All Episodes

March 19, 2025 • 43 mins

đź’ˇ How do you scale a SaaS company from SMB customers to billion-dollar enterprise deals?

In this Prime Venture Partners Podcast episode, we sit down with Praerit Garg, President of Product & Innovation at Smartsheet, to uncover the secrets of scaling SaaS, AI’s role in work management, and the game-changing lessons from Smartsheet’s journey.

⏳ Timestamps:

00:00 - Introduction 


01:28 - Praerit Garg’s Career Journey: From Microsoft → AWS → Smartsheet


04:46 - What is Smartsheet? How It Serves SMBs & Enterprises


07:11 - The Land & Expand Strategy: How Smartsheet Scaled Enterprise Deals


10:27 - Finding the "Magic Metric" That Drives SaaS Growth 


12:55 - Smartsheet’s IPO Journey & Why It Later Went Private Again


15:37 - AI’s Role in Work Automation & How Smartsheet Uses It 


21:03 - The Enterprise AI Trust Challenge – Why Big Companies Are Cautious


24:58 - What VCs Look for in AI SaaS Startups 🚀


36:30 - Why Learning from Non-Customers Unlocks New Market Opportunities


43:00 - Closing Thoughts 


🔥 Inside This Episode:
âś… How Smartsheet transitioned from PLG to enterprise sales
âś… The pricing strategy that maximized SaaS revenue
âś… Why AI is transforming work management & automation
âś… The #1 mistake SaaS founders make when scaling
âś… How learning from non-customers can drive new product innovation
âś… What VCs look for when investing in AI-driven SaaS startups

📢 This isn’t just a SaaS success story—it’s a must-listen masterclass on scaling, pricing, AI, and product innovation.

đź”” Subscribe & Turn on Notifications for more expert insights!

Follow Prime Venture Partners:
Instagram: https://www.instagram.com/primevp_in/ 
LinkedIn: https://www.linkedin.com/company/primevp/ 
Twitter: https://twitter.com/Primevp_in 

#SaaS #ScalingSaaS #Smartsheet #StartupGrowth #AI #TechInnovation #EnterpriseTech #VentureCapital #FounderMindset #Entrepreneurship #B2BTech #SaaSStartups #BusinessGrowth #FutureOfWork #PrimeVenturePartnersPodcast

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
If you're a SaaS business right, you earn your
customer's business every day,every hour.
I'm one of the three presidentsof the company.
Now, MomSheet is a workmanagement platform.
So think, projects, programs,processes yeah, I think the
magic is in product.
We organize the product orgaround the personas we have
served.
The job of product manager isto be the voice of the customer.

(00:22):
Everybody, even the smallest ofmom shop, wants to have an
enterprise-grade experienceright.
Every morning you want to wakeup thinking about okay, what do
they need and how do I servethem?
Technology exists ultimately toserve customers.
Microsoft had lost its hunger.

Speaker 2 (00:35):
I know you're setting up a brand new office in India
for Smartsheet.
Welcome to the Prime VenturePartners Podcast.
I'm Amit Somani, your host, andI am delighted to have with us
today Prerit Garg, a dear friendand president of innovation
products and tech at Smartsheet.

(00:57):
Welcome to the show, prerit.
Thanks, amit, it's great to behere.
So Prerit and I met each othermany, many decades ago we won't
say how many so as to not dateeither of us, but he's had a
very illustrious career, youknow, starting out with his grad
school at Purdue, working at avariety of tech companies, then
for a long stint at Amazon andnow at Smartsheet.

(01:19):
Maybe you can walk ourlisteners and our viewers
through a little bit of yourcareer, praveen.

Speaker 1 (01:32):
Oh, that may take 45 minutes, no, but I think you
kind of summarized it.
We met when we were in gradschool and I went to Microsoft
right out of grad school andthat was a long stint, for 12
years and I eventually decidedthat you know, it's a groundhog
day, every day is a groundhogday.
I better get out of there anddo something.
So that was fun.
I did a startup for six yearsand then we sold that company

(01:54):
and I thought I was going to doanother startup, but then AWS
came calling and so I ended upjoining AWS for a few years and
I thought I was going to retireafter that.
And then I met Mark Mader, whoconvinced me to join Smartsheet.
So I've been six years now at.

Speaker 2 (02:11):
Smartsheet, Fantastic .
So tell us a little bit aboutthe most recent two journeys One
at Smartsheet.
What is your role at Smartsheet?
What does Smartsheet do?
And then we'll go a little bitfurther back in history.

Speaker 1 (02:23):
Sure sure, yeah.
So I joined Smartsheet in 2019,february, after about eight
months of quote-unquoteretirement, and so I joined as
the CTO.
Initially, mark sort of cameand said, hey, I'm running
engineering myself.
I need somebody who reallyknows how to run engineering.

(02:44):
Can you help me out?
So I, who really knows how torun engineering, can you help me
out?
So I ended up joining him torun engineering.
That's where it started.
Of course, the company had justgone public and it was super
interesting, right Like how you,where the team was, where the
product was, like the entireservice was in a data center.
It was not in the cloud in 2019when I joined Wow, and so one

(03:08):
of the big things I did was toactually mobilize the team, sort
of restructured them and thentook the service into the cloud.
So we moved everything to AWSand that was sort of the one
first big thing.
Then we created another regionin Europe for Smartsheet and at
that point, my partner in crime,who was running product at that

(03:29):
time, decided to leave and gobecome a CEO of a startup, and
so Mark and I had theconversation and I'd always run
product and engineering andevery other role, and so Mark's
like should we bring somebodyelse, or do you want to just
take over the whole thing?
I said you get to make thatdecision, I don't get to make
that decision, and so I tookover both of them at that time.

(03:50):
And then my role evolved againlast year where I took over many
other functions, including corpdev strategy, digital marketing
pieces as well on that.
So that's sort of so.
I'm one of the three presidentsof the company.
Now I'm responsible foreverything that's product and
digital.
So as long as there is nodirect human interaction, it

(04:13):
sits with me.
If there's direct humaninteraction, that sits with Max.
So all our go-to-marketfunctions like field marketing
and sales and customer success,and then Mark's the CEO
president.

Speaker 2 (04:24):
Got it.
So what is the core offeringfrom Smartsheet and what are the
?
A lot of our listeners andviewers are like early stage
entrepreneurs, right?
And one of the things that weoften think about when you're
building companies cross borderpowerhouse out of India or dual
homed in India and US is how doyou sell to and how do you build
for the mid market andenterprise, right?

(04:44):
So maybe some lessons learnedfrom Smartsheet and I'm not
really sure.
Is it only enterprise customersyou guys have, or you have SMB
as well, or just mid-market?
Maybe a little bit on thatwould be helpful.

Speaker 1 (04:56):
Yeah, so Smartsheet is a work management platform,
right?
So think projects, programs,processes being managed in an
organization, right?
We have the smallest ofcustomers, and I like giving my
personal example.
We were remodeling our houseover COVID, oh, wow.
And so the architect as well asthe general contractor both

(05:18):
happen to be Smartsheetcustomers, small boutique shops
but they use Smartsheet tomanage all of their projects,
right, I did not know that.
I found out when they sharedthe Smartsheet to manage all of
their projects.
I did not know that.
I found out when they sharedthe Smartsheet with me as their
client.
Amazing, amazing moment.
And then, on the other end, wehave customers like Amazon.
Many of the Amazon's divisionsuse Smartsheet for managing

(05:40):
their projects and programs.
So the largest of customers inthe world use Smartsheet for.

Speaker 2 (05:48):
So pretty.
Very few companies have beenable to scale both at the
product and the GTM level, allthe way from SMB, like the
contractor that redid your home,to like somebody running a
large division in Amazon orwhatever Walmart or whichever
enterprise customer you have.
How has that really worked out,in the sense of both the
product side and thego-to-market side?

(06:09):
And do you consciously, whenyou are running the org, are you
thinking like one customerpersona, or you know?
Because like scaling a PLG withlike $20 a month for some
contractor versus a milliondollar account with a larger
client, like it just seems likevery different.

Speaker 1 (06:25):
They are very different.
I mean, there's no questionabout that or anything.
And for a platform which servesthe smallest of customers to
the largest, you have to sort ofbe very intentional about how
are you going to go to market,how are you going to serve
customers at the differentsegments, and how much?
Because it's very much a landexpand product offering right.

(06:46):
So you land with a customer fora specific use case and then,
because of collaboration acrossthe organization, new use cases
get discovered right, and sosmall customers you can only go
so far and the large customersthere's a lot of opportunity to
expand across division, acrossdepartments.
So SmartShare has gone on a veryinteresting journey.

(07:07):
It originally started as a PLGoffering right, there was a and
Smartsheet always had the trialmotion and so it started as that
.
But at some point Mark made thedecision this was before I had
joined them right that hestarted experimenting, hiring
salespeople to go sell to largermid-market and enterprise

(07:28):
customers and those deals tendedto be larger and there was a
very different level ofsophistication of what was being
managed.
So the business heavily grewbecause of the enterprise
penetration, mid-market andenterprise.
We kept our PLG DNA and that'swhy we continue to have a lot of

(07:48):
SMB customers as well, and soyou have to be very thoughtful
about how do you run those twomotions, and we've had our set
of learnings along the way.

Speaker 2 (07:59):
Can you talk about the product side of this?
Because what a mom-and-pop SMBcustomer would demand versus a
typical, you know a largeenterprise customer?
The five, nines availability,this failover, all that would
not match.
So how do you do the productand the tech org to match that?

Speaker 1 (08:17):
Yeah, I think there are some aspects which are
consistent.
Right, everybody, even thesmallest of mom shop, wants to
have an enterprise gradeexperience.
If it's a work managementproduct, they don't want the
service going down theirdependency on tracking work and
being able to report on work.
We often say that if you're aSaaS business, you earn your

(08:40):
customer's business every day,every hour.
Regardless of the smallest ofcustomers to largest, the level
of sophistication of whatthey're managing changes, right,
like a large customer ismanaging a portfolio typically
of hundreds, if not thousands,of projects.
Right, like, if you're managingwind farms, you're probably
hundreds of wind farms andyou're trying to actually manage

(09:03):
and maintain that.
So the scale and the complexitychanges right when you're a
small business to a largebusiness, and so a lot of our
functionality is common, the enduser functionality is common.
But then we provide these highvalue, large scale portfolio
management capabilities thatessentially that are really
targeted to our end pricecustomers and to your product

(09:23):
point.
Right, you have to when you'rebuilding a platform that is so
horizontal in terms of serving,you have to be.
You can't sort of purely do itby segmenting the market.
You have to focus on thepersona, right, and so product
org, because I just restructuredthe product org and we can talk
about that as well.

(09:45):
So we organized the product orgaround the personas we are
serving.
So the three core personas thatSmartsheet serves today is what
I call a work manager.
A core work manager Somebodywho's managing a project or a
program in the organization.
To an enterprise work managerthat's managing a portfolio of
hundreds, if not thousands, ofprojects right.

(10:07):
And then the collaborator, thestakeholder that's participating
in the work right.
It's a very importantstakeholder that collaborates
and they're doing the actualwork, working with either the
enterprise portfolio manager orthe work manager right.
So we're organized around thepersona because it's all about
how do you delight the persona,how do you serve them.

(10:27):
Every morning you want to wakeup thinking about okay, what do
they need and how do I servethem?

Speaker 2 (10:33):
So let's say I'm a SaaS entrepreneur right From
anywhere really, but nominally,say, cross-border, based out of
India and the US, and I'mserving SMB customers.
I'm at a couple of million ARRand the US and I'm serving SMB
customers.
I'm at a couple of million ARRand now my VCs, unfortunately,
are pushing me to go up marketright, go mid-market, go
enterprise, try to get 50K deals, try to get 250K deals.

(10:53):
How do I make that transitionIf I'm already there, I've got
real customers, I've got realtraction, but I need to scale up
Any thoughts or lessons or tipsof what I might go through.

Speaker 1 (11:07):
Yeah, I think the magic is in product right.
So the magic is do you have aproduct team that actually
deeply understands the customerand the customer need right,
like Smartsheet went throughthat journey as an example, I'll
give you.
Yes, I remember when I joinedSmartsheet.
One of the questions I askedMark at that time was okay, what

(11:28):
led to the IPO?
What was that secret sauce thatenabled you to scale and scale
rapidly enough that you could?

Speaker 2 (11:34):
actually go IPO and what stage were you at when you
IPO'd revenue scale?

Speaker 1 (11:38):
It was a couple of hundred million dollars.
So it was super interesting.
He referenced a very specificcapability in the product it's
called the control center whichwas discovered essentially by
the product managers talking tothe actual customers.
They saw this pattern over andover again, which is these

(11:59):
portfolio managers.
What they were doing is theywere making copies of their
standard Smartsheet templates tomanage hundreds or thousands of
these projects in a consistentway, and so they discovered this
sort of little secret, which is, hey, what really, at scale,
customers want to do is managethings consistently across large

(12:20):
number of projects.
So they built a specificcapability to target that
persona, and that was a highvalue capability, right?
And so you have to continuouslylisten to the customer, right?
One of the things I often sayabout product management is it's
actually really poorly named.
Right, because the productmanagement we think that, oh,

(12:42):
it's about managing the product.
It's actually not right.
The job of a product manager isto be the voice of the customer
, right?
Like?
One of the things I ask myproduct managers is how much
time are you spending withcustomers in a given week?
Right?
I'm a big believer of weeklyrhythms.
Like how much time do you spendwith customers If you're not
spending 30 to 40% of your timetalking to real customers or

(13:04):
talking to your go-to-marketteam that talks to your
customers.
You're not doing productmanagement, because product
management often gets focused onfeatures and functions and
that's not the job of productmanagers, got it?

Speaker 2 (13:18):
So talk to us a little bit, both about the IPO
you were there before the IPO,or just about, just about.

Speaker 3 (13:23):
Just after.

Speaker 2 (13:24):
And then obviously you guys recently went private
again, right with the privateequity.
So how was the journey post ipo, dealing with the public
markets, delivering to a certaintarget every quarter, every
year, etc yeah it's, it's superinteresting.

Speaker 1 (13:37):
I learned a lot right um this I was a section 16
officer of a public company forthe first time in my career and
so there's a lot to learn everyquarter.
The earnings statement thatMark had to say I was part of
that journey of sort of creatingthat.
I think there are lots ofbenefits of the public market
but at the same time thedynamics and the expectations of

(14:00):
the public market require acertain kind of consistency in
results.
So if you want to make pivots,if you want to restructure the
company not great to be inpublic markets right Because
it's very focused on quarterlyoutcomes and public market are
not as involved in the company.
They're sort of assessing thecompany from far away right.

(14:24):
And so it's very hard to makebets that are multi-year out
bets, whereas working withprivate equity changes that
equation.
We're in this together now,right, Our investors and us.
We are in this together tocreate more value so you can
make longer bets.
You can actually do therestructuring and changing some
of the things you want to gochange.

Speaker 2 (14:43):
Awesome.
We can't but not talk about AIand quite a bit.
But before that, just one lastthing on the SMB versus
mid-market versus enterprise.
How about packaging?
How about pricing?
Like you said, I love the thingabout product managers spending
a lot more time or 30 to 40% oftheir time with customers.
How do you figure out pricediscovery?
Another of my favorite topics.

Speaker 1 (15:05):
Please go right ahead .
We just changed Smartsheets,pricing and packaging.
That was one of therestructuring things we did.
I'm a big believer pricing isone of the strongest levers you
have in the business, right, andespecially once you figured the
mousetrap out.
In terms of what customers need, pricing is a big lever and I

(15:25):
learned a lot about pricing andpackaging at AWS when I was four
years there.
That company has the art andthe science of pricing down.
So the way I always talk aboutpricing and packaging especially
if you have our kind of productoffering, which is you want to
land and then you want to expand, right.

(15:46):
So AWS was very much like thatas well.
It was very much a land, expandright and client business, and
so you have to price.
What you have to find is thismagic, what I call the magic
metric, the value metric.
Like that, the customer clearlysees that they are getting that
value right.
And when you find that valuemetric, you have to price it

(16:07):
such a way that it's easy to geton it right and then, as the
adoption grows and scales, youget paid for the value the
customer is actually getting.
And that's the magic right.
And there are lots of differentmetrics Like in AWS, right S3
storage price point, right On aunit price point.
It was super small yeah Easy toget started.

(16:28):
Right Easy to get started.
Compute Easy to compute yeahEasy to get started.
But the more you consumed,clearly, the more value you were
getting and more you paid right.
And so it has to be simpleenough that the customer
connects the dot on value beingrealized right, because
customers don't really want topay when they can connect the
dot to the value they're getting.
It's hard to argue against that.

Speaker 2 (16:52):
So let me double click just on that one last
second before we move on to adifferent topic.
Let's say in enterprise you'redoing a sale brand new first
time and there's enterpriseproduct manager or whatever
right program manager persona.
There is the collaboratorpersona, there's like a bunch of
different like the wind, wind,windmills, farm kind of thing.
There you don't have thatluxury right of starting small

(17:14):
and scaling up because you'regoing to land right off the bat
with a much higher price point,potentially right.
How would you do that?
Or you'll just do theextrapolation from other clients
actually.

Speaker 1 (17:24):
no, it's super interesting.
Each one one of those scenarios, right, like the wind farm
scenario, as an example.
Typically, what happened is forSmartsheet was one specific
team that was managing just onewind farm started using
Smartsheet.
Right, we would see that inwarehouses as well One team
starts using Smartsheet.

Speaker 2 (17:42):
This is like HubSpot or Dropbox or one of those, like
it's the department level.

Speaker 1 (17:49):
Department level person signs up because you, you
know, typically they have beenusing something like
spreadsheets and it's likethey're struggling trying to
keep up with and spreadsheetsare not really designed for
managing work.
Yeah, right, and so whathappens is that they switch,
they start using it, see thepower of it, and then they start
talking to their colleaguesabout it, or typically start
sharing the sheets with theircolleagues, and then they sort
of adopt it and at some pointsomebody says, okay, we're going

(18:11):
to manage the whole thing withthat.
So a lot of our adoption, evenin the enterprise, has been sort
of this you land with specificpeople and then expand it
through that.
Now that to your point.
That's not necessarily true forevery product, of course, right
, there are some products youhave to go in um with the, the
full artillery.
And that's sort of very much anenterprise sales-led motion.

(18:33):
So we found kind of thatbalance.
We do that enterprise sellingas well as land and expand.

Speaker 2 (18:41):
All right, Moving to the buzzword of the decade,
maybe the century AI.
So how does AI change what ishappening at Smartsheet?
How are you guys thinking aboutagentic AI?
How are you thinking abouteverything AI with respect to
Smartsheet?

Speaker 1 (18:55):
I think we live in a very privileged time, right Like
you and I.
Multiple decades, that's right.
I often tell people that youknow, in my career, right, we've
seen several suchtransformations.
Right like the personalcomputer to client server
computing, to the internet, tothe cloud, to mobile and now the

(19:17):
generative ai right like it's.
It's incredible, right, it'slike the.
The first neural network paperwas 1983, right?
Yeah, I think you and I werelike, yeah, we probably read it
Sixth grade maybe, right?
So 40 years later, right, it'sprobably the best gift we've

(19:38):
gotten, like at Smartsheet, wetruly believe that it's like one
of the best gifts we could havegotten from technology.
Because, when you think aboutwho we serve, we serve work
managers and people who areactually doing the work.
They're typically businessusers.
They're not technologists,they're not developers, they
don't want to write code, and sowe pride ourselves in being

(20:00):
that no-code work managementsystem that you can configure.
But still, there are some hardthings in it Writing formulas
people don't wake up everymorning wanting to write
formulas or analyzing whichprojects are at risk, which
projects are over budget.
They're not data analysts,typically, so they want a
dashboard that tells them what'sat risk and what's over budget.

(20:22):
So we have capabilities in theproduct that up until generative
AI were required a lot of whatI call cognitive load.

Speaker 2 (20:32):
Yeah, but you have to engage with it.

Speaker 1 (20:33):
Yeah, you have to become experts at writing
formulas and you have to becomeexperts at sort of building
these charts and widgets.
So we added capabilities withgenerative AI where you can,
with natural language, now asklike calculate, give me the
formula for calculating overbudget projects.
Right, literally generates theformula for you and plugs it
into your sheet.

(20:54):
Now I don't have to do that,right?
Same thing with analyze dataright, we have an analyze data
capability with natural language.
You can ask the question.
It will analyze your sheets andcreate your chart that you can
literally, with a click of abutton, put it on your dashboard
, so dramatically lowering theburden.
We have customers like Collier,which is using these.

(21:15):
They've created thesepersonalized dashboards now for
each of the agents simplybecause now they have these
tools that make it super easy toset things up.

Speaker 2 (21:26):
How about the role of automating the role of the work
manager?
Are you thinking one is theengaging you know helping the
work manager do a smart sheetbetter.
Are you doing things toautomate that Absolutely?
And maybe some examples of whatare the?
Kinds of things you guys arethinking about.
I think it's introduction,right?

Speaker 1 (21:44):
Well, I think you have to.
Often technology comes aroundand people think that.
So I think often technologycomes around and people think
that, oh, I can get users toadopt technology quickly.
That doesn't actually happen,right, People have to go through
a journey of gettingcomfortable with technology.
Generative AI is a classicexample where, if you start
automating things because it's astochastic system and not an

(22:06):
algorithmic system it will makemistakes, Of course, and so that
trust with your users is supercritical to get right right.
So I think we're on a journey.
We're not at the place where wecan turn things on and people
are willing to let it automateand do that autonomously for you
.

Speaker 2 (22:23):
In fact, we've heard the opposite that the enterprise
clients are very picky aboutensuring that there is
visibility into what the systemis going to do Exactly right.

Speaker 1 (22:32):
And when we added capabilities like analyze data
and built a chart, the commonquestion was how do I trust that
it's there?
So we had to add capabilitieswhere you can actually say OK,
show me how you came up withthis chart so people could go
read that stuff right.
So I think we are on a journey.
We are absolutely going to getto autonomous capabilities, but

(22:53):
we're starting with hey, thereare on-demand capabilities where
I can ask for it to help me andit'll help me, right.
And then there are what I callproactive capabilities, where it
starts making suggestions.
And then there will be theautonomous capabilities where
you can just say okay, I trustyou now enough that you can just
do this for me, right?
So we are on this journey ofsort of enabling that for our

(23:15):
customers.
Over the next couple of years,I think you'll see a lot more
autonomous capabilities beingturned on as our users become
comfortable with that.

Speaker 2 (23:26):
Let's say, I'm an early stage SaaS or or you know
whatever, software founder andI'm starting out now, circa 2025
.
What would you advise me to doin terms of my mvp or my 1.0, as
it pertains to ai, as itpertains to sas?
Of course you need tounderstand the customer.
Is there a pain point, all ofthat?

(23:46):
But in terms of actuallybuilding, would you go like AI
first, right off the bat, and doyou think there'll be customer
adoption?
Or, like you're saying, there'smaybe a little bit of assist
model where you're, you know,still leaving the human in the
loop to build the conviction andtrust?
How do you think about it?

Speaker 1 (24:04):
I think it's no different than any other
technology.
I mean, right, like when cloudcame about, people were like,
okay, well, am I ready to adopt,right?
I think AI is.
It's another technology likethat.
Now it's a tool in our toolboxto go serve customers, right?
So the first technology existsultimately to serve customers.
That's sort of so if you're anew founder, like you should

(24:29):
absolutely be looking as like oh, here's another tool in my
toolbox to serve my customers inan even better way.
So I think it would be amistake to not have that in your
toolbox.
Experiences that are justamazingly delightful and solve
the customer problem and thecustomer pain in sort of

(24:51):
incredible ways, in adifferentiated way.
You should absolutely go dothat right?
There's no reason to kind ofthink, but at the end of the day
, you have to keep listening toyour customers, right?
So, yeah, trying to go too muchfaster than where your customer
is also is not necessarilygoing to make you successful,
right?
Because you have to bring thecustomer on a journey with you.

(25:11):
So work backwards from yourcustomer.

Speaker 2 (25:14):
Got it, since you also now head CoopDev and I know
you used to do angel investingI don't know if you still do
angel investing or not.
Let's say, 10 different SaaS AIcompany founders are pitching
you.
What will attract yourattention in terms of at least
the initial laugh test, to say,ah, this is real value being
created, versus you knoweverybody's, you know

(25:35):
everythingai right Coffeeai.

Speaker 1 (25:38):
I always sort of ask the customer question Okay, who
have you talked to?
Who's you ideally, who's usingyour stuff right?
Are they able to pull out theirwallet and want to pay you for
it?
Like those are the kinds ofquestions you want to ask.
And if there is and then youknow you are much more of an
expert at this than I am so I'llask what do you think is the

(25:58):
size of the market that you cango penetrate?
But at the same time I willalso assess the founders
themselves, because I thinkdoing startups is extremely hard
.
You work with so many founders.
Do you have that perseveranceto go on that journey and do you

(26:24):
have that ability to listen andadapt to the customers and sort
of go on that journey?
That takes a lot right, thattakes a lot of conviction right
to actually go do that.
And so I think there's a lotthat goes into what
differentiates between successand failure in that particular
case.

