Ryan Glasgow, CEO and founder of Sprig, and Kevin Mandich, Head of Machine Learning at Sprig, discuss key lessons from Sprig's founding story, product development in the pre vs. post-LLM world, how to overcome AI skepticism, evaluating new models, the importance of ML engineers, Sprig's 'AI Squad' team structure, and upskilling team members on AI.

Saumil Mehta, GM of Square’s flagship point-of-sale business, discusses the principles of effective org design, signs your company needs a re-org, Square’s GM-led org design, and lessons on incentive-design, pricing, planning, and decision-making at scale. He also shares the step-by-step process behind a recent re-org at Square and 5 lessons from Alyssa Henry, CEO at Square.

Guest Kellan Elliott-McCrea, Head of Engineering at Adobe, previously VPE at Dropbox and CTO at Etsy, discusses the changes in software engineering, the future of AI, achieving alignment, enabling engineering productivity, culture lessons from Adobe, Dropbox, and Flickr, tips for better management, and rituals for building business literacy throughout an organization.

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: https://www.dock.us/ Lattice: https://lattice.com/ Jack Altman: https://www.linkedin.com/in/jackealtman J Zac Stein: https://www.linkedin.com/in/jzacstein Where to find Alex Kracov:Twitter: https://twitter.com/kracov/LinkedIn: https://www.linkedin.com/in/alexkracovWebsite: https://www.kracov.co/Where to find Brett Berson:Twitter: https://twitter.com/brettbersonLinkedIn: https://www.linkedin.com/in/brett-berson-9986094/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

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: https://www.loom.com/ Navan (formerly TripActions): https://navan.com/ Teach for America: https://www.teachforamerica.org/ Uber: https://www.uber.com/ Where to find Anique Drumright:Twitter: https://twitter.com/aniquedLinkedIn: https://www.linkedin.com/in/anique-drumright-53978a1aWhere to find Brett Berson:Twitter: https://twitter.com/brettbersonLinkedIn: https://www.linkedin.com/in/brett-berson-9986094/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

Noah Desai Weiss is the Chief Product Officer of Slack, and has an accomplished track record inside and outside of the company. He started Slack’s Search, Learning, and Intelligence division, led the Self-Service (SMB) Business, and led the Expansion and Virtual HQ product areas (responsible for Huddles, Clips, and more). Before joining Slack, Noah was the SVP of Product Management at Foursquare (raised over $390m), and was a Product Manager at Google.In today's episode, we discuss: When to use intuition vs data to drive decisions The most underrated traits in a remote work environment How Slack runs product reviews The importance of a team’s “vibe” Managing pace vs accuracy in decision-making Balancing "big swings" with incremental improvements Advice on product-led vs sales-led growth Curious to learn more about Slack? You can try Slack Pro and get 50% off using this link.Referenced:Creative Selection - Inside Apple's Design Process During the Golden Age of Steve Jobs: https://www.amazon.com/Creative-Selection-Inside-Apples-Process/dp/1250194466Salesforce acquires Slack: https://slack.com/blog/news/salesforce-completes-acquisition-of-slackThinking in Bets - Making Smarter Decisions When You Don't Have All the Facts: https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions-ebook/dp/B074DG9LQFWhere to find Noah Weiss:Twitter: https://twitter.com/noah_weissLinkedIn: https://www.linkedin.com/in/noahw/Where to find Brett Berson:Twitter: https://twitter.com/brettbersonLinkedIn: https://www.linkedin.com/in/brett-berson-9986094/Timestamps:[2:46] Not all decisions should be data-driven[3:46] When to use data vs intuition to drive decisions[9:15] Taste and judgment are learnable[11:47] How Slack scales intuition across their product org[14:58] Challenges of intuition-led product building[16:43] Matching people to data vs intuition-driven work[19:19] underrated qualities for remote workers[21:34] What's special about Slack's approach to product?[23:33] Which products should focus on end-users versus executives[26:38] What Slack learns from Salesforce[31:44] Pricing lessons from Salesforce and Marc Andreessen[34:10] How Slack runs product reviews[37:02] What creates good vibes in a product team[40:17] Managing pace vs accuracy in decision-making[46:29] Rituals for good decision-making[50:20] Balancing "big swings" with incremental improvements[55:30] Slack's biggest philosophy change[60:05] Slack's humility and why it matters[61:43] Advice for thinking about product-led vs sales-led growth[01:08:14] How to build product with a product-focussed founder[01:12:46] People who made an outsized impact on Noah's career

