All Summaries for In Depth

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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

AI Hot Takes and Unusual Twitter Fundraising Strategies with Dan Siroker (Rewind AI)
Dan Siroker is the co-founder and CEO at Rewind AI, a personalized AI powered by everything you’ve seen, said, or heard. Dan launched Rewind to an emphatic response on Twitter, and used a public pitch video to fundraise at a $350m valuation. Prior to starting Rewind, Dan co-founded Optimizely, which reached $120m ARR before being acquired by Episerver, a content management company. Dan was also the Director of Analytics for Obama’s first presidential campaign. In today’s episode, we discuss: Rewind’s journey to Product Market Fit Lessons from Optimizely and being a second time founder Dan’s one-of-a-kind Twitter fundraising strategy Dan’s hot takes on the future of AI Where to build in AI, and what makes a “wrapper” thin versus thick Referenced: Apple’s Silicon: ChatGPT: Dan publicly sharing his own 360 performance reviews: Dan’s public Twitter fundraise: Dan’s Rewind demo tweet: Google Glass: Google Wave: Maslow's Hierarchy of Needs: Optimizely: Paul Graham: Rahul Vohra’s framework for measuring and optimizing Product Market Fit: Rewind AI: Scribe (which morphed into Rewind): The Mom Test book: Where to find Dan Siroker: Twitter: LinkedIn: Personal website: Blog: Where to find Todd Jackson: Twitter: LinkedIn: Where to find First Round Capital: Website: First Round Review: Twitter: Youtube: This podcast on all platforms: Timestamps (02:25) Rewind's origin story (04:04) How Rewind works (07:24) Managing scope when building Rewind (13:47) How Dan thought about early user feedback (17:08) Rewind's cultural mantra for shipping and validating fast (18:35) Product positioning as a category creator (20:39) Lessons from being a 2nd time founder (26:11) Cultural values at Optimizely and Rewind (28:22) How Dan defines and operationalizes Product Market Fit (32:06) Audience segmentation (34:32) Measuring Product Market Fit (36:23) Dan's take on the current AI hype (38:11) What makes a "wrapper" thin vs thick? (39:50) Where founders should and shouldn't build within the AI ecosystem (43:22) Trends in consumer expectations around data privacy (46:59) What AI might look like 10 years from now (51:09) Dan's one-of-a-kind public Twitter fundraise (59:40) What's next for Rewind? (61:26) The influence of Paul Graham (62:47) Dan's #1 piece of advice (64:23) Dan's #1 book recommendation
Thu, September 14, 2023
A guide to building product in a post-LLM world | Ryan Glasgow and Kevin Mandich from Sprig
Sprig is an AI-powered user insights platform that has raised over $88m. Today’s discussion features two key individuals in Sprig’s journey so far: Ryan Glasgow, Sprig’s CEO and founder; and Kevin Mandich, Sprig’s Head of Machine Learning. Before Sprig, Ryan was an early PM at GraphScience, Vurb, and Weeby (all of which were acquired), and Kevin was an ML Engineer at Incubit, and a Post-Doctoral Researcher at UC San Diego. In today’s episode, we discuss: Key lessons from the Sprig founding story Product development in the pre vs. post-LLM world How to overcome AI skepticism How to evaluate new models and how to know when to switch Why you need an ML engineer Sprig’s “AI Squad” team structure How Sprig upskills all team members on AI Referenced: Auto-GPT: Chat GPT: Google’s BERT model: Jira: Jobs to Be Done Framework: Langchain: Sprig: Where to find Ryan Glasgow: Twitter: LinkedIn: Where to find Kevin Mandich: Twitter: LinkedIn: Where to find Brett Berson: Twitter: LinkedIn: Where to find First Round Capital: Website: First Round Review: Twitter: Youtube: This podcast on all platforms: Timestamps (02:50) Intro (04:57) What attracted Kevin to Sprig (05:53) Kevin's background before Sprig (07:56) How Ryan gained conviction about Kevin (09:55) Key technical challenges and how they solved them (18:46) How to overcome AI skepticism (21:47) The early difficulties of building an ML-enabled product (25:06) Evaluating new models and knowing when to switch (35:09) Using Chat GPT (37:23) Product development in the pre vs. post-LLM world (39:53) The impact of AI hype on Sprig's product development (45:36) Balancing AI automation with user-psychology (48:47) Do recent LLMs reduce Sprig's competitive advantage? (51:00) The importance of "selling the vision" to customers (54:40) How Sprig structures teams (57:25) How Sprig upskills all team members on AI (60:25) 3 key tips for companies trying to navigate AI (66:05) Major limitations with LLMs right now (70:27) The future of AI and the future of Sprig
