Second Acts with Krish Subramanian

Chargebee

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 month 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. Miro CEO on reaching 100m users + 250k orgs, permission to win, hybrid pricing, more | Andrey Khusid

    30. JAN.

    Miro CEO on reaching 100m users + 250k orgs, permission to win, hybrid pricing, more | Andrey Khusid

    In this episode of Second Acts, Krish is joined by Andrey Khusid, founder and CEO at Miro. Andrey shares notes on: Miro's AI-native second act and how it's enabling them to expand horizontally and vertically at once while serving 100m users and most of the Fortune 500, the inputs that help Andrey constantly assess and intuit market fit, Miro's portfolio of bets approach, what strategic enterprise AI deployments actually demand, why monetization has long been a cross-functional team effort at Miro and why Andrey has always been part of it, how Miro is evolving beyond per-seat pricing, why he's back in founder-led sales mode, shifting from role-based to skill-based "maker teams", re-earning product-market fit: "it's not constant, we have to win it again and again," why Andrey is turning to Brian Balfour's Four Fits framework as they chart their “best-of-suites” path with AI, and much more. — Chapters: 00:00 - Episode highlights 01:28 - Episode intro 04:27 - Broad and deep JTBD 09:57 - A best-of-suite strategy 13:40 - Data behind Andrey’s intuition 16:14 - A portfolio of bets 19:40 - “PLG is not a business model” 24:16 - Evolving beyond per-seat pricing 28:50 - Miro’s monetization team 31:10 - The AI-led enterprise shift 34:28 - Founder mode redux 41:00 - Re-earning PMF 49:14 - Hiring former founders 56:00 - “Discipline is critical” 59:50 - 0-1 maker teams 01:01:38 - The enduring Four Fits 01:04:50 - Resilience — Referenced: Miro MCP (Model Context Protocol) Menlo Ventures 2025 report Slack OpenAI/ChatGPT Anthropic/Claude Gemini Granola Jeff Chow Jakob Knutzen Butter Tony Beltramelli Uizard Brian Balfour The Four Fits framework (updated for the AI era) — Connect with Andrey: LinkedIn — Connect with Krish: LinkedIn X...

    1 Std. 8 Min.
  2. Pendo CEO on category creation, differentiated platforms, pricing MAUs, and more | Todd Olson

    18.12.2025

    Pendo CEO on category creation, differentiated platforms, pricing MAUs, and more | Todd Olson

    In this episode of Second Acts, Krish is joined by Todd Olson, CEO and Founder of Pendo. Todd talks about: why investors pushed him to sell to marketers in 2013 but he stubbornly built for product managers instead (a persona without a proven budget line), the decade-long journey of creating a new category from scratch, why raising minimum price from $99/m to $1,500/m overnight accelerated their growth, the platform vision that's been core to Pendo since 2014 and Todd’s "innovate at the intersections" philosophy, how AI is fundamentally reshaping product analytics (as "the incremental value of a click" has declined in the post-ChatGPT era), the innovator's dilemma facing scale-ups today, lessons from Bill Walsh's The Score Takes Care of Itself and why leading indicators matter more than lagging ones, running one’s own race, and so much more. — Chapters: 00:00 - Episode highlights 01:51 - Episode intro 04:25 - How Pendo created a budget line item 08:14 - Questions for AI-native product teams 10:14 - Devs vs PMs: JTBDs and inclinations 13:24 - New paradigms for product analytics 21:14 - Why charge for MAUs? 22:21 - A trajectory-shifting price change 27:19 - “We’ve been a platform since 2014” 31:57 - Differentiating on intersections 37:21 - Living the innovator’s dilemma 43:19 - “Run your own race” 46:24 - The Score Takes Care of Itself — Referenced: Amp It Up (Frank Slootman) Marty Kagan Silicon Valley Product Group Receptive (acquired by Pendo) Crossing the Chasm (Geoffrey Moore) ChatGPT OpenAI Claude Code Lovable Airtable: Intercom: Net Promoter Score Product Operating Model Innovator's Dilemma (Clayton Christensen): The Score Takes Care of Itself (Bill Walsh) — Connect with Todd: LinkedIn: https://www.linkedin.com/in/toddolson/ — Connect with Krish: LinkedIn: https://www.linkedin.com/in/krishs/ X: https://x.com/cbkrish — About Chargebee: a href="https://www.chargebee.com/" rel="noopener noreferrer"...

    49 Min.
  3. v0’s GM on powering the next 100m builders, monetizing infra products, and more | Zeb Hermann

    13.11.2025

    v0’s GM on powering the next 100m builders, monetizing infra products, and more | Zeb Hermann

    In this episode of Second Acts, Krish is joined by Zeb Hermann, General Manager of v0 at Vercel. Zeb unpacks: the biggest lessons from his time at Segment and Sequoia Capital, why he joined Vercel (makers of Next.js and AI SDK) to lead initiatives (such as pricing and packaging) with “asymmetric upside,” v0’s origins (as Vercel’s second act) and how it has exploded to reach millions of users in the most intensely competitive competitive of AI categories, how the v0 team is structured as customer zero within Vercel, why it takes Caltech PHDs to scale their infrastructure pricing, v0’s deep vertical adjacencies and the differentiation that that unlocks, what he envisions as the ideal monetization model for AI, some amazing book recs via lectures he attended at The Long Now Foundation, and so much more. — Chapters: (00:00) Episode intro (03:39) v0: Vercel’s magisterial second act (04:59) “What’s the scale of your ambition?” (10:23) Asymmetric upside  (12:20) No (long-term) random acts of AI (14:16) Being customer zero  (15:51) v0 as a startup within Vercel (19:55) v0’s unique PLG-enterprise barbell (23:48) Vercel’s deep vertical differentiation (29:35) Value, Caltech PHDs, and Vercel’s pricing (35:35) Expanding to adjacent product lines (38:56) “Should this even be a separate product?” (41:41) Margins and value-aligned AI monetization (43:43) Zeb’s radical, two-year vision for v0 (47:11) Zeb’s favourite books on scaling decisions  — Vercel Guillermo Rauch Next.js by Vercel ShadCN UI Tailwind CSS Nikita Shamgunov Segment Zhenya Loginov Sequoia Capital Miro Opendoor CEO’s AI memo Caltech Harpreet Arora Malte Ubl Fluid compute Fluid compute pricing Algorithms to Live By (Brian Christian & Tom Griffiths) Scale (Geoffrey West) The Long Now Foundation Magic...

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

    09.10.2025

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

    25.09.2025

    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...

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

    11.09.2025

    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...

    1 Std. 15 Min.
  7. Optimizely CEO on suites, pricing AI agents, scaling through M&A, and more | Alex Atzberger

    28.08.2025

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

    14.08.2025

    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...

    1 Std. 12 Min.
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Info

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 month 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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