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 tea...
What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Head of Global Product at Stripe)
Eeke de Milliano is the Head of Global Product at Stripe, helping drive innovation and success in the company's product line. Before this role, she was Head of Product at Retool and co-founded Constellate. Eeke previously spent 6 years as Product Lead at Stripe, working with the company during their hyper-growth era.
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In today’s episode, we discuss:
Eeke’s wealth of experience as an executive leader
The challenges companies face when hiring new executives
Common hiring red flags and pitfalls
Practical advice for measuring success
Why learning your strengths is an underrated piece of the process
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Referenced:
ASML: https://www.asml.com/en
Claire Hughes Johnson: https://www.linkedin.com/in/claire-hughes-johnson-7058/
Constellate: https://constellate.team/
John Collison: https://www.linkedin.com/in/johnbcollison/
Mike Maples Jr.: https://www.linkedin.com/in/maples/
Patrick Collison: https://www.linkedin.com/in/patrickcollison/
Retool: https://retool.com/
Stripe: https://stripe.com/
Will Gaybrik: https://www.linkedin.com/in/william-gaybrick-5730347/
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Where to find Eeke:
LinkedIn: https://www.linkedin.com/in/eeke-de-milliano-3b05a629/
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Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
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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
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Timestamps:
(00:00) Should you ‘buy or build’ a leader
(03:45) Why do executive hires fail so often?
(09:35) Why the stakes are so high for leadership hires
(12:26) The hardest document Eeke ever wrote
(14:06) Two red flags in a new hire
(17:27) An example of an outstanding leader
(21:40) What creates dysfunctional exec relationships
(22:38) The three steps towards hiring successful leaders
(30:30) What you should know about outside hires
(33:12) Eeke’s advice for easing leadership transitions
(42:06) How to notice success patterns
(47:21) Why high-functioning executive teams are like parents
(52:02) The most surprising lesson from Eeke’s first stint at Stripe
(55:11) The leadership data Eeke wishes we had
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59:59
Inside Guideline's mission to modernize 401(k)s | Building from first principles, finding strategic edges, and rewiring retirement | Kevin Busque (Co-founder and CEO)
Kevin Busque is the co-founder and CEO of Guideline, a 401(k) management company revolutionizing the retirement space for small and medium-sized businesses. Prior to Guideline, Kevin co-founded Taskrabbit, where he encountered firsthand the complexity and low participation rates of traditional 401(k) plans—largely due to confusing fee structures.
After launching Guideline to address those problems head-on, the company has seen remarkable growth, hitting $120 million in ARR by June 2024. In this conversation, Kevin shares pivotal moments that shaped Guideline’s trajectory, including a strategic partnership with Gusto. He also explains how his “Do the hard thing first” mindset helped the team build an industry-leading platform and disrupt an entrenched market.
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Referenced:
ADP: https://www.adp.com/
Aydin Senkut: https://www.linkedin.com/in/aydins/
CalSavers: https://www.calsavers.com/
DoorDash: https://www.doordash.com/
Fidelity: https://www.fidelity.com/
Guideline: https://www.guideline.com/
Gusto: https://gusto.com/
Intuit: https://www.intuit.com/
Jeremy Caballero: https://www.linkedin.com/in/jeremycaballero/
John Zimmer: https://www.linkedin.com/in/johnzimmer11/
Josh Reeves: https://www.linkedin.com/in/joshuareeves/
Mike Nelson: https://www.linkedin.com/in/mnelsonio/
Leah Solivan: https://www.linkedin.com/in/leahsolivan/
Paychex: https://www.paychex.com/
Plaid: https://plaid.com/
Taskrabbit: https://www.taskrabbit.com/
Tomer London: https://www.linkedin.com/in/tomerlondon/
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Where to find Kevin:
LinkedIn: https://www.linkedin.com/in/kevinbusque/
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Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
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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
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Timestamps:
(00:00) Teaser: “I don’t believe in stealth mode”
(02:51) Inspiration behind Guideline
(07:56) Lessons from a year’s research before Guideline
(10:44) Identifying market pull for Guideline
(14:28) What Kevin learnt before shipping their first product
(19:10) How Guideline set their fees up
(27:51) The surprising range of Guideline’s early customers
(31:48) Kevin’s insights from the Gusto integration
(39:48) Guideline’s first year
(44:44) Working with Plaid as Guideline’s first customer
(53:28) Guideline’s auto-enrollment feature
(57:53) Lucky 8: Kevin’s unexpected pricing strategy
(62:04) Franchise opportunities
(64:49) Kevin’s reflections on Taskrabbit
(71:36) Will Guideline ever go multi-product?