Thu, September 7, 2023
An org-design masterclass from a Square GM | Saumil Mehta
Saumil Mehta is the GM of Square’s flagship point-of-sale business, as well as CRM, Square Staff, and Square Online. Before Square, Saumil was the Founder and CEO of LocBox, which raised over $5.1M, and helped offline/local businesses run multi-channel marketing campaigns, all from one universal dashboard. Saumil has now been a leader at Square for 8+ years, and has overseen many complex re-orgs. These experiences have shaped Saumil into an all-round org-design expert. In today’s episode we discuss: The principles of effective org design Signs your company needs a re-org Square’s GM-led org design, and the reasoning behind it Lessons on incentive-design, pricing, planning, and decision-making at scale The step-by-step process behind a recent re-org at Square 5 lessons from Alyssa Henry, CEO at Square Referenced: Alyssa Henry, CEO at Square: Saumil’s 6 key principles for effective re-orgs: Saumil’s blog post about “Building Better Products with Escalation”: Square: Where to find Saumil Mehta: Twitter: Linkedin: Blog: Where to find Brett Berson: Twitter: LinkedIn: Where to find First Round Capital: Website: First Round Review: Twitter: Youtube: This podcast on all platforms: Timestamps [00:02:22] Intro [00:04:20] The principles of effective org design [00:04:32] #1 Align on goals [00:06:14] #2 Separate design considerations from human considerations [00:08:03] #3 Define clear reasons each team exists [00:09:21] #4 Design for durability [00:09:49] #5 Be very intentional with comms [00:10:14] Some stories behind the principles [00:13:55] How to know when you need a re-org [00:16:14] Managing inevitable tradeoffs in org design [00:20:45] Square's "GM-led" structure [00:23:05] Why Square centralized GTM [00:25:39] Managing pricing and packaging across a complex org [00:29:28] Examples of Square's written principles [00:31:19] How Square determines what each GM owns [00:38:35] Collaboration across GMs and products [00:40:32] Key lessons on planning and decision-making at scale [00:43:15] Designing incentives across a massive org [00:49:03] Two reasons GM structures go wrong [00:52:03] 6 Step re-org walkthrough [00:52:37] Step 1: Triggering the re-org [00:53:59] Step 2: Sketching a proposed org design [00:56:17] Step 3: Checking against key criteria [00:59:22] Step 4: Finalizing approach with leadership [01:00:04] Step 5: Planning comms [01:01:58] Step 6: Executing comms [01:04:20] Signals a re-org worked vs failed [01:07:13] 5 lessons from Alyssa Henry, CEO at Square
Thu, August 31, 2023
How to supercharge your engineering org | Kellan Elliott-McCrea (Adobe, Dropbox)
Kellan Elliott-McCrea is a Head of Engineering at Adobe, overseeing, a newly acquired video review and collaboration platform. He is known for his experience and expertise as an engineering leader. He was previously a VPE at Dropbox, and CTO at Etsy where he built and led a team of 300 people, from tech and platform reboot through to IPO. Kellan also built and scaled teams at Flickr, and has a coaching and advising practice for companies looking to supercharge their engineering teams.  In today's episode, we discuss: How software engineering has changed in the last 10-15 years The future of software engineering, and the impact of AI The importance of alignment and tactics for achieving it How to think about and enable engineering productivity Lessons on culture from Adobe, Dropbox, and Flickr Concrete tips for being a better manager Rituals for building business literacy throughout an org Referenced: Adobe: Dropbox: Flickr: Frame: How Complex Systems Fail, by Richard I. Cook, MD: How Etsy Grew their Number of Female Engineers by Almost 500% in One Year Where to find Kellan Elliott-McCrea: Twitter: LinkedIn: Website: Personal blog: Where to find Brett Berson: Twitter: LinkedIn: Timestamps: [00:02:58] Engineering orgs now vs 15 years ago [00:05:57] Why engineering teams are bigger despite better tools [00:10:45] How to think about engineering productivity [00:15:50] Questioning common compensation models [00:19:39] Slow teams are misaligned teams [00:23:56] How to achieve alignment in engineering teams [00:29:12] How to co-ordinate better across teams [00:35:23] Why so few companies successfully go multi-product [00:38:02] Which elements of successful orgs replicate? [00:41:53] How to approach a new org system at a new company [00:45:48] The value of information sharing and coaching [00:48:55] Best practices for communicating with and across teams [00:51:05] How to approach disagreements [00:54:27] What high-quality engineering management looks like [00:58:37] How to increase organizational capacity [00:63:20] Tactics and rituals for enabling effective teams [00:66:05] How to build business literacy [00:68:30] Kellan's biggest inspirations
