Webflow

Jessica Fain is a product leader at Webflow and former Chief of Staff to the CPO at Slack, where she worked alongside April Underwood and many past podcast guests including Stewart Butterfield, Annie Pearl, Tamar Yehoshua, and Noah Weiss. She’s spent her career learning how executives actually make decisions—and why most people completely misunderstand the process. We discuss: 1. Why great ideas often don’t get buy-in 2. Why executive calendars are “like strobe lights” and why the first 30 seconds of a meeting matter so much 3. Why executives are usually optimizing for a global maximum while you are often optimizing locally 4. The best question Jessica uses when a leader says something that seems wrong: “That’s so interesting. What led you to believe that?” 5. Why you should go in to learn, not to convince 6. Why showing only one option is a mistake 7. Why AI will make influence more important, not less — Brought to you by: Omni—AI analytics your customers can trust Lovable—Build apps by simply chatting with AI Vanta—Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Jessica Fain: • LinkedIn: https://www.linkedin.com/in/jessica-fain-79b8989 — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jessica Fain (03:53) Why influence is the highest-leverage skill in product (04:47) Why great ideas fail without executive buy-in (06:00) How executives actually think (09:05) The fundamentals: context-setting, communication, and empathy (10:22) Stop pitching for approval—start co-creating with execs (12:59) Influence vs. politics (and why people get it wrong) (15:44) How to disagree with execs without losing trust (17:20) Going in to learn, not to convince (19:08) How to present ideas (26:05) The Minto-style approach and tailoring your communication to each exec (28:22) Why Jessica doesn’t like the question “What’s top of mind for you?” (30:24) Understanding incentives to unlock buy-in (32:10) Aligning product work with company strategy (35:10) Quick summary (37:31) Disarming the executive (40:49) Speed matters: why fast follow-up builds momentum (43:32) How to run high-impact meetings (the 60-second rule) (47:00) Why influencing execs is part of your job (49:15) Asking for more resources and thinking in 10x bets (52:23) What to do when your idea gets rejected (54:18) Clarifying information (56:50) How to build trust and make ideas stick (58:30) Shrinking big ideas into experiments (01:02:27) Common mistakes people make when influencing leaders (01:06:00) How to grow into your next role (01:09:32) How AI is changing influence and product work (01:17:55) Using AI to simulate exec feedback and improve pitches (01:21:15) Protecting our brains from overwhelm (01:22:44) Lightning round and final thoughts — Referenced: • Box: https://www.box.com • Slack: https://slack.com • Brightwheel: https://mybrightwheel.com • Webflow: https://webflow.com • April Underwood on LinkedIn: https://www.linkedin.com/in/aprilunderwood • Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua (Product at Glean, ex-Google and Slack): https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua • Atlassian: https://www.atlassian.com • Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO): https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid • Calendly: https://calendly.com • Glassdoor: https://www.glassdoor.co.in/index.htm • The 10 traits of great PMs, how AI will impact your product, and Slack’s product development process | Noah Weiss (Slack, Foursquare, Google): https://www.lennysnewsletter.com/p/the-10-traits-of-great-pms-how-ai • Ethan Eismann on X: https://x.com/eeismann • Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield • Ilan Frank on LinkedIn: https://www.linkedin.com/in/ilanfrank • Checkr: https://checkr.com • Ali Rayl on LinkedIn: https://www.linkedin.com/in/alirayl • Rachel Wolan on LinkedIn: https://www.linkedin.com/in/rachelwolan • How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan: https://www.lennysnewsletter.com/p/how-webflows-cpo-built-an-ai-chief • Barbara Minto’s website: https://www.barbaraminto.com • How Slack invests in big little details through Customer Love Sprints: https://slack.design/articles/sweating-the-small-stuff • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • The Enneagram Institute: https://www.enneagraminstitute.com/type-descriptions • The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD • Towel warmer: https://www.amazon.com/FLYHIT-Large-Towel-Warmer-Bathroom/dp/B0CB5K34L2 • Casa: https://getcasa.com • Jimi Hendrix: https://en.wikipedia.org/wiki/Jimi_Hendrix • Greek Theatre: https://en.wikipedia.org/wiki/Greek_Theatre_(Los_Angeles) — Recommended books: • Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927 • Homegoing: https://www.amazon.com/Homegoing-Yaa-Gyasi/dp/1101971061 • A History of Burning: https://www.amazon.com/History-Burning-Janika-Oza/dp/1538724243 • The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jessica Fain

