My Prime 10 Errors In 10 Years: Gainsight CEO Nick Mehta

So I wished to kick off a brand new collection that productized one thing we’ve been doing for 10+ years at SaaStr … getting prime leaders share their errors.  So the remainder of us can get to $100m+ ARR sooner, with much less stress and extra success.  We’ve accomplished a ton of this content material through the years, however by no means on a constant foundation, so I reached out to one in all SaaStr’s longest-time contributors, Nick Mehta, CEO of Gainsight, to replicate on his prime 10 errors taking Gainsight from a tiny startup one doing properly greater than $100m ARR.

I actually thought this primary one was really wonderful and hit house.  Take a learn. — Jason, ed.

“I by no means make the identical mistake twice. I make it 5 or 6 occasions, simply to make sure.” -Random quote I discovered on the Web

If that doesn’t describe the CEO expertise, I don’t know what does.

In February 2023, I hit my 10-year anniversary (or “Gainaversary,” as we are saying) of operating Gainsight. After receiving my gold watch and Silicon Valley AARP card, I had an opportunity to reflect on a decade of community-building, tacky music movies, and #CustomerSuccess. 

However way more attention-grabbing than the quick listing of Kodachrome-colored successes which are straightforward to recall are the gloomier-toned failures I attempt to neglect. Whereas I struggled to provide 10 issues I acquired proper in a decade, the listing of errors flowed a lot simpler. Listed here are my 10 biggest (worst?) hits, in no explicit order:

Mistake: Not holding my leaders to the best normal

Considered one of our firm values is the Golden Rule—deal with folks the best way you’d need to be handled. As such, we at all times attempt to discover the most effective in every individual at Gainsight. Usually, this implies working laborious to see in the event that they aren’t succeeding in a given position, whether or not one other one can be higher. A lot of our most vital Gainsters in our historical past are ones that rotated from a suboptimal job into one during which they thrived.

Early on, I attempted to use the identical mantra to leaders. We must always give them an opportunity. They’re people too. Perhaps they’re misunderstood. Perhaps they want extra teaching. Perhaps they simply want extra time. And people maybes might be proper. However what I realized, after years of procrastinating on powerful strikes for our management workforce, is that the leaders’ groups endure vastly by means of that inaction.

Lesson: I would like to carry our leaders at Gainsight to the best potential normal. This implies it’s actually powerful to be a pacesetter at Gainsight, and I’m unapologetic about that. I wrote up a doc of what I anticipate from our leaders, in excessive element. I stroll them by means of this after I rent them. And over time, I acquired higher at parting methods shortly once we weren’t aligned. Because the saying goes, “to those that a lot is given, a lot is anticipated.”

Mistake: However… not betting on the workforce that acquired me there

“All the pieces will probably be tremendous as soon as we get a brand new head of [X]” -every startup CEO ever (additionally me, incessantly)

While you launch an organization, the preliminary workforce is normally whoever you may get. It’s sometimes a bunch of scrappy underdogs seeking to show themselves. Sooner or later, both by means of exterior prompting or inner contemplation, CEOs suppose “perhaps I must ‘improve’ the workforce.” This thought is normally accompanied by a obscure assertion like “this individual isn’t scaling.”

After all, generally that’s certainly true. There are a lot of tales of legendary exec hires. Over time at Gainsight, we’ve had a number of—our first Chief Monetary Officer and our first Chief Folks Officer, to call two—that had a large affect. However way more typically, I swung and missed. I employed the individual with an excellent resume however who didn’t get our enterprise, tradition, or group. And inevitably, these of us ended up not understanding, regardless of being very gifted in different settings.

On the flip facet, we’ve had unbelievable success with inner promotions and “up and comers,” together with our first Chief Advertising Officer (began as a Director of Advertising, with no advertising and marketing expertise), our first Chief Working Officer (began in Enterprise Operations), our third Chief Income Officer (began as a gross sales rep), our present Chief Monetary Officer (began as our head of FP&A) and our present Chief Buyer Officer (began as an enterprise CSM).

Lesson: Many occasions, I assumed, “I would like to rent for the position I’ll want 4 years from now.” In actuality, I wanted to guess on the one that had believed in Gainsight for the final 4 years.

Mistake: Not scaling based mostly upon main indicators

We’ve had 3 durations in historical past the place we scaled up means too quick:

  • Early on, once we thought the enterprise alternative for Gainsight’s Buyer Success product was big after closing *1* enterprise deal!
  • Afterward, once we thought a brand new acquisition of uncooked expertise was able to scale (it wasn’t – it’s now)
  • In 2022 (like many firms), once we misinterpret the “COVID bump” of 2021 for a secular change in software program

In every case, the error wasn’t being aggressive. To run a startup, you must make bets. However I ought to have appeared extra rigorously at main indicators and had a transparent system to guage if we had been on monitor or not. As a substitute, I set a giant gross sales quantity for every of these years (based mostly upon the most important lure ever—a gross sales rep capability mannequin) and completely missed every time!

Lesson: “Fireplace bullets, not cannonballs,” as Jim Collins says. I must always run small experiments and scale solely based mostly upon clear main indicators. 

Mistake: Not standardizing pricing and associated techniques early

Each enterprise-oriented startup, together with Gainsight, can fall into the identical lure. For this one deal, we simply must do X. Ultimately, you find yourself with 2000 contract varieties for 1000 prospects. And when you didn’t make investments proactively in techniques like CPQ early, you create a byzantine mess that’s unattainable to scale. This causes many issues:

  • Complexity for patrons
  • Frustration for client-facing groups
  • Problem in analyzing the enterprise

Inevitably, firms like Gainsight then find yourself going by means of a large venture to “simplify” insurance policies, pricing, and sophisticated techniques. However it doesn’t matter what occurs, it’s nearly unattainable to get again to the extent you’d have had if we had accomplished issues proper from day 1.

Lesson: Be REALLY cautious about customized offers and ensure they’re price it. Put money into back-office techniques early. BTW, this helps you will have higher main indicators for resolution making (see earlier mistake!)

Mistake: Not investing in Digital Buyer Success early

The cobbler’s children typically don’t have any sneakers. In our case, as a result of we centered on an excellent high-touch expertise for our purchasers, we had a high-touch CSM-led mannequin. This labored nice for a lot of of our purchasers – and led to very robust Gross Retention – however made it more durable for us to scale over time.

They are saying, “When you’ve got a hammer, every thing appears like a nail.” The identical will be true for CSMs and this is the reason firm CSM groups typically get stretched too thinly.

Lesson: Make investments early in Digital CS capabilities for all prospects – like self-service, group, in-app engagement, telemetry, digital journeys, and product-CS suggestions loops.

Mistake: Not parting methods properly at all times

In startups, relationships finish. Teammates and purchasers will depart. It’s powerful, however it’s a part of the circle of life.

Over time, I adopted the philosophy that I need to deal with folks properly in all phases of our relationship, aligned to our Objective “to be dwelling proof you could win in enterprise, whereas being Human-First.”

However I can bear in mind two conditions (early on) with teammates and two with purchasers the place I didn’t apply what I preach. Within the teammate case, I made the parents leaving really feel responsible—“How will you do that?” Within the purchasers’ case, I didn’t take it properly and burned two relationships within the course of.

Lesson: Finish each relationship in a Human-First means. When a teammate leaves, my solely response is (1) thanks for what you’ve accomplished right here, (2) congratulations on what’s subsequent and (3) what can we study to proceed to get higher. When a consumer leaves, we need to assist them on the best way out, as a result of they typically come again.

Mistake: Not being prescriptive sufficient, early sufficient

Within the early days of Gainsight, I bear in mind purchasers asking us, “How ought to we implement your product?” TBH, we didn’t know, since we had been nonetheless figuring it out. So our response was one thing like, “I don’t know—how would YOU like us to implement it?”

That works for some time with early adopter purchasers. However finally, you run into issues:

This back-and-forth results in very long time to worth.

Each consumer makes use of you slightly in a different way.

It’s laborious to ramp new teammates in CSM and PS.

Since purchasers use you in a different way, they’ll’t at all times use new performance that you simply develop.

And so forth.

For us, probably the greatest issues we did (which we should always have accomplished sooner!) is create a Prescriptive Methodology. In the event you’re a Gainsight nerd, at varied occasions, this was known as V3D, Parts, and now O2. However the spirit was the identical: We’re the consultants on learn how to get worth from our software program. Lead our purchasers to the result.

However this course of was additionally laborious:

We needed to get alignment throughout Product, Advertising, Gross sales, CS, and PS on what our end-to-end worth (from 30K ft to 30 ft).

We wanted the proper granularity for every stakeholder.

We needed to discover a method to preserve it up to date.

Most significantly, we needed to coach our teammates (from Gross sales to PS to CS) to be “courageous” (within the phrases of the nice Allison Pickens) and inform our purchasers one of the best ways to get worth.

Lesson: It wasn’t with out its flaws, however Prescriptive Methodology, to me, is without doubt one of the most crucial step capabilities for any SaaS firm in a brand new class.

Mistake: Not beginning Act II quick sufficient

Gravity is brutal when you fall whereas snowboarding. And progress deceleration—startup gravity—is equally painful for entrepreneurs.

Within the early days, you’re employed off small numbers. Your new logos develop quickly. You have got a small base, so churn isn’t an element. However finally, you hit the frontier of your preliminary Complete Addressable Market and your new logos per 12 months flatten out. In the meantime, even with a hard and fast Gross Retention Price, your base grows, so your churn {dollars} develop 12 months after 12 months. This poisonous combo can flip a hyper-growth firm right into a stalled one right away.

This stall will occur to all firms finally. For a fortunate few, it occurs previous $1B of ARR. For a lot of, it occurs between $50M and $100M. And for some, it happens earlier than.

For Gainsight, we began seeing a slowdown round $50M in ARR. Our new bookings stopped rising, as we had been an enormous chunk of the marketplace for Buyer Success Platform software program and thus had been TAM-bound. However we had no second product – no “Act II” in sight. So we stored making an attempt to scale stuff that was maxed out – see a earlier mistake for extra!

Ultimately, we expanded to develop into a platform firm (including on Product Analytics and Buyer Communities as a part of our resolution) and this re-accelerated our progress. However alongside the best way, we slowed down, so our price and attractiveness did to buyers, too. As I’ve written about before, we had a “Sequence F” that was a real F— each investor turned us down!

In hindsight, we should always have began a lot earlier. We must always have had a pipeline of natural and M&A merchandise to increase into adjacencies. We must always have understood the bounds of our TAM and seen the wall coming.

Lesson: Monitor your TAM vigilantly and begin your second act— natural or M&A—properly earlier than progress stalls.

Mistake: Not being affected person and never ignoring FOMO

Each mistake I revamped time will be attributed to 1 subject: lack of endurance. And that impatience ties to 1 human vice: Worry of Lacking Out.

Over time, I noticed lots of of firms increase cash at valuations greater than ours, go public in spectacular trend, and announce large progress charges. Each time, I assumed, “Why not us?” And this comparative emotion drove me to lots of the ill-conceived selections above.

Almost each untimely scaling, pressured exec rent, pressured buyer deal, in hindsight, turned out to be a giant mistake. We needed to unwind the scaling earlier than its time. The execs that we employed too shortly moved on. And the purchasers that purchased too shortly ended up churning.

And guess what? A lot of my FOMO friends flamed out too. In spectacular collapses, some IPOs went bust and progress charges decelerated off a cliff. Don’t get me incorrect—many did higher than us. However many extra fell off the map.

Lesson: In lots of markets, the affected person tortoise beats the over-anxious hare. Stick with your values and imaginative and prescient and, within the phrases of Lin Manuel Miranda from Hamilton, “Look forward to it.”

Mistake: Not being myself

Our first Pulse convention – which grew to become the business occasion for Buyer Success – was in a small San Francisco ballroom in 2013. After the preliminary occasion exceeded our expectations, I made a decision to up my sport for 2014.

I employed a talking coach (who was nice in her personal proper, regardless of this story). She watched me converse and mentioned, “You’re too casual, and also you converse too quick. Attempt writing out your speech and studying from a teleprompter. Attempt to have extra gravitas.”

So at Pulse 2014, I grew to become a “grown-up CEO.” I wore a boring swimsuit. I learn from the boldness monitor. I spoke slowly in a measured tempo. And you’ll see the results. Pulse 2014 was by far my worst keynote of all time.

The following 12 months, I went again to my “excessive power,” “frenetic,” “tacky,” but genuine self. After which at Pulse 2016, I made a decision to take one other leap. In our closing keynote, I channeled Brene Brown’s vulnerability and talked about being lonely as a child—consuming lunch alone day-after-day from kindergarten to twelfth grade. I shared that I nonetheless really feel insecure about whether or not folks like me to today.

After the speech, I obtained tons of accolades, however a number of Gainsters mentioned, “That’s not very CEO-like. I would like my CEO to be powerful and never have points.” I wrote concerning the expertise here.

However fortunately, I leaned additional into myself through the years, speaking about unhappiness, loneliness, my dad’s dementia, fears about my oldest daughter rising up and, after all, Taylor Swift. I spotted that the most effective model of myself is myself.

Lesson: Being your self is fairly highly effective. Nothing can maintain you again when you discover the boldness to indicate up with authenticity and vulnerability.


Penning this publish was like a painful remedy session. I appeared within the mirror and noticed all of the pimples and pimples and hair loss and graying of a flawed human being. However through the years, I’ve grown to like this model of myself as a result of I do know it’s all I can really be. And my solely aim is to maintain making errors and studying from them—after at a minimal 4 makes an attempt!

Printed on April 2, 2023

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