Thu, August 17, 2023
The zero to one B2B marketing playbook | Alex Kracov (Lattice, Dock)
Alex Kracov is the CEO and Co-Founder at Dock, and the former VP of Marketing at Lattice. Alex joined Lattice as the first marketer and third employee, and he helped to grow the business from seed to 1850+ customers. Prior to Lattice, Alex was a consultant at Blue State Digital — the team that elected President Obama and orchestrated projects at Google. Since leaving Lattice in 2021, Alex co-founded Dock, a B2B platform that has streamlined the customer buying experience for clients like Loom, Origin, and Instabug.  In today's episode, we discuss: The 2023 SaaS marketing playbook How to start your early-stage B2B marketing How to prioritize resources across multiple marketing bets How to think about attribution Lattice’s unorthodox million-dollar marketing campaign How to hire for early marketing roles What makes a standout marketer Advice for building your first website Referenced: Dock: Lattice: Jack Altman: J Zac Stein: Where to find Alex Kracov: Twitter: LinkedIn: Website: Where to find Brett Berson: Twitter: LinkedIn: Timestamps: [00:00:00] Intro [00:02:45] The challenges and opportunities in early-stage B2B marketing [00:05:13] How to think about short-term versus long-term marketing goals [00:07:31] Allocating resources across marketing bets [00:09:13] Signs your marketing is working [00:11:20] The most underutilized marketing strategy [00:13:03] Creating your company’s first website [00:14:22] How Lattice formed its brand messaging and positioning [00:18:22] Dock’s innovative approach to marketing software [00:20:14] The first thing people should see on your website [00:23:10] Lattice’s most successful early-stage marketing tactics [00:28:05] Determining which marketing strategies are still relevant [00:30:25] Lattice’s unorthodox million-dollar marketing campaign [00:33:26] Why Alex had an outsized impact at Lattice [00:37:05] Lessons from his first marketing hires [00:39:41] When to scale your marketing team [00:40:55] Building an effective early-stage marketing team [00:42:30] A tough conversation with the CEO & Co-founder of Lattice [00:44:46] Achieving early-stage marketing alignment [00:46:20] Transitioning from employee to entrepreneur [00:49:19] Getting the most out of conferences [00:50:47] Selecting marketing channels in the early stages [00:52:44] Hiring marketers for experience versus potential [00:56:34] The 2023 SaaS marketing stack [00:58:19] Advice for Zero to One marketing [00:60:46] What successful B2B marketing looks like
Thu, August 10, 2023
Lessons from Loom on product strategy, organizational leadership, and cross-functional performance | Anique Drumright (COO at Loom)
Anique Drumright is the COO at Loom, a video communication tool for streamlining workflows. Loom has raised over $200M, and was last valued at $1.5B. Anique has a proven track record across product development, executive leadership, and building high-performing organizations. Before joining Loom, Anique was the VP of Product at TripActions, where she scaled the team over 8x globally, and she has also held multiple roles at Uber. In today's episode, we discuss: Best-practice product management How to achieve alignment at scale The importance of cross-functional performance Anique's unique approach to finding top organizational talent How to hire for roles outside your area of expertise Common fail cases with internal and external recruitment Tactics for effective interviews Referenced: Loom: Navan (formerly TripActions): Teach for America: Uber: Where to find Anique Drumright: Twitter: LinkedIn: Where to find Brett Berson: Twitter: LinkedIn: Timestamps: [00:03:00] The similarities and differences between PM and executive leadership roles [00:06:53] How Loom uses storytelling when launching a product [00:10:01] Managing cross-functional scope and performance [00:13:41] Goal-setting with functional leads [00:16:59] The importance and difficulty of organizational alignment [00:20:40] How Uber achieved alignment at scale [00:24:06] Rituals for staying aligned [00:25:23] Loom's