Product Leader

Webflow

SaaStr 834: Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott, and Harry Stebbings, Founder of 20VC Discover how OpenAI's unique approach to B2B sales compensation is changing the game. In this interview with Harry Stebbings, Founder of 20VC, Maggie Hott, OpenAI GTM leadership, shares her experience at OpenAI, including why they don't pay sales commissions, and what B2B sales leaders can learn from this disruptive model. --------------------- This episode is Sponsored in part by HappyFox: Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr --------------------- Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year. But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

Maggie Hott

GTM Team Member

OpenAIWebflow

Harry Stebbings

Founder & General Partner

20VC

SaaStr 814: How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott Join Maggie Hott, GTM Leader at OpenAI, as she shares her extensive experience in building top-performing sales organizations at SaaStr. With a remarkable career history at Eventbrite, Slack, Webflow, and OpenAI, Maggie distills 15 years of insights into a tactical playbook for building and scaling sales teams. Learn key principles for hiring the right candidates, fostering thriving teams, maintaining customer obsession, and driving sustainable growth. Discover common pitfalls to avoid, the importance of storytelling, and how to align your teams for maximum impact. Whether you're a startup founder or a seasoned leader, these practical lessons will help you scale your sales team effectively. ------------------ Hey everybody, SaaStr AI's next stop takes us to London on December 2nd and 3rd! It's Christmas with SaaStr and 2,000 of the best SaaS and AI leaders. The biggest names will be there. The best networking. Early adopter tickets are selling faster than we expected. So don't wait. With only 5 months until the event, we expect this year's SaaStr London event to sell out to capacity. Use my code jason20pod for exclusive savings. Get your tickets now at podcast.saastrlondon.com or use code jason20pod at checkout. SaaStr AI London – where SaaS Meets AI in London. See you there. ------------------ This episode of the SaaStr podcast is sponsored by: get.tech The best .coms are taken or overpriced. So you settle on a workaround domain for your website. Don't compromise. Get a clean, sharp .tech domain that instantly says: this is a tech startup. Grab yours at get.tech/saastr or via domain registrars like GoDaddy.

Maggie Hott

GTM Team Member

OpenAIWebflow

SaaStr 788: Going Multi-Product in the Age of AI with Webflow, Rubrik, Zoom, and ProductBoard At SaaStr Annual's AI Summit, we asked product leaders from some of the fastest-growing SaaS companies to share their insights on navigating the AI revolution while scaling multi-product strategies. This panel of product leaders featured Anneka Gupta, CPO at Rubrik, Mahesh Ram, Head of AI Product at Zoom, Hubert Palan, CEO at Productboard, and Rachel Wolan, CPO at Webflow. -------------------------------------------------------------------------------------------- SaaStr hosts the largest SaaS community events on the planet. Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code JASON50 for an extra discount on our very best pricing. --------------------------------------------------------------------------------------------

