Episodes

  • Why founders should invest in coaching, communication & leadership mechanisms before you scale w/ James Birchler

    Why founders should invest in coaching, communication & leadership mechanisms before you scale w/ James Birchler
    Aug 14 2025
    Founders often delay leadership coaching until a major crisis hits, leading to significant costs in productivity, team churn, and poor decisions. In this episode, James Birchler (Technical Advisor & Executive Leadership Coach) argues that early coaching is a game-changer for a startup's success. We explore the hidden costs of waiting and the benefits of intentionally installing leadership and communication systems before you scale. James shares specific self-awareness mechanisms, like advisory groups and feedback loops, to help founders design their day and create accountability. You'll also learn practical strategies like the "5-Minute Alignment Loop" for spotting communication breakdowns & for reinforcing clarity. Plus insights on how to "install your leadership OS" so it can scale with your company.ABOUT JAMES BIRCHLERJames Birchler is an executive leadership coach and technical advisor who specializes in helping engineering leaders and founders develop greater self-awareness and build high-performing teams. He combines deep technical expertise with practical leadership development, making him particularly valuable for technical leaders scaling their organizations.As both a founder and engineering leader, James has more than 20 years of experience leading teams at companies ranging from early-stage startups to Amazon, where his current role is Technical Advisor to the VP of Amazon Delivery Routing and Planning. Most recently, he founded NICER, a premium natural personal care company, and Actuate Partners, his executive coaching and technical advisory practice. He also held VP of Engineering roles at companies including Caffeine (backed by Greylock and Andreessen Horowitz), SmugMug (where his team acquired Flickr), and IMVU.At IMVU, James implemented the Lean Startup methodologies alongside Eric Ries, author of The Lean Startup and creator of the methodology, literally the first company to apply these principles. His team helped pioneer the DevOps movement by building infrastructure to ship code to production 50 times per day and coining the term "continuous deployment." This experience in systematic experimentation and continuous improvement now informs his coaching approach through frameworks like CAMS (Coaching, Advising, Mentoring, Supporting) and the Think-Do-Learn Loop.James completed his executive coaching certification at UC Berkeley Haas School of Business Executive Coaching Institute. His coaching practice focuses on self-awareness, integrity, accountability, and fostering growth mindsets that support continuous learning and high performance. He writes the Continuous Growth newsletter and offers both individual executive coaching and peer learning circles for technical leaders.Through his advisory work with growth-stage startups in the US and Europe, James helps leaders navigate common scaling challenges including hiring and interviewing, implementing development methodologies, establishing operational cadences, and developing other leaders. His approach treats leadership development like product development—with systematic feedback loops, measurable outcomes, and continuous improvement.You can find James at jamesbirchler.com, LinkedIn, and Substack. ToolHive Unlocks the Full Value of MCP & Your AI AgentsSo you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems.ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP).ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe.Leaders trust ToolHive to put MCP into production and put their AI agents to work.ToolHive is open source, so get started for free at toolhive.dev Join us at ELC Annual 2025ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections!🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES:Why founders should seek coaching earlier rather than waiting for a crisis to occur (2:47)The high stakes of ignoring this critical advice & how this leads to communication & Scaling problems (4:50)The importance of effective communication channels & leadership mechanisms before pressure increases (6:31)How investing a small amount in coaching early on can prevent hundreds of thousands of dollars in future costs (8:07)Frameworks for cultivating self-awareness / leadership blind spots (11:06)James's practice of "designing your day" around a desired identity, not just a list of tasks (12:30)Why designing your day is about intentionality (15:13)How this practice leads to better relationships & opportunities to reflect (17:44)...
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    51 mins
  • Balancing shifting priorities, leveraging your founder network, and navigating cost vs. value w/ Sumeet Vaidya @ Crafting

    Balancing shifting priorities, leveraging your founder network, and navigating cost vs. value w/ Sumeet Vaidya @ Crafting
    Jul 31 2025

    In this episode, we cover some of the most important founder challenges, including engineering management, prioritization / time management principles, analyzing the market, and making the decision to sell to enterprise early on with Sumeet Vaidya, Co-founder & CEO @ Crafting. He unpacks the story behind Crafting & the decision to found it along with how he knew he was the right person to lead this org. Patrick & Sumeet dissect GTM strategies when it comes to enterprise sales, how funnel optimization for sales works, and making business decisions while navigating cost vs. value. We also chat about the importance of forming founder-to-founder connections as you navigate the founder journey – it’s definitely better with others than alone.

