Second Acts with Krish Subramanian

In this episode of Second Acts (a first for season two; welcome back!), the table turns as Krish is interviewed by Chargebee’s CMO, Guy Marion.

They talk about: Chargebee’s founding theses, strengths, and constraints, *the* characteristic patterns (not to be found in “innovation labs”) that propel second acts, how pricing of AI products must draw on familiar monetization principles yet demand a markedly different view of costs and value, the baffling absurdity of once-a-year pricing changes, Krish’s introspections on “inspired problems” and scaling himself, billing for time travellers, and much, much more!

Krish: “The good news is you have so much data [on pricing]. Which you can use to be more precise about it or understand it and then being able to make much better decisions where it’s no longer an art. It can be a science, provided you’re leaning into wanting it to be a science.”

Guy: “I think that's one of the differentiators of founder-led businesses still is that… beginner’s mindset where you're looking at every problem, looking at how to improve it in an honest and transparent way.”

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Chapters:

(03:43) How Krish described Chargebee’s mission five years ago (and where it’s headed now)

(05:54) On billing’s expansive, transformative role in an AI-driven world 

(08:03) How AI is changing the value exchange question 

(10:17) How a customer-first approach to growth shaped Chargebee’s early years

(13:34) How founding strengths continue to inform Chargebee’s approach to products

(16:00) Stacking S-curves (or defining second acts of scale) 

(17:52) The defining characteristic of companies that get second acts right 

(23:10) Krish reflects on the founder’s journey and scaling himself

(28:55) On founder mode and what the current, uncertain moment demands 

(32:57) How each era of software has been driven by the core economics of delivery 

(36:12) Why the urgency around AI innovation is fast shifting towards urgency around monetizing that innovation 

(39:12) Why treating pricing as a science is central to enduring businesses

(41:53) Why the future of software monetization is hybrid (and still driven by a standard evolution of the value chain) 

(45:19) Why AI monetization is still rooted in pricing fundamentals 

(46:55) The table-stakes instrumentation that modern monetization demands

(49:01) Why monetization experiments can no longer be a once-a-year exercise

(52:31) How Zapier, Personio, and other Chargebee customers solve pricing with rapid iteration  

(55:10) Why monetization has been an underutilized growth lever 

(56:25) The “Partner > Build > Buy” M&A framework (and applying that to Chargebee’s own product bets)

(01:02:41) An API-first approach to everything; or why Chargebee built a time machine 

(01:05:07) Creating an environment for scaling people’s contributions (also: their lessons, challenges, and happiness)

(01:10:17) Where “inspired problems” come from 

(01:15:57) Krish’s move to Amsterdam and on the beautiful gains of operating in a globally distributed org 

(01:19:47) The role of luck in the scaling journey 

(01:22:51) Guy’s closing note  

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Mentioned/Resources:

Invisible asymptotes

Joel on Software

Girish Mathrubootham

Second Acts; Episode 1: Nick Mehta, Gainsight

The Dream Machine

Wardley map

Zapier

Personio

DeepL

Hostinger

Chargebee Time Machine

Moments of Truth

Rajaraman Santhanam

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Connect with Guy:

LinkedIn

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Connect with Krish:

LinkedIn

X

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About Chargebee:

Chargebee is a Revenue Growth Management platform that helps thousands of recurring revenue businesses unlock second acts of scale. Learn more.

In this episode of Second Acts, Krish is joined by Guru’s co-founder and CEO, Rick Nucci.

Rick recounts how they rediscovered product-market fit at his previous startup, Boomi (the first iPaaS that foresaw cloud’s preeminence, exited to Dell, and was last valued at $4b), the many evolutions of Guru’s all-in-one (AI Search + Intranet + Wiki) position, three principles for building in an AI-first enterprise world, how they’ve thought through pricing experiments that serve both PLG and SLG motions, and much more!