Anneka Gupta

Chief Product Officer

Rubrik

Mahesh Ram

Head of AI Product

Zoom

Hubert Palan

Founder & CEO

Productboard

Rachel Wolan

CPO

WebflowDropbox

Jiaona "JZ" Zhang is the Chief Product Officer at Linktree, the world's leading link-in-bio platform empowering 45M+ creators, brands and SMBs. JZ joined Linktree from Webflow, where she served as SVP of Product. Before that, she spent four years at Airbnb where she built and led numerous teams on the host side. JZ's also held leadership roles at the likes of Wework, Dropbox and teaches at Stanford University and Reforge. In Today's Episode with Jiaona Zhang We Discuss: Entry into the World of Product How did JZ first fall in love with product? Why does JZ believe the best PMs have experience in the gaming industry? Does JZ think Linktree could be a $100BN business? How could Linktree become a $100BN business? Mastering Product Metrics Why does JZ think product is the most chameleon role? Where does product start & end? Why does JZ think every function should have tension with product? What is a KPI tree? How does JZ branch business & product metrics? When does JZ think startups should set up a metric infrastructure? What are the three levers of product? How does JZ determine which ones to trade off? How to Run Product: Planning, Strategy, & Rituals Why does JZ think planning should not exist? What are strategy and rituals? When should founders do either? What are JZ's three core rituals? What is the scorecard method? How do they help team transparency? What are product jams? When does it work? When does it not work? Product Career Advice When does JZ think founders hire a product person? What are the most common mistakes early stage founders make when hiring for product? Does JZ think domain expertise is important? What does she look for in product hires? What is JZ's advice to PMs who want to get promoted today? What is JZ's advice to young people who want to get into product?

Jiaona Zhang

SVP of Product

WebflowLinktree

SaaStr 707: The Where, When, and How of AI with Theory Ventures, Open AI, MotherDuck and Lamini Hear the latest insights on AI from leading VC Tomasz Tunguz of Theory Ventures Theory Ventures, joined by Jordan Tigani, Founder and CEO of Mother Duck Maggie Hott, GTM at OpenAI, and Sharon Zhou, Co-Founder and CEO of Lamini. Together they discuss the new architecture for building Software as a Service (SaaS) applications with data & machine learning at their core, moderated by Tomasz. The focus of the episode centers around the transformative role of data, which has become an integral part of the production stack. The speakers also delve into the implications of this shift and explore how leveraging data within the architecture empowers developers to create more robust, intelligent, and scalable SaaS solutions. -------------------------------------------------------------------------------------------- SaaStr hosts the largest SaaS community events on the planet. Join us in 2024 at: SaaStr Annual: Sept. 10-12 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Podcast listeners can grab a discount on tickets here: https://www.saastrannual2024.com/buy-tickets?promo=fave20 SaaStr Europa: June 5-6 in London. We'll be hosting the 5th SaaStr Europa in London for two days of content and networking. Join 3,000 SaaS and Cloud leaders. Podcast listeners can grab a discount on Europa tickets here: https://www.saastreuropa2024.com/buy-tickets?promo=fave200 -------------- This episode is sponsored by: Northwest Registered Agent When starting your business, it's important to use a service that will actually help you. Northwest Registered Agent is that service. They'll form your company fast, give you the documents you need to open a business bank account, and even provide you with mail scanning and a business address to keep your personal privacy intact. Visit https://www.northwestregisteredagent.com/saastr to get a 60 percent discount on your next LLC.