(72:37) Kevin’s take on product-market fit
(73:30) Guideline’s compounding advantage
(78:51) The challenges faced by introverted leaders
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1:24:49
Inside Braze’s blitz to $500M in CARR | Building broad, going global, and outfoxing the competition | Bill Magnuson (Co-founder & CEO) and Kevin Wang (CPO)
Bill Magnuson is the co-founder and CEO at Braze, along with Kevin Wang, who joined as employee #8 and serves as the CPO. The two MIT graduates have built Braze into a publicly listed customer engagement platform with a $4.4B market cap. In 2023, Braze surpassed $500M in CARR, and serves over 2,200 customers worldwide. Before Braze, Bill spent time at Bridgewater Associates. Kevin’s academic background is in brain & cognitive sciences, and prior to joining Braze he worked at Accenture and Brewgene.
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In today’s episode, we discuss:
The Braze founders’ early insights into the mobile revolution
How a TechCrunch Hackathon sparked Braze's creation
The journey from 1,000 beta signups to 2,200+ paying customers
Breaking traditional lean startup rules
Navigating early fundraising challenges
Finding product market fit by “fishing in every pond”
Approaching competition strategically like a boxer
Much more
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Referenced:
Accenture: https://www.accenture.com/
Appboy: https://www.braze.com/resources/articles/appboy-social-network-for-mobile-apps
Bipul Sinha: https://www.linkedin.com/in/bipulsinha/
Braze: https://www.braze.com/
Bridgewater Associates: https://www.bridgewater.com/
Jon Hyman: https://www.linkedin.com/in/jon-hyman/
Mark Ghermezian: https://x.com/markgher
MIT: https://www.mit.edu/
Rubrik: https://www.rubrik.com/
WeWork: https://www.wework.com/
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Where to find Bill:
LinkedIn: https://www.linkedin.com/in/billmagnuson/
Twitter/X: https://x.com/billmag
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Where to find Kevin:
LinkedIn: https://www.linkedin.com/in/kevin-wang-96131916/
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Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
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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
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Timestamps:
(00:00) Teaser: Finding “terminal value” product market fit
(00:24) Introduction
(02:34) Bill's insights into the mobile revolution
(04:43) Lessons from Bridgewater Associates
(09:12) First principles thinking in action at Braze
(14:14) Meeting co-founders at an NYC Hackathon
(24:35) Braze’s scrappy scaling
(33:37) Early product development
(39:37) From 1,000 beta signups to 2,200+ paying customers
(43:51) Braze’s fundraising struggles
(47:01) Breaking the rules of a lean startup
(53:02) Riding the mobile wave to success
(60:02) Building a global customer base
(64:04) The never-ending quest for PMF
(70:29) 3 things every founder needs to know
(73:56) Navigating competition like a boxer
(79:03) When scale helps or hurts
(80:32) 1 thing they’ve learned from each other
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1:23:07
Inside Clay's unconventional path to $1.25B: Rethinking GTM, pricing, and enterprise sales | Varun Anand (Co-founder and Head of Operations)
Varun Anand is the co-founder and Head of Operations at Clay, a GTM development environment that combines data and AI to help over 5000 companies power everything from CRM enrichment to highly targeted outreach campaigns. Clay recently announced their Series B expansion, raising $40M at a $1.25B valuation. Before Clay, Varun was the Director of Operations at Newfront and the Head of Expansion at Candid. Varun also spent four years working on Hillary Clinton’s presidential campaign.