winning one-on-one format [00:27:49] When and how to help functional leads [00:29:13] Hiring for roles outside your area of expertise [00:32:55] Go-to interview questions for prospective leaders [00:33:55] Changing the hiring process for roles outside your area of expertise [00:36:09] Common patterns of failed external hires [00:37:40] Common patterns of failed internal hires [00:39:05] Avoiding over-promotion in your organization [00:40:51] What inspires people in a company [00:45:40] Tactics for getting honest answers in interviews [00:47:12] Asking the right questions during reference checks [00:51:29] A month in the life of a COO [00:52:52] The importance of employee energy levels [00:54:53] Loom's leadership dynamics and why it works [00:57:30] People who had an outsized impact on Anique's career
Thu, August 3, 2023
Lessons from Stripe on adding new products - Assessing ideas, structuring teams, and tactics for product reviews | Tara Seshan (Watershed, Stripe)
Tara Seshan is the Head of Product at Watershed, a climate platform that companies use to measure, report, and reduce their carbon emissions. Before joining Watershed, Tara was Head of Product at Stripe throughout the launch of Stripe Billing and Stripe Treasury. As a Thiel Fellow and experienced multi-product builder, Tara brings a wealth of experience with 0-1 SaaS products. In today's episode, we discuss: The different types of multi-product strategies. Stories from Stripe’s multi-product success. How to allocate resources across new and existing products. How to structure teams for launching new products. The best personas for building new products and the hiring tactics for finding those people. Common challenges when going from single to multi-product. How to assess and prioritize new product ideas. How to measure success when launching new products. The 12 questions Tara asks for better product reviews. Tactics for collecting and interpreting user feedback. Referenced: First Round Capital's Newsletter: The 'Wins Above Replacement' metaphor: Zero to One by Peter Thiel & Blake Masters: Companies Referenced: Atlassian: Cash App: Figma: First Round Capital: Lattice: Notion: Paypal: Stripe: Watershed: People Referenced: Jack Dorsey: Patrick Collison: Shreyas Doshi: Where to find Tara Seshan: LinkedIn: Twitter: Where to find Brett Berson: Twitter: LinkedIn: In this episode, we cover: (0:00) Intro (3:55) How Stripe navigated the path from single to multi-product (6:00) How to allocate resources across a primary product and secondary bets (7:46) How to launch products using small teams (12:25) What makes a great early-stage product thinker (13:08) Key indicators for spotting early-stage product talent (16:33) A common fail-case when hiring for potential over experience (18:32) 5 interview questions to unearth hidden talent among product candidates (20:35) What Stripe got wrong when it first launched Billing (26:00) How Stripe adapted to new buyer profiles (28:50) Why new product teams should be treated like a startup within a company (30:35) The importance of “definite optimism” (31:44) How Watershed prioritizes new products in an early market (33:53) The methodical versus analytical approach to picking new products (40:08) Setting goals and evaluating new product bets (41:55) How Tara runs new-product reviews (42:10) “The Enterprise Rent-A-Car Story” and why it matters (43:56) The 12 questions Tara asks in product reviews (46:17) How to use product review questions pre-meeting (46:34) The rationale behind Tara’s 12 questions (48:13) How Tara re-focusses the questions when building products for net-new-customers (49:43) How to collect and leverage user feedback when building new products (51:58) Why product development must start with problem validation (53:52) Two people who had an outsized impact on how Tara thinks about product (54:50) Outro
Thu, June 22, 2023
How to design a high-impact growth org for a PLG startup — Webflow & Dropbox’s Melissa Tan
Our guest today is Melissa Tan, GM of Self-Service and Head of Growth at Webflow and formerly Head of Growth and Monetization for Dropbox Business. In today’s conversation, she unpacks the nuances between the two PLG businesses and how growth strategy changes for a more complex product like Webflow, including:  Designing and structuring a growth org The right way to tackle goal-setting How Webflow’s pricing and packaging has evolved How to calibrate pricing feedback You can email us questions directly at or follow us on Twitter @firstround and @brettberson.  