    ABOUT SUMEET VAIDYA

    Prior to co-founding Crafting, Sumeet has scaled engineering teams and built products at Meta, Uber, and Discord. He has worked on developer platforms, consumer products, marketplaces, enterprise integrations, and more. He also angel invests and advises startup founders, motivated by helping sharp people solve real problems to build successful businesses.

    Join us at ELC Annual 2025

    ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections!

    🔗 Get your ticket now → https://sfelc.com/annual2025

    SHOW NOTES:
    • The origin story behind Crafting & challenges in eng management (2:56)
    • Dissecting Sumeet’s decision to found the company (5:28)
    • Questions & processes for analyzing founder conviction from an investor POV (7:00)
    • How to know if you’re the right person to lead this org (8:45)
    • Analyzing the market / competitors & determining your product’s differentiators (11:34)
    • Go-to-market strategy & enterprise sales (14:07)
    • Optimizing for enterprise sales early on / understanding PMF (16:15)
    • Why you need to leverage your founder network for advice (17:45)
    • Frameworks for determining gaps in the sales funnel (20:55)
    • Exploring happiness and connection (22:31)
    • Sumeet’s perspective on prioritization & time management as a founder (24:45)
    • Balancing cost vs. value in business decisions (27:11)
    • Remote vs. in-person team dynamics for eng & sales (31:00)
    • Hiring the first non-engineer (34:45)
    • Rapid fire questions (38:54)
    LINKS AND RESOURCES
    • https://www.themarginalian.org/

    This episode wouldn’t have been possible without the help of our incredible production team:

    Patrick Gallagher - Producer & Co-Host

    Jerry Li - Co-Host

    Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

    Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

    Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/
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    43 mins
  • Early team building and pivoting to competitive advantage as a solo founder w/ Tony Dong @ Propel

    Early team building and pivoting to competitive advantage as a solo founder w/ Tony Dong @ Propel
    Jul 17 2025
    Tony Dong (Founder & CEO @ Propel) shares how he navigated the early days of solo founding, hired eight engineers in a month, and rapidly built early momentum. We explore how he leveraged existing relationships, storytelling, and competitive advantage analysis to pivot Propel’s focus, providing value quickly in your product, and building credibility for early sales. Plus, support systems for early founders, strategies for going broad vs. narrow, and how Tony’s current tech stack / AI tools are accelerating how they build.ABOUT TONY DONGTony is the Founder & CEO of Propel, an AI engineering agent that integrates into your team’s workflows to automate engineering tasks and elevate developer productivity.Before Propel, Tony served as the VP of Engineering at Rippling, where he led the development of the company's Platform and HR products. As a seasoned entrepreneur, Tony was also the founder and CTO of a YC-backed startup and held key engineering roles at Periscope, TellApart, and Twitter.Join us at ELC Annual 2025ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections!🔗 Get your ticket now → https://sfelc.com/annual2025SHOW NOTES:Tony’s journey transitioning from eng leader to founder (2:29)Lessons learned from founding Pershop & working @ Rippling (3:47)The origin of Propel & turning frustration into a startup idea (5:58)Recognizing the right moment to pivot your product (7:55)Incorporating competitive advantage analysis into strategic decision making (10:29)Accelerating user research & establishing credibility in your product area (12:32)The process of pivoting / solving highly valuable problems (14:15)Examples of how a product can quickly prove its value to customers (16:35)Strategies for proving value quickly during the early product building stages (17:51)Dynamics of being a solo founder & early team building (19:30)Pitching Propel as a solo founder / building support systems (21:13)How Tony hired a team of eight within one month, using relationships and public storytelling (23:32)How hiring contractors & sharing publicly helped drive early team building (25:19)Frameworks for attracting talent as a competitive advantage (27:44)Assessing hiring candidates: using every available AI tool, real projects & hands-on collaboration (31:09)Tony’s current stack & AI tools enhancing team productivity and innovation (33:49)The impact of AI on early-stage company building (35:39)Tony’s thoughts on capturing a broad market @ Propel (37:03)Understanding today's fundraising landscape (39:00)Rapid fire questions (40:48)LINKS AND RESOURCESUnreasonable Hospitality: The Remarkable Power of Giving People More Than They Expect - Today, every business can choose to be a hospitality business—and we can all transform ordinary transactions into extraordinary experiences. Featuring sparkling stories of his journey through restaurants, with the industry’s most famous players like Daniel Boulud and Danny Meyer, Will Guidara urges us all to find the magic in what we do—for ourselves, the people we work with, and the people we serve.The Secret Life of Groceries: The Dark Miracle of the American Supermarket - In this exposé, author Benjamin Lorr pulls back the curtain on this highly secretive industry. Combining deep sourcing and immersive reporting, Lorr leads a wild investigation in which we learn the secrets of Trader Joe's success from Trader Joe himself, why truckers call their job "sharecropping on wheels," what it takes for a product to earn certification labels like "organic" and "fair trade," the struggles entrepreneurs face as they fight for shelf space, including essential tips, tricks, and traps for any new food business, the truth behind the alarming slave trade in the shrimp industry and much more.CAFEC Pour-Over Flower Dripper DEEP 27 - Tony’s favorite coffee dripper!This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/
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    46 mins
  • Building insight engines, emotionally intelligent AI products & blending PLG / enterprise GTM w/ Aiswarya Sankar @ Entelligence.AI

