Saying yes to everything: How customer obsession built Samsara | Kiren Sekar (CPO)
Kiren Sekar is the CPO of Samsara, a company that brings real-time visibility, analytics, and AI to physical operations. Before Samsara, Kiren was an early leader at Meraki, which was acquired by Cisco for $1.2B.
In this episode, he walks us through Samsara’s origin story: from hardware hacking in a basement to scaling a cross-industry IoT platform. He shares how early customer feedback loops led to the company’s first product, why starting with the mid-market was a deliberate choice, and how Samsara kept a startup mindset even as it scaled.
In this episode, we discuss:
Lessons from Meraki’s acquisition by Cisco
How Kiren hires for intrinsic motivation
Why Samsara was built for operations industries
The early hardware prototype and the Cowgirl Creamery insight
Building broad vs. niche from day one
The shift from founder-selling to a scalable sales motion
Organizing product teams around revenue vs. experience
How Samsara uses LLMs and AI today
What Kiren learned from longtime co-founder Sanjit Biswas
Where to find Kiren:
LinkedIn: https://www.linkedin.com/in/kirensekar/
Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
References:
Cisco: https://www.cisco.com/
Clay: https://www.clay.com/
Cowgirl Creamery: https://cowgirlcreamery.com/
IBM: https://www.ibm.com/
Meraki: https://meraki.cisco.com/
Microsoft: https://www.microsoft.com/
Salesforce: https://www.salesforce.com/
Samsara: https://www.samsara.com/
Sanjit Biswas: https://www.linkedin.com/in/sanjitbiswas/
Uber: https://www.uber.com/
Timestamps:
(01:27) Meraki’s growth and acquisition by Cisco
(03:25) The "evaporating" exit strategy from Meraki
(04:42) Identifying the IoT market gaps
(07:38) The early keys to success at Samsara
(09:39) What does quality mean to Kiren?
(10:54) Building a customer-centric roadmap
(17:34) Early customer research and the failed fridge monitoring idea
(20:57) How a cheese producer helped create Samsara’s first prototype
(28:06) Balancing depth and breadth in customer profiles
(33:45) Developing customer trust to build feedback loops
(40:27) How “ease of use” became a growth secret
(44:23) Pricing strategies and market positioning
(51:51) How Meraki influenced Samsara’s GTM strategy
(57:19) Helping customers navigate change management
(1:00:48) How Samsara’s team evolved during rapid growth
(1:04:03) What AI means for an IoT giant
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1:08:57
Starting an education giant in a “bad market” | ClassDojo’s story | Sam Chaudhary (Co-founder and CEO)
Sam Chaudhary is the co-founder and CEO of ClassDojo, a multi-product education platform used in 95% of U.S. schools and over 180 countries globally to connect teachers, students, and families. In this episode, Sam shares the full arc of building ClassDojo, from early skepticism about education and a failed group-making tool, to creating a communication platform loved by millions.
In this episode, we discuss:
Why ClassDojo was built for consumers (teachers, students and parents) instead of schools
How ClassDojo grew entirely by word-of-mouth
Sam’s unusual approach to building multiple new businesses
The founder mindset required to build an industry leader
Why relentless resourcefulness is an underrated skill
And much more…
References:
Accel: https://www.accel.com/
Airbnb: https://www.airbnb.com/
Bill Gates: https://www.linkedin.com/in/williamhgates/
Brendan Kereiakes: https://www.linkedin.com/in/product/
ClassDojo: https://www.classdojo.com/
Dominick Bellizzi: https://www.linkedin.com/in/dominickbellizzi/
Geoff Ralston: https://www.linkedin.com/in/geoffralston/
Gonzalo Aguilar Málaga: https://www.linkedin.com/in/gonzalodecheck/
Hamilton Helmer: https://www.linkedin.com/in/hamilton-helmer-42983/
Imagine K12: https://www.imaginek12.com//
Khan Academy: https://www.khanacademy.org/
Liam Don: https://www.linkedin.com/in/liamdon/
McKinsey: https://www.mckinsey.com/
Paul Graham: https://x.com/paulg
Plaid: https://plaid.com/
Reid Hoffman: https://www.linkedin.com/in/reidhoffman/
Roblox: https://www.roblox.com/
Sal Khan: https://www.linkedin.com/in/khanacademy/