Tomasz Tunguz

Founder and Partner

Theory VenturesRedpoint Ventures

Jordan Tigani

Founder and CEO

MotherDuck

Maggie Hott

GTM Team Member

OpenAIWebflow

Sharon Zhou

VP of AI

AMDLamini

Vlad Magdalin is the Co-founder and CEO of Webflow, software that empowers designers to build websites without code. Vlad started the company with his co-founders Sergie Magdalin and Bryant Chou in 2013, and has since raised roughly $335 million supported by investors like Accel, Khosla Ventures, YCombinator, Capital G, and Eric Bahn. — — — — Brought to you by Mercury, the bank built for startups. Join more than 100,000 startups and venture capital firms on Mercury, the powerful and intuitive way for ambitious companies to bank.Sign-up now: https://bit.ly/46ImCuD Disclaimer: Mercury is a financial technology company, not a bank. Banking services are provided by Choice Financial Group and Evolve Bank & Trust; Members FDIC. — — — — Topics discussed include: • The history of web browsers, websites, and web design • Why websites are the ultimate economic enablers • How Webflow empowers anyone to design websites without code • Why website design is a gateway into programming • How the movement to CSS and web standards in the 2000’s and 2010’s created the opportunity for Webflow to build a product around responsive design • Moving to the US with his parents and five siblings as refugees from the USSR at nine years old • How losing half of their luggage and immigration documents in the move enabled his dad to buy the family’s first computer • The first website Vlad ever designed for a Brad Pitt movie • How his experience dropping out of a computer science degree to work in 3D animation at Pixar, then going back to school gave him the idea for Webflow • Failing to build Webflow three times between 2005 and 2008 • Why the spouses and partners of founders are the unsung heroes of startups • The moment he immediately quit his job and attempted Webflow for the fourth time • Burning three months of runway on a Kickstarter that never went live • Liquidating his retirement account, paying rent with credit cards, and selling and leasing back the family car’s to keep the business running • Vlad’s exuberant optimism that kept him going for 10 years • Failing to get into YC, and the crazy story behind getting accepted the second time • The trajectory-altering customer and fundraising advice they got from Paul Graham • The “Investing on Principle” contract they signed with Accel who led Webflow’s Series A • Why Vlad thinks every startup founder should operate with the assumption they’ll never be able to raise money again Referenced: • Inventing on Principle (Video): https://www.youtube.com/watch?v=PUv66718DII • Inventing on Principle (Transcript): https://jamesclear.com/great-speeches/inventing-on-principle-by-bret-victor • The Infinite Game: https://simonsinek.com/books/the-infinite-game/ Where to find Vlad: • Twitter: https://twitter.com/callmevlad • LinkedIn: https://www.linkedin.com/in/vladmagdalin Where to find Turner: • Newsletter: https://www.thespl.it • Twitter: https://twitter.com/TurnerNovak Production and distribution by: https://www.supermix.io Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Vlad Magdalin

Founder and CEO

Webflow

Vlad Madgalin is the co-founder and CEO of Webflow, a platform with 3.5 million users that helps people develop websites and web applications. He shares Webflow’s journey as an integral player in the no-code movement, as well as why he's grateful for the opportunity to start this company in the United States. Vlad tells many sincere stories including immigrating from Russia at age 9, starting Webflow four times before succeeding, going through a rollercoaster experience with YCombinator, and much more.  Show Notes: Inventing on Principle Talk: https://youtu.be/PUv66718DII?si=FQgWF4018HGpin7a https://youtu.be/PUv66718DII?si=FQgWF4018HGpin7a (0:00) Intro (1:56) Essentialism (6:01) No one is a natural great manager (15:01) The Freedman Doctrine (22:42) Distinction between behavior and core values (26:23) Two sides to any coin (32:31) Choosing who to do business with (38:31) Working remote (44:57) Early days of Webflow (57:07) Looking for silver bullets but finding lead bullets (1:05:57) The YC interview and walking out of Oblivion (1:10:01) Joining YC (1:14:57) From Skype calls to brand ambassadors (1:24:02) Product roadmap and development (1:27:24) Graduation vs churn (1:37:10) Taking your time raising money (1:24:17) Big product market fit (1:44:59) Pros and cons of venture capital (1:52:10) Not a zero sum (1:57:01) B2C versus B2B (2:04:22) Immigrating from Russia (2:11:24) Influence of Pixar (2:15:07) Favorite interview question   Mixed and edited: Justin Hrabovsky Produced: Rashad Assir Executive Producer: Josh Machiz Music: Griff Lawson   🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839 Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1 Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg   🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1   Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 🐦 Twitter - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow   About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes. Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