    Building insight engines, emotionally intelligent AI products & blending PLG / enterprise GTM w/ Aiswarya Sankar @ Entelligence.AI
    May 29 2025

    How do you build an AI product that engineers actually enjoy? ****Aiswarya Sankar, co-founder of Entelligence.AI, reveals how her team is creating an AI-powered “insight engine” that supports (and celebrates) the work of engineering teams. We explore how Entelligence.AI evolved from code search to a full-stack insight engine that reduces merge times, improves code quality, and makes teams more effective. Aiswarya explains how personalization, context awareness, and positive reinforcement drive adoption. Plus Aiswarya unpacks the psychology of feedback, how to make AI feel collaborative (not corrective), and their dual GTM strategy blending product-led growth with enterprise sales. Whether you’re building an AI-native product, leading an eng org, or just curious about the future of developer tools, this episode is packed with insights.

    ABOUT AISWARYA SANKAR

    Aiswarya Sankar is the co-founder of Entelligence.AI, an AI-powered engineering intelligence platform that streamlines development, enhances collaboration, and accelerates engineering productivity. Previously, Aiswarya has held roles at Intel, Google, and Uber. She has a degree in Electrical Engineering and Computer Science from UC Berkeley.

    Join us at ELC Annual 2025

    ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections!

    🔗 Get your ticket now → https://sfelc.com/annual2025

    SHOW NOTES:
    • Aiswarya’s eng leadership background & founder journey (3:22)
    • The early “mini search engine” project that ignited Entelligence.AI (6:23)
    • Behind the decision to start with code search and what it unlocked (7:44)
    • From Uber to full-time founder: the leap into AI entrepreneurship (9:03)
    • What Entelligence.AI does & who it serves (10:12)
    • Deconstructing engineering pain points into product strategy (12:04)
    • Insights from engineering users that informed the product’s direction (13:52)
    • Building customizable, context-aware intelligence for teams (16:47)
    • Lessons learned on balancing proactive feedback and team culture (19:24)
    • Use sprints & rituals to surface hidden team contributions (21:05)
    • Emerging trends in how software is being built and how teams are measured (23:45)
    • Key principles for designing AI-based systems to align with evolving workflows (26:49)
    • Strategies for measuring qualitative & quantitative impact (29:27)
    • Frameworks for humanizing AI & creating enjoyable AI experiences (31:42)
    • Identifying the psychological needs / drivers of your users (33:14)
    • Rapid fire questions (36:47)
    This episode wouldn’t have been possible without the help of our incredible production team:

    Patrick Gallagher - Producer & Co-Host

    Jerry Li - Co-Host

    Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

    Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

    Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/
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    41 mins
  • The Startup Epoch: Rethinking Company Building & Defensibility in an AI World w/ Craig McLuckie @ Stacklok

    The Startup Epoch: Rethinking Company Building & Defensibility in an AI World w/ Craig McLuckie @ Stacklok
    May 1 2025

    AI is reshaping the fundamental economics of startups—lowering product development costs, compressing GTM cycles, and rewriting the rules of competition. In this episode, Craig McLuckie (Co-Founder & CEO @ Stacklok, co-creator of Kubernetes) unpacks “the epoch of the startup,” a moment of massive disruption where fast-moving founders have a unique edge over incumbents. We explore how Craig is navigating this new era from rethinking cost structure, value capture and defensibility to leveraging open-source, community, and asymmetric advantages as core pillars of Stacklok’s strategy. Craig shares lessons from pivotal product shifts, frameworks for identifying moats, and the broader societal implications of AI-driven disruption. Whether you’re leading a startup, pivoting in the face of AI, or thinking about your next big move, this conversation offers a strategic playbook for thriving in today’s shifting landscape.

    ABOUT CRAIG MCLUCKIE

    Craig is the CEO and co-founder of Stacklok, where his team is working to tip AI code generation on its side, from vertical, closed solutions to horizontal, aligned systems. Craig was previously CEO and co-founder of Heptio, which was acquired by VMware in 2018; he has also led product and engineering teams at Google and Microsoft. Craig is a co-creator of Kubernetes and he bootstrapped and chaired the Cloud Native Computing Foundation.

    ABOUT STACKLOK

    Stacklok is working to tip AI code generation on its side — transforming vertically integrated (and closed) solutions into horizontal, open systems. Their CodeGate.ai project is an important step in this direction; it's a bridge between AI assistants and LLMs that gives developers control of their privacy and delivers richer results.

    Join us at ELC Annual 2025

    ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections!

    🔗 Get your ticket now → https://sfelc.com/annual2025

    SHOW NOTES:
    • Why this moment is “the epoch of the startup” (2:03)
    • How AI shifts startup economics: from cost structures to value capture (4:18)
    • Why incumbents struggle during disruption—and how startups can win (8:17)
    • The origin story behind Stacklok & lessons from Craig’s pivot (11:04)
    • Frameworks for identifying asymmetric advantages as a founder (14:48)
    • How to map your unique asymmetric advantages to new opportunities and secure stakeholder buy-in (16:34)
    • Rethinking defensibility & value capture in the AI era (16:29)
    • How Craig applied cost, GTM & product perspectives to strategic pivots @ Stacklok (18:07)
    • Building investment theses: Aligning cultural strengths & asymmetric advantages with evolving opportunities (20:05)
    • Determining your startup’s investment themes (22:53)
    • Structuring experiments & validating opportunities (24:15)
    • Defensibility & building community-driven moats in early ideation phases (26:54)
    • Signals of early community-product alignment (31:24)
    • Conversation frameworks to assess asymmetric advantages (32:22)
    • Societal implications of AI disruption & the “startup epoch” (35:14)
    • Rapid fire questions (38:12)
    This episode wouldn’t have been possible without the help of our incredible production team:

    Patrick Gallagher - Producer & Co-Host

    Jerry Li - Co-Host

    Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

    Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

    Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/
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    42 mins
  • Building platforms, ecosystems & open-source communities: Lessons from Viam & MongoDB w/ Eliot Horowitz @ Viam

    Building platforms, ecosystems & open-source communities: Lessons from Viam & MongoDB w/ Eliot Horowitz @ Viam
    Apr 10 2025
    How do you build a platform that accelerates innovation by 10x-100x? Eliot Horowitz (CEO & Founder @ Viam) shares how insights from building MongoDB are shaping Viam’s approach to platform ecosystem development, user-centricity and open-source strategy. We explore the origin story behind Viam, principles for platform design for hardware/software development, modular systems, seamless APIs, and finding the right abstraction layers for your product. Plus we cover cultivating developer communities, and frameworks to anchor your business-model and pricing. This episode is packed with insights on platform building, fostering ecosystems, driving user-centric innovation.ABOUT ELIOT HOