In Depth

Latest Episodes:

The fastest way to learn is to run two competing bets | Jay Parikh (EVP CoreAI, Microsoft) Aug 27, 2026

Show notes

In the latest episode of Executive Function, Brett sits down with Jay Parikh, Executive Vice President of CoreAI at Microsoft. Before joining Microsoft, Jay spent over a decade as Facebook's global head of engineering, scaling the company from a few hundred engineers to billions of users, then ran the cybersecurity company Lacework as CEO through its acquisition by Fortinet. In this conversation, he breaks down the five ingredients of great engineering leadership, discusses why he'd rather run two competing bets in parallel than forecast a winner, and explains why company culture remains more important than ever for teams to get right.

In today's episode, we discuss:

The five ingredients that separate excellent engineering leadership from the rest
How to protect your team from large shifts in public perception
The mindset shift organizations need to maintain speed at scale
How every layer of the organization needs to stay connected to the customer
Why Jay runs "brain trusts" of senior ICs with zero managers in the room

References

Akamai: https://www.akamai.com/
AWS: https://aws.amazon.com/
Facebook: https://www.facebook.com/
George Conrades: https://www.linkedin.com/in/georgeconrades/
Mark Zuckerberg: https://x.com/finkd
Microsoft: https://www.microsoft.com/
Paul Sagan: https://www.linkedin.com/in/paul-sagan-59654a1/
Tom Leighton: https://www.linkedin.com/in/tleighton/

Where to find Jay

LinkedIn: https://www.linkedin.com/in/jayparikh/
Twitter/X: https://x.com/jayparikh

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

00:00 Introduction

00:36 How leadership changes through exponential growth

02:21 The five ingredients that define excellent engineering leadership

07:51 What actually drives culture at a company as it scales

12:05 The physics behind why everything slows down at scale

18:57 The fastest team of Jay's career, and why size mattered

22:44 Why every team should think like an FDE

26:20 Managing a team through wild swings in public perception

29:07 What's different about leading through the steepest S-curve moments

33:58 Why onboarding well means going slow to go fast

37:41 Is AI actually new, or is history just repeating?

41:35 What actually counts as a "big bet" worth taking

45:01 The concrete big bets that reshaped Facebook's entire technology stack

47:35 Why vertical integration keeps being the right call as companies scale

51:46 How being a startup CEO reshaped Jay as a leader

1:01:26 Why Jay overruled Zuckerberg's instinct to skip efficiency

What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr) Jul 30, 2026

Show notes

In the latest episode of Executive Function, Brett sits down with Lindsey Scrase, COO of Checkr. Before joining Checkr as CRO and later stepping into the COO seat, Lindsey spent nearly a decade at Google Cloud as global managing director for SMB, mid-market, and startups. In this conversation, she breaks down why moving upmarket into enterprise trips up so many startups looking to scale, how Checkr rebuilt its sales compensation model to keep pace with growth, and where AI is already reshaping her operations and go-to-market teams.

In today's episode, we discuss:

Why operators who thrive at massive-scale companies often struggle when they join a startup
The hard-won lessons from Checkr's early enterprise push that nearly failed
Why Checkr’s C-suite meets every morning with no specific agenda
The surprising challenges moving from CRO to COO
How Checkr turned AI experiments into operating systems

References

Amazon: https://www.amazon.com
Checkr: https://checkr.com
Claude: https://claude.com
Daniel Yanisse: https://www.linkedin.com/in/yanisse/
DoorDash: https://www.doordash.com
Google: https://www.google.com
Lovable: https://lovable.dev
Microsoft: https://www.microsoft.com

Where to find Lindsey

LinkedIn: https://www.linkedin.com/in/lindsey-scrase-0702442/
Twitter/X: https://twitter.com/Lscrase

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

00:00 Introduction

00:06 Why big-company executives often struggle in startups

02:18 What Checkr's first CRO needed to accomplish

03:33 How to take on an entrenched category leader

06:58 Why leaders underestimate how hard the jump to enterprise really is

10:23 Separating a true deal-blocker from a customer's nice-to-have request

18:30 Why Lindsey hired enterprise-scarred sales leader over a market leader's résumé

22:08 The biggest challenges of moving from CRO to COO

28:03 Why Checkr names a single decision-maker for every major decision

34:42 Why Checkr rebuilt their sales compensation model

40:39 What actually separates a team's best seller from everyone else

45:03 Inside Checkr’s daily, no-agenda, c-suite meeting

50:23 How following data can sometimes lead you in the wrong direction

57:27 Why hitting 130% of a goal isn’t always a good thing

58:57 Where AI has changed how Checkr's teams operate day to day

1:04:33 Advice for all aspiring COOs

How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma) Jul 24, 2026

Show notes

In this episode of In Depth, Brett sits down with Jon Noronha, co-founder and CPO of Gamma, the AI-native presentation platform used by more than 100 million people. In this conversation, he walks through Gamma’s distinct eras of product-market fit: from a pre-AI struggle with a year of runway left, to an overnight AI-fueled explosion, to today’s unplanned scramble into enterprise sales. Jon also unpacks his hard-won lessons on horizontal versus vertical bets, monetizing AI products, and why nailing onboarding turned out to be the whole game.

In today's episode, we discuss:

Why Gamma's all-in AI launch in March 2023 saved their startup
How fixing a simple onboarding problem accidentally uncovered Gamma’s entire product-market fit
Why Jon bet Gamma on a horizontal product against the advice of nearly every investor
How Gamma's daily signups climbed from hundreds to over 100,000 with zero paid marketing
What building three pricing tiers taught Jon about monetizing AI

References

Where to find Jon Noronha

LinkedIn: https://www.linkedin.com/in/jonnoronha/
Twitter/X: https://twitter.com/thatsjonsense

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:

00:00 Introduction

01:47 Gamma’s three-era journey to product-market fit

03:41 Spotting the blank page problem pre-ChatGPT

05:11 How Gamma survived with only one year of runway

07:17 How onboarding fixes revealed the whole product

09:31 Choosing horizontal over investors' vertical playbook

13:41 Prototyping by hand before AI coding

15:36 How Gamma builds with future models in mind

20:06 The Kool-Aid mistake of a late PowerPoint export

24:31 Why the presentation industry hadn't evolved since 1987

33:30 How Gamma solves evals for taste, not just data

40:21 Jon's hardest lessons monetizing AI since 2023

44:16 The fast leap from prosumer to enterprise

47:01 Why product still beats distribution

52:06 The metric that proved product-market fit

57:36 Pricing advice for prosumer AI founders

59:01 The toils and realities of founder life

Why Plaid’s COO cold-calls new hires | Eric Sager (COO of Plaid) Jul 16, 2026

Show notes

In the latest episode of Executive Function, Brett sits down with Eric Sager, COO of Plaid, following stints as CRO of Bluevine and Head of Sales at Square. During his seven-year tenure at Plaid, Eric has helped lead the business through a pandemic, Visa's collapsed acquisition, a fintech downturn, and the AI boom. In today’s conversation, he unpacks how he kept teams focused during turbulent times, why he refuses to run at 100% capacity, and how he re-architected the go-to-market function as Plaid scaled.

In today's episode, we discuss:

How Plaid stayed focused after the Visa acquisition fell through and then raised at nearly 3x the price
Why great COOs deliberately make themselves obsolete
Why Eric treats speed, risk, and cost as a three-way trade-off, and why sometimes going slower wins
How refusing to run at 100% capacity helped Plaid win OpenAI, Perplexity, and Replit
Why Eric personally cold-calls brand-new employees