Vlad Magdalin

Founder and CEO

Webflow

Brought to you by Brave Search API—An independent, global search index you can use to power your search or AI app | Miro—A collaborative visual platform where your best work comes to life | Superhuman—The fastest email experience ever made — Jiaona Zhang (JZ) is a product leader with a strong background in consumer products and extensive hiring and management experience. She is currently SVP of Product at Webflow as well as a lecturer at Stanford, where she teaches a graduate-level course on product management. Before Webflow, JZ was Head of Product for the Homes Platform at Airbnb and has also led product teams at Airbnb, WeWork, and Dropbox. In today’s episode, we discuss: • Building a “minimum lovable product” rather than a minimum viable product • How to create better roadmaps through storytelling • Top lessons from Dropbox, Airbnb, WeWork, and Webflow • The importance of setting ambitious OKRs • JZ’s first 90 days playbook: how to succeed in a new role • Advice for early-career PMs — Find the transcript at: https://www.lennysnewsletter.com/p/building-minimum-lovable-products — Where to find Jiaona Zhang: • Reforge: https://www.reforge.com/managing-your-pm-career • LinkedIn: https://www.linkedin.com/in/jiaona/ • Website: https://www.jiaonazhang.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) JZ’s background (04:22) Common mistakes new PMs make (06:44) Why Airbnb Plus didn’t work out, and takeaways from that experience (10:51) Executing big dreams step-by-step (13:45) The right way to push back against founders (16:54) Minimum lovable product vs. minimum viable product (20:53) What makes a product lovable (22:20) Advice on roadmapping and prioritization (28:04) Tips for new PMs to accelerate their career (29:16) JZ’s top skills and how they have evolved over her career (31:37) Designing crisp OKRs (36:09) Lessons from WeWork (43:01) Winning the first 90 days at a new company (48:34) Why trust is crucial (51:48) High-level lessons from Dropbox, Airbnb, WeWork, and Webflow (56:38) The one piece of advice that transformed JZ’s career (58:39) Lightning round — Referenced: • Mike Lewis on LinkedIn: https://www.linkedin.com/in/mikelewis/ • “What working at Figma taught me about customer obsession,” VP of Product Sho Kuwamoto: https://www.lennysnewsletter.com/p/what-working-at-figma-taught-me-about • WeWork: https://www.wework.com/ • WeCrashed on AppleTV+: https://tv.apple.com/us/show/wecrashed/umc.cmc.6qw605uv2rwbzutk2p2fsgvq9 • Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-Solve-Problems-Test-Ideas/dp/150112174X • The Making of a Manager: What to Do When Everyone Looks to You: https://www.amazon.com/Making-Manager-What-Everyone-Looks/dp/0735219567 • Tress of the Emerald Sea: A Cosmere Novel: https://www.amazon.com/Tress-Emerald-Sea-Brandon-Sanderson/dp/1250899656/ • Arcane on Netflix: https://www.netflix.com/title/81435684 • Snoo: https://www.happiestbaby.com/ • Midjourney: https://www.midjourney.com/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jiaona Zhang

SVP of Product

WebflowLinktree

Brought to you by AssemblyAI—Production-ready AI models to transcribe and understand speech | Mixpanel—Product analytics that everyone can trust, use, and afford | Eppo—Run reliable, impactful experiments — Melissa Tan is an advisor, investor, and growth expert. She’s worked with fast-growing startups like Dropbox, Canva, Grammarly, and Miro, and for the past 2.5 years has been the Head of Growth at Webflow. There, she led the company's self-service business across Product, Marketing, and Growth, in addition to leading the charge on pricing and packaging. Prior to Webflow, she was Head of Growth for Dropbox’s B2B product, where she played a pivotal role in propelling their growth. In today’s episode, we discuss: • Attributes of high-performing teams • Tips for developing talent and seeking a mentor • How to create a strong culture of ownership • Frameworks for hiring PM and growth talent • Common pitfalls companies face when implementing growth strategies • Lessons from scaling Dropbox • The DACI framework for increasing team velocity • How to actually embrace first-principles thinking — Find the full transcript at: https://www.lennysnewsletter.com/p/building-high-performing-teams-melissa — Where to find Melissa Tan: • Twitter: https://twitter.com/melissamtan • LinkedIn: https://www.linkedin.com/in/melissamtan/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Melissa’s background (04:12) What’s next for Melissa (06:45) Lessons learned from Dropbox (11:49) When to add sales to product-led products and vice versa (14:28) Managing people with a people-focused and results-oriented approach (17:14) An example of people-focused leadership (20:26) The importance of talent development and why Melissa invests in it (22:26) Tips for finding a mentor (24:58) Specific questions to ask when you are interviewing for a role (27:49) Companies Melissa has worked with (28:33) Attributes of high-performing teams (31:38) Creating a sense of ownership among team members (34:36) Building a team-first culture (36:54) Avoiding burnout by knowing your limits (39:24) Developing talent and unlocking potential within your organization (42:45) Melissa’s hiring practices and what she looks for in a product manager (44:40) The exact interview sequence Melissa utilizes (49:58) Common pitfalls when creating growth teams (53:43) “Flying formation” and the DACI framework (56:48) Who should own revenue (58:19) When to invest in growth (1:01:06) What to look for in your first growth hire (1:04:35) When it’s appropriate to hire an advisor (1:06:19) First-principles thinking (1:09:50) Lightning round — Referenced: • Jiaona Zhang on LinkedIn: https://www.linkedin.com/in/jiaona/ • Lean In: Women, Work, and the Will to Lead: https://www.amazon.com/Lean-Women-Work-Will-Lead/dp/0385349947 • Tim Ferriss: How to Find a Great Mentor: https://www.youtube.com/watch?v=RVo1aZCyfO4 • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375/ • How to Monetize a Freemium Business: https://www.ycombinator.com/blog/how-to-monetize-a-freemium-business • DACI framework: https://www.productplan.com/glossary/daci/ • Leaders Eat Last: Why Some Teams Pull Together and Others Don't: https://www.amazon.com/Leaders-Eat-Last-Together-Others/dp/1591848016/r • The Untethered Soul: The Journey Beyond Yourself: https://www.amazon.com/Untethered-Soul-Journey-Beyond-Yourself/dp/1572245379/ • The Four Agreements: https://www.amazon.com/Four-Agreements-Practical-Personal-Freedom/dp/1878424319 • Winning Time: The Rise of the Lakers Dynasty on HBO: https://www.hbo.com/winning-time-the-rise-of-the-lakers-dynasty • ChatGPT: https://chat.openai.com/ • Webflow: https://webflow.com/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Melissa Tan