Jack Altman is the co-founder and CEO of Lattice, a people success platform for building engaged, high-performing teams. Lattice has raised over $330M, and was last valued at $3B. He is an expert in building company culture, and wrote a book on the topic, titled: “People Strategy”.In today's episode, we discuss: The importance of self-awareness and how to develop it The value of difficult conversations and advice for having them Common mistakes when scaling a company How to approach firing decisions and the associated internal optics How to think about low-performing but “well-liked” employees How to get drastically more out of your team members Adapting to the challenging new economic environment Referenced:Jack’s book: https://www.amazon.com/People-Strategy-Culture-Competitive-Advantage/dp/1119717043Jack’s company, Lattice: https://lattice.com/First Round Capital's Newsletter: https://review.firstround.com/newsletterWhere to find Jack Altman:LinkedIn: https://www.linkedin.com/in/jackealtmanTwitter: https://twitter.com/jaltmaWhere to find Brett Berson:Twitter: https://twitter.com/brettbersonLinkedIn: https://www.linkedin.com/in/brett-berson-9986094/In this episode, we cover:(2:40) Founders must continually grow with their company(7:23) How to identify hiring errors vs management errors(9:46) Managing the tension of delegation vs control(11:51) How to cultivate self-awareness(14:59) The one thing founders should never give up(17:22) How to build a product org(19:06) Hot take on micro-management(21:05) The importance of context setting as CEO(22:09) What founder transparency actually means(23:43) Examples of “context setting” as a leader(26:09) The value of uncomfortable conversations(27:16) How to have uncomfortable conversations(28:30) Founders must own their most difficult decisions(31:48) Optimizing speed vs accuracy in decision-making(33:50) The hidden biases in group discussions(35:05) When Jack experimented with removing himself from all meetings(37:48) The most unusual element of Jack’s leadership approach(38:34) 4 pieces of advice for CEOs(41:20) How to talk to customers(42:59) The many sources of learning for CEOs(46:45) Instructive framework for maximizing employee performance(49:56) When long-time employees don’t scale with the company(55:07) How to think about low-performing but “well-liked” employees(58:19) Identifying team members that “aren’t a fit”(59:57) Should you tell people why someone was let go?(62:42) Managing in the challenging new economic environment(68:18) Aligning an employee’s career goals with company goals(74:27) You're probably underestimating your team's potential

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: https://review.firstround.com/newsletter The 'Wins Above Replacement' metaphor: https://en.as.com/mlb/wins-above-replacement-war-baseball-statistic-explained-n/ Zero to One by Peter Thiel & Blake Masters: https://www.amazon.com.au/Zero-One-Notes-Startups-Future/dp/0804139296 Companies Referenced: Atlassian: https://www.atlassian.com/ Cash App: https://cash.app/ Figma: https://www.figma.com/ First Round Capital: https://firstround.com/ Lattice: https://lattice.com/ Notion: https://www.notion.so/ Paypal: https://www.paypal.com/ Stripe: https://stripe.com/ Watershed: https://watershed.com/ People Referenced: Jack Dorsey: https://twitter.com/jack Patrick Collison: https://twitter.com/patrickc Shreyas Doshi: https://twitter.com/shreyas Where to find Tara Seshan:LinkedIn: https://www.linkedin.com/in/tarstarr/Twitter: https://twitter.com/tarstarrWhere to find Brett Berson:Twitter: https://twitter.com/brettberson?lang=enLinkedIn: https://www.linkedin.com/in/brett-berson-9986094/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

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 review@firstround.com or follow us on Twitter @firstround and @brettberson.  

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 review@firstround.com or follow us on Twitter @firstround and @brettberson.