References

Bain & Company: https://www.bain.com
Bluevine: https://www.bluevine.com
Chase: https://www.chase.com
Citibank: https://www.citi.com
Eyal Lifshitz: https://www.linkedin.com/in/eyallifshitz/
Françoise Brougher: https://x.com/FrancoiseBr
Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/
Jack Dorsey: https://x.com/jack
Michael Mankins: https://www.linkedin.com/in/michaelcmankins
OpenAI: https://openai.com
Perplexity: https://www.perplexity.ai
Plaid: https://plaid.com
Replit: https://replit.com
Sarah Friar: https://www.linkedin.com/in/sarah-friar/
Square: https://squareup.com
Visa: https://www.visa.com
William Hockey: https://www.linkedin.com/in/william-hockey-04536710
Zach Perret: https://www.linkedin.com/in/zperret/

Where to find Eric Sager

LinkedIn: https://www.linkedin.com/in/eric-sager-a529516

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

00:00 Introduction

00:40 Leading a company through turbulent times

04:24 How to build a resilient team culture

08:33 How Plaid avoids bureaucracy, while operating at scale

10:58 The speed-quality tradeoff: Going faster isn't always better

15:32 When to move from generalists to specialized customer segments

20:14 Why Plaid has one owner for entire customer relationships

22:06 The "quarterback" model: one owner, experts on call

24:08 Why you should never run your org at 100% capacity

29:47 "Always available, never needed": the support mantra

36:49 Eric’s unusual "hit by a bus" test to measure job success

43:57 Why Eric cold calls brand-new employees

52:14 Eric's week: 25% ecosystem, 50% business, 25% team

55:15 How to spot fake mission alignment in interviews

59:04 The one thing a founder has that no hire can replicate

How Supabase became the essential infrastructure for the AI era | Paul Copplestone (Co-founder, CEO) Jun 25, 2026

Show notes

In this episode of In Depth, Brett sits down with Paul Copplestone, co-founder and CEO of Supabase, the open-source Postgres platform now serving more than seven million developers. Before Supabase, Paul launched a Thumbtack-style marketplace in Southeast Asia and co-founded an office-management startup called Nimbus, experiences that taught him to separate fundraising from building and to find product-market fit before blitzscaling. He breaks down how a single tagline change for Supabase unlocked product-market fit, why he runs a fully distributed async team with near-zero attrition, and how he turned PLG signals into a product-led sales motion comped only on incremental uplift.

In today's episode, we discuss:

How changing one tagline helped Supabase go to #1 in Hacker News - an early sign of product market fit
Why Paul ran Supabase like it had only $100K in the bank despite raising real money
How Supabase rode three distinct AI waves, from pgvector to Bolt and Lovable, to Claude Code
Why Supabase built a sales team comped only on the incremental uplift over a control group
What the Toyota production system's "kaizen" taught Paul about unblocking a scaling team

References:

Ant Wilson: https://www.linkedin.com/in/ant-wilson-46179937
Bolt: https://bolt.new/
Claude Code: https://www.anthropic.com/claude-code
Codex: https://openai.com/codex/
Entrepreneurs First: https://www.joinef.com/
Firebase: https://firebase.google.com/
Lovable: https://lovable.dev/
MongoDB: https://www.mongodb.com/
Next.js: https://nextjs.org/
PostgreSQL: https://www.postgresql.org/
Supabase: https://supabase.com/
Thumbtack: https://www.thumbtack.com/
Y Combinator: https://www.ycombinator.com/

Where to find Paul:

LinkedIn: https://www.linkedin.com/in/paulcopplestone
Twitter/X: https://x.com/kiwicopple

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:

00:00 Introduction

01:32 Why Paul's earlier startups were never destined to be huge

07:14 Unlearning the "tall poppy" mindset and going all-in on async

09:54 Reverse-engineering why Supabase was an outstanding idea

12:04 The accidental Hacker News launch and tagline lesson

13:58 Where the early roadmap came from: demand vs. technical taste

17:28 Skill vs. luck, and operating like you have $100K in the bank

21:42 What actually makes a great developer experience

23:10 Solving the "graduation problem" Firebase never could

24:58 The role of open source in Supabase's success

26:10 The three distinct AI tailwinds: From pgvector to Claude Code

35:24 Supabase’s egoless, hyper-competitive open-source culture

42:58 A tactical playbook for raising capital

48:37 Product-led sales comped on incremental uplift only

59:27 The production philosophy behind Supabase’s operations

How to build a beloved tech brand | Sheila Joglekar Vashee (CMO, Figma) Jun 04, 2026