Head of Growth

Webflow

Today's 20Sales is a special Mother's Day edition where we are joined by 6 of the best sales leaders who also happen to be rockstar mothers. The Profiles Maggie Hott is on the GTM Team (Go-To-Market) at OpenAI. Before OpenAI, Maggie was Director of Sales @ Webflow and before Webflow spent an incredible 6 years at Slack. Stevie Case is the CRO @ Vanta. Prior to Vanta, Stevie spent an immensely successful 6 years at Twilio as VP of Mid-Market Sales. Renu Gupta is an advisor and sales consultant to some of the fastest-growing SaaS companies today. Previously she has held sales leadership roles at Slack, Thrive and Dropbox. Lauren Schwartz is the VP Enterprise Sales @ Fivetran. Before Fivetran, Lauren spent 4 years at Segment as Senior Director of Enterprise Sales leading to their acquisition by Twilio. Julie Maresca is the Head of Global Accounts at Atlassian. Prior to Atlassian, Julie spent an immensely successful 6 years at Slack in numerous roles including Head of Enterprise Sales for North America. Jessica Arnold is the VP of Global Sales Development @ Amplitude. Before Amplitude, Jessica was the Senior Director for Inside Sales North America at Dropbox for close to 6 years. In Today's 20Sales Mothers Day Episode We Discuss: 1.) How have you navigated growing in your career at the same time, growing your family? 2.) How do you balance your career and being a mother - when do you lean in and out? 3.) What are some specific strategies or tools that have helped you maintain a work-life balance? 4.) How do you prioritize your mental health and wellbeing while juggling your responsibilities at work and at home? 5.) How do you handle the guilt that many working mothers experience when they have to focus on their career? 6.) What are the unique challenges and advantages of being a mother in a sales leadership role? 7.) How has your experience as a mother influenced your leadership style and decision-making? 8.) How have you navigated going out on maternity leave without it having an impact on your career? 9.) America has one of the worst parental leaves of any country in the world. How can you advocate for parental leave if the existing policy isn't up to par? 10.) What are some ways that companies can create a more inclusive and supportive environment for working mothers in sales leadership roles?

Maggie Hott

GTM Team Member

OpenAIWebflow

Stevie Case

CRO

Vanta

Renu Gupta

Advisor and Sales Consultant

Thrive Global

Lauren Schwartz

VP Enterprise Sales

Fivetran

Maggie Hott is the Director of Sales @ Webflow where she leads their Sales Dev, Account Executive, and Solution Engineering orgs. Prior to Webflow, Maggie spent an incredible 6 years at Slack in a period of hypergrowth for the company having joined as the founding AE scaling to a Sr Enterprise Leader. Before Slack, Maggie was the founding Sales hire at Eventbrite. If that was not enough, Maggie is also an active angel investor, an advisor to Cowboy Ventures, Scribble Ventures, and is a Founding Operator and LP @ Coalition Partners. In Today's Episode with Maggie Hott We Discuss: 1. The Cold Email that Led to a World-Class Sales Career: How a cold email to Kevin Hartz @ Eventbrite led to Maggie's career in sales? What are the 1-2 biggest takeaways from her time at Slack? How did they impact her mindset? What does Maggie know now that she wishes she had known when she entered sales? 2. The Sales Playbook: PLG and Enterprise: How does Maggie define the sales playbook? What is it? What is it not? Is it possible for early-stage companies to do both enterprise and PLG at the same time? When is the right time to add enterprise to a PLG motion? What are the steps to build an outbound sales engine in enterprise? Where do many go wrong? 3. Building the Bench: Hiring Your First Sales Team: Should founders look to hire a Senior Head of Sales first or a more junior sales rep? Should they be hired one at a time? What are the benefits of hiring many at the same time? What is the right process to hire your first sales hire? What are the core traits and habits that make the first 10x sales hire? What are the right questions to ask to unveil those characteristics? 4. Making the Machine Work: The Process: What can sales leaders do to proactively build relationships with other parts of the org? How can more junior sales reps build relationships with other functions? Why does Maggie believe that mis-hiring can be a $1M mistake? What are the early signs that a new hire is not working out in sales? How does this differ for outbound? Why is it dangerous to make your self-serve product too good?

Maggie Hott

GTM Team Member

OpenAIWebflow

Product-led scaling isn't about growth hacking. Scaling 10X is really hard…no matter if you are starting at $1M, $10M, $100M or $1B ARR. Join Dropbox GM, Rachel Wolan, as she shares hard-earned, practical lessons learned through product-led scaling at Dropbox, LiveRamp, and Talkdesk. Blog post and video: https://www.saastr.com/beyond-product-led-growth-7-lessons-learned-in-product-led-scaling-podcast-490-and-video/ Sponsors: https://www.invoca.com/ https://stripe.com/ https://www.ontheclock.com/

Rachel Wolan

CPO

WebflowDropbox

Webflow, a no-code website builder, doubled its customer base last year, pushing the company's valuation to $2.1 billion. Webflow CEO Vlad Magdalin openly shares the struggles and triumphs they endured along the way to their success. Video + blog post: https://www.saastr.com/webflow-ceo-vlad-magdalin-on-building-a-four-billion-dollar-company/

Vlad Magdalin

Founder and CEO

Webflow

In this episode, we talk about using no-code tools to aid in your coding journey and your work, with David Hoang, director of design at Webflow. David talks about how he got into code through the fine arts, the utility of using no-code tools both for learning to code as well as in your career, and what some of his favorite no-code tools are. Show Links Partner with Dev & CodeNewbie! (sponsor) Webflow Macromedia Adobe Dreamweaver HyperCard Apple II Commodore 64 Microsoft Excel HTML CSS Myspace Adobe Photoshop Adobe Illustrator Codeless innovation: experience prototyping with visual programming One Medical Bubble Airtable Quartz Composer Makerpad Ruby on Rails David Hoang David Hoang is a design leader, technologist, teacher, and startup advisor. He's currently the Director of Design at Webflow and User Experience Design Instructor at General Assembly.

David Hoang

Director of Design

Webflow

Vlad Magdalin (@callmevlad) might just be the most principled founder I've had on the podcast. "When it came to making hard decisions, I've leaned more on my morality rather than my business sense. That's what I regret the least." Sticking to his heart has paid off. Not only has he built a company that's changing and improving lives by the millions, but he's also grown it to millions in revenue and 155 employees. In this episode Vlad and I talk about the ups and downs of raising money from investors, the impact of building something that empowers your customers to create, and the compounding benefits of focusing on people and relationships over profit and product. Transcript, speaker information, and more: https://www.indiehackers.com/podcast/144-vlad-magdalin-of-webflow

Vlad Magdalin

Founder and CEO

Webflow

We're back with Season 3, brought you by Microsoft: The latest episode of My First Million, Shaan sits down with Vlad Magdalin (@callmevlad), Co-Founder & CEO of Webflow: a visual tool to build web apps. Vlad shares the several attempts in 6 years to get his no-code brainchild going. Persistence paid off as it quickly got to $20MM in revenue and raised a monster $72M Series A round led by Accel. He talks about the emotional rollercoaster of getting into Y-Combinator, the video that made him quit his high paying job immediately, kickstarter kicking him off their platform and the trick to get investors interested without changing anything.  See acast.com/privacy for privacy and opt-out information.

Vlad Magdalin

Founder and CEO

Webflow

We're joined by Webflow's Co-Founder and CEO, Vlad Magdalin, talking about how he started the company (over a decade, trying three times), how to nail the timing of your startup, and the future of the "no-code movement." Vlad took his company through YCombinator in 2013, and raised only $3m in the following six years, before closing a $72m Series A from Accel earlier this year. He gives his perspective on why now is the only time Webflow could have worked (not in 2009, the last time he tried to start it), what's changed in browser technology, and how he was inspired by one of the original designers of the iPhone software. Vlad also shares his wisdom for other founders and opportunities he thinks will be available for entrepreneurs in the next five years when robust "no-code" infrastructure is built out. “The differentiator between No-Code and Low-Code is that Low-Code makes this implicit admission that in order to really finish a project, I’m going to need a developer. Or I am going to need to know how to take it across that last mile. In No-Code, the aspiration is that for the vast majority of cases, you will not that. Or, if you do, that one or a few developers that can create the No-Code version that abstracts away the Low-Code version and put it into the hands of millions.” -Vlad Magdalin, @callmevlad Sponsors: Sierra: https://bit.ly/acquiredsierra   Be sure to follow the Acquired Podcast: Acquired.fm @AcquiredFM   Show Links: Bret Victor – The Future of Programming (YouTube) Bret Victor – Inventing on Principle (vimeo) Paul Graham – Default Alive or Default Dead Essay

Vlad Magdalin

Founder and CEO

Webflow

Vlad Magdalin is the Founder & CEO @ Webflow, the startup that allows you to build better business websites, faster, without coding. To date, Vlad has raised over $73m with Webflow from some dear friends of the show including Accel, Ron @ Rainfall, Brianne @ Work Life, Benjamin Ling and Y Combinator to name a few. Prior to founding Webflow, Vlad was a Senior Software Engineer @ Intuit. Before Intuit, Vlad co-founded Chatterfox, a web application allowing people to stay in touch with groups of friends, family, or co-workers. In Today's Episode You Will Learn: 1.) How Vlad made his way into the world of startups? How did the original idea to democratise the world of design and site creation with Webflow come about? 2.) Webflow has had an unorthodox funding path with their recent $73m Series A, how was it for Vlad raising the seed round with Webflow? What lessons did he learn from that raise? Why did they drive to be breakeven so much earlier than others might? Why did Vlad believe now was the right time to go big and raise the Series A? 3.) Vlad chose to partner with Accel, what advice does Vlad give to founders in determining which funding partner to choose? What makes for the best VC <> founder relationships? What is the optimal way to build those relationships? Where does Vlad believe that VCs can strategically move the needle? Where do many think VCs can really help but they most often cannot? 4.) What have been Vlads biggest lessons when it comes to successful board management? What advice would Vlad give Harry when it comes to joining boards as new board member? What does Vlad mean when he says, the best board members come to the board with the mindset of "servant leadership"? How do they show that in their actions? How can investors create an environment of trust at the board? 5.) Vlad AMA: Why does Vlad believe that it is a distraction for founders to be angel investing alongside their role as a founder? How does he believe this creates a wedge between them and the team? How has having kids impacted how he thinks about operating today? What have been the big takeaways from fatherhood? Items Mentioned In Today's Show: Vlad's Fave Book: Leaders Eat Last: Why Some Teams Pull Together and Others Don't As always you can follow Harry, The Twenty Minute VC and Vlad on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Vlad Magdalin

Founder and CEO

Webflow