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. Notion co-founder on malleable software, monetizing agentic work, reinvention, more | Akshay Kothari

    2D AGO

    Notion co-founder on malleable software, monetizing agentic work, reinvention, more | Akshay Kothari

    In this episode of Second Acts, Krish is joined by Akshay Kothari, co-founder at Notion. Akshay shares notes on: The founding insight behind his first startup, Pulse (acq. by LinkedIn in 2013) and how that led him to Notion, the now-storied Kyoto reset that transformed a flailing, early version of the product, how the idea of building “malleable software” can be traced back to the origins of modern computing, what’s informing Notion’s agent-native second act and its multi-layered moat, learning to price work/intelligence over seats/platforms, how Notion's Custom Agents made usage-based monetization an incontestable choice, why Akshay turns to the necessary pragmatism of Buffet and Munger, defiant narratives, and much more. — Chapters: 00:00 — Episode highlights 03:31 — Pulse 06:12 — The Kyoto reset 08:58 — “Everything is a block” 11:16 — Malleable software 13:27 — Sugar-coated broccoli 15:26 — Selling work 19:15 — Switzerland of LLMs 23:32 — Pricing intelligence-as-a-service 31:22 — Margins and agents 35:02 — Think Together 38:39 — Freeing demos 42:13 — Munger’s valley — Referenced: Notion Pulse Ivan Zhao Douglas Engelbart Alan Kay Augmenting Human Intellect Malleable software Custom Agents Notes from Token Town Landing on usage-based pricing Think Together Notion Media Fellows Poor Charlie's Almanack — Connect with Akshay: LinkedIn X — Connect with Krish: LinkedIn X — About Chargebee: Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative AI monetization infrastructure.

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

    JAN 30

    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 — About Chargebee: Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra.

    1h 8m
  3. Pendo CEO on category creation, differentiated platforms, pricing MAUs, and more | Todd Olson

    12/18/2025

    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: Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra.

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

    11/13/2025

    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 Patterns Greedy algorithm — Connect with Zeb: LinkedIn X — 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.

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

    10/09/2025

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

    09/25/2025

    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 HashiCorp Google ChatGPT Lovable Cursor 5 Mistakes SaaS Startups Often Make with Pricing Explore vs. Exploit in Agentic Coding Barr Moses How Monte Carlo's Daily Revenue Model Rewrote Their Strategy The Market Size Mistake Gainsight Why There's Never Been a Better Time to Found a SaaS Startup A Challenge to SaaS Orthodoxy Extreme PMF : Sustaining Success with Scale My Favorite Books of 2024 Chronicles of a Liquid Society Breakneck: China’s Quest to Engineer the Future — Connect with Tomasz: LinkedIn X Tomasz Tunguz — 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.

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

    09/11/2025

    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 Cursor Google: How the Best Business in Human History Happened The Next Great Distribution Shift ChatGPT-5 We've Raised $21M To Grow Reforge Clouded Judgement Paul Graham The Coming Wave Andrew Matthews Izzy the Inventor (children’s book) — Connect with Brian: LinkedIn X Brian Balfour — 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.

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

    08/28/2025

    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
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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 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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