
resist the temptation to go through everything that's really
cool and unique. Like take a deep breath,
remember to stick to 1 customer,one problem, one outcome, right?
And kind of let the story breathe, if you will.
So it sounds simple. It's really hard, right?
You have to practice this stuff.It doesn't.
Just just because you remember those things doesn't mean you've
(20:23):
mastered it, right? So practice.
Yeah, less, less is more is really true in many, many
situations, right? It's like because they're not
going to remember everything. You know, you, you talked a lot
about credibility and trust as being part of it and you know,
dropping, you know, examples andthings and, and just how you ask
questions that all contributes to that.
But there's still times where, you know, even though they
(20:45):
understand that this is a good goal to get to etcetera, there's
they're kind of skeptical about either the real value of it or
if if they can accomplish it or things of that because people
are resistant to change a lot. What would you say, you know, to
help address those types of customers or those people are
(21:05):
struggling a little bit to really see how they bridge to
the future? You know, I also get pitched by
a lot of different companies with solutions.
So there's a good chance that, you know, if I'm typical of
people, they've heard it all before, right?
And many were burned. They adopted something, right?
AI in particular, it's often seen as a buzzword.
So just the other day I receiveda message from a swag vendor
(21:29):
stating that they're using AI tosuggest what I could buy.
And I was thinking, oh, gosh, I really want a human who's been
at recent shows, who's seen what's popular to suggest
something. I don't want AI, right?
But but that that tells you an example of how everybody is, is
dropping the word AI into their offering, whether it's real or
whether it's not. So yeah, I can understand that,
(21:51):
you know, a certain amount of skepticism, it's healthy, but
that's where you should take that as your cue to ground the
conversation and results, not the hype.
Like AI is nice, but what can itreally do for that, for that
prospect and then back to related to what they care about
and not just or it does this. So in terms of strategies that
(22:12):
work to increase that trust and to resist that resistance, if
you will, or reduce that resistance, show them what
doesn't change as well, right? So for example, like in with our
solution, we tell them you don'tneed a data scientist to use
this. We walk them through real world
transitions like of wait, if youadopt this, here's what you can
expect in the 1st 30 days. Here's how others have succeeded
(22:34):
that have used this solution. What to avoid?
Even if you point out some things that are difficult with
your product or things to avoid,they trust you more because
they're like, OK, this person is, is, is being realistic.
They're not saying that the world is perfect once we adopt A
solution, that there are some things to think about and
there's some consideration, but this person's going to help me
(22:55):
get through that, that that I find really helps.
And it reduces that resistance because it's not just you sign
the contract, we're going to cutand run.
It's like, no, we're going to bewith you.
We're going to be your partner. So I do think that that helps.
And then last thing is around the balance between aspirations
and kind of grounded in reality,if you will, for your messaging.
(23:16):
Aspiration definitely gets attention, but grounded stories
wins deals, right? So it's good to say, oh, AI is
going to solve the world, but but let's make it grounded in
reality like, well, it's going to help you with these things.
And these are the things, hopefully those are the things
that the prospect cares the mostabout.
So the sweet spot is kind of showing a bold vision, but power
(23:37):
it by tangible, incredible stepsTo get there.
You have to be believable. You need to earn that trust by
keeping it as real as possible and also pointing out some
flaws, right? Again, hopefully those flaws
aren't the ones they care about.But if you drop in a nugget here
or there, they tend to believe you more because they're like,
what? This person's not just painting
a picture of this is going to solve World Peace.
(23:59):
They're saying, well, no, it's not going to solve World Peace,
but it will solve peace in your little corner of the world.
And that's. I think that's absolutely
critical because, oh, let's faceit, in many verticals to say
that the the term AI has been used and abuse would be, would
be generous. It's been a buzzword for a long
time and and half the people I think we're using it didn't even
know what it really meant. So with respect to that, I agree
(24:21):
with you. Being painfully honest in some
respects with the customers is really critical to get that
credibility with them. But at the speed that some
organizations are dealing with, like Matt and I are talking with
organizations all the time and some of them are very early on
in their development phase wherethey haven't even really built a
(24:42):
body of customers yet. How do how does somebody in that
stage development where they don't have a lot of customers
they can point back to as proof points.
How would they approach that that Crucible of truth with the
customer to come forward saying here's what's good and here's
where things might be wobbly? Yeah.
(25:03):
If you don't have many customers, the assumption is
that you have at least a few. And most companies that are in
their earlier stages usually will have design partners that
have agreed to speak to them or speak on their behalf, if you
will. So you you go off of that,
right. And ideally, those customers are
relevant to the ones you're talking to such that you could
(25:25):
share that example. I don't think anything is gained
by pretending you have dozens and dozens of customers that are
that are doing this. Be honest and upfront.
It's back to credibility, right?If they believe you and they
trust you and you have their best interests in mind.
I don't want to over emphasize this, but the rest of the
process can be easier once you have that trust.
(25:47):
But if you don't have that trust, you don't have a shot.
You do not, you do not have permission to continue, if you
will, right. So it's OK to be real.
It's OK to say we have a few, but guess what, These customers
have real results and this is very relevant to you, Mr. Or
Misses Prospect and let's talk about those.
Yeah. One thing that you mentioned
(26:07):
that we've talked about on previous podcasts, but I think
it's so important that we circleback to it is as I progressed in
my career, having a very clear path about how it's going to be
implemented, deployed and adopted has become so much more
critical because that is the final stages of the journey, if
you will. But that is ultimately where you
(26:29):
provide the most credibility because they're like, I see it's
done. And being upfront and saying
some of this is going to be hard, some of this is going to
take effort and it's going to take this amount of effort, you
know, and you set that stage. So it's not like, Oh yeah, one
click button, it's all integrated, you're good.
Those days are gone. So I really can't emphasize
enough, you know, that portion of it of being, you know, that's
(26:52):
where you really become a trusted partner.
And when you don't have perhaps all the customer stories and
things in the past, helping themknow that you have a well
thought out way to get them to value can provide that
credibility you need. I love that point because you're
right, a smaller companies have that advantage, which is we're
(27:13):
going to hand hold you to the process.