Speaker 2 (26:44):
So I'm going to switch gears, Prate and talk a
little bit about, you know,three amazing companies you
worked at, right.
What were some of the lessonslearned from Microsoft, from
Amazon and, of course, now stillat Smartsheet right From
Smartsheet that you wouldrecommend, Because these are all
ginormous companies, right?
Certainly, the first two aremulti-trillion dollar companies

(27:05):
and hopefully Smartsheet alsosomeday becomes an equally large
company.
So what were some of thelessons learned from each of
those companies that might behelpful?

Speaker 1 (27:14):
I think the lessons I learned I mean were the most
brutal lessons I learned wereactually doing a startup Okay we
should include that Mostrelevant for our audience.
I thought that might be.
Microsoft is already big andalready had customers, and I
often used to say that, hey, I'mvery customer-centric product

(27:37):
leader.
And because I would go spendtime in the executive briefing
center a couple of times a month, when I started doing the
startup, I realized one of oneof the recent learnings was well
, at Microsoft, customers cameto us.
Right, I never had to go tocustomers.
Customers came to us and Iwould go present and feel like

(27:57):
I'm very customer connected.
You become a startup.
Nobody comes to you.
I would give out business cardsat Microsoft, people would call
you.
I would give out business cardsat Microsoft.
People would call you.
I would give out business cards.
Nobody calls you, right.
And so one of the biggest youhave to go find your customers
and, as a technologist, it'svery easy to sit in your little
office with your computer andimagine what the customers need.

(28:20):
My biggest learning was onenight.
You know this is 2008.
Economy had crashed, right.
And so, as founders, you havethat choice where are you going
to go back to corporate jobs orare you going to actually make
this company real?
And I stayed up at night, builta list of customers in a
25-mile radius and I literallynext day morning started cold

(28:41):
calling them and then found timewith them and over the next
couple of weeks I actually drovearound to go show them what we
had and whether they wouldactually pay for that.
And that's what it takes toactually right I mean, it was
one of those hard learnings.
Right Is that you have to goactually chase down your

(29:02):
customers and to learn from them.
So this is obviously extremelyvaluable you have to go actually
chase down your customers ifyou're, and to learn from them.

Speaker 2 (29:05):
So I'm going to.
So this is obviously extremelyvaluable.
Uh, I'm going to go back to themicrosoft and uh and amazon
thing.
I mean mac microsoft, of course, very large, successful company
, went from being a sleeperright to suddenly being, at
least at one, of the kind of uh,you know, forefront kind of
leaders in in ai.
Right, how the heck did thathappen?

(29:26):
Right, and you know this islast 10 years.
I know satya nadella iscredited with a lot of it, but
uh, that.
And then, of course, amazon.
I mean they keep expanding intoa variety of different things.
So so, maybe less about youknow, just startup founders, but
as they think of building scale, building scale.
I worked at google, I worked atibm and there were a lot of
things I learned from thosecompanies which someday would be

(29:46):
very valuable to a startupfounder maybe not the first
hundred customers.

Speaker 1 (29:51):
Right.
I think so scaling a businessare things you learn at
companies like Microsoft andAmazon and, like I told you, the
pricing and packaging.
I had a lot of tremendousamount of learning at Amazon
around pricing and packaging,how to price it to be able to
scale the business right.
As an example.
Right, microsoft, I had someincredible learnings around

(30:15):
go-to-market, for example.
Right, like Microsoft, washeavily channel-driven business,
right?
Microsoft basically neverreally sold anything directly to
customers.
It was either through OEMs orthrough this large ecosystem of
channel partners.
And so how do you reach yourcustomers, how do you deliver

(30:36):
value to customers?
Different companies have donethat.
Amazon is exactly the opposite.
It's like directly selling tocustomers, all direct, right.
The key thing in those culturesyou learn is are you hungry?
You talked about how Microsoftsort of lost its way, and I
think one of the things I usedto say, one of the reasons I

(30:57):
left Microsoft at that time, wasMicrosoft had lost its hunger
and hunger to serve customersand so it sort of became very
insular and inward facing as anorganization.
And that's the danger you runup.
I think Satya a lot of creditto Satya and sort of turning
that around and make the companyhungry again, and I think
that's why, whether it waschasing the cloud bet or getting

(31:21):
ahead in the AI, it's like youhave to constantly be hungry and
be looking for what's the nextthing.
How are we going to almostcommoditize our last thing and
do the next best thing?
And Amazon is inherently hungry.
That culture is justmind-blowingly hungry, yeah

(31:44):
absolutely so.

Speaker 2 (31:46):
let's move from companies to people, right?
What, when you are hiringproduct leaders or tech leaders
or grooming them, right?
I mean, you already have themin a startup, your first product
manager, whoever you couldafford the right horsepower and
hunger.
What do you look for?
How do you nurture them?
You know, maybe talk a littlebit about building the tech and

(32:08):
product org, particularly at aleadership level.

Speaker 1 (32:11):
Yeah, so I think hunger is definitely a key
element, right, I always sayattitude is 80% of the job, and
so there are sort of core thingslike that.

Speaker 2 (32:23):
And how do you assess hunger in an interview setting?
Or whatever, especially in astartup.
Think startup, not late stagecompany.

Speaker 1 (32:30):
Tricky, tricky Interview like one hour
conversation.
How much can you actually gleansomebody through that?
So usually experientiallearning is what I seek for.
I look for those examples whereyou failed, why you failed,
what you learned from that right, what bets you made and whether
they succeeded or not.

(32:51):
So you're constantly lookingfor is this person going to push
themselves and push theorganization to go do more and
better?
So I think that's one of thecore things I look for.
There are, of course, skillsright, like as a product manager
.
If you are enamored withcreating features versus

(33:11):
enamored with actually talkingto customers and reaching out to
customers, you can tell thedifference.
Yes, that's one of those bigthings.
It's like I need productmanagers who are going to be out
there talking to customers, notin the kitchen as much.
Right.
I often say that you need to bein the dining hall, not in the
kitchen.
Oh, nice, got it.

Speaker 2 (33:34):
How about just the roadmap of managing product,
right, like you just said?
Look, you sometimes have tokind of go out, not just be
inward focus or even cannibalizeyour own products and so on.
So do you have any frameworksin terms of you know what is new
stuff that you launch, what isexisting stuff that just needs

(33:55):
to keep getting better, rightand maybe something in between
right?
So how do you manage the kindof product kind of roadmap as it
?

Speaker 1 (34:03):
were yeah, another thing, that's art, a balance
between art and science?

Speaker 2 (34:09):
yes, hence asking you those questions so we can get
clarity yeah again.

Speaker 1 (34:15):
No, no, no magic.
But there is a prioritizationframework.
Right, like taking care of yourexisting customers comes is
paramount.
Right, like as a SaaS business.
Right, like I said earlier, weearn our customers' business
every day, every hour.
Right, it's a subscriptionbusiness.
It's not like they paid us somelicenses and now they're stuck
with us.
No, they can walk away tomorrow, right, and so if our current

(34:40):
customers are not happy, we haveto prioritize that portion of
that right.
So now you have to be carefulenough to not let all of your
investment dollars essentiallyget sucked into just that piece.
So you have to figure out, okay, what are the most painful set
of things that you must goaddress to not risk losing
customers.

(35:00):
Right, because churn is superdamaging.

Speaker 2 (35:03):
That's the core right .

Speaker 1 (35:06):
Service availability sits in that bucket.
Right Like it's a SaaS business.
So if the service is notavailable or there's a risk of
scaling issues or serviceincidents, got to take care of
that.
Right Like it's prettyfundamental right, because if
your customers don't trust youthat you're going to be there,
you're going to lose them,regardless of how fancy features
you might have, and so that'spretty fundamental.
And then, after that, yourproduct team and the time they

(35:31):
spend with customers to seekingthose pain points that will
create real value for yourcustomers are the opportunities.
I'm a big believer of the workbackwards from your customers,
right, amazon, so we usesomething equivalent and, like a
PR FAQ, we call it them acustomer problem definition

(35:52):
documents.
So I expect product managers towrite a customer problem
definition doc or a CPD, and CPDhas to have real quotes from
multiple customers that can tellus, okay, what are some of the
challenges they are facing inmanaging work at scale, and
those are the things that driveprioritization on the bets we'll
make right.

Speaker 2 (36:13):
How would that work, pradeep, for new products or new
companies, right.
So I'm going to go talk toprospects.
This is like the Henry Fordthing.
If I'd asked customers, theywould have said faster horses or
more horses right.
How would you do that for newproducts?
Like you're launching somethingnew from Smartsheet from
scratch?

Speaker 1 (36:30):
Yeah, I think so.
Sometimes new product journeys,amit, start actually walking
away from your product andthinking, okay, right product
and thinking okay, right.
And and often startups are agreat place to go learn right,
because the disruption ishappening when you are, when
you're not looking right, and soyou're absolutely right about

(36:52):
that.
So one of the things havingCorpDev as a function is that we
are constantly looking atwhat's happening in the market
right.
How is somebody doing it betterand differently from us?
Because there is, there's a lotof learning that can happen
that just looking at yourexisting customers is not going
to give you.
It's like all those people whoare not your customers are also

(37:13):
the places to go learn from, andso we have a CorpDev team that
is sort of adjunct to ourproduct team that creates other
learnings that are happening andone of the ways and you can do
through that learning you canidentify new opportunities of
adjacent offerings that you cango create.
Sometimes it's actually betterto do an acquisition right.

(37:35):
So, because there is a set offounders and a team that has
spent several years that are,you know, wallowing in that
particular domain and thatparticular need, and that's a
faster path to bringing them on.
So we've done a couple ofacquisitions.
Like, resource management wasan area we were deep in managing
work and we said, hey, managingwork and managing people that

(37:58):
are doing the work is an equallyimportant adjacent domain.
We did an acquisition in that.
We learned that, oh, managingcontent a lot of work generates
content.
Or, like in marketing,generating video and images and
things like that.
So content was highlyassociated.
So we went and did anacquisition in that area as well
.
So you have to look at whetheryou are going to make an
investment internally or you cando an acquisition and bring an

(38:21):
adjacent offering through that.
So many ways to go innovate andmove that forward.

Speaker 2 (38:27):
Awesome.
I know you're setting up abrand new office in India for
Smartsheet, but maybe expandinga little bit more.
What is your view of startupsfrom India, talent from India?
In your past companies perhapsAmazon and Microsoft you
probably hired people from here.
And what would you recommendthat we do to get India on the
global kind of product map?

(38:48):
India has a good global productmap Awesome.
How do we get a larger share ofthat?

Speaker 1 (38:54):
Absolutely.
I think India has, like what1.4 billion people.
Right, like the talent is here,like by all statistical
measures, right, there's adomination in talent in the
country, right?
So I think Freshworks is anexample of a company that I look
up to Girish, I know, and youknow was started here and had a

(39:18):
highly PLG motion.
His customers took him tovarious parts of the world and
and the company has doneextremely well, right.
So.
So I don't think the beautifulthing about the internet is that
you know, as long as yourcustomers can discover and get
started and use you, you'll findyour customers and it can be
global.
Right, my, my daughter, youknow, she, she has a business of

(39:40):
her own and it's completelyonline, selling clothes, and her
customers are everywhere.
So, the, so, the nothing isstopping you.
I think the world is now anoyster in terms of reaching your
customers and going global,absolutely, but I will also say
that I think the indian marketitself is massive, so there's
like you have a massive marketthat you can serve right here.

(40:02):
You don't even need to worryabout global like you can.
Actually serving that marketcan teach you so much and set
you up for going and serving therest of the world does part
sheet have a lot of revenue fromindia?
not a lot of revenue not not alot but we do sell through a
couple of channel partners hereand um, and so we, we would love

(40:22):
to grow our market in India.
Right, but that's.
I often tell people thatgrowing into international
markets you have to understandcultural aspects of those
markets and how to best servecustomers.
Right, japan's very differentthan Australia, is very
different from India, and sogrowing internationally requires

(40:44):
that connection with the localculture.
Got it?

Speaker 2 (40:49):
So, preet, as we come to a wrap here, just maybe talk
a little bit about yourself andyour personal journey, right,
in terms of what lessons haveyou learned as you evolved into
these various roles?
What has inspired you, whetherit's people or books, or
frameworks or whatever that, ifsomebody was listening in who is

(41:09):
20-something, two, three, fiveyears out of college, that might
benefit them over the next 20years.

Speaker 1 (41:18):
So a lot of things, Amit.
I think we've gone through.
We have time Books.
One of my favorite books isSapiens, I don't know if you've
read Noam.

Speaker 3 (41:28):
Harari's book Sapiens .

Speaker 1 (41:32):
It was one of those transformational books for me
and as a leader.
There's another book that Ilearned a lot from.
It's called Leadership on theLine.
That's a great book.
I highly recommend it.
Lots of amazing stories in thatbook about what leadership is
about, and often peopleassociate leadership with

(41:56):
corporate environments.
Leadership is any individual canbe a leader, right.
It's about having a mission andgoing pursuing that mission and
bringing people along on thatmission.
So there's a lot that you canlearn right through those things
.
I think, as I've evolved in mycareer and become much more of a

(42:17):
people leader, it's beenfascinating, right.
I used to say that when Istarted my career, when you and
I were sort of coming out ofcollege, it was all about hey,
what's the technology that we'reworking on, what's the business
context in which we're workingon?
And people were like thedistance third and I became, I

(42:39):
think a few years later gotmarried and became a dad and I
didn't learn this thing.
My priorities flippedcompletely.
It's all about the people.
If you have the right peopleand you can create the right
culture, magic happens andtechnology is, like now, a
distant third.
It's the people, the businesscontext and technology.
We'll figure the technology out.

(42:59):
If you have the right peopleand the right business, problem
we're going after and so Well,awesome, thank, right people and
the right business problemwe're going after, and so Well,
awesome.

Speaker 2 (43:05):
Thank you so much, prit.
It has been delightful to talkto you.
I know we can go on for a while, but thanks for being on the
podcast, of course.

Speaker 1 (43:14):
It was fun, thank you for having me.

Speaker 3 (43:19):
Dear listeners, thank you for listening to this
episode of the podcast.
Subscribe now on your favoritepodcast app for free and you'll
be the first one to know whennew episodes are available.
Just search for Prime VenturePartners Podcast in Apple
Podcast, Spotify, CastBox orhowever.
You get your podcasts, Then hitsubscribe and, if you have

(43:40):
enjoyed the show, we would bereally grateful if you leave us
a review on Apple Podcast.
To read the full transcript,find the link in the show notes.
Advertise With Us

Popular Podcasts

Crime Junkie

Crime Junkie

Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

24/7 News: The Latest

24/7 News: The Latest

The latest news in 4 minutes updated every hour, every day.

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.