Podcasts from around the Web

After 30 years in marketing, Melissa Puls, CMO and SVP, Customer Success & Renewals at Ivanti, has seen it all: the highs, the lows, and the evolution of marketing itself. In this episode, she shares how she’s built her career around people-first leadership, purpose-driven strategy, and performance that actually moves the business forward. Melissa breaks down why B2B and B2C are outdated concepts, why it’s time to think “business-to-human,” and how aligning marketing, customer success, and renewals can transform growth. She also opens up about lessons learned from failure, how AI is reshaping efficiency and personalization, and why transparency and data-driven decisions are a CMO’s real superpowers. Whether you’re a rising marketing leader or a seasoned exec, this episode delivers practical insights on building teams, earning trust, and driving measurable impact across the entire customer lifecycle.

What if marketing didn’t just support company strategy, but shaped it from the start? 8x8 CMO Bruno Bertini breaks down how today’s marketing leaders can elevate their role through goal-driven alignment, end-to-end customer experience, and real-world applications of AI. Bruno shares his approach to building marketing-led OKRs, driving measurable outcomes like LTV and retention, and using AI to streamline enrichment, targeting, and creative production. It’s a must-listen for CMOs who want to operate as true business leaders and make marketing central to growth.

How do you thrive in private equity while maintaining local autonomy and driving growth? Meghann McNally, CMO of Wrench Group, shares her unique approach to leading marketing in a fast-growing, private equity-backed company. From scaling brand strategies in 27 markets across 14 states to navigating the challenges of a male-dominated industry, Meghann emphasizes the importance of hands-on leadership and data-driven decision-making. She also reveals how fostering curiosity, maintaining local connections, and balancing efficiency with personal touch have been key to Wrench Group’s success.

In this episode of the State of Customer Storytelling podcast, DailyPay Director of Client Advocacy Maria Braune shares how to truly listen to your customers and get the best testimonials possible.

In this episode of the State of Customer Storytelling podcast, Chief Outsiders Partner and CMO Jeff Loeb shares how to gather customer insights and share them with the rest of your team.

In this episode of the State of Customer Storytelling podcast, Airtable Customer Marketing Programs lead Valeria Gomez shares how to show love to your customers the way you want them to show love to your company.

Thank you to the folks at Sustain for providing the hosting account for CHAOSSCast! CHAOSScast – Episode 125 In this final episode of the year from CHAOSScast, hosts Alice Sowerby and Harmony Elendu welcome members of the CHAOSS Board, Sean Goggins, Anita Ihuman, Georg Link, and Elizabeth Barron, for an in-depth discussion on the project's developments and future. They share their reflections on key events and trends in the open-source community over 2025. Topics include the impact of AI on open source, shifts in funding, community engagement, and the importance of psychological safety. The panelists also spotlight various CHAOSS working groups, including education, design, and technical writing, while sharing their wishes for the CHAOSS Project in 2026. Press download now! [00:00:49] The hosts and guests introduce themselves and their backgrounds. [00:02:28] Georg announces CHAOSScon in Brussels, Jan 29, 2026, Co-located with FOSDEM. [00:04:51] The guests talk about factors affecting OSS communities in 2025. [00:11:39] We hear where CHAOSS grew the most in 2025 such as regional chapters, global reach, CHAOSS Asia, with shout-outs to Divvya Mohan and Rowland Mosbergen, how metrics are being used, Design Working Group, accessibility, Practitioner Guides, and two new working groups. [00:19:45] The panel shares project and working groups they’re most proud of: Package Management, AI Alignment, Alice and Harmony for keeping CHAOSScast podcast active and alive, Paul and Peachtree Sound for editing the podcast and keeping episodes on track, Education Project, Practitioner Guides, and shared ownership of community growth. [00:28:55] What is some work that went under the radar in 2025? The guests talk about DEI Working Group, DEI Badging, Harmony and the Technical Writers Working Group, and AI’s impact on maintainers. [00:35:41] Georg and Sean have additional thoughts on AI identity and bots. Current tooling assumes human contributions, but AI agents and bots break those assumptions and there’s a need for better identity solutions and metrics that distinguish humans, bots, and multi-account actors. [00:39:33] Elizabeth would love people to give CHAOSS more feedback on engagement for newcomers to make onboarding smoother and encourages people to use the Education Project as a starting point. [00:42:07] Georg, Sean, and Anita talk about CHAOSS board priorities for 2025-2026. [00:45:25] Everyone shares their wishes for CHAOSS in 2026.