We're going to make sure you're successful where as a larger
companies like you know, you're 1 of many, you know, we'll give
you our standard package, but smaller companies can provide
that hand holding to make sure they're successful.
And that's an advantage. That's an advantage over those
large established folks. So I like that point that you
emphasize. It is important and it's OK to
(27:35):
it's OK to you don't have to be shy about it.
Every company at one point was smaller.
Nothing wrong with that, right? Everybody starts from somewhere,
but highlight what's relevant for that customer.
No, I wholeheartedly agree. And I think it really comes down
to, but you're talking about credibility and that trust with
the customer that is probably the most valuable commodity you
(27:57):
have as a seller when you're talking with them is the honesty
of what you're approaching them with.
And it's also very fragile currency, right?
You lose it, It's almost impossible to get it back once
you've lost it, right? Yeah, I so agree.
Yeah. So with that being that being
said, so obviously we want to sell with integrity.
We want to sell with honesty and, and be frank about where we
(28:19):
are, but also aspirational with respect to what we can provide
them in terms of solution and where we can get them to best
laid plans of mice and men. Things don't always work out.
You don't always win everything.You win a few and you lose a
few. I know that you're really big on
the concept of doing the post mortems, which is kind of a
(28:39):
morbid term for it, but the likethe after action report, if you
want to use more of a militaristic term after a deal,
why? I have really strong and Matt
does too, really strong opinionsabout why that's so important,
but I'd love to hear your perspective as a marketer on
that. Yeah, win loss analysis is
important. You know, often times when you
win something, it's easy to not realize there things have gone
(29:01):
wrong, right? Because you're so caught up in
the oh, we won, so everything I had done must have worked well.
So it's important losses are actually more important for that
because losses reveal what went wrong such that you can improve
on it, right? So structured reviews help you
find those patterns, right? Misaligned messaging, maybe
competitive positioning, right? Maybe there's what's better or
(29:24):
any internal friction, right? Maybe the handoffs weren't great
or we fell down during onboarding.
I don't know, you know, whateverthose things are.
But that analysis is important because it's, it's a mirror,
right? And and and growth requires
looking into that mirror and being brutally honest, I
actually find more value from the ones we lost than the ones
(29:44):
we won. Because of that, yeah, I mean
that's been our staple in our journey as sellers is that after
everything we have a post more even after every meeting, you
know, just how, what went well, what didn't go well, what do you
think how it should go, etcetera.
So that's been part of our process for a long time.
But from the marketing side, it's very rare that a marketing
(30:06):
person is involved in these meetings.
I'm just curious because obviously you can't be on every
of those calls, but at what point are you kind of looking at
it and what's your engagement with the sales team for their
feedback or can you do it all remotely just by looking at the
the videos and things like that?What does that process look like
I guess for you? Yeah.
So from the market side, I'm thinking of product marketing,
(30:27):
and it is absolutely product marketing's job to do the win
loss analysis. And you know, with the video
recording features, you can see the video, you know, you can
dump the transcript into an LLM,right?
ChatGPT, Claw, Gemini, whatever,and be able to find the
patterns, the sentiment. That's something that you know,
(30:49):
you'd have to go through the recording to see.
These are the words they use. But how was it said, right?
So you can get that kind of analysis so quickly, so easily,
right, that it has become a lot easier.
And so I do think marketing has a role in it as well as as as
customer success, right? Because if you think about it,
they both could be affecting that deal, right?
(31:09):
Maybe it's the messaging that's upfront.
Maybe it's the positioning that that caused a disconnect with
this CS team. Maybe it's the onboarding.
Maybe it's the, you know, the regular check insurance, the the
MBRS or whatever you do or something fell down.
Maybe, you know, adoption wasn'tthere or support or whatever
that is. And so there are many reasons or
(31:30):
many ways that a customer could be lost even after it was
closed. One, if you will.
I think the most important stuffis to actually conduct that
analysis because I know oftentimes everybody's so busy,
we forget. We're like, oh, we're doing
well, we'll put it off. And it's like, you don't want to
make assumptions because you don't know what will be
revealed, right? Did we confuse them?
Did we share too much information?
(31:51):
So it could be the marketing, you know, the messaging, the
targeting, it could be just the mismatch of what they needed and
what we actually provided in terms of service and support.
Every company's at a different place in the maturity, if you
will, right? And they need something
different. So we don't want to assume, and
I think that's where the post mortem analysis helps.
That said, you need to have a sufficient number that you've
(32:13):
done to see those patterns. It can't be like 3 or 4, it has
to be more. And so once you have a
sufficient number, then you can start to see themes in
objections, in clarity, gaps in positioning or in
differentiation where maybe the differentiation didn't land.
And so sometimes it's not the deck that was shared, the sales
deck, it's the disconnect between the pain and the promise
(32:34):
that we made. And that's where the win loss
analysis helps. Yeah, I think that understanding
that gap is so critical. And to your point about bringing
in customer success and the service delivery people into
part of that analysis, one of the things that I'm a big
proponent of is to bring them invery early because we're talking
(32:56):
about the initial sale here in this conversation.
But the renewal is just as important, if not more so
because you're trying to grow inmany cases where the land and
expand. And it's been my experience that
when we bring customer success and they're like you promised
the wrong thing based on what their problem was.
(33:17):
So you were you were hamstringing yourself for your
renewal before the ink ever hit the contract.
What would you say with organizations, particularly
young ones that are trying to find out and acid test their
value, what are some strategies that they can take on trying to
really document and understand and validate their value
(33:41):
proposition from that perspective?
And I know that's a big question.
Yeah, it is a big question. There's lots of ways to attack
it. You know, that's where I find
out that a few trusted customerswhere they can be honest and
frank. If you're able to get their
attention, maybe it's through a customer Advisory Board or maybe
it's just you built a good relationship, or maybe it's the
E staff meeting with a customer,you know, where they have no
(34:06):
agenda. They're like, I just want to
hear from you what the experience is.
But if you can get some frank and honest conversations going
with customers, you'll get more of that insight because
sometimes maybe people are too polite or they're too busy or
whatever that is. So I find that those are a
couple of ways to get that information.
Is is earn the trust, have get afrank conversation where you
(34:28):
tell them you know, nothing's off the plate.
You know, like we really want tohear and understand and that
might help. I'm sure there are many, many
other ways to do this, but that's a tough one.
I think that's a great one, getting out there and actually
talking to the people who are using the solution and getting
getting them to give it to you with no sugar, no sugar on it at
all, right? Because you can't fix it if they
(34:50):
don't tell you. Yep, agreed.
Yep, Janet, I would love to keeptalking because these are very,
these are very exciting topics for, for with Matt and I, but we
do have to bring our episode to a close.
So before we do that, I wanted to ask if, you know, if somebody
was looking to kind of get into your area, what kind of advice
(35:10):
would you give to somebody who maybe is just starting out in
your field about how to deal with the kind of changing
landscape in the world today? Well, that's a tall order, but
you know what, you start with step one, right?
I think we can learn from any experience.
And so the main thing is to get started.
And then you start to figure outwhat you like, what you don't
(35:33):
and what you've learned and whatelse you need to learn.
And then just kind of continue that path.
Go to your next role, go to yournext company and, and collect
those kinds of experiences. But really the biggest advice is
just start right. And it doesn't matter where you
start. Every experience is relevant,
but there's so much happening that it, it is tough to keep up.
And so, you know, definitely getadvice from people who've been
(35:56):
in your shoes, right? Save yourself some time, right?
Like, why learn things the hard way if you're able to cultivate
a network, able to read and learn from others books,
podcasts like this one, right? Like, learn from other folks
who've been there and who have done that.
Might save yourself a little bitof time and heartache.
Mentorship and connection, that's what it's all about.
(36:18):
There's a lot of great experiences out there and we
won't ever experience them all over the course of our careers.
So reaching out to those who maybe have seen and done things,
we haven't great advice from that perspective.
So if people wanted to reach outand connect with you, Janet,
what's the best way for them to do that?
If they wanted to try and and collaborate or get some of your
(36:40):
thought? Yeah.
Real easy, just go to LinkedIn and look up my first name, last
name. So far no one else appears under
Janet Jaswal. So yeah, just reach out.
Happy to help wherever I can. Fantastic we will include in
your bio and a link inside of the description on most of the
platforms this is going to be showing on anyone wants to click
on that you'll be able to go directly over to Janet and
(37:02):
communicate with her and I can tell you from personal
experience it it's always fulfilling and you will always
learn something as a result so Janet, thank you so much for
coming onto the show this week really enjoyed it and I hope
that you had a great time here as well you're.
Welcome. I enjoyed the conversation, so
thank you for the fantastic questions.
Thank you so much for the fantastic answers, Matt Sir,
(37:25):
always great to spend a little bit of time with you virtually
online. Anything you'd like to share
before we close down for today? Yeah.
I'd really appreciate your perspective coming from
marketing because most of the people we have on here are in
sales. And I gotta be honest, in my
career, there's a lot of finger pointing back and forth between
marketing sales. For healthy.
No, never happened. But also I think they're
(37:47):
rightfully so there was a disconnect for a lot of years
between marketing sales and I'm glad to see that it's kind of
come back around to be more integrated and holistic in terms
of really everyone understandingevery step of that customer
relationship, right. So that's it's really nice to
hear your insights and thoughts around this.
So thanks, Janet. You're welcome.
Now I wholeheartedly concur withthat.
(38:08):
And ladies and gentlemen, with that having been said, that
brings us to a close on this episode.
Please come back and join us next week where we'll have
another guest right here on the very same spot.
If you would like, please subscribe, like, follow,
comment. It does us a world of good on
the different algorithms for theplatforms we're on.
Please take a moment to do that if you don't mind.
And if you would like to learn more about the methodology you
(38:30):
hear Matt and I talking about onour show, you can go to our
website where you find a you canpurchase your very own copy of
our book. But until then, we will see you
next week right here on this same channel.
And with that having been said.
To Software Sales simplified Move to success, your weekly
podcast for software sales professionals who want to sell
better. Whether you're a seasoned
professional or just getting started, make Software Sales
simplified your first stop for the latest and greatest in
insights, developments and news from the world of software
sales. I'm Kevin Donville.
I'll be your Co host today and I'm joined by my good friend and
(00:32):
partner in crime, Matt Long. Matt, how you doing today?
I'm doing great. How is everyone doing?
Doing fantastic together, Matt and I have over over 50 years of
experience in software sales, implementation and services
teams, and we're going to bring that together to you here inside
of our podcast. Today we've been joined by a
wonderful guest, a person that both Matt and I have had the
(00:54):
pleasure of working with in the past, Janet Joswal.
She is going to be joining us and sharing some of her
experiences and perspectives on what it means to be a software
sales professional these days. But before we go ahead and get
into the meat of our session today, just want to remind
everybody, if you like what you hear on our show, please take a
moment to like, subscribe, follow, and comment on the
(01:15):
podcast on whatever platform it is that you're listening to us
here today. That having been said, Janet,
thank you so much for joining us.
It was a real treat to see that you're going to be able to join
us on the call today. How are you doing?
Good. Good to see both you and Matt.
Thanks for having me. Well, we're really glad to have
you and I know you have very busy schedule your CMO and
(01:36):
Global VP of Marketing over a blue shift and we've walked a
few miles together with some of the past organizations that
we've worked with. Take a moment, take the floor,
tell everybody a little bit about your background and where
you are presently. So I'm Janet Chaswell.
I'm currently leading the marketing function at Blue
Shift. And Blue Shift helps brands to
intelligently engage with their customers using AI and real time
(01:59):
data. It turns the background.
I've spent my career helping B to B&B to C companies connect
with customers more effectively.It's so that could be launching
new categories, building AI solutions, telling better
stories. And so I'm excited to share how
marketing and sales intersect, right, especially around
storytelling, empathy, and positioning.
Yeah, that's a area that both Matt and I are very, very close
(02:22):
to. We're big on the concepts of
messaging and storytelling and being able to communicate with
the prospects about not just what the value of the software
is and what it can do, but how that relates to them.
So that whole thing about storytelling to make it
relatable and empathy so they understand that you get where
they're coming from. Now, when we were kind of
(02:43):
talking about how we were going to prep for today, you were
mentioning a few topics along those lines that you thought
were particularly interesting. And one of them really stood out
to me because it's something a lot of people ask us about when
we're talking with them, which is with respect to those types
of skills and emphasis. You were just talking about how
(03:03):
can software companies, companies like Blue Ship that
you're working with now, How canthey stand out?
What makes them different in these almost overcrowded market
that we're finding ourselves in these days?
Yeah, that's a tough one and every company wrestles with
that. Some are more effective than
others. But you know, what I've seen
time and time again is that great companies, they don't
(03:26):
leave with features. They lead with Impact, right?
Impact to their prospects, whoever they're targeting,
right? And the best preparation is
really aligning your differentiation to real customer
pain points, which means you really have to understand your
customers and the buyer personas, right?
But when they align those differentiations, they support
(03:47):
it also with proof points that show measurable outcomes, don't
just make claims, but show that,hey, you can measure it.
And here's here's what comes outof it.
So at Blue Shed, for example, weposition ourselves around
enabling smarter customer engagement through AI.
So not just faster, but more autonomous, more predictive,
more effective. And so that helps us to stand
out from all the other customer engagement platforms, which you
(04:10):
know they all have some form of data management, whether that's
ACDP and then you know orchestration and activation
through a cross channel marketing platform.
So our customer AI is what differentiates us.
That's that's a key thing. I mean, AI is very much
obviously a major buzzword today.
Security and AI are like the topics you're constantly hearing
everybody talking about. And those two industry areas,
(04:32):
those verticals are moving extremely fast, right.
So when you talk about how do you communicate the value you
want to, you want to come in andhave those conversations with
the customer early? When you're talking about market
fit, solution fit, are you sometimes like literally
throwing track in front of the train with respect to how you
put together that message? Because it's got to be a
(04:54):
constantly evolving thing. Yes, yeah.
And so we do test to see what resonates.
We're constantly testing whetherthat's sales conversations where
maybe we'll try a different pitch and that could be a
different pitch deck. It could be the messaging that
we provide on the website, right?
Because often times it's not what you and I think are are
right. Let the people who are targeting
(05:15):
make that determination. It it takes kind of the not the
ambiguity, but it takes a guesswork out of it.
Let the target audience decide what works.
Yeah. I have a question.
So, you know, we worked with a lot of different marketing
organizations at the companies I'm at, right?
And it seemed a while ago there was a shift towards just very
general statements to the point that you go on three competitors
(05:38):
websites and they're all saying the exact same thing, right?
And I think things have turned alittle bit since then, you know,
because it's always like we're going to improve your ROI by
maximizing your efficiencies across your sales team to
improve revenue. It's like something like that,
just like, yes, everyone does that.
I have, I have no idea what you do, right.
So can you talk a little bit howmaybe messaging from the
(05:58):
marketing side has changed? So it's not like these blanket
broad statements about strategy and stuff, but very pinpoint in
terms of what value we're going to deliver to you.
Yeah. And so allow me to expand what I
said earlier where we differentiate ourselves through
AI. We don't just say AI because
every company says AI, right? Like it's so overused.
We go into the details, right? We talk about the components of
(06:22):
it. It's predictive AI, it's
generative AI, it's agentic. But more importantly, we make
sure that the outcomes are prominent, right?
Outcomes make the message believable, right?
So when we talk about enabling a300% increase in revenue per
campaign or reducing time to campaigns by 80%, we're not
selling software, selling success and what that success
(06:44):
feels like to our customers who are marketers who are running
campaigns. And we backed that up with proof
points, right? So we show them real outcomes
from customers and how their situation is similar such that
they could also relate to and say, Oh yeah, I'm in that same
situation and they did XY and Z and they got to this.
(07:06):
I can get to that, right? And so while our software
provides a lot of other benefits, we only highlight the
ones that are relevant for that customer and not the 1200 things
that the software does. Like we're all excited about
what we, you know, what we market, what we sell, but that
doesn't mean the customer is excited about it or is even
cares about it, right? Stick to what's relevant.
(07:26):
So from the perspective of people like Matt and I who you
know primarily let on the pre sell side and one of the major
proof points I would imagine then in that strategy that you
have is going to be how you present something like the
solution demo to folks. Is that correct?
Yes, you know, and and somethingimportant when you're in that
(07:47):
pre sales processes, you know it's it's trust, right?
It's when you've gained that person's trust, meaning you
understand their world, you understand their pain points and
you can relate to it. That's the moment where that
trust happens. If your answer sounds like
everyone else's, you've kind of lost the right to a deeper
conversation. So it's not just about standing
out, it's, it's about being relevant to their priorities.
(08:09):
And that really does start way in the beginning, way before
they even contact you, right? And it continues when they
contact you and you're building up that that relationship over
time such that it comes to hopefully a happy outcome.
How engaged then do you feel that marketing should be, even
in today's day and age with how fast everything's moving?
How involved does marketing needto be in the collection of data,
(08:32):
preparation of data and then servicing of that data to the
sales team as an enabling feature?
Yeah. I think it's that partnership is
very important and both parties,the left and the right hand, if
you will have access to different data and it's
important to be able to collect that data and look at it
objectively, right? And not just, I've been doing
(08:54):
this for 20 years, I know what it is.
And it's like, yes, but not it doesn't mean that that
experience is going to be 100% relevant to that situation,
right? Of course we all have experience
that we rely on, but let the data do the talking.
So on the marketing side, we, you know, we try to test
everything at every step of the way.
(09:14):
It's kind of, it's like the adage trust but verify, right?
Like, yeah, I think I got it, but let's just make sure that
the customers have that. So, you know, we run surveys, we
run test, we tried different messaging.
And our partnership with sales is such that they are willing to
also trial some different thingssuch that then we're able to
say, OK, yeah, this work, this didn't, then maybe it wasn't the
(09:35):
message, maybe it was a delivery.
So like, you know, you look at all those different things and
they're all important. Yeah.
And how do you kind of convey this kind of approach to the
sales team? Because I there's some sellers
that innately will do this and make sure that they're
connecting and there's a sense of empathy pre salespeople as
well in the demo. But, you know, are there
messaging that you helped conveyso that they can actually lead
(09:57):
these things in a much more personal level?
Yeah. So you're right.
Not everybody will agree to doing that testing.
So you start small, you start a pilot, like most things, right?
Like get a few people that are excited about it, get them to
try things out. They'll share the results.
And if it comes, you know, if you're talking to sales, another
seller is more credible than someone in marketing, right?
(10:18):
So it's like, that's cool, that's all right.
But have them pilot it, have them share.
And soon you'll start to see that adoption because everybody
wants to improve. Everybody wants to up their game
and do better. And so start small, do a pilot
and then take your learnings andthen expand.
You don't need to involve everybody right away.
Yeah. Do you leverage a lot of like
just, you know, video recording or meeting recording technology
(10:39):
and things to help with the messaging and cross pollination
and and things like that? Absolutely, yeah.
And nowadays it's so much easierto do that, right.
There's about 1001 different tools that'll do recording.
They'll show share the transcript.
You can, you know, dump that into an LLM and be able to
analyze it. So it's become much easier than
it used to be even 10 years ago,heck, two years ago.
(11:02):
So yeah, that makes things a loteasier.
It helps us to go faster. One of the things that you know,
we've had several people on on the show talking about
strategies around those kinds ofrecordings and I'm curious as to
your thoughts on this. Do you guys over at your
organization utilize calls with not just the sales and marketing
teams, but also the customer success teams who are doing the
(11:23):
actual service delivery to the customers?
And if if you are, what would your advice be with to somebody
who is maybe considering or on the fence about whether or not
to to, to incorporate those kinds of elements in their
analysis? Yeah, definitely right.
It's not just sales, it's the post sales process and there's a
lot of cross sell upsell happening with our CSM.
(11:45):
So they get the same sort of enablement that we do.
If your question is how do we gain adoption, I think everybody
wants to improve or at least I'mmaking that assumption.
Everybody wants to be more effective.
Not everybody will adopt it because maybe their perspective
is they've had a bad experience or maybe it's something didn't
work. So we allow that flexibility as
(12:07):
well, which is we're going to recommend it, but we're not
going to force feed it. Now for folks that have
something else that's cool. We're going to show you
something that we as a company are going to adopt, but
ultimately the results show for themselves.
So they're not seeing the results.
There might be more open to it if they're seeing the results
because they have some other method that's OK as well.
No, I think it's really important to have that
flexibility for sure and to be able to adapt.
(12:29):
You know, it's, and this is the,I think this is the thing that
we can do now because there are data points that are easily
consumable where we can take those and then pivot quickly as
necessary. So I think that's definitely
something that's come about morerecently.
It would circle back a little bit.
You mentioned as a marketer a lot of Times Now you're trying
to tell a good story. You know, it's about telling
(12:50):
stories conveying that. Could you talk a little bit
about what makes up a good storyyou know, and what your approach
is there? I think it's really around
demonstrating understanding of the customers unique needs and
really empathy. And empathy starts, you know,
way before the demo, right? It's, it's the research, it's
asking what's frustrating your team today.
(13:11):
And then it involves tailoring that walkthrough to show, not
tell, but to show how you're solving their struggles, right.
Great demos rarely go through the features and functionality
of a product. They're not going to remember
here's, you know, all buttons. It's like they're not going to
remember. It's the first time they've seen
it. They're overwhelmed.
But what they will remember is how that demo that you did, how
(13:35):
quickly and easily that customeris able to solve the problem
using your product, right? After all, people don't remember
the product features and functionality, but they will
remember how easy it was, how intuitive it was and how they
were able to get to that end state that will they will
remember for sure and how it made them feel right.
(13:57):
If you can get them to a point where they're like, Oh my God,
that was easier, then you know, you've got a good opening right
for for that next stage, if you will.
Yeah, it's kind of like the the old adage, like people remember
how you made them feel, not whatyou said, right?
And that's really what lasts because I got to admit being on
the receiving end of demos and vendors coming in, I gotta
(14:19):
admit, sometimes after you're done, you're talking about a
vendor and it's the opposite vendor.
You're talking about the features like you, you can't
even keep them straight ahead, right?
You do remember not the featureslike that team just really
seemed on it. They seemed like they were
answering your questions and really going down the right
paths. And that's that's what really
resonates, I think. That's absolutely fair.
(14:39):
So, so Janet, to kind of extend on that, so for anybody who's
listening into the show today and are wondering, well, what
should I be considering about how our demo strategy might,
might be rethought? I really think you struck the
nail on the head when you said the whole whole thing about
establishing empathy with the customer starts before the demo
even happens, with doing your research and understanding who
(15:02):
they are and what they do. What do you think is the biggest
challenge then about taking whatyou learned ahead of time and
packaging that as messaging thatcan be reused with other sellers
inside the organization, like Matt and I would do that
instinctively as part of our prep, but you're in a different
(15:23):
role and you're packaging that in a broader sense.
What are some of the things thatyou would do in order to be able
to make that an effective bit ofkit for the rest of the team?
Yeah. So it definitely involves
acknowledging the customer's struggle during the demo because
it it's, you know, it's back to relating to them, right?
(15:44):
You get their trust when you acknowledge and you say it out
loud. OK, here's what you might be
struggling with because if you don't, you're just another
vendor pitching features. Everybody does that.
So acknowledging that struggle humanizes the conversation.
It shows that you understand their world.
It shows that you understand their struggle.
It builds rapport, right? And it makes them feel seen.
And when people feel seen, they're more likely to listen.
(16:07):
So then you've earned the right to continue that conversation,
right? And you know, in terms of just,
you know, what's the difference between showing features versus
creating confidence? Confidence is when it is built,
when you connect features to outcomes, right?
You know, the features very welltie it to tangible outcomes that
they care about, right. So instead of here's our
(16:29):
campaign builder, it's here's how a retail marketer like you
use this to reduce card abandonment rate by 40% or
whatever that is, right? So that then the retail marketer
is like, oh, I do care about card abandonment and yes, you
can help me reduce it. OK, I'm listening, right?
So then all of a sudden you've got their attention and.
(16:52):
Yeah, in some of our prep conversation, we talked a little
bit about, you know, the customer is the hero.
I mean, I have certainly my thoughts around that just in
terms of basic storytelling structure, right.
But what? What?
Could you elaborate a little bitof what you mean by that?
Yeah, the story has to, you know, it has to mirror a buyer's
reality, right? It's the using the before and
(17:14):
after storyline arc, if you will, right.
So first you talk about the challenge.
What is the challenge that the prospect is facing?
Then you talk about the shift, what caused them to look into a
specific solution or a differentway of doing things, hopefully
your solution. And then you talk about the
results, right? What was the result of adopting
the new solution? Basic stuff, but how you
(17:35):
delivered is what's hard, right?So you want to keep it specific,
you want to keep it short, you want to keep it relatable, and
you want to reference industry peers in the story.
You want to show the KPIs that are involved.
Hopefully those are the KPIs that your customer cares about
and examples of real impact, right?
So if you can pull all of that in there and make it seeing like
(17:57):
a conversation instead of something that's rehearsed, then
I think you have you built that credibility and you show that
they are the hero because guess what?
They solve this using your or people like them solve this
using your solution. And so they.
Feel good, obviously. I mean wholeheartedly agree with
that idea. Storytelling, such a much more
(18:17):
commutative and effective way ofbeing able to have a
conversation with another person, especially in a sales
situation. Sadly, a lot of organizations
struggle with that and as they're putting their material
together, it becomes this feature function dump.
Especially with folks that are early in their development
stages, what advice would you give them on how to look at what
(18:39):
they're really doing critically and how to course correct if
they're off the mark with respect to that?
That's a tough one. I would encourage them to shift
from a product first mindset to a customer first mindset.
Ask them to put themselves in the customer's seat and remind
them, hey, they are looking at 2-3 other of your peers or
(19:00):
competitors, right? So, so don't just jump to we do
this and this is really neat andit's a differentiator.
Forget about that. Forget the product stuff, right?
Ask them what does success look like for your prospect?
Start with that and then show how your product enables that
success, right? Use phrases like here's what our
(19:21):
customers achieved instead of here's what our product does.
Like, don't do that, right? And then, you know, a big
mistake, especially for folks that are maybe newer to this is
they try to fit too much into that demo, right?
And it's very tempting to communicate all of your unique
features and how much better your product might be.
(19:41):
But the value gets lost, right? They, they lose their power when
they're bloated with too much jargons, logos, or every
feature. It's just, it's overwhelming.
And you have to remember it's the first time they're seeing
your product or the second time and they've just come from
another meeting. They don't remember, right?
So keep it, keep it simple and keep it to just the most germane
(20:02):
points. And then resist, you know,
resist the temptation to go through everything that's really
cool and unique. Like take a deep breath,
remember to stick to 1 customer,one problem, one outcome, right?
And kind of let the story breathe, if you will.
So it sounds simple. It's really hard, right?
You have to practice this stuff.It doesn't.
Just just because you remember those things doesn't mean you've
(20:23):
mastered it, right? So practice.
Yeah, less, less is more is really true in many, many
situations, right? It's like because they're not
going to remember everything. You know, you, you talked a lot
about credibility and trust as being part of it and you know,
dropping, you know, examples andthings and, and just how you ask
questions that all contributes to that.
But there's still times where, you know, even though they
(20:45):
understand that this is a good goal to get to etcetera, there's
they're kind of skeptical about either the real value of it or
if if they can accomplish it or things of that because people
are resistant to change a lot. What would you say, you know, to
help address those types of customers or those people are
(21:05):
struggling a little bit to really see how they bridge to
the future? You know, I also get pitched by
a lot of different companies with solutions.
So there's a good chance that, you know, if I'm typical of
people, they've heard it all before, right?
And many were burned. They adopted something, right?
AI in particular, it's often seen as a buzzword.
So just the other day I receiveda message from a swag vendor
(21:29):
stating that they're using AI tosuggest what I could buy.
And I was thinking, oh, gosh, I really want a human who's been
at recent shows, who's seen what's popular to suggest
something. I don't want AI, right?
But but that that tells you an example of how everybody is, is
dropping the word AI into their offering, whether it's real or
whether it's not. So yeah, I can understand that,
(21:51):
you know, a certain amount of skepticism, it's healthy, but
that's where you should take that as your cue to ground the
conversation and results, not the hype.
Like AI is nice, but what can itreally do for that, for that
prospect and then back to related to what they care about
and not just or it does this. So in terms of strategies that
(22:12):
work to increase that trust and to resist that resistance, if
you will, or reduce that resistance, show them what
doesn't change as well, right? So for example, like in with our
solution, we tell them you don'tneed a data scientist to use
this. We walk them through real world
transitions like of wait, if youadopt this, here's what you can
expect in the 1st 30 days. Here's how others have succeeded
(22:34):
that have used this solution. What to avoid?
Even if you point out some things that are difficult with
your product or things to avoid,they trust you more because
they're like, OK, this person is, is, is being realistic.
They're not saying that the world is perfect once we adopt A
solution, that there are some things to think about and
there's some consideration, but this person's going to help me
(22:55):
get through that, that that I find really helps.
And it reduces that resistance because it's not just you sign
the contract, we're going to cutand run.
It's like, no, we're going to bewith you.
We're going to be your partner. So I do think that that helps.
And then last thing is around the balance between aspirations
and kind of grounded in reality,if you will, for your messaging.
(23:16):
Aspiration definitely gets attention, but grounded stories
wins deals, right? So it's good to say, oh, AI is
going to solve the world, but but let's make it grounded in
reality like, well, it's going to help you with these things.
And these are the things, hopefully those are the things
that the prospect cares the mostabout.
So the sweet spot is kind of showing a bold vision, but power
(23:37):
it by tangible, incredible stepsTo get there.
You have to be believable. You need to earn that trust by
keeping it as real as possible and also pointing out some
flaws, right? Again, hopefully those flaws
aren't the ones they care about.But if you drop in a nugget here
or there, they tend to believe you more because they're like,
what? This person's not just painting
a picture of this is going to solve World Peace.
(23:59):
They're saying, well, no, it's not going to solve World Peace,
but it will solve peace in your little corner of the world.
And that's. I think that's absolutely
critical because, oh, let's faceit, in many verticals to say
that the the term AI has been used and abuse would be, would
be generous. It's been a buzzword for a long
time and and half the people I think we're using it didn't even
know what it really meant. So with respect to that, I agree
(24:21):
with you. Being painfully honest in some
respects with the customers is really critical to get that
credibility with them. But at the speed that some
organizations are dealing with, like Matt and I are talking with
organizations all the time and some of them are very early on
in their development phase wherethey haven't even really built a
(24:42):
body of customers yet. How do how does somebody in that
stage development where they don't have a lot of customers
they can point back to as proof points.
How would they approach that that Crucible of truth with the
customer to come forward saying here's what's good and here's
where things might be wobbly? Yeah.
(25:03):
If you don't have many customers, the assumption is
that you have at least a few. And most companies that are in
their earlier stages usually will have design partners that
have agreed to speak to them or speak on their behalf, if you
will. So you you go off of that,
right. And ideally, those customers are
relevant to the ones you're talking to such that you could
(25:25):
share that example. I don't think anything is gained
by pretending you have dozens and dozens of customers that are
that are doing this. Be honest and upfront.
It's back to credibility, right?If they believe you and they
trust you and you have their best interests in mind.
I don't want to over emphasize this, but the rest of the
process can be easier once you have that trust.
(25:47):
But if you don't have that trust, you don't have a shot.
You do not, you do not have permission to continue, if you
will, right. So it's OK to be real.
It's OK to say we have a few, but guess what, These customers
have real results and this is very relevant to you, Mr. Or
Misses Prospect and let's talk about those.
Yeah. One thing that you mentioned
(26:07):
that we've talked about on previous podcasts, but I think
it's so important that we circleback to it is as I progressed in
my career, having a very clear path about how it's going to be
implemented, deployed and adopted has become so much more
critical because that is the final stages of the journey, if
you will. But that is ultimately where you
(26:29):
provide the most credibility because they're like, I see it's
done. And being upfront and saying
some of this is going to be hard, some of this is going to
take effort and it's going to take this amount of effort, you
know, and you set that stage. So it's not like, Oh yeah, one
click button, it's all integrated, you're good.
Those days are gone. So I really can't emphasize
enough, you know, that portion of it of being, you know, that's
(26:52):
where you really become a trusted partner.
And when you don't have perhaps all the customer stories and
things in the past, helping themknow that you have a well
thought out way to get them to value can provide that
credibility you need. I love that point because you're
right, a smaller companies have that advantage, which is we're
(27:13):
going to hand hold you to the process.
We're going to make sure you're successful where as a larger
companies like you know, you're 1 of many, you know, we'll give
you our standard package, but smaller companies can provide
that hand holding to make sure they're successful.
And that's an advantage. That's an advantage over those
large established folks. So I like that point that you
emphasize. It is important and it's OK to
(27:35):
it's OK to you don't have to be shy about it.
Every company at one point was smaller.
Nothing wrong with that, right? Everybody starts from somewhere,
but highlight what's relevant for that customer.
No, I wholeheartedly agree. And I think it really comes down
to, but you're talking about credibility and that trust with
the customer that is probably the most valuable commodity you
(27:57):
have as a seller when you're talking with them is the honesty
of what you're approaching them with.
And it's also very fragile currency, right?
You lose it, It's almost impossible to get it back once
you've lost it, right? Yeah, I so agree.
Yeah. So with that being that being
said, so obviously we want to sell with integrity.
We want to sell with honesty and, and be frank about where we
(28:19):
are, but also aspirational with respect to what we can provide
them in terms of solution and where we can get them to best
laid plans of mice and men. Things don't always work out.
You don't always win everything.You win a few and you lose a
few. I know that you're really big on
the concept of doing the post mortems, which is kind of a
(28:39):
morbid term for it, but the likethe after action report, if you
want to use more of a militaristic term after a deal,
why? I have really strong and Matt
does too, really strong opinionsabout why that's so important,
but I'd love to hear your perspective as a marketer on
that. Yeah, win loss analysis is
important. You know, often times when you
win something, it's easy to not realize there things have gone
(29:01):
wrong, right? Because you're so caught up in
the oh, we won, so everything I had done must have worked well.
So it's important losses are actually more important for that
because losses reveal what went wrong such that you can improve
on it, right? So structured reviews help you
find those patterns, right? Misaligned messaging, maybe
competitive positioning, right? Maybe there's what's better or
(29:24):
any internal friction, right? Maybe the handoffs weren't great
or we fell down during onboarding.
I don't know, you know, whateverthose things are.
But that analysis is important because it's, it's a mirror,
right? And and and growth requires
looking into that mirror and being brutally honest, I
actually find more value from the ones we lost than the ones
(29:44):
we won. Because of that, yeah, I mean
that's been our staple in our journey as sellers is that after
everything we have a post more even after every meeting, you
know, just how, what went well, what didn't go well, what do you
think how it should go, etcetera.
So that's been part of our process for a long time.
But from the marketing side, it's very rare that a marketing
(30:06):
person is involved in these meetings.
I'm just curious because obviously you can't be on every
of those calls, but at what point are you kind of looking at
it and what's your engagement with the sales team for their
feedback or can you do it all remotely just by looking at the
the videos and things like that?What does that process look like
I guess for you? Yeah.
So from the market side, I'm thinking of product marketing,
(30:27):
and it is absolutely product marketing's job to do the win
loss analysis. And you know, with the video
recording features, you can see the video, you know, you can
dump the transcript into an LLM,right?
ChatGPT, Claw, Gemini, whatever,and be able to find the
patterns, the sentiment. That's something that you know,
(30:49):
you'd have to go through the recording to see.
These are the words they use. But how was it said, right?
So you can get that kind of analysis so quickly, so easily,
right, that it has become a lot easier.
And so I do think marketing has a role in it as well as as as
customer success, right? Because if you think about it,
they both could be affecting that deal, right?
(31:09):
Maybe it's the messaging that's upfront.
Maybe it's the positioning that that caused a disconnect with
this CS team. Maybe it's the onboarding.
Maybe it's the, you know, the regular check insurance, the the
MBRS or whatever you do or something fell down.
Maybe, you know, adoption wasn'tthere or support or whatever
that is. And so there are many reasons or
(31:30):
many ways that a customer could be lost even after it was
closed. One, if you will.
I think the most important stuffis to actually conduct that
analysis because I know oftentimes everybody's so busy,
we forget. We're like, oh, we're doing
well, we'll put it off. And it's like, you don't want to
make assumptions because you don't know what will be
revealed, right? Did we confuse them?
Did we share too much information?
(31:51):
So it could be the marketing, you know, the messaging, the
targeting, it could be just the mismatch of what they needed and
what we actually provided in terms of service and support.
Every company's at a different place in the maturity, if you
will, right? And they need something
different. So we don't want to assume, and
I think that's where the post mortem analysis helps.
That said, you need to have a sufficient number that you've
(32:13):
done to see those patterns. It can't be like 3 or 4, it has
to be more. And so once you have a
sufficient number, then you can start to see themes in
objections, in clarity, gaps in positioning or in
differentiation where maybe the differentiation didn't land.
And so sometimes it's not the deck that was shared, the sales
deck, it's the disconnect between the pain and the promise
(32:34):
that we made. And that's where the win loss
analysis helps. Yeah, I think that understanding
that gap is so critical. And to your point about bringing
in customer success and the service delivery people into
part of that analysis, one of the things that I'm a big
proponent of is to bring them invery early because we're talking
(32:56):
about the initial sale here in this conversation.
But the renewal is just as important, if not more so
because you're trying to grow inmany cases where the land and
expand. And it's been my experience that
when we bring customer success and they're like you promised
the wrong thing based on what their problem was.
(33:17):
So you were you were hamstringing yourself for your
renewal before the ink ever hit the contract.
What would you say with organizations, particularly
young ones that are trying to find out and acid test their
value, what are some strategies that they can take on trying to
really document and understand and validate their value
(33:41):
proposition from that perspective?
And I know that's a big question.
Yeah, it is a big question. There's lots of ways to attack
it. You know, that's where I find
out that a few trusted customerswhere they can be honest and
frank. If you're able to get their
attention, maybe it's through a customer Advisory Board or maybe
it's just you built a good relationship, or maybe it's the
E staff meeting with a customer,you know, where they have no
(34:06):
agenda. They're like, I just want to
hear from you what the experience is.
But if you can get some frank and honest conversations going
with customers, you'll get more of that insight because
sometimes maybe people are too polite or they're too busy or
whatever that is. So I find that those are a
couple of ways to get that information.
Is is earn the trust, have get afrank conversation where you
(34:28):
tell them you know, nothing's off the plate.
You know, like we really want tohear and understand and that
might help. I'm sure there are many, many
other ways to do this, but that's a tough one.
I think that's a great one, getting out there and actually
talking to the people who are using the solution and getting
getting them to give it to you with no sugar, no sugar on it at
all, right? Because you can't fix it if they
(34:50):
don't tell you. Yep, agreed.
Yep, Janet, I would love to keeptalking because these are very,
these are very exciting topics for, for with Matt and I, but we
do have to bring our episode to a close.
So before we do that, I wanted to ask if, you know, if somebody
was looking to kind of get into your area, what kind of advice
(35:10):
would you give to somebody who maybe is just starting out in
your field about how to deal with the kind of changing
landscape in the world today? Well, that's a tall order, but
you know what, you start with step one, right?
I think we can learn from any experience.
And so the main thing is to get started.
And then you start to figure outwhat you like, what you don't
(35:33):
and what you've learned and whatelse you need to learn.
And then just kind of continue that path.
Go to your next role, go to yournext company and, and collect
those kinds of experiences. But really the biggest advice is
just start right. And it doesn't matter where you
start. Every experience is relevant,
but there's so much happening that it, it is tough to keep up.
And so, you know, definitely getadvice from people who've been
(35:56):
in your shoes, right? Save yourself some time, right?
Like, why learn things the hard way if you're able to cultivate
a network, able to read and learn from others books,
podcasts like this one, right? Like, learn from other folks
who've been there and who have done that.
Might save yourself a little bitof time and heartache.
Mentorship and connection, that's what it's all about.
(36:18):
There's a lot of great experiences out there and we
won't ever experience them all over the course of our careers.
So reaching out to those who maybe have seen and done things,
we haven't great advice from that perspective.
So if people wanted to reach outand connect with you, Janet,
what's the best way for them to do that?
If they wanted to try and and collaborate or get some of your
(36:40):
thought? Yeah.
Real easy, just go to LinkedIn and look up my first name, last
name. So far no one else appears under
Janet Jaswal. So yeah, just reach out.
Happy to help wherever I can. Fantastic we will include in
your bio and a link inside of the description on most of the
platforms this is going to be showing on anyone wants to click
on that you'll be able to go directly over to Janet and
(37:02):
communicate with her and I can tell you from personal
experience it it's always fulfilling and you will always
learn something as a result so Janet, thank you so much for
coming onto the show this week really enjoyed it and I hope
that you had a great time here as well you're.
Welcome. I enjoyed the conversation, so
thank you for the fantastic questions.
Thank you so much for the fantastic answers, Matt Sir,
(37:25):
always great to spend a little bit of time with you virtually
online. Anything you'd like to share
before we close down for today? Yeah.
I'd really appreciate your perspective coming from
marketing because most of the people we have on here are in
sales. And I gotta be honest, in my
career, there's a lot of finger pointing back and forth between
marketing sales. For healthy.
No, never happened. But also I think they're
(37:47):
rightfully so there was a disconnect for a lot of years
between marketing sales and I'm glad to see that it's kind of
come back around to be more integrated and holistic in terms
of really everyone understandingevery step of that customer
relationship, right. So that's it's really nice to
hear your insights and thoughts around this.
So thanks, Janet. You're welcome.
Now I wholeheartedly concur withthat.
(38:08):
And ladies and gentlemen, with that having been said, that
brings us to a close on this episode.
Please come back and join us next week where we'll have
another guest right here on the very same spot.
If you would like, please subscribe, like, follow,
comment. It does us a world of good on
the different algorithms for theplatforms we're on.
Please take a moment to do that if you don't mind.
And if you would like to learn more about the methodology you
(38:30):
hear Matt and I talking about onour show, you can go to our
website where you find a you canpurchase your very own copy of
our book. But until then, we will see you
next week right here on this same channel.
And with that having been said.
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