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In today’s episode, we discuss:
Clay’s unconventional GTM machine
3 changes that unlocked Clay's upmarket motion
Layering enterprise customers on top of PLG
Scrappy sales tactics: WhatsApp groups, Reddit threads, and reverse demos
Thinking long-term about brand and content
Building an elite team of people who are “technical enough”
Clay’s contrarian take on compensation
Much more
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Referenced:
Anthropic: https://www.anthropic.com/
Clay: https://www.clay.com/
Clay’s Series B expansion: https://www.clay.com/blog/series-b-expansion
Eric Nowoslawski: https://www.linkedin.com/in/outboundphd/
Figma: https://www.figma.com/
Jesse Ouellette: https://www.linkedin.com/in/jesseoue/
Kareem Amin: https://www.linkedin.com/in/kareemamin/
Nick Merrill: https://www.linkedin.com/in/nick-merrill-64562310/
Notion: https://www.notion.com/
Oyster: https://www.oysterhr.com/
Pave: https://www.pave.com/
Rippling: https://www.rippling.com/
Snowflake: https://www.snowflake.com/
Verkada: https://www.verkada.com/
Webflow: https://webflow.com/
Yash Tekriwal: https://www.linkedin.com/in/yashtekriwal/
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Where to find Varun:
LinkedIn: https://www.linkedin.com/in/vaanand/
Twitter/X: https://x.com/vxanand
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Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
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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
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Timestamps:
(00:00) Teaser + Introduction
(03:13) Turning traditional GTM on its head
(05:37) How Clay hustled for its first customers: Reddit threads & WhatsApp groups
(08:53) Unpacking Clay's credit-based pricing
(14:29) Building Clay's self-serve engine
(16:54) Why Clay rejected the usage-based model
(19:04) Clay’s big bet on content
(23:59) How "reverse demos" win enterprise deals
(27:49) 3 changes that unlocked Clay's upmarket motion
(36:59) How to build trust with enterprise buyers
(38:49) Applying the land and expand model
(40:40) Hiring people who are “technical enough”
(46:33) Inside Clay’s hands-on interviewing process
(48:15) Why Clay invested in brand from day-one
(50:21) Clay’s contrarian take on compensation
(58:35) The person who shaped Varun’s career
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1:02:31
Building a 4 billion dollar data platform: Inside dbt Labs’ unconventional path | Tristan Handy (Co-founder and CEO, ex-RJMetrics, Squarespace)
Tristan Handy is the Founder and CEO at dbt Labs, a cloud-based data management platform that has raised over $400M to date, and was last valued at $4.2B in 2022. Dbt Labs has grown from just three companies using its free tool in 2016 to an ecosystem of 30,000+ enterprise users. Before founding dbt Labs, Tristan was the VP of Marketing at RJMetrics and the Director of Operations at Squarespace.
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In today’s episode, we discuss:
Dbt’s explosive growth
The strategic pivot from consulting to a software company
Unexpected strategies for building a tech category from scratch
The critical moment: Why and when dbt Labs sought venture funding
How to drive commercial adoption after open-sourcing
Two things every founder CEO should do
Much more
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Referenced:
Amazon Redshift: https://aws.amazon.com/redshift/
Bob Moore: https://www.linkedin.com/in/robertjmoore/
Crossbeam: https://www.crossbeam.com/
dbt Labs: https://www.getdbt.com/
Drew Banin: https://www.linkedin.com/in/drewbanin/
Jerry Colonna: https://www.reboot.io/team/jerry-colonna/
RJMetrics: https://en.wikipedia.org/wiki/RJMetrics
SeatGeek: https://seatgeek.com/
Steve Ritter: https://www.linkedin.com/in/steve-ritter-69495210/
Squarespace: https://www.squarespace.com/
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Where to find Tristan:
LinkedIn: https://www.linkedin.com/in/tristanhandy/
Twitter/X: https://x.com/jthandy
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Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
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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
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Timestamps:
(00:00) Introduction
(02:56) The critical oversight in data analysis
(05:41) Becoming an “accidental founder”
(07:04) Inside the unique decision to start a consultancy
(08:17) The game-changing principle behind dbt Labs’ rapid growth
(11:20) Finding dbt Labs’ first customers
(15:52) Consulting's hidden scalability
(17:25) How dbt Labs created a new category
(21:03) The anti-demo strategy
(23:59) Community hacking: the Slack group that changed everything
(26:00) The open source philosophy
(27:39) When growth went exponential
(28:49) How consulting engagements shaped the roadmap
(30:02) Fundraising only when “things started to break”
(32:40) Consultancy superpowers: the hidden advantages
(34:04) Pivoting from consulting to software
(40:00) Key monetization strategies
(48:56) Why “begrudging” CEOs can be successful
(51:02) Advice for finding PMF: “It’s not a playbook”
(51:59) Lowering your standards is a hack
(53:30) Navigating emotional overwhelm
(54:25) Every CEO needs a coach
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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