[00:48:52] If anyone has any ideas, topics, questions, and guests for future CHAOSS episodes please send us an email. Merry Christmas and Happy New Year! Panelists:

Alice Sowerby

Harmony Elendu Guests:

Sean Goggins

Anita Ihuman

Georg Link

Elizabeth Barron Links:

CHAOSS

CHAOSS Project X

CHAOSScast Podcast

CHAOSS YouTube

podcast@chaoss.community

Georg Link Website

Harmony Elendu X

Alice Sowerby LinkedIn

Sean Goggins X

Elizabeth Barron X

Anita Ihuman GitHub

CHAOSScon 2026 Brussles, Belgium

FOSDEM 2026

CHAOSS Education Project

CHAOSS Onboarding Courses-GitHub

CHAOSS Practitioner Guides

First Person Project White Paper

The Road Ahead For Identity Management In Open Source: Humans, Bots, AI Agents-And The Future Of Attribution by Diane Mueller (Bitergia)

CHAOSScast Podcast-Episode 121: Package Metadata Working Group with Andrew Nesbitt and Damián Vicino CHAOSScast Podcast-Episode 100: Celebrating 100 episodes of CHAOSScast

CHAOSScast Podcast-Episode 76: CHAOSS Goals for 2024 and Beyond

CHAOSScast Podcast-Episode 71: What’s New in CHAOSS: Podcast Reboot Episode

CHAOSScast Podcast-Episode 49: CHAOSS Community Year 2021 in Review

CHAOSScast Podcast-Episode 1: Hello, World!

Peachtree SoundSpecial Guest: Anita ihuman.Support CHAOSScast

Thank you to the folks at Sustain for providing the hosting account for CHAOSSCast! CHAOSScast – Episode 124 This episode of CHAOSScast kicks off a new Practitioner Guide series focused on “Building Diverse Leadership” in open source communities. Harmony Elendu hosts with co-host Georg Link and guests Dawn Foster and Peculiar Umeh, exploring why diverse leadership matters, how CHAOSS’ practitioner guides turn “walls of metrics” into practical action, and how three specific metrics: Board/Council Diversity, Sponsorship, and Inclusive Leadership, can help projects become more welcoming, representative, and sustainable. Hit download now to hear more! [00:00:35] Dawn, Peculiar, Georg, and Harmony share their backgrounds. [00:02:57] Dawn gives us an overview of the Practitioner Guide series and emphasizes that the guides focus on how to improve projects using metrics, not just on measuring. [00:05:13] Georg asks Peculiar what inspired her to write the “Getting Started with Building Diverse Leadership” guide. She describes working on CHAOSS metrics templates and wanting to help non-data science people use them. [00:08:09] Harmony connects the topic to broader industry conversations on diversity and inclusion. Peculiar explains that diverse leadership brings different perspectives, experiences, and voices into decision making and uses CHAOSS as an example. [00:10:30] Dawn expands on how seeing leaders “who look like you” motivates people to participate and aspire to leadership. [00:11:28] Georg talks about diversity as social justice and explains benefits for the projects: resilience, innovation, and better products for diverse users. [00:14:25] Peculiar shares the three metrics and why there were chosen. Dawn adds that guides are designed to change projects, not just describe them. [00:18:09] Georg notes Board/Council Diversity is the most intuitive to measure and Dawn cautions that many aspects of identity are invisible and the guide recommends surveys to ask community members whether they feel represented and heard. [00:21:03] Georg explains sponsorship vs. mentorship. Peculiar shares her own experience of being advocated for and supported in open source. Dawn tells the story of Danese Cooper sponsoring her showing how sponsorship accelerates careers. [00:25:27] Georg explains Inclusive Leadership as the governance scaffolding and Peculiar describes what the guide offers. [00:27:50] Harmony asks how they can implement the guide and monitor progress. Peculiar highlights some implementation steps and Dawn re-emphasizes using recurring surveys as monitoring tools.

