Second Acts with Krish Subramanian

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

Fri, 30 Jan 2026 10:45:00 +0100

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.

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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

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Referenced:

Miro

MCP (Model Context Protocol)

Menlo Ventures 2025 report

The Four Fits framework (updated for the AI era)

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Connect with Andrey:

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Connect with Krish:

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About Chargebee:

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

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

Thu, 18 Dec 2025 16:00:00 +0100

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.

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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

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Referenced:

Amp It Up (Frank Slootman)

Marty Kagan

Silicon Valley Product Group

Receptive (acquired by Pendo)

Crossing the Chasm (Geoffrey Moore)

Product Operating Model

Innovator's Dilemma (Clayton Christensen):

The Score Takes Care of Itself (Bill Walsh)

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Connect with Todd:

LinkedIn: https://www.linkedin.com/in/toddolson/

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Connect with Krish:

LinkedIn: https://www.linkedin.com/in/krishs/

X: https://x.com/cbkrish

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About Chargebee:

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

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

Thu, 13 Nov 2025 16:55:00 +0100

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.

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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

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Opendoor CEO’s AI memo

Fluid compute pricing

Algorithms to Live By (Brian Christian & Tom Griffiths)

Scale (Geoffrey West)

The Long Now Foundation

Magic Patterns

Greedy algorithm

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Connect with Zeb:

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Connect with Krish

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About Chargebee:

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

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

Thu, 09 Oct 2025 20:13:00 +0100

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.

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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

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Referenced:

Docebo

NASDAQ

Edugo

“From System of Record to System of Intelligence:”

The Five Dysfunctions of a Team

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Connect with Alessio:

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Connect with Krish

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About Chargebee:

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

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

Thu, 25 Sep 2025 17:52:00 +0100

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.

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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

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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

The Second-Order Effects of AI

Several Short Sentences About Writing

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

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Connect with Tomasz:

Tomasz Tunguz

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Connect with Krish

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About Chargebee:

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

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

Thu, 11 Sep 2025 18:59:00 +0100

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.

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(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

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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

Izzy the Inventor (children’s book)

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Connect with Brian:

Brian Balfour

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Connect with Krish

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About Chargebee:

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

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

Thu, 28 Aug 2025 04:30:00 +0100

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.

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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

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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

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Connect with Alex:

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Connect with Krish:

LinkedIn:

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About Chargebee:

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

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

Thu, 14 Aug 2025 15:47:00 +0100

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.”

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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”

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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

Introducing the Model Context Protocol

commercetools Commerce MCP

MACH alliance

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Connect with Dirk:

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Connect with Krish:

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About Chargebee:

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

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

Thu, 31 Jul 2025 18:55:00 +0100

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.”

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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

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Referenced/resources:

American Dreamers: Tracy Young Has The Eye Of The Tiger

TigerEye

PlanGrid

Tracy Young, Co-founder & CEO of PlanGrid (The Social Radars)

Procore

Part II: The failure points from $5m to $100m in ARR

Mid-market is no man’s land

Do Things that Don’t Scale

Cursor

GitHub Copilot

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Connect with Tracy:

Tracy writes

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Connect with Krish:

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About Chargebee:

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

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

Thu, 17 Jul 2025 17:20:00 +0100

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

Chargebee Time Machine

Moments of Truth

Rajaraman Santhanam

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Connect with Guy:

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Connect with Krish:

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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.

Episode 10: Rick Nucci, Guru

Mon, 25 Nov 2024 04:30:00 +0100

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:

Connect with Krish:

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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.

Episode 9: Ted Elliott, Copado

Thu, 07 Nov 2024 04:30:00 +0100

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:

Connect with Krish:

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Episode 8: Andrew Lau, Jellyfish

Thu, 24 Oct 2024 04:30:00 +0100

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:

Connect with Krish:

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Episode 7: Bob Moore, Crossbeam

Thu, 10 Oct 2024 04:30:00 +0100

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:

Twitter

Connect with Krish:

Twitter

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Episode 6: Jonas Ruyter and Vidya Peters, DataSnipper

Thu, 26 Sep 2024 04:30:00 +0100

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:

Connect with Vidya:

Connect with Krish:

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Episode 5: Jason Cohen, WP Engine

Thu, 12 Sep 2024 16:30:00 +0100

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

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Connect with Krish:

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Episode 4: Bo Jiang, Lithic

Thu, 29 Aug 2024 04:30:00 +0100

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:

Connect with Krish:

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About Chargebee:

Episode 3: Allison Pickens, The New Normal Fund

Thu, 15 Aug 2024 04:30:00 +0100

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:

Allison Pickens' Newsletter

Connect with Krish:

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About Chargebee:

Episode 2: Brendan Schwartz and Chris Savage, Wistia

Thu, 01 Aug 2024 15:00:00 +0100

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:

Connect with Chris:

Talking Too Loud

Connect with Krish:

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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.

Episode 1: Nick Mehta, Gainsight

Thu, 18 Jul 2024 17:00:00 +0100

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 the CRM market was so big. However…the reason Salesforce is worth a couple of hundred billion dollars and not 20/50 is Service cloud. They said, act one is Sales Cloud. Act two is Service Cloud. Then act three was Marketing Cloud and some other things.”

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Chapters:

0:38: An introduction to Nick

1:57: Premise of this podcast series

6:10: Why most companies need a second act (way) sooner than they think

8:38: How to figure out when you need the second act (mathematically)

14:01: Two factors that dictate this transition: cycle time and org charts

15:52: The M&A patch

18:13: Why a top-down motion can prove incredibly advantageous

21:28: How to approach different rights-to-win/product adjacencies

28:38: The art of layering S-curves

33:50: The four things scale-ups need to be good at

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Mentioned:

So You’ve Raised a SaaS Mega Round: Now What?

Invisible asymptotes

My Top 10 Mistakes In 10 Years: Gainsight CEO Nick Mehta

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Connect with Nick:

MehtaPhysical

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Connect with Krish:

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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.

Introducing: Second Acts with Krish Subramanian

Mon, 15 Jul 2024 21:30:00 +0100

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.