Superhuman: https://superhuman.com/
Tim Brady: https://www.linkedin.com/in/tim-brady-7a632510/
Y Combinator: https://www.ycombinator.com/
Where to find Sam:
LinkedIn: https://www.linkedin.com/in/samchaudhary/
Twitter/X: https://x.com/samchaudhary
Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
Timestamps:
(01:36) Why education is a “bad market”
(02:52) Why enterprise education is broken
(03:35) Building for families, not schools
(06:53) Early challenges and insights
(09:45) Sam’s unusual background
(11:42) Meeting co-founder Liam at a hackathon
(13:22) Getting into Imagine K12 with a group-making tool
(19:47) The conversation with Reid Hoffman that changed everything
(21:52) Building a network to reach more families
(23:30) Scaling by building a community
(33:18) Designing for delight and word-of-mouth growth
(40:09) Launching the first monetization feature after 7 years
(41:35) How to pick markets and when to go broad
(46:04) The explosive expansion into the tutoring industry
(55:11) Creating safe online spaces for kids
(58:01) Harnessing AI in education
(59:52) Lessons from ClassDojo’s playbook
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1:12:29
From Chrome extension to $5B platform | Postman’s journey | Abhinav Asthana (Co-founder & CEO)
Abhinav Asthana is the co-founder and CEO of Postman, the world's leading API collaboration platform used by millions of developers and thousands of companies. What began as a personal itch, a simple Chrome extension Abhinav built to make his own API work easier, became a global phenomenon within weeks.
In this episode, we discuss:
Making the leap from India to Silicon Valley
The moment Abhinav realized Postman could win
His principles behind building for developers and non-developers alike
The early monetization experiments that led to their SaaS model
The value of progressive complexity in product design
How community building became a powerful growth lever
And much more…
References:
Abhijit Kane: https://www.linkedin.com/in/abhijitkane/
Adobe: https://www.adobe.com/
Ankit Sobti: https://www.linkedin.com/in/ankit-sobti/
Figma: https://www.figma.com/
Kong Inc.: https://konghq.com/
National University of Singapore: https://nus.edu.sg/
Postman: https://www.postman.com/
Ram Gupta: : https://www.linkedin.com/in/ram-gupta-39b9711/
Slack: https://slack.com/
Stripe: https://stripe.com/
Stewart Butterfield: https://www.linkedin.com/in/butterfield/
Yahoo: http://yahoo.com/
Where to find Abhinav:
LinkedIn: https://www.linkedin.com/in/abhinavasthana/
Twitter/X: https://x.com/a85
Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
Where to find First Round Capital:
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps:
(01:18) Why early computer access changed everything
(03:39) The first taste of the entrepreneurial bug
(09:58) Building BITS360 in college
(11:14) Curating entrepreneurial taste
(15:49) The ventures that didn’t make it
(20:53) The problems that preceded Postman
(29:56) How Postman’s team was formed
(34:01) Why clear roles prevent chaos
(34:50) Scrappy startup life in the early days
(36:26) Postman’s path to monetization
(39:59) Building a truly collaborative platform
(43:00) Navigating market and customer needs
(46:02) Cracking the go-to-market code
(49:39) Bridging the developer-enterprise divide
(54:43) The open-source dilemma
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1:06:20
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1:06:20
How Canva leveraged unconventional growth levers to grow to $42B | Cameron Adams (Co-founder & CPO)
Cameron Adams is the co-founder and Chief Product Officer at Canva, the design platform valued at $42B as of July 2025, used by over 230 million people every month.
Before starting Canva, Cameron was a designer and engineer at Google and co-founded Fluent, an email startup. In this episode, Cameron walks through Canva’s earliest days — from the remarkably fast courtship with co-founders Melanie Perkins and Cliff Obrecht, to the counterintuitive product decisions that helped Canva instantly resonate with users who thought they would never design anything.