Show notes

In today's conversation, Brett sits down with CMO of Figma, Sheila Joglekar Vashee. Previously the second marketing hire at Dropbox, where she helped scale the company past $1 billion in revenue, she now leads marketing at Figma fresh off its IPO. In an industry that has spent a decade trying to turn marketing into something closer to hedge fund trading, Sheila argues the art was always the point — we just stopped talking about it. She unpacks how to run marketing as a portfolio of moonshots, why giving teams different goals breeds dysfunction, how to scale taste across an organization, and why old playbooks are obsolete, even as the fundamentals hold.

In today's episode, we discuss:

How to run marketing like a portfolio of moonshots
The value of disruptive energy for senior marketers
Why "Ubiquity is the opposite of cool"
How to actually scale taste across an organization
What great marketing looks like in the AI era

Referenced:

Apple: https://www.apple.com/
Dennis Woodside: https://www.linkedin.com/in/dennis-woodside-341302/
Dropbox: https://www.dropbox.com/
Dylan Field: https://www.linkedin.com/in/dylanfield/
Figma: https://www.figma.com
Francoise Brougher: https://www.linkedin.com/in/francoise-brougher-341a72/
Gap: https://www.gap.com/
Google Chrome: https://www.google.com/chrome/
Harley-Davidson: https://www.harley-davidson.com/
HubSpot: https://www.hubspot.com/
Notion: https://www.notion.com/
Opendoor: https://www.opendoor.com/
Pinterest: https://www.pinterest.com/
Square: https://squareup.com/
The Web Is What You Make of It (Dear Sophie): https://www.youtube.com/watch?v=pzOBOuyr-EU
Urban Outfitters: https://www.urbanoutfitters.com/
Yamini Rangan: https://www.linkedin.com/in/yaminirangan/

Where to find Sheila:

LinkedIn: https://www.linkedin.com/in/sheilavashee/
X: https://x.com/sheilavashee

Where to find Brett:

LinkedIn: https://www.linkedin.com/in/brett-berson-9986644/
X: https://x.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:

00:00 Introduction

00:07 What excellent marketing actually is in 2026

01:36 Why giving teams different goals creates dysfunction

02:36 The most important decision Sheila made as CMO last year

04:26 The real difference between an SVP and a CMO

06:05 Marketing is one engine - not separate pieces

07:15 The tension between brand and growth

09:25 The decisions a CMO should never be making

09:55 Running marketing like a portfolio of moonshots

12:46 "Ubiquity is the opposite of cool"

15:11 Why a few companies get a flywheel of momentum

16:44 The Silicon Valley clock and irrational perception cycles

19:25 How to actually scale taste across an org

21:09 What changes for a CMO in a post-LLM world

23:15 Why the artistic side of marketing never really left

26:05 Whether taste can ever be encoded in software

27:15 Telling an optimistic, yet realistic story about AI

30:50 You need to make people care

32:11 What surprised Sheila about being a public-company CMO

33:46 Why Figma won enterprise where Dropbox couldn't

35:25 Sheila’s favorite campaign ever

37:10 Why announcement videos full of humans, lack humanity

38:55 Playbooks are obselete, but the fundamentals are not

40:25 Why marketing in 2026 demands disruptive energy

41:54 How Sheila architects her week

48:55 Where corporate politics actually come from

53:55 "Sheila, are you going to change the world in this job?"