[00:33:27] Dawn notes that every practitioner guide includes a Cautions and Considerations section, and Georg reminds us that interpersonal relationships are crucial for understanding how people experience the community. Value Adds (Picks) of the week: [00:35:25] Harmony’s pick is n8n and automations.
[00:36:10] Georg’s pick is looking forward to the holidays with his family.
[00:37:54] Dawn’s pick is watching chunky squirrels play outside her window.
[00:38:24] Peculiar’s pick is taking time to rest.
Panelists:

Harmony Elendu

Georg Link Guests:

Dawn Foster

Peculiar Umeh Links:

CHAOSS

CHAOSS Project X

CHAOSScast Podcast

CHAOSS YouTube

podcast@chaoss.community

Georg Link Website

Harmony Elendu X

Dawn Foster X

Peculiar Umeh LinkedIn

CHAOSS Practitioner Guide: Getting Started with Building Diverse Leadership

About the CHAOSS Practitioner Guides

The Linux Foundation Report -Diversity, Equity, and Inclusion in Open Source

The Linux Foundation-Decentralized innovation. Built on trust.

Inclusive Leadership: Effecting change: Introduction | OpenLearn-Open University

CHAOSS Data Use Awareness Recommendation: Privacy and Ethics

n8n

Previous Practitioner Guide Episodes:

Episode 85: Introducing CHAOSS Practitioner Guides: #1 Responsiveness

Episode 88: Practitioner Guides: #2 Contributor Sustainability

Episode 89: Practitioner Guides : #3 Organizational Participation

Episode 97: Practitioner Guides: #4 Security

Episode 120: Practitioner Guides: #5 Demonstrating Organizational Value

Episode 123: Practitioner Guides: #6 Sunsetting an Open Source ProjectSpecial Guest: Peculiar Umeh.Support CHAOSScast

Thank you to the folks at Sustain for providing the hosting account for CHAOSSCast! CHAOSScast – Episode 123 This episode of the CHAOSScast features hosts Harmony Elendu and Alice Sowerby, along with guests Stefka Dimitrova and Dawn Foster, discussing the process of sunsetting open source projects. Dawn and Stefka share their extensive experiences and the importance of managing the lifecycle of open source projects responsibly. They delve into the specifics of the 'Getting Started with Sunsetting an Open Source Project' guide from Dawn's series of practitioner guides, which aim to help practitioners, not just experts, interpret data and improve their project health. Key topics include identifying inactive projects, the responsible steps for sunsetting, and the crucial role of communication within the community. The episode also touches upon metrics to determine project activity and archive responsibly, highlighting that the process goes beyond simply pressing an 'archive' button. Hit download now to hear more! [00:00:23] The hosts and guests introduce themselves. [00:02:09] Dawn explains the purpose of the CHAOSS Practitioner Guides. [00:04:54] Harmony asks Dawn what inspired her to write the “Getting Started with Sunsetting an Open Source Project” guide. She highlights the problem of inactive, unarchived projects creating security and reputational risks and being inspired by VMware’s internal sunset process let by Stefka when they both worked there. [00:06:23] Dawn explains why projects shouldn’t remain unarchived and who the guide is intended for. [00:07:30] Stefka shares her background and how she got started with sunsetting projects while she was at VMware. [00:10:33] Dawn discusses the three Primary metrics: Change Requests, New Issues, and Technical Forks. [00:12:10] Harmony asks how to identify a functionally abandoned project and Dawn explains if there’s no updates or security patches it’s likely abandoned. [00:13:07] Stefka outlines some responsible “sunsetting” steps. [00:16:16] Harmony asks what to do if an active project decides to wind down and Stefka says it’s better to decide proactively while still active, plan and communicate early, re-evaluate priorities, and prepare alternatives. [00:17:31] Dawn adds within companies, it must involve PR and customer teams to manage impact and have a transition plan and timeline. [00:18:20] Alice summarizes the dual responsibility of both OSPOs and maintainers to recognize when it’s time to sunset and Stefka shares an example that was helpful for the teams she worked with. [00:21:17] Alice reflects that open source is about people as much as technology and managing emotional transitions is vital. [00:21:58] Final takeaways: Dawn encourages listeners to read the guide and follow its step-by-step approach for responsible project sunsetting and Stefka encourages people to be ready for the sunset form the start of a project and keep the guide handy as a reference for your teams. Value Adds (Picks) of the week: [00:23:36] Dawn’s pick is her 3D printer.
[00:24:47] Harmony’s pick is talking a walk after the rain.
[00:25:52] Stefka’s pick is working with people at the Playback Theatre*.*
[00:26:59] Alice’s pick is Vitamin B3 for skin cancer prevention. Panelists:

Harmony Elendu

Alice Sowerby Guests:

Dawn Foster

Stefka Dimitrova Links:

CHAOSS

CHAOSS Project X

CHAOSScast Podcast

CHAOSS YouTube

podcast@chaoss.community

Harmony Elendu X

Alice Sowerby LinkedIn

Dawn Foster X

Stefka Dimitrova LinkedIn

CHAOSS: Practitioner Guide: Getting Started with Sunsetting an Open Source Project

CHAOSS: About the CHAOSS Practitioner Guides

When and How to Deprecate an Open Source Project by Stefka Dimitrova

Deprecating an Open Source Project, Part 2 by Stefka Dimitrova
Simple Steps for a Calm “Sunset”- Stefka Dimitrova’s video from the Open Source Summit in Europe (2022)

Dos and don’ts when sunsetting open source projects (GitHub Blog)

Shutting Down An Open Source Project (TODO Group Guide)

When to Send Flowers? End of Life and End of Support Across the Ecosystem-Allen Friedman’s video Open Source Summit

10 quick tips for making your software outlive your job (white paper)

Playback Theatre Network

Vitamin B3 can help protect against skin cancer. Here’s who may benefit (npr)Special Guest: Stefka Dimitrova.Support CHAOSScast

Molly Graham has worked for some of tech’s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community for leaders navigating rapid scale, growth, and change. She’s best known for her “Give away your Legos” framework and her collection of practical mental models for leading through hypergrowth.We discuss:1. “Give away your Legos”: a framework for scaling yourself as a leader2. “J-curves vs. stairs”: the two paths of career growth, and why you should pick the scarier path3. “The waterline model” for diagnosing team problems (and why you should “snorkel before you scuba”)4. Six rules for creating effective goals (and aligning everyone around them)5. Rules of thumb for leading through rapid scale and change6. Her biggest leadership lessons from Mark Zuckerberg, Sergey Brin, Larry Page, Sheryl Sandberg, and Bret Taylor—Brought to you by:DX—The developer intelligence platform designed by leading researchersBrex—The banking solution for startupsGoFundMe Giving Funds—Make helping a habit—Transcript: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182877855/my-biggest-takeaways-from-this-conversation—Where to find Molly Graham:• X: https://x.com/molly_g• LinkedIn: https://www.linkedin.com/in/mograham• Substack: https://mollyg.substack.com• Website: https://glueclub.com—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 Molly Graham(04:28) Molly’s background at Google, Facebook, Quip, and CZI(11:29) The “Give away your Legos” framework(16:44) Managing your inner monster(19:49) When not to give away your Legos(21:28) Embracing a long career(23:25) The J-curve vs. stairs approach to career growth(32:00) The gift of knowing yourself(34:28) Learning to be a professional idiot(38:30) The waterline model: snorkel before you scuba(47:16) Six rules for creating strong alignment around goals(57:15) Rules of thumb for leading through rapid scale(01:07:49) Investing in high performers vs. low performers(01:10:54) Lessons from Zuckerberg, Sandberg, and Bret Taylor(1:21:15) Pivoting from ambition to purpose(1:26:32) Finding stability in instability(01:29:44) Final thoughts—Referenced:• Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG): https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652• Elliot Schrage on LinkedIn: https://www.linkedin.com/in/elliotschrage• Quip: https://quip.com• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• Chan Zuckerberg Initiative: https://chanzuckerberg.com• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths• ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups• The Muppets: https://muppets.disney.com• Sara Caldwell on LinkedIn: https://www.linkedin.com/in/saramcaldwell• J-Curves vs. Stairs: Two Approaches to Career Growth: https://mollyg.substack.com/p/j-curve• Forget the corporate ladder—winners take risks: https://www.ted.com/talks/molly_graham_forget_the_corporate_ladder_winners_take_risks• Chamath Palihapitiya on LinkedIn: https://www.linkedin.com/in/chamath• Lori Goler on LinkedIn: https://www.linkedin.com/in/lori-goler-6b96921• Joseph Campbell’s quote: https://www.goodreads.com/quotes/192665-the-cave-you-fear-to-enter-holds-the-treasure-you• Zevi Arnovitz on LinkedIn: https://www.linkedin.com/in/zev-arnovitz• Peopling 101: The Waterline Model: https://christinehaskell.com/blog/peopling-101-the-waterline-model• Introduction to NVC: https://www.cnvc.org/learn/what-is-nvc• I hate OKRs... and other thoughts about goal setting: https://mollyg.substack.com/p/i-hate-okrs-and-other-thoughts-about• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics• James Clear’s quote: https://www.goodreads.com/quotes/9614600-problem-1-winners-and-losers-have-the-same-goals• Founder mode: https://paulgraham.com/foundermode.html• Stripe: https://stripe.com• Patrick Collison on X: https://www.linkedin.com/in/patrickcollison• John Collison on X: https://x.com/collision• Seth Godin’s best tactics for building remarkable products, strategies, brands and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow—Recommended books:• The Artist’s Way: https://www.amazon.com/Artists-Way-25th-Anniversary/dp/0143129252• Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212• Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299—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

Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn’t, and how the GTM landscape is quickly being transformed.We discuss:1. How AI is fundamentally changing the sales function2. Why most SDRs and BDRs will be “extinct” within a year3. What Jason is observing across his portfolio about AI adoption in GTM4. How to become “hyper-employable” in the age of AI5. The specific AI tools and tactics he’s using that have been working best6. Practical frameworks for integrating AI into your sales motion without losing what works7. Jason’s 2026 predictions on where SaaS and GTM are heading next—Brought to you by:DX—The developer intelligence platform designed by leading researchersVercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the webDatadog—Now home to Eppo, the leading experimentation and feature flagging platform—Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation—Where to find Jason Lemkin:• X: https://x.com/jasonlk• LinkedIn: https://www.linkedin.com/in/jasonmlemkin• Website: https://www.saastr.com• Substack: https://substack.com/@cloud—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 Jason Lemkin(04:36) What SaaStr does(07:13) AI’s impact on sales teams(10:11) How SaaStr's AI agents work and their performance(14:18) How go-to-market is changing in the AI era(19:19) The future of SDRs, BDRs, and AEs in sales(22:03) Why leadership roles are safe(23:43) How to be in the 20% who thrive in the AI sales future(28:40) Why you shouldn't build your own AI tools(30:10) Specific AI agents and their applications(36:40) Challenges and learnings in AI deployment(42:11) Making AI-generated emails good (not just acceptable)(47:31) When humans still beat AI in sales(52:39) An overview of SaaStr's org(53:50) The role of human oversight in AI operations(58:37) Advice for salespeople and founders in the AI era(01:05:40) Forward-deployed engineers(01:08:08) What's changing and what's staying the same in sales(01:16:21) Why AI is creating more work, not less(01:19:32) Why Jason says these are magical times(01:25:25) The "incognito mode test" for finding AI opportunities(01:27:19) The impact of AI on jobs(01:30:18) Lightning round and final thoughts—Referenced:• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org• SaaStr Annual: https://www.saastrannual.com• Delphi: https://www.delphi.ai/saastr/talk• Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/• Vercel: https://vercel.com• What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Replit: https://replit.com• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• ElevenLabs: https://elevenlabs.io• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack• Bolt: https://bolt.new• Lovable: https://lovable.dev• Harvey: https://www.harvey.ai• Samsara: https://www.samsara.com/products/platform/ai-samsara-intelligence• UiPath: https://www.uipath.com• Denise Dresser on LinkedIn: https://www.linkedin.com/in/denisedresser• Agentforce: https://www.salesforce.com/form/agentforce• SaaStr’s AI Agent Playbook: https://saastr.ai/agents• Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan• Brian Halligan’s AI: https://www.delphi.ai/minds/bhalligan• Sierra: https://sierra.ai• Fin: https://fin.ai• Deccan: https://www.deccan.ai• Artisan: https://www.artisan.co• Qualified: https://www.qualified.com• Claude: https://claude.ai• HubSpot: https://www.hubspot.com• Gamma: https://gamma.app• Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b• Brex: https://www.brex.com• Outreach: https://www.outreach.io• Gong: https://www.gong.io• Salesloft: https://www.salesloft.com• Mixmax: https://www.mixmax.com• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr• Clay: https://www.clay.com• Owner: https://www.owner.com• Momentum: https://www.momentum.io• Attention: https://www.attention.com• Granola: https://www.granola.ai• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• Palantir: https://www.palantir.com• Databricks: https://www.databricks.com• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan• Rippling: https://www.rippling.com• Cursor: https://cursor.com• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna• Pluribus on AppleTV+: https://tv.apple.com/us/show/pluribus/umc.cmc.37axgovs2yozlyh3c2cmwzlza• Sora: https://openai.com/sora• Reve: https://app.reve.com• Everything That Breaks on the Way to $1B ARR, with Mailchimp Co-Founder Ben Chestnut: https://www.saastr.com/everything-that-breaks-on-the-way-to-1b-arr-with-mailchimp-co-founder-ben-chestnut/• The Revenue Playbook: Rippling’s Top 3 Growth Tactics at Scale, with Rippling CRO Matt Plank: https://www.youtube.com/watch?v=h3eYtzBpjRw• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—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

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you’ve gone too far3. Matt’s transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.com—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 Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion’s success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling’s vision and success(01:17:48) AI’s impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway’s law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman’s website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I’m Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459—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.

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What happens when your referral program participants are literally trained to find holes in systems? How do you protect your program without making it so complicated that nobody wants to use it? To explore this, we welcome Mariana Doncel to The Advocacy Channel. Mariana leads B2C product marketing at Hack the Box, a cybersecurity training platform where users learn ethical hacking through hands-on challenges. When your customers spend their days breaking into systems for fun, you learn pretty quickly what actually works for fraud prevention. In this episode, Mariana and host Will Fraser get into the reality of protecting your referral program from abuse. Spoiler: it's not about building an airtight system with rules for every scenario. Mariana shares the pragmatic approach Hack the Box has taken, focusing on damage control and smart incentive design rather than trying to prevent every possible exploit. In this episode, Mariana walks us through: Why trying to close every possible loophole often backfires by making your program too complex for legitimate users The "accept and mitigate" approach: acknowledging that some people will try to game the system while capping your exposure How tying rewards to actual monetary actions creates natural fraud deterrence Setting per-person limits so even if someone does find a workaround, the damage is contained Thinking about fraud prevention as risk analysis rather than absolute protection How to balance moving fast with protecting your program from abuse Mariana also shares how this mindset extends beyond referral programs to everything her marketing team puts out at Hack the Box, where every campaign has to account for users who will look for alternative interpretations. Connect with Mariana on LinkedIn: https://www.linkedin.com/in/marianadoncel/  Connect with us:  Get more customer marketing insights and strategies at impact.com/blog/  Connect with host Will on LinkedIn: www.linkedin.com/in/wifraser/   Have a question? Suggestion? Email us at advocacychannel@impact.com   Loving this show? Explore impact.com's other podcasts packed with insights: The Partnership Economy The Publisher's Playbook

