Episode Transcript
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This episode of Closing Time
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Now let's get to Closing Time.
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Hi I’m DaveOsborne, chief Sales officer at Insightly.
Welcome to Closing Time. The show forGo to Market Leaders.
I'm joined today by Jason Bay,founder and CEO of Outbound Squad.
Welcome, Jason.
What's up?Good to jam here with you, David.
Yeah, absolutely.
So, Jason, you and I were talkinga little bit before the session, right?
Like, I think outbound is almost
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the holy grail of buildingpipeline and has been for a long time.
And I know a lot of folks outthere are deadly focused on either
adding that to their skillset or to their,you know,
their pipe gen strategyor they're trying to just amplify it.
Right.
So I think this is going to be a really,really relevant topic for a lot of folks.
But, you know, looking at your past,you've always some big, big brands
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at Outbound Squad, right?
You've worked with Zoom, Gong, CBRE.
The list goes on. Right.
So by that list, I mean, I assume thatthat means that the challenges
with building self-source pipelineisn't just limited to small startups.
Is that fair?
Definitely not.
If you kind of step back
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and think about, you know,why is this so hard and why do so
few people do it.
I mean, it's filled with rejection.
I mean, worse than selling,you know, the average win rates,
you know what, ten or 20%,depending on your industry,
that means you lose 80%plus of the deals that you work.
Well with outbound, It'sone of those things where, hey,
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if you have a 95 to 98% rejection
rate, you're actually doing okay.
Yet, The mindset behind
dealing with thatamount of rejection is crazy.
You know,when you apply for an Ivy League school,
the rejection rate is not 95%usually, Right?
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You know, there's all kinds of rejectionthat an individual faces
in sales with prospecting, thatif anyone had that in their daily job,
it would be so unhealthy for them.
You know, I think that's a really big partthat as a sales organization,
if you're treating outbound like,Hey David and team, just go make calls
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and go send emails and you providevery little enablement or direction
or guidance, you're going to have peoplethat pick up the phone and get met
with a lot of rejection and resistanceand who would want to continue doing that.
So I think shifting into an approachthat's more customer centric,
that isn't talking all about my productand pitching people who I have
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not met before, like shifting to somethingthat has less rejection
and is more customercentric is a start in the right direction.
Right.
So let's talk aboutlike how we kicked this off.
So let's kind of pretend that,
you know, I'm a sales leader, I'mjust getting started.
We’re about to do a stand up to do aan outbound motion, right?
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So we have a meeting to geteveryone pumped up about outbound, right?
And everyone is being hyped.
And then you check in a few weeks laterand there's absolutely no movement.
Like, yeah,what is the disconnect that happens there
between like an AE's desire to self source
and build their own pipeline to themactually executing and getting it done?
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Yes, I think that's step numberone is sitting down
with your account executives,and I call it the sales math.
So we have a sales mathcalculator that we use and we say, Hey,
you want to make X amount of dollarsin commissions?
Let's backtrack that into the revenuethat you need to close
with your commission rate and say, hey,based on how inbound and SDRs
like that portion of your pipeline,you're going to get 70% of the way there.
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So that 30% that you need to self
source is worth $60,000 in your pocket,let's say.
And then why is that number important?
You need to have that wholewhy conversation and that needs to be done
with a managerindividually with each of their reps
so that you're not about to dostep number two and pull out an
arbitrary activity target and say,All right, David and team,
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everyone needs to make 30 coldcalls a day.
No, you want that to be.
Hey, David, based on your number, if weback, you know, reverse engineer the math.
It looks likeyou need to make 26 of these calls
every single daybecause your pick up rate is 10%.
That's going to give you twoor three conversations.
And we know with your conversion rate,that's going to be one meeting per day.
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So that's five meetings
a week of which you're probably goingto close one of those deals.
So if you can make it very real,that's step number one.
Step number two, the kind of framework,I call it
the outbound equation,there's three kind of components to it
on the quality side of the equation.
So there's a qualityand then quantity side.
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So I need to have activity no different
than if I'm working outand trying to lose weight.
I need to exercisefor a certain number of minutes, right?
There has to be an activity.
I focus a lot on the qualityside of the equation,
so there's three parts on the qualityside.
It's fit, So who am I reaching out to?
Message, What am I saying?
Three is delivery, which isI know the what the message should be.
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What are my soft skills and my ability
to When the prospect says hello, executea great call?
To write a compelling email,to handle an objection,
to secure our meeting,to get them to show up, etc.
So where I would start is the fit piece.
I think the number one mistake.
I was just on a callright before this with a sales leader
and we were joking aroundbecause he just joined a new team around
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how the worst way to approacha set of accounts is to just go top
to bottom in your Salesforce or Insightlyor your whatever.
What you want to do is you want to saythat 100 accounts that you're going after,
how do we say, hey, we know that health
care is the industry where we're closingthe most work right now.
We know that VPs of IT
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Are the best place to get a meetingstarted.
Now let's cherry pick and look at allthe health care accounts.
Let's get on LinkedIn SalesNavand look for newly appointed IT leaders.
Let's see if there's anyone
that used to be a previous customerthat moved to one of these places.
Like let's go through that exerciseof the fit component
and say outbound is really hard.
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It's a lot of work.
Let's make sure our effort is focusedin the right direction.
So I'll pause there.
That's the most critical thing to nailfirst is where is my effort
going to be directed and at what?
How much of that?
Also, Jason is like a factor of, you know,I don’t have the stats in front of me,
but there's always a certain amountof touchpoints before you potentially do
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get a response, right?
So I think conceptually,if this is your fourth or fifth or sixth
call or email or touch point, whateverthat looks like versus the first one,
are you prioritizing like those follow upsor those subsequent calls first versus
is that somethingthat you're keeping in mind
or is that not necessarily as relevantas like title, etc.?
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Yeah.
So I think first decidingwhat account am I going to go after
and who are the individuals that I'm goingto target doing that activity first.
Sure.
Second, we can start to thinkabout our contact strategy.
So our sequence cadence,whatever you want to call it,
Orum, Bridge Group, Outreach, Salesloft,all of the sales
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engagement vendors, all of their datawill generally tell you the same thing.
It takes somewhere between 12and 15 touches to get in touch
with most prospects.
So the most important thing is thatwhatever you do, it needs to
be multi-channel.
So it needs to be phoneplus email, plus social.
Your contact rate will literally tripleby having three channels versus one.
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If you guys listening could guesswhich channel gets neglected the most it’s
definitely the phone.
People don't pick up the phone.
Multi-day is, I can't do 12 touches
in one day it needs to be spread outover 2 to 4 weeks.
So multi-channel, multiday,
those are the most kindof key components to it
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and the way that you want to thinkabout spreading out the touches
is a weekly touchpattern could look like this.
It's a Tuesday.
Today I do phone, email, LinkedIn,I do all of those at once.
I do a triple touchand then I wait two days.
On a Thursday,I do an email and a follow up phone call.
So that same weekly patternI follow three weeks in a row
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that's going to get my 15 touches.
That's a great starting point.
Now, the FIT piece,what you want to think about
is how you segment and prioritizewho you're spending effort on.
It's like, David, you're a VP of sales.
Like in terms of my target market,you're the person really ultimately
that I want to meet with.
I might be meeting with a sales manageror a director of sales first,
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but ultimately I know a VP ofsales is a champion.
Like that's going to be
someone that can mobilizea training engagement to their CRO.
So if I'm reaching out to you, David,I'm going to do that
full 15 touch sequence because it'sworth it to spend extra time on you
becausethat meeting is really high value to me.
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Now, if I don't mind meetingwith the sales manager, let's say
one of your managersto get the deal started.
I'm probablynot going to exert that much effort,
so I might taper off on some of the phonecalls,
like the manual elements of thisthat require my manual work.
I might taper off on those.
So it's really important to think aboutwhat accounts are most valuable to you,
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what types of jobtitles will typically be most valuable?
And it's about putting more effort
in the areas where the return is higherand less effort in the areas.
Honestly, where I just
a sales manager
is not getting as much cold outreachas someone like you, right, or a CRO.
So I need to work harderto get that meeting.
And it's also worth more.
Do that answer your question.
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That was kind of a roundabout, really longwinded answer, but that's, that's how
I think about the sequencingand like the contact strategy.
No, that's perfect.
And, you know, I was I was thinking aboutand I can remember the word you used,
but like the combo, right,where historically or even today,
maybe phone callsare the least high contact rate.
But having that multi-channel strategyis super impactful.
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So let's talk aboutmaybe taking a step back.
Talk about activity targets.
Which gets a bad rep from a lot of folks.
But I think we're I'm curiousto understand is, again,
if I'm a sales leader, getting an outboundmotion out for the first time.
You talkedabout looking at historical data
and kind of kind of backing your wayinto a prescriptive approach.
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But let's saywe don't have a lot of historical data.
So how would you recommend leadersarchitect
the initial activity targetsand adapt from there?
Yeah.
One, I wouldn't just
pull that number out of thin air,which you'd be very surprised.
The larger the company, the morethey just pull numbers out of thin air.
Like are totally arbitrary numberthat they talk to their peers
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and that's just what they saidtheir activity target was.
You could just use industry benchmarks.
So if we were going to work backwards,like you should know,
you should at least know your win rates
and you should know what percentageof like an intro calls turn into,
you know, a weighted pipelineor a qualified opportunity,
you should at least know those metrics.
So if we work backwards to
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how many people would I need to getin touch with in order to get a meeting,
I'll give you some benchmarksthat you could work off of.
So with the total number of contactsthat you're reaching out
to booking meetingswith, somewhere between five and 10%
of the everyone that you reach out to,that's a good starting point to use.
And if you wanted to dial it inper channel,
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the averagepick up rate for a cold call is 5%.
The average conversion rate of connected
cold call into a meeting is around 10%.
Your best reps should be in that 25 to 30%range.
Email, Your open rates should be around35% on average.
Your reply ratesgoing to probably be around 1 to 3%.
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The average called email replyrate is actually 1% according to Clearbit,
that's honestly being a little generousfrom what I see in a lot of companies.
So you could use those benchmarksas a starting point
to kind of work backwards around the math.
And you need to explain the whybehind the math if you're speculating
and don't have like real numbersto work off of.
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Yeah.
I think people sometimeslike sales leaders I find
they kind of treat their repslike they're idiots or something.
You know what I mean?
It's like, dude explain the why behind it,get them excited about the number,
but also like show themthat you're like using
an objective analysisto come up with the numbers.
I think this era of like,especially with younger
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sales reps coming in Gen Z
and this is the case
with all younger generations typically,but I think very much so a Gen Z and I'm
a millennial,
this like I'm going to
blindly followauthority, just doesn't work anymore.
Like that's how I was led as a sales rep.
It just doesn't work.
Like explain the logic behind the number
and what you're asking your reps to doand you'll have a lot more buy in.
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100% agree.
Maybe just to wrap up, I'd love to hearyour thoughts on personalization.
I think that's a nice young dovetail fromwhat we were just talking about there.
So obviously you talked about quantityand quality both being important, right?
And when doing prospecting,we do need to cast a wide net,
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but would love to kind of understandhow you think about casting a big net
versus using kind of a sniper rifle.
Right, in some situations.
So, you know,
feels like the one to many approachis a little bit behind in the past.
So is that what you're seeing with yourclient base or how do you approach that?
The question really is not likewhether you should personalize or not.
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It's it's really kind of like,how do I do this
and still remain productiveand get out emails, right?
So the way that you personalize at scale,as you know, that term has been coined is
how do I find common patternsin the people that I'm reaching out to?
So if I was to give you an example,
I worked with a companythat sells into DevOps leaders.
DevOps is essentially the equivalentof sales enablement for reps.
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They do it for engineers,they make an engineer's life easier.
So when they're reaching outto these DevOps leaders, it's like,
Hey, the situations you're looking for,are they hiring engineers right now?
Did they recently release a product?
Did they recently go through M&A?
There's like all this really commonlike 5 to 10 triggers,
but you should have an email sequenceprepped and ready to go that you can add
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slight customizationto around all of those situations.
So situation based outreachis how you can really prepare
for the most common scenariosand have a game plan that's repeatable.
So when you're goingthrough your account list
and you're going through the peopleto reach out to you, you're
looking for peoplethat fit into the different situations
that are really common so that you don'treally have to customize that much.
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That's that's the big idea.
That's how you do that at scale.
That's perfect.
It's not about looking at the person'sLinkedIn profile
to see where they went to schoolor the content they post.
Make it about the company.
Love it, love it.
All right, folks,
that's all the time we have for thisthis episode of Closing Time.
Really appreciate taking the time, Jason.
Really, really relevant content.
Appreciate it.
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Yeah, absolutely.
All of our stuff is at outboundsquad.com.
We have a podcastas well, Outbound Squad Podcast
so make sure to check it outif you're looking for more tips
or how to make a lot of what we talkedabout today more actionable for you.
And a special thanks to all be listeningtoday.
Be sure to tune in every weekfor new episodes with luminaries
in sales, marketing and customer successfields.
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I'm your host,Dave Osborne. I'll see you next time.