In this episode, we cover:
How Canva turned social media managers into early evangelists
Balancing a huge vision with scrappy execution
Hard lessons from their near-silent launch day
The two growth levers that changed everything
And much more…
References:
Adobe: https://www.adobe.com/home
Atlassian: https://www.atlassian.com/
Campaign Monitor: https://www.campaignmonitor.com/
Canva: https://www.canva.com/
Cliff Obrecht: https://www.linkedin.com/in/cliff-obrecht-79ba9920/
Dave Greiner: https://www.linkedin.com/in/davegreiner/
Lars Rasmussen: https://www.linkedin.com/in/larserasmussen/
Melanie Perkins: https://www.linkedin.com/in/melanieperkins/
Mike Cannon-Brookes: https://www.linkedin.com/in/mcannonbrookes/
New York Stock Exchange: https://www.nyse.com/
Pinterest: https://pinterest.com/
Scott Farquhar: https://www.linkedin.com/in/scottfarquhar/
Where to find Cameron:
LinkedIn: https://www.linkedin.com/in/themaninblue/
Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
Where to find First Round Capital:
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
X/Twitter: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps:
(01:24) The birth of Canva
(04:32) Meeting Canva’s co-founders
(11:22) Building the first iteration of Canva
(15:26) The discovery that changed prototyping
(20:48) Why onboarding was the unlock for retention
(27:36) The anticlimactic launch day
(32:43) How word-of-mouth spurred early retention
(36:33) Targeting different user personas
(41:02) Building a community on social media
(43:38) Two impactful growth levers
(47:14) Why Canva should have gone mobile sooner
(48:12) What underpins Canva’s dominance today
(53:37) Rebuilding for enterprise
(58:38) Lessons from Canva’s tough times
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1:04:26
Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)
Parag Agrawal is the co-founder and CEO of Parallel, a startup building search infrastructure for the web’s second user: AIs. Before launching Parallel, Parag spent over a decade at Twitter, where he served as CTO and later CEO during a period of intense transformation, as well as public scrutiny.
In this episode, Parag shares what he learned from his time at Twitter, why the web must evolve to serve AI at massive scale, how Parallel is tackling “deep research” challenges by prioritizing accuracy over speed, and the design choices that make their APIs uniquely agent-friendly.
We also discuss:
Why Parallel designs for AI as the primary customer
Lessons from 11 years at Twitter and applying them to a startup
Potential business models to keep the web open for AI
Hiring philosophy: balancing high potential and experienced talent
The evolving role of engineers in an AI-assisted world
Why “agents” are finally becoming useful in production
And much more…
References:
Bloomberg launch coverage: https://www.bloomberg.com/news/articles/2025-08-14/twitter-ex-ceo-parag-agrawal-is-moving-past-his-elon-musk-drama
Clay: https://www.clay.com/
Index Ventures: https://www.indexventures.com/
Josh Kopelman: https://www.linkedin.com/in/jkopelman/
KLA: https://www.kla.com/
OpenAI: https://openai.com/
Parallel: https://parallel.ai/
Patrick Collison: https://www.linkedin.com/in/patrickcollison/
Stripe: https://stripe.com/
Where to find Parag:
LinkedIn: https://www.linkedin.com/in/paragagr/
X/Twitter: https://x.com/paraga
Where to find Todd:
LinkedIn: https://www.linkedin.com/in/toddj0/
X/Twitter: https://x.com/tjack
Where to find First Round Capital:
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
X/Twitter: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps:
(1:26) Founding Parallel with an AI-first mission
(3:23) From Twitter CTO/CEO to startup founder
(6:20) What the AI era spells for companies
(7:58) The CEO to founder pipeline
(11:18) Reflections on Twitter’s transformation
(17:48) How Parallel was born
(22:31) Early use cases for Parallel
(31:42) How has Parallel’s ICP changed?
(34:37) AI’s impact on competitor dynamics
(36:06) When should founders launch?
(37:43) Parag’s fundraising framework
(40:14) Building a high-impact engineering team
(44:49) Counterproductive uses of AI
(47:35) How will the software engineer role evolve?
(49:10) How are Parallel’s customers using AI?
(53:27) Defining agents in 2025
(55:02) Parallel’s long-term vision
(1:03:43) Parag’s growth as a founder
Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. We hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com
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