Second Acts with Krish Subramanian

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 mode...

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...

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 g...

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 th...

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 decis...

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 distr...

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 emergin...

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...

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 com...

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 ult...

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 ma...

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 en...

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....

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 hel...

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 als...

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 t...

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 fo...

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 pha...

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...

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 st...

In this inaugural episode of Second Acts, Krish sits down with Gainsight’s CEO, Nick Mehta, to arrive at the very heart of this “mission-critical," post-PMF stage of scaling a SaaS business. Nick: “If you’re not careful and you don’t watch that bookings growth and drive it, you’re going to hit a wall. Some markets don’t hit a wall quickly. For example, Salesforce kept going for a long time because...

Join Chargebee's co-founder and CEO, Krish Subramanian, as he documents how veteran SaaS leaders navigate the make-or-break setting up of new, transformative growth engines: Second Acts. Hear the tactical, strategic, and deeply personal takes on this foundational phase of scaling SaaS companies.