58:09 What's unique about the CMO and CEO relationship

Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel) May 21, 2026

Show notes

In the latest episode of Executive Function, Brett sits down with Graham Moreno, Head of GTM at Parallel Web Systems. Before Parallel, Graham scaled Windsurf's GTM organization from three sellers to seventy-five in under a year, served as President through the Cognition acquisition, and earlier built and led enterprise sales teams at Grafana Labs and MongoDB. In this conversation, he unpacks why the AI-era backlash against structured enterprise sales misreads the data, how to design a process that raises the floor for ordinary reps without capping the ceiling for stars, and why selling to AI-native customers compresses an eight-week cycle into five business days.

In today's episode, we discuss:

Why in-person enterprise rollouts still beat product-led motions
Building a robust sales process that still leaves room for unscripted moments
Why the three highest-leverage early sales hires aren't sellers at all
The case for outsized commission accelerators for star sellers — and the kind of person they attract
Why most AI companies are skipping the in-person sales work that enterprise customers actually want

References:

Ahead: https://www.ahead.com
Amazon: https://www.amazon.com
Anthropic: https://www.anthropic.com
Attio: https://www.attio.com
Augment Code: https://www.augmentcode.com/
Cognition: https://cognition.ai
Cursor: https://cursor.com
Dani McCabe: https://www.linkedin.com/in/danielle-mccabe/
Datadog: https://www.datadoghq.com
GitHub Copilot: https://github.com/features/copilot
HubSpot: https://www.hubspot.com
Jeremy Powers: https://www.linkedin.com/in/jeremypowers/
JPMorgan: https://www.jpmorgan.com
Matt McClernan: https://www.linkedin.com/in/mattmcclernan/
MongoDB: https://www.mongodb.com
Nicole Rettinger: https://www.linkedin.com/in/nicole-rettinger-23b20465/
Notion: https://www.notion.com
OpenAI: https://openai.com
Parag Agrawal: https://www.linkedin.com/in/paragagr/
Parallel: https://parallel.ai
Snowflake: https://www.snowflake.com
University of Chicago: https://www.uchicago.edu
Windsurf: https://windsurf.com

Where to find Graham:

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

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:

00:00 Introduction

00:32 Has the sales playbook changed in the AI era?

02:13 Why "showing up" beats letting the marketplace decide

06:50 Why great salespeople sell to engineers and executives in one motion

11:37 Selling to AI-native buyers who grew up on ChatGPT

13:49 Same seller, different tempo: 8 weeks vs. 8 business days

15:57 How AI-native buyers handle build vs. buy decisions

17:48 The rep who taught a champion's son guitar over Zoom

19:03 Raising the floor without capping the ceiling

22:09 Why too much process narrows the kind of seller you attract

25:46 The three pillars of GTM excellence

31:00 Building peers who are 80% aligned, not 100%

38:03 Whether AI is changing what good enablement looks like

41:35 Selling against direct and implied competitors at once

42:45 Instrumenting the funnel from stage zero to close

45:57 Why post-sales should always roll up to the revenue leader

48:19 The case for outsized commissions

52:02 The 96 hours of panic before Cognition acquired Windsurf

53:04 How far out should a GTM leader be planning?

57:53 What a normal week looks like in hypergrowth

Why founders should bet on first-time executives | Praveer Melwani (CFO, Figma) May 14, 2026

Show notes

In this latest episode of Executive Function, Brett sits down with Praveer Melwani, CFO at Figma. Praveer joined Figma in 2017 as the company's first business operations and finance hire—when the team was around 30 people and not yet charging for the product—and stepped into the CFO seat in 2022, helping to lead the company’s IPO in 2025. In today’s conversation, Praveer breaks down the step functions that took him from IC to CFO, why Figma started acting like a public company three years before IPO, and how AI is rewriting capital allocation and the CFO job itself.