Want to build a customer advisory board that actually drives business value? Struggling to figure out where to start or how to prove the ROI? To help, we welcome Cate Vanasse to The Advocacy Channel. Cate leads customer marketing at TalkDesk, where her team's mission is "igniting raving fans, driving growth, and building customers for life."  With extensive experience building and scaling customer advisory boards across multiple companies, Cate shares her practical framework for creating CABs that strengthen relationships, influence revenue, and create real brand advocates. In this episode, Cate walks us through: How to identify the right CAB members by balancing ideal account logos with the right human personalities in the room The art of balancing "give vs get" so it doesn't feel transactional Why in-person meetings matter for executive CABs versus when virtual works better for technical advisory boards Cate also shares insights from TalkDesk's CX Innovators Awards program, including how industry recognition has helped customers get promoted and secure internal resources.  Her closing advice? The best customer marketing programs don't start with a spreadsheet. They start with empathy. Connect with Cate on LinkedIn: https://www.linkedin.com/in/catevanasse/  Connect with us:  Get more customer marketing insights and strategies at impact.com/blog/  Connect with host Will on LinkedIn: http://www.linkedin.com/in/wifraser/  Have a question? Suggestion? Email us at advocacychannel@impact.com  Loving this show? Explore impact.com's other podcasts packed with insights: The Partnership Economy The Publisher's Playbook  

Want your referral program to succeed?  Start with the foundation first. Make sure your product infrastructure is solid and can handle growth before you launch. In this episode, we're excited to welcome Ashley Stead, Director, Growth Product at Nesto Group, a leading Canadian tech company building the mortgage ecosystem of the future. With over 15 years of experience spanning product management, UX research, marketing, and operations, Ashley brings a unique full-stack perspective to customer marketing and advocacy initiatives. In this episode, Ashley and our host Will Fraser dive into what it means to think about advocacy as infrastructure rather than one-off campaigns. Ashley shares her framework for creating product-led advocacy programs that integrate seamlessly into the customer journey.  From understanding the "micro-yeses" approach to breaking down complex customer paths, to navigating build vs. buy decisions and fostering collaboration between marketing and development teams, this conversation is packed with practical insights. In this episode, you'll discover: How to map customer journeys and identify the right moments for advocacy messaging without competing with other business priorities.  The framework for deciding when to build custom solutions versus buying existing platforms, and how to create hybrid approaches.  Strategies for empowering marketing teams to move quickly while keeping technical infrastructure robust and scalable.  The importance of breaking down big conversions into micro-yeses and understanding the data behind each step.  How to use AI tools and prompts to become more full-stack in your marketing role, even without technical resources. Listen to this episode to hear more about how infrastructure thinking can transform your advocacy programs and help you avoid the common mistakes marketers make with referral programs.  Connect with Ashley on LinkedIn: https://www.linkedin.com/in/ashley-stead/ AI prompt from Ashley: The Advocacy Channel | Season 2 Episode 9 AI Prompt Connect with us:  Get more customer marketing insights and strategies at impact.com/blog/  Connect with host Will on LinkedIn: http://www.linkedin.com/in/wifraser/  Have a question? Suggestion? Email us at advocacychannel@impact.com  Loving this show? Explore impact.com's other podcasts packed with insights: The Partnership Economy The Publisher's Playbook