Thu, June 8, 2023
Why is the transition from IC Engineer to Manager so tricky (and how to get it right)? — Marcel Weekes, VP of Product Engineering at Figma
Our guest today is Marcel Weekes, VP of Product Engineering at Figma and former VP of Engineering at Slack. In today’s conversation, he unpacks why most startups get it wrong when they uplevel someone from IC engineer to eng manager and unfurls what stellar engineering management looks like at high-growth companies, including: Setting appropriate expectations and goals  Turbocharging the team’s effectiveness  Delivering high-impact feedback Going from a peer to a manager What leaders risk when they drag their heels on managing out low-performers You can email us questions directly at or follow us on Twitter @firstround and @brettberson.  
Thu, May 25, 2023
How to pull off the ‘zoom-in pivot,’ and other lessons in early-stage building with Luminai’s Kesava Kirupa Dinakaran
Todd Jackson is back on the mic to guest host another product-focused episode. This time, he chats with Kesava Kirupa Dinakaran, co-founder and CEO of Luminai, a B2B software tool that helps automate any manual process down to just one click.  Dinakaran’s personal and professional story is one that you do not want to miss. A former Rubik’s Cube champion and back-to-back Hackathon winner, Dinakaran’s foray into the world of building software products is anything but conventional. The founders stumbled on the idea for its automated “one-click” product started on accident, at a corporate hackathon.  But it’s exactly this unique worldview and introspective strategies that make Dinakaran’s advice on the path to finding product-market fit for Luminai so fascinating. Formerly called Digital Brain, Luminai is a Series A startup that’s raised nearly $20 million since its launch out of Y Combinator in 2020.  In this episode, we explore the psychology behind the sales process, why sales leaders should consider pitching straight to the CEO and Dinakaran’s decision to scrap hundreds of lines of written code to focus on building out their most beloved customer feature.  On the surface, Luminai may seem like just another B2B SaaS startup, but with nearly half the team comprising of former founders (seven of which are ex-YC founders), Luminai is a true example of how the co-founders can really make their mark on shaping their company on the path to product-market fit.  
Thu, May 18, 2023
The go-to-market guide for open-source companies — Douglas Hanna, COO Grafana Labs
Our guest today is Douglas Hanna, Chief Operating Officer at Grafana Labs.  Grafana Labs is an observability stack built around Grafana, a leading open-source technology for dashboards and visualization. Douglas is a seasoned revenue leader, previously leading operations and GTM strategy at Zendesk. At Grafana Labs, Douglas has been instrumental in scaling GTM at the open-source company — building up both team headcount and its revenue model.  In our conversation today, Douglas dives deep into the process of bringing products to market at an open-source company. We explore the different facets of building and scaling a revenue model at an open-source company. Douglas opens up the GTM playbook at Grafana Labs sharing:  When to commercialize a feature vs. switch to a hosted version of a product Tried and tested frameworks for pricing and packaging  How Grafana Labs thinks about what to put behind a paywall  How the GTM team was built over time.,  You can follow Douglas on Twitter at @douglashanna. You can email us questions directly at or follow us on Twitter @firstround and @brettberson.
Thu, May 11, 2023
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