Second Acts with Krish Subramanian

Chargebee
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Second Acts chronicles the risky, exacting, and ultimately foundational shifts that propel SaaS businesses forward. Whether it’s expanding into new geos/segments/verticals, releasing adjacent product lines, devising the next set of GTM/monetization models and org structures, scaling up requires pursuing these (often tricky) transformations (read: Second Acts) all at once. In this second season, tune in every other Thursday as Chargebee’s co-founder and CEO, Krish Subramanian, sits down with senior founders and CXOs to capture the urgent, never-before-seen second acts that AI’s all-out enterprise embrace is bringing about.

  1. Docebo CEO on steady growth, systems of intelligence, pricing's value chain, and more | Alessio Artuffo

    9 OCT

    Docebo CEO on steady growth, systems of intelligence, pricing's value chain, and more | Alessio Artuffo

    In this episode of Second Acts, Krish is joined by Docebo’s (NASDAQ: DCBO) CEO, Alessio Artuffo. Alessio talks about: Docebo’s many second acts from the early days of bootstrapping to their recent AI-native reinvention, what they have learned about sustaining balanced growth as a public SaaS company, how “clear, unarguable” enterprise value (not AI hype) drives their product and monetization decisions, the internal idea-to-execution value chain of pricing ownership, why focus (not TAM) is the big constraint in horizontal markets, a Lencioni classic he keeps going back to, and more. — Chapters: (00:01) Episode highlights (03:13) Episode intro (05:40) A brief note on Docebo’s 20-year path (07:14) Docebo’s many second acts (12:14) A philosophy of balanced growth (17:56) The post-COVID reset (21:39) System of record → System of intelligence (28:10) Real AI adoption starts with customer problems (31:57) Rewiring Docebo’s GTM for an AI-led future (34:23) AI, FedRAMP, and unlocking new markets (40:33) SI partnerships as multipliers (43:00) A methodical approach to AI monetization (46:54) Pricing “clear, non-arguable value” with simplicity (50:14) A hypothesis-led, cross-functional pricing process (55:54) Alessio recommends a Lencioni classic — Referenced: Docebo NASDAQ Edugo “From System of Record to System of Intelligence:” Accenture Deloitte Kyle Lacy Mark Kosoglow FedRAMP The Five Dysfunctions of a Team — Connect with Alessio: LinkedIn — Connect with Krish LinkedIn X — About Chargebee: Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra. Learn more.

    58 min
  2. Theory Ventures founder on GTM leverage, AI margins, real enterprise TAM, and more | Tomasz Tunguz

    25 SEPT

    Theory Ventures founder on GTM leverage, AI margins, real enterprise TAM, and more | Tomasz Tunguz

    In this episode of Second Acts, Krish is joined by Theory Ventures founder and General Partner, Tomasz Tunguz. Tomasz talks about: the three infinite learning curves that originally drew him into venture, the tricky thing that is advising operators, writing lessons that have made him one of SaaS’s most prolific and admired public thinkers, why he has long believed in the compounding power of distribution, the current case for pursuing uneconomic growth, why pricing is continually in flux, Looker’s extreme PMF and second acts, three reasons why this is the best time in history to start a SaaS business, Umberto Eco, and more. — Chapters: (05:22) A walk along Embarcadero (07:58) Venture’s three infinite learning curves (09:05) “Advice is a tricky thing” (11:53) Dalio, Munger, and effective board members (13:58) Product limited/GTM limited? (16:00) Situation, Complication, Question, Answer (19:33) Several short sentences (21:00) Writing as a way to think better about AI (23:02) Krish’s fun, clarifying AI use case (24:51) A distribution-first thesis (29:38) How AI changes GTM (32:08) The past and present of category creation (34:30) The generalist-specialist pendulum (36:00) “Pricing is a perennial” (39:09) The inevitability of better AI margins (41:52) Uneconomic growth as a valid bet (46:44) Monte Carlo’s radical daily revenue model (50:34) Never been a better time to start a SaaS business (54:17) “PMF is grease” (56:53) The year of Looker 500 (59:07) Why the growth bar keeps moving (01:00:51) Umberto Eco and explaining China — Referenced: Tomasz Tunguz on raising Theory Ventures’ $450 million second fund The Decade of Data with Tomasz Tunguz Joel on Software Poor Charlie's Almanack Principles by Ray Dalio Mike Volpi Tomasz Tunguz on Venture Capital Intercom Des Traynor McKinsey & Company SCQA The Second-Order Effects of AI Several Short Sentences About Writing Copyblogger MongoDB a...

    1h 4m
  3. Reforge CEO on PMF expansion, retention laws, AI pricing's figuring-out phase, and more | Brian Balfour

    11 SEPT

    Reforge CEO on PMF expansion, retention laws, AI pricing's figuring-out phase, and more | Brian Balfour

    In this episode of Second Acts, Krish is joined by Reforge’s founder and CEO, Brian Balfour.
 Brian dives into: early years of Reforge’s breakout—“the strongest PMF I’d ever felt”—education business, what led to their recent AI-native second act, launching a whole suite of products within a couple of quarters as a lean team, what real-world enterprise adoption requires, retention laws, the emerging breaking points in the Four Fits to $100m, why AI monetization strains past SaaS growth models and is still being figured out (and why people are wrong about Cursor and others), startup-within-a-startup lessons from HubSpot, Izzy the Inventor, and much more. — (00:01) Episode intro (06:24) Second acts aren’t all the same (08:00) “The most instant PMF I’d ever felt” (09:35) Whiplash (10:26) Reforge’s second act (15:10) “People overbuild for the SV tech company” (17:56) Unifying the product stack for humans (and AI) (21:20) How Reforge ships absurdly fast (24:20) The foundational law of retention (32:14) What made HubSpot’s seminal second act work (39:27) How AI is reshaping the Four Fits (43:35) Why AI monetization breaks traditional SaaS growth (49:17) Three checks every monetization model must pass (54:08) How Reforge is pricing multiple AI-native products (55:28) Why pricing today requires rapid iteration (58:03) The next great distribution platform (01:05:48) Capital and the company you want to build (and grow) (01:10:08) Notes from Brian’s operator reading list (01:13:04) Storytime: Brian and Krish swap kids’ book recs — Referenced: Why Retention Is The Silent Killer Growth Loops are the New Funnels AI User Interviewer Monterey AI HubSpot Christopher O'Donnell Michael Pici Mark Roberge The Feedback Fragmentation Tax: How Product Teams Lose Touch (And How To Fix It) The Foundational Laws of Retention That Haven’t Changed in the AI Era Calm Why Product Market Fit Isn't Enough Four Fits for $100m Growth Get Out of the ARPU-CAC Danger Zone with Channel Model Fit tokens are getting more expensive...

    1h 15m
  4. Optimizely CEO on suites, pricing AI agents, scaling through M&A, and more | Alex Atzberger

    28 AUG

    Optimizely CEO on suites, pricing AI agents, scaling through M&A, and more | Alex Atzberger

    In this episode of Second Acts, Krish is joined by Optimizely’s CEO, Alex Atzberger. Alex shares notes on: why deeply integrated suites win in enterprise (and will continue to do so with AI), scaling Optimizely into an AI-powered platform (and past $400M+ in ARR), pricing AI agents that span vastly different use cases, treating monetization as a reversible decision, lessons from more than a decade of M&A, building with long-term discipline under PE, hot chocolate, and much more. — Chapters: (00:00) Episode intro (04:45) Lessons from The Wonderbon Chocolate Co. (09:10) Principles shaping Optimizely today (12:36) “The suite always wins” (17:14) Avoiding platform sprawl (19:56) Defensibility in a world of overlapping suites (25:00) What are you really pricing for? (28:46) Pricing is never a one-shot decision (30:00) Enterprise AI is about the unsexy stuff (35:35) Test and learn: How Optimizely prices AI agents (40:35) The hard thinking behind successful M&A bets (44:44) Building a “long-term healthy” business with PE (50:20) Team of Teams — Referenced: Optimizely SAP Ariba The Wonderbon Chocolate Co "The suite always wins" "Enterprise AI is not all alike." "The great bundle brawl (Brian Balfour)" OpenAI Optimizely Opal Insight Partners Three things I learned from my past five years running a Private Equity owned business — Connect with Alex: LinkedIn — Connect with Krish: LinkedIn: X — About Chargebee: Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra. Learn more.

    51 min
  5. Building for adaptability (headless to agentic), scaling enterprise pricing, and more | Dirk Hoerig

    14 AUG

    Building for adaptability (headless to agentic), scaling enterprise pricing, and more | Dirk Hoerig

    In this episode of Second Acts, Krish is joined by Dirk Hoerig, founder of commercetools. Dirk reflects on: coining “headless commerce” and the architectural decisions that let them stay ahead of wave after wave of platform shifts (including the recent agentic one), standardizing a consumption-based pricing model for wildly varying customer types, having a clear-eyed view of different eras of competition, handing off the CEO title after 14 years (plus scaling past $150m in ARR), staying obsessed with what’s next, and much more. Dirk: "My experience on building companies and business models is that you have to monetize around what your buyers understand and what's driving value for your business. So you can have a great product that has a lot of customer demands. If your pricing isn't matching what the customer perceives as value driver, and you don't have clear KPIs that they are also able to track, then it will be challenging for you as a business to grow." Krish: “The [gross margin] discipline that you are referring to—I think is even more applicable in today's world, because with AI, one of the things we are observing is every feature is becoming like a micro-product, and you have to be very conscious of the winners and your fillers... because it's going to cost you a lot more, and it can erode the gross margins.” — Chapters: (05:12) commercetools’ early insight 
 (06:46) Challenging legacy enterprise commerce vendors that monetized maintenance not innovation
 (07:42) Wired magazine’s The Web Is Dead issue (and how it affirmed commercetools’ founding thesis) (09:45) commercetools today: a composable ecommerce platform that serves every potential touchpoint (including AI agents) 
 (10:47) How commercetools defines their enterprise segment (12:42) 200-item, two-year-old backlogs and the cost of dated enterprise systems  (19:14) Dirk's monetization philosophy (and why some value drivers remain hard to monetize) (23:54) How commercetools iterated their way to a standard, order-consumption-based pricing model (27:23) Conducting rigorous, gross margin analyses across customer tiers (29:60) How AI features demand a similarly disciplined approach to costs  
 (31:55) Building with an unwaveringly counter-intuitive premise; "independent of the category" (34:45) How a truly API-first architecture has paid off across several—from mobile to voice to agentic—technological shifts  (41:22) On competition: Legacy giants, segment-expanding players, and the coming AI-native wave (50:28) A brief snapshot of commercetools’ Commerce MCP launch, from an internal prototype to a standard-defining release 
 (57:05) Dirk acknowledges the need to celebrate business milestones better, while there’s always the founder’s urge to move to the next thing  (59:32) Adapting org design and operating models for serving a sophisticated, at-scale enterprise motion  (01:03:16) Dirk’s transition to a Chief Innovation Officer role as commercetools prepares for its next decade (01:08:36) Sports, crunch times, and Dirk’s central advice to founders: “don’t quit”  — Referenced/Resources: The Web Is Dead. Long Live the Internet (Wired Magazine) Why headless commerce will continue to boom after a decade of innovation Customer Keynote: Path to Composable Commerce - John Lewis Migration Journey a...

    1h 12m
  6. From a $875m exit to building again, the AI opportunity, pricing trade-offs, and more | Tracy Young

    31 JUL

    From a $875m exit to building again, the AI opportunity, pricing trade-offs, and more | Tracy Young

    In this episode of Second Acts, Krish interviews TigerEye’s (previously PlanGrid’s) co-founder and CEO, Tracy Young. Tracy talks about: her big insights from scaling one of the most formative vertical SaaS businesses (PlanGrid, acquired by Autodesk for $875m), winning with technological shifts (and where she sees TigerEye’s AI-native opportunity), how PlanGrid’s best-in-class pricing model was ultimately outplayed by a now-public competitor, the mid-market “no man’s land”, why to zealously slice TAM when growth stalls, and much more. Tracy: “I think it’s really easy to increase prices…Changing the shape, and how you charge is much harder. And the reason it’s hard is because you have to look at what percentage of your current revenue that might not renew because of the new pricing. And you always want to protect every dollar of revenue. And that’s the hard trade-off, even if you know this is a better pricing for your customers and for the company.” Krish: “…It is normally accepted that with scale your growth rate tends to fall. But what you are actually referring to [is] that by deliberately not just looking at an overall business, but slicing it in every dimension, you actually continue to think about the potential in each one of those segments to layer those S curves.” — Chapters: (01:06) Episode intro (03:18) Tracy’s kind, founder-to-founder note of praise (04:06) TigerEye’s founding premise (06:58) Why Tracy started PlanGrid (a vertical SaaS pioneer that sold for $875m) (07:56) Why Tracy chose a horizontal path with TigerEye (10:10) Reimagining a competitive enterprise category with the AI shift (12:17) There are (still) at least 10 good startup ideas in every enterprise category (17:16) Why changing the shape of how you charge is much harder than changing price points (18:37) How PlanGrid’s exceptionally successful (netting 130-140% NRR) seat-based motion was still bested by a different approach of a now-public competitor (22:00) Tracy explains how (in the construction space between 2011-20) landing logos faster was more important than the average contract value (22:55) PlanGrid’s freemium, mobile-SEO driven top of funnel (23:25) Why Tracy picked a one-price-for-everything (including unlimited seats) for TigerEye (25:20) How AI allows TigerEye to do things that don’t scale with the depth of best-in-class consulting firms; “insanely fast and at a fraction of the cost” (28:04) How a painstakingly precise view of segments is critical for understanding where a business is struggling and where it’s headed (31:40) The “gnarly” data issues PlanGrid encountered post the Autodesk acquisition and how that informed TigerEye (33:24) Tracy’s three distinct flavours of mid-market (and why the classical definition of that segment fails most founders) (37:20) Having built SaaS scale-ups in the past decade, Tracy and Krish reflect on the possibilities of building AI-native teams (42:55) How Tracy sees AI-driven enterprise business models evolving over the next couple of years (45:00) Why TigerEye is training their own tailored AI models — Referenced/resources: American Dreamers: Tracy Young Has The Eye Of The Tiger TigerEye PlanGrid Tracy Young, Co-founder & CEO of PlanGrid (The Social Radars) a...

    46 min
  7. Ep 11: Notes on second acts, building Chargebee, figuring AI monetization, and more | Krish and Guy

    17 JUL

    Ep 11: Notes on second acts, building Chargebee, figuring AI monetization, and more | Krish and Guy

    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.” — 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   — Mentioned/Resources: Invisible asymptotes Joel on Software Girish Mathrubootham Second Acts; Episode 1: Nick Mehta, Gainsight a...

    1h 24m
  8. Episode 10: Rick Nucci, Guru

    25/11/2024

    Episode 10: Rick Nucci, Guru

    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.” — (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” — 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…” — Connect with Rick: X a...

    56 min
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About

Second Acts chronicles the risky, exacting, and ultimately foundational shifts that propel SaaS businesses forward. Whether it’s expanding into new geos/segments/verticals, releasing adjacent product lines, devising the next set of GTM/monetization models and org structures, scaling up requires pursuing these (often tricky) transformations (read: Second Acts) all at once. In this second season, tune in every other Thursday as Chargebee’s co-founder and CEO, Krish Subramanian, sits down with senior founders and CXOs to capture the urgent, never-before-seen second acts that AI’s all-out enterprise embrace is bringing about.

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