Rick: “We put an enormous amount of effort into listening to the market. And I would say 80% of listening to the market for us means listening to all active customer conversations. We certainly look at and understand what competitors are doing. I think that’s very important. I think it’s especially important these days. [With] AI there [are] constant new entrants and so you really do need to spend time and be aware of them. That pendulum can over-swing though and I think where it can become unhealthy is if you lose your North Star of what you’re doing and what your purpose in the world is, so we do try to balance that carefully.”

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(03:57) Charting Guru’s evolution as a product

(11:30) How Boomi (Rick’s previous venture) bet big on the cloud transition and differentiated against MSFT and other well-funded giants

(14:32) Connecting a huge problem with a [new] technology, a clear need, and a first mover’s advantage

(17:18) How (much) Rick and team think about competition

(18:06) Guru’s relentless customer listening rituals to keep levelling up in a competitive space

(21:02) A customer-first ritual Krish is trying to bring back and his favourite internal Slack channel

(22:35) How Guru serves customers of different sizes with a core product insight and 2 GTM motions

(27:36) Moving to a company-wide problem from departmental problems — The 3 arcs of Guru’s product-market fit

(34:20) How Guru’s path reminded Krish of Chargebee’s own opportunities and challenges

(36:24) Lessons from Guru’s old, short-lived pricing experiment

(38:51) Why Guru’s current pricing model is framed around a “dead-simple” price-point that serves an all-in-one package

(40:20) How Rick and team empower themselves to make pricing changes

(41:30) How pricing is a compass for continuously finding the right customers

(43:25) “Focus on outcomes, not algorithms” and other notes on making sense of the AI hype cycle

(49:35) Krish’s experience of the great possibilities of AI-first interfaces

(51:15) “It’s possible to have a culture of urgency that doesn’t burn people out”

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Mentioned/Resources:

Dell Discovers Internet Mojo in … Philadelphia?

The GURU of Philly Tech: CEO Rick Nucci

What AI means for the future of SaaS: Reality vs. hype

“We recently had our 100th Townhall at Guru. This is one of my favorite rituals…”

“Guru turned 10 this week…So, here are 10 learnings from the last 10 years…”

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Connect with Rick:

X

LinkedIn

Connect with Krish:

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LinkedIn

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Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.

In this episode of Second Acts, Krish speaks with Copado’s CEO, Ted Elliott.

Ted shares (with refreshing wit and candor): the pivots that defined Jobscience (the previous business he helmed for 18 years), a veteran’s view of building and scaling software (Copado has raised over $300m for its DevOps platform) within the Salesforce ecosystem, what causes M&A disasters, Mungerisms, and much more.

Ted: “What caused the disaster acquisitions? Lack of alignment. Lack of having the same interests. Lack of wanting to be here for the long game to make it happen. You really cannot acquire…If you want to acquire a businesses because they are cheap and you think you can just pick up something on the fly and press them in a box you should be a private equity firm. When you’re a growing venture-backed business, you’re doing acquisitions to get bigger faster, to get some innovation you couldn’t build…”

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Chapters:

(02:57) An introduction to Copado

(04:32) A brief snapshot of Ted’s path before Copado

(05:16) The 3 kinds of pivots that shaped Jobscience (Ted’s previous, 18-years-in-the-making bootstrapped venture)

(06:44) “…you really never want to burn bridges”

(08:09) A heart-to-heart on the peculiarities of (startup) time and life itself

(11:45) Learning to balance “founder mode” style involvement by scaling “people, processes, and products”

(17:22) Why Ted believes Salesforce is still largely misunderstood as a cloud platform

(22:26) How Copado’s grasp of the Salesforce ecosystem has helped them spot a compelling gap

(23:22) The 3 stages (one being the “Valley of Death”) of building on Salesforce

(26:18) Why opportunistic, financials-driven M&A deals don’t work for mission-driven, high-growth companies

(32:37) Remembering a Mungerism: “Tap dancing to work”

(33:47) Working with a massive platform? Know your swim lanes

(37:19) Why Ted hires for “speed of trust” and how he decided on leading Copado

(43:44) Hiring a CFO early and 2 other impactful decisions Ted made in his first year as Copado’s CEO

(46:38) A talent insight Ted realized while working with his father

(49:27) Taking away the right (hard) lessons from this down cycle

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Mentioned/Resources:

Copado Celebrates 10 Years of DevOps for Enterprise SaaS Solutions

Meet the CEO of a Salesforce DevOps $1B Unicorn [Interview]

Ted Elliott of Copado: I Survived Cancer and Here Is How I Did It

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Connect with Ted:

X

LinkedIn

Connect with Krish:

X

LinkedIn

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Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.

In this episode of Second Acts, Krish is joined by Jellyfish’s co-founder and CEO, Andrew Lau.

Andrew begins the conversation with a modest admission: "Part of this is the entrepreneurial journey, probably a little impostor syndrome (we’re not done yet)... it’s hard to draw a line or make declarations around things definitively working or not. But I’m excited to share what we’ve done if that’s helpful for others to learn from along the way."

But, with stints at Microsoft and IBM in the late 90s, being an engineering leader at a startup (Endeca) that turned into a billion-dollar exit, and multiple ventures of his own under his belt, Andrew's discerning lessons cut across different eras of SaaS.

He revisits standard “binaries” (PLG vs enterprise, saturated vs white-space categories, and founders vs markets) and illustrates how a nuanced understanding of each of those and 25 years of common context with his co-founders have helped shape Jellyfish’s scaling path.

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Chapters:

(02:50) “We’re not done yet”

(03:18) An introduction to Jellyfish 

(05:02) Why startups are the by-products of founders’ experiences

(07:09) How Andrew and his co-founders arrived at Jellyfish’s core thesis and values with 25 years of shared context 

(16:17) The quiet, services-mindset-informed early years of Jellyfish 

(21:59) Choosing a GTM motion — why they decided against both an SMB-first, PLG play and a seven-figure, enterprise play

(27:59) The foundations that allowed Jellyfish to accelerate during the pandemic 

(29:39) Creating a category vs picking a mature market — “People think that something like Salesforce is preordained, it’s not” 

(33:45) Figuring go-to-market operations as technical founders 

(39:53) Managing reserves of capital and patience to address the inherent unpredictability of markets

(46:15) Understanding central forecasting levers as a way to unlock next acts of growth 

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Mentioned/Resources:

Jellyfish aims to ‘do for engineering what Salesforce did for sales’

Navigating 2024: Engineering management principles to tackle the unknowns & challenges ahead

How to Translate Engineering to the CEO

MGMT Boston - The Endeca Effect - Special Report (1/5)

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Connect with Andrew:

LinkedIn

Connect with Krish:

LinkedIn

X

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Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.

In this episode of Second Acts, Krish is joined by Crossbeam’s co-founder and CEO, Bob Moore. Bob traces a captivating line of inflection points across the three different SaaS startups (RJMetrics; acquired by Magento, Stitch; acquired by Talend, and Crossbeam; they recently acquired their biggest, most kindred-spirited competitor, marking a major second act) he has co-founded. In doing so, he also expounds — with lively analogies — on the line that ties product-market fit and breakthrough scale.

Bob: “I will say, shamelessly, that being a repeat founder is an extreme cheat code to having a short-cut to product-market fit. Because not only do you have a lot of very real, tactile experiences inside of an operating company to pull from that give you a lot of conviction around your idea, not just in academic theory, which is what we came to the table with at RJ[Metrics]. But, actually, in practice, based on real-world interactions with real companies. You get that head start. But then, you also have relationships.”

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Chapters:

(03:20) Falling out of PMF (despite a glorious head start) with RJ Metrics

(15:12) “2 ways to make money in business: One is to bundle; the other is unbundle.”

(18:56) Why Bob thinks being a repeat founder is an extreme cheat code for PMF

(25:34) How Stitch and Crossbeam came about in quick, high-energy succession

(30:32) How ecosystem signals can unlock the stacking of next S-curves

(35:22) Why taking ecosystem-led growth beyond the partnerships team is a force multiplier

(42:42) Bob’s earnest reflection on raising “pandemic-fuelled” mega rounds of capital

(47:12) How the Crossbeam-Reveal merger is shaping their future second acts

(55:45) The fantastically similar paths that brought Bob and Simon (Reveal’s co-founder) together

(58:05) “Suffer pain early” — Why Bob feels M&As are set up to fail and how he has approached them

(01:04:44) How poker and improv have deeply informed Bob’s sense of the core binaries of starting up

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Mentioned/Resources:

I’m Bob Moore. I’m the CEO and Co-founder at Crossbeam, and a serial SaaS founder, AMA!

My $2.6 Billion Ecosystem Fail

How to Succeed in Business by Bundling – and Unbundling

Breaking: Stitch acquired by California-based Talend in $60M deal

Whoa: RJMetrics just got acquired

It’s Happening! Crossbeam and Reveal are Joining Forces to Disrupt Go-To-Market Strategy As We Know It

This Founder Built Startups in 2008, 2016 and 2018. Here’s What He’s Learned About Resiliency

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Connect with Bob:

LinkedIn

Twitter

Connect with Krish:

LinkedIn

Twitter

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Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.

In this episode of Second Acts, Krish is joined by DataSnipper’s co-founder, Jonas Ruyter, and their CEO, Vidya Peters. They shed introspective light on how they thoughtfully underwent (what often is) among the most exactingly strained transitions for scaling SaaS businesses: hiring an external leader as the CEO. 

Jonas: "Always, indeed, be laser focused on product and how you can add stuff to the product that your users want. But also look at your pricing, because most first-time founders price too low and you can tweak around with that. Not to say you have to be very expensive, but I do see, in the beginning you need to close your first deals and that's not always the actual value you deliver or far from it."

Vidya: "Growth papers over talent; it papers over strategy; it papers over processes. All of those can be broken and you wouldn’t know because growth just kind of papered over all of it exactly as you said. And it’s so easy to assume, ‘okay, don’t touch anything, you may mess with growth,’ but actually what you don’t realize is you could be driving into a wall unless you change something now."

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Chapters:

(02:36) An introduction to DataSnipper

(07:16) Deciding on hiring an external CEO

(10:42) How DataSnipper co-founders landed on their focus areas

(12:35) “It’s easier if someone has already seen the movie”

(14:53) How their search for a CEO led them to Vidya

(16:18) Why they didn’t hire a COO in their biggest market instead

(17:51) Managing the (often) tense founder-to-CEO transition

(22:23) Vidya’s 3-point rubric for assessing a leadership opportunity (and a business)

(24:54) What questions did Vidya ask even before speaking with DataSnipper co-founders

(26:39) Why Vidya feels 90-day plans take too damn long

(30:05) How growth papers over all sorts of cracks

(32:43) Expanding the core segment, finding new ones, and accelerating the product

(33:58) Why Jonas believes “charge more” is perennially relevant advice

(37:55) The 3 types of changes that scaling demands and how to approach them

(41:30) From Taleb to Aurelius — Jonas and Vidya recommend their favourite books

(44:57) How Jonas keeps the passion alive in his new role

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Mentioned/Resources:

#26 Hiring Company Leaders | Vidya Peters | Slush 2023

Leading a Company Through Self-Disruption

Zero to One

Skin in the Game

Trillion Dollar Coach

The Five Dysfunctions of a Team

How to Win Friends and Influence People

The Daily Stoic

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Connect with Jonas:

LinkedIn

Connect with Vidya:

X

LinkedIn

Connect with Krish:

X

LinkedIn

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Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.

In this Second Acts episode, WP Engine’s (previously: ITWatchDogs’ and SmartBear’s) founder, Jason Cohen joins Krish to discuss: how predictability becomes required to withstand the pressures of scale, how Jason has consistently sought different roles (from CEO to CTO to Chief Innovation Officer) to contribute as a founder, how WP Engine set up all functions anew for the enterprise segment save for one (and how they’ve followed a similar path with other second acts), and other well-examined insights from 24 years of building B2B software.

Jason: “We didn't layer on an enterprise business until four years in. And when we did, one of the things we did is we had entire teams devoted only to it. We had whole sales teams only for enterprise… And one of the nice things about us is we didn't need different engineering teams, because the same product is what people buy. So we didn't need a separate engineering team. That's part of why it made sense for us to do it. It was a different go-to-market, but not a different product. That's part of why it made sense to do it. But what we didn't do is just put on the website, ‘we [sell] to the enterprise, and that's it.”

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Chapters:

(03:20) The post-PMF, everything-demands-predictability mode

(09:29) The external CEO as a “late-joining co-founder”

(11:53) How Jason’s role has evolved across the 14 years of WP Engine

(13:09) The (whole) org design puzzle

(18:58) Scaling cross-team prioritization with planned debates

(27:10) How WP Engine layered on an enterprise bet

(28:26) A framework for approaching potential adjacencies (and second acts)

(35:54) WP Engine’s practical — “map, not the terrain” — competitive strategy

(46:44) Operationally living up to the one defining truth of strategy

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Mentioned/Resources:

WP Engine passes $100M in revenue and secures $250M investment from Silver Lake

The fundamental forces of scale

Letter to Customers – Founder/CEO

What is the argument for staying with SMB while going up-market?

What makes a strategy great

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Connect with Jason:

A Smart Bear

X

LinkedIn

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Connect with Krish:

X

LinkedIn

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Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.

In this Second Acts episode, Krish speaks with Lithic’s co-founder and CEO, Bo Jiang; who breaks down how Lithic (a fast-scaling, B2B infrastructure play in the card issuing space) came about as a compelling second act while running a cash-efficient, B2C startup.

Bo: “Infrastructure businesses tend to trend as being horizontal vs verticalized businesses. And if you think about the transitional phases of a company, everyone starts somewhat horizontal. Or a lot of companies start somewhat horizontal. But, in order to scale, in order to differentiate and to build bespoke businesses over time and cross the chasm, you have to verticalize the business.”

Krish: “…it’s a new learning for us to not reject the idea [of professional services] but to embrace it and ask, ‘what makes a customer successful?’ Incentivizing even the sales process to, say, leave enough room for professional services to be monetized later, because the customer has a particular budget for the first year…[then] making sure that the implementation is actually successful while you discount the first year’s platform fee.”

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Chapters:

(3:37) Going from a lean team of 20 to raising $100m+ 

(7:47) How their own B2C startup has been Lithic’s first (and foundational) customer

(10:28) Questioning general startup wisdom with the right whys 

(11:10) Why most infrastructure businesses make the horizontal-to-vertical shift

(12:03) How Privacy.com has continued to inform Lithic despite their ICP evolution

(13:22) How the technology adoption curve explains verticalization

(15:44) The traps of an “unlimited TAM”

(18:07) Revisiting the strong pull of promising verticals

(20:48) One of the hardest things to balance as a founder

(21:44) Why expanding to new segments/verticals requires a beginner’s mindset

(24:18) How to build products that both devs and other business stakeholders love

(26:55) How to think about (and structure) the value of professional services in SaaS

(31:04) Assessing potential exec hires for adaptability and the ability to altitude-shift

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Mentioned/Resources:

Lithic's New Customer

Amazon’s New Customer

Lithic's 10-Year Anniversary Episode

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Connect with Bo:

X

LinkedIn

Connect with Krish:

X

LinkedIn

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About Chargebee:

Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.

In this Second Acts episode, Krish speaks with The New Normal Fund’s founder and GP, Allison Pickens; who draws on her time as the former COO of Gainsight and her work with several remarkable (pre-seed to pre-IPO) SaaS companies, to illuminate some of the foundations (across people, product, and GTM) necessary for scaling up.

Allison: “If you put… a great generalist in front of a customer and you say ‘make them successful’ they might again be able to use their heroics to make that customer successful. But those heroics may not be scalable because the product has a real gap. I think there was a period where the involvement of our generalists actually prevented the product from getting better, which is the opposite of what you would hope.”

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Chapters:

(03:00) GTM-strategy-market fit 

(03:38) Hiring for the scale phase 

(04:58) Two reasons behind B2B’s recent (pre Gen AI) efficiency gains

(06:10) What generalists enable 

(08:01) Charisma and playbooks 

(09:22) Why great generalists can obscure the reality of a product 

(10:41) Codifying all the hats that generalists wear

(13:30) Why one should map product features to actual customer processes

(17:55) Ego vs spirit 

(22:26) Why Gainsight plateaued despite best-in-class growth and culture

(25:22) How well they understood the coming resurgence 

(27:12) The four types of COOs 

(31:37) The COO role that can best drive second acts

(33:21) The principles (and routines) that inform a successful CEO-COO relationship 

(37:40) Shared context or why a founder should constantly download their brain

(39:27) The act two pitfalls that prevailing tech headwinds have exposed

(44:30) How some companies have revisited their playbooks post ZIRP

(46:38) How Gainsight helped create a new role (and an org structure)

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Mentioned/Resources:

Why You Should Hire for Your Stage

Scaling Your Startup…Through Your Best Nature

Is Your Market Growing Fast Enough?

The Rise of the COO Role

The Customer Success Economy: Why Every Aspect of Your Business Model Needs A Paradigm Shift

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Connect with Allison:

X

LinkedIn

Allison Pickens' Newsletter

Connect with Krish:

X

LinkedIn

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About Chargebee:

Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.

In this Second Acts episode, Krish is joined by Wistia’s co-founders, Brendan Schwartz and Chris Savage, as they thoughtfully recount lessons from a path-altering decision (buying out their investors) in Wistia’s exemplary, 18-year history.

Brendan: “The other thing that’s surprising is, how hard and how much work it is to build great software at scale…We’re super psyched right now that we have started back on this path and we’re shipping a lot faster and the product is getting faster, and I will say it gives me a lot more respect for really enormous companies who make great products.” 

Chris: “I just think that that’s like a mistake that’s very — and a surprise — it’s very easy to make as an entrepreneur: to see your journey as the journey of the market. And the truth is the market doesn’t care one leg. It doesn’t matter at all.”

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Chapters:

(02:08) The unaddressed scaling phase 

(03:33) What Brendan and Chris realized the one time they decided to sell Wistia

(07:26) Overscaling and the storied, clarifying buyback

(10:55) How Krish has learned to think about past mistakes

(12:49) Deploying speed as a tool to deliver quality

(19:09) The midwit meme and how Wistia hires execs

(25:16) Trillion Dollar Coach

(26:07) The long game and seeing what others don’t

(28:32) How Wistia’s market has evolved (dramatically) over the years

(32:26) Going from aiming for the “best damn point solution” to an all-in-one approach

(35:50) Two scaling lessons that have surprised Brendan the most 

(37:38) Why the market doesn’t care how long you’ve been at it

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Mentioned/Resources:

How an Offer to Sell Wistia Inspired Us to Take On $17M in Debt

Savage Mindset: Secrets to Moving Fast

Trillion Dollar Coach

I’m Brendan Schwartz, Co-Founder and CTO of Wistia. AMA 💞

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Connect with Brendan:

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LinkedIn

Connect with Chris:

X

LinkedIn

Talking Too Loud

Connect with Krish:

X

LinkedIn

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About Chargebee:

Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale. Learn more.