In today's episode, we discuss:

What separates a world-class finance leader from a traffic-cop CFO
How Praveer went from Figma's first biz ops hire to CFO of a public company in nine years
Why Figma started acting like a public company three years before its IPO
What Praveer has learned working alongside Dylan Field for nine years
Why Figma intentionally cut its 90% gross margin to invest in AI

References:

Adobe: https://www.adobe.com
Brendan Mulligan: https://www.linkedin.com/in/brendanmulligan
Cloudflare: https://www.cloudflare.com
Dropbox: https://www.dropbox.com
Dylan Field: https://www.linkedin.com/in/dylanfield/
Fidelity: https://www.fidelity.com
Figma: https://www.figma.com
GIC: https://www.gic.com.sg
NerdWallet: https://www.nerdwallet.com
Shaunt Voskanian: https://www.linkedin.com/in/shauntvoskanian/

Where to find Praveer:

LinkedIn: https://www.linkedin.com/in/praveer-melwani

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:

00:00 Introduction

02:13 From banking to Dropbox to Figma

04:14 The phase shift when Figma's COO left

05:36 Hiring leaders in functions you don't understand

07:18 Selling the exec team on AI consumption pricing

09:48 Using Claude Code to learn new things as CFO

11:36 Building an internal board of peer CFOs

13:52 Inside Figma's CFO job description

16:38 What separates good CFOs from world-class CFOs

18:42 Capital allocation and risk in a post-ChatGPT world

21:45 Why Praveer wants to take more bets

24:32 How AI is materially changing the CFO role

25:36 The nine-year working relationship with Dylan Field

29:12 How deeply in the details should a CFO be?

31:47 What Dropbox taught Praveer about building strong teams

33:24 Praveer’s first-principles test for hiring VPs

38:47 Why Figma acted like a public company in 2022

Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero) Apr 30, 2026

Show notes

In the latest episode of Executive Function, Brett is joined by Diya Jolly, Chief Product and Technology Officer at Xero. Before Xero, Diya was CPT at Okta and led YouTube's advertising monetization products at Google. In this conversation, she unpacks her three-bucket framework for delegating decisions, why the most important part of a CPO’s role is to drive team-wide ambition, and why the best executives need to spend half their time thinking, not doing.

In today's episode, we discuss:

Why a CPO's number one job is raising their team’s ambition, not shipping features
How to demand the best from your team without creating a fear-based culture
Why organizational politics is actually an incentives problem
How Diya is “militant” with her calendar to carve out dedicated thinking time
Why you should avoid chasing titles in your career - and what to chase instead

References:

Google: https://www.google.com
Melio: https://meliopayments.com
Okta: https://www.okta.com
Sukhinder Singh Cassidy: https://www.linkedin.com/in/sukhinders/
Xero: https://www.xero.com

Where to find Diya:

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

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:

00:12 How an excellent CPO makes an impact on the business

02:01 How the CPO role shifts under founders vs hired CEOs

03:38 Influencing a founder without going deferential

07:37 How adding value to customers is always a net positive

08:45 Why roadmaps need more risk in the AI era

12:30 How to shelter innovation teams from the existing system

15:12 What's different about being a great CPO in 2026

17:34 How AI has changed the concept of an app

18:28 It’s essential for CPOs to fly at a low altitude

20:34 How misaligned incentives cause organizational politics

25:13 Being demanding without creating a fear-based culture

28:10 Why raising ambition is a CPO's number one job

31:39 The boss who taught Diya to keep raising the bar

32:43 The hardest part of being a CPO

35:28 The three buckets Diya uses to delegate

36:30 How Diya protects deep-work time on her calendar

42:45 Xero’s game-changing early bet on AI insights

44:58 How far into the future should CPOs plan for?

47:14 What it takes to be an excellent C-suite member

48:53 Why ambitious PMs should chase impact, not titles

50:28 The four bottlenecks that stall career growth

Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis) Apr 21, 2026

Show notes

In this episode of In Depth, First Round Partner Josh Kopelman sits down with Shachar Hirshberg and Dan Shiebler, co-founders of Artemis, the AI-native security platform that just emerged from stealth with $70M in combined seed and Series A funding. Shachar and Dan unpack how they built a 30-person team in seven months, why AI-native companies are outperforming their AI-enabled counterparts, and why they plan to stay on a texting basis with every customer, even at scale.

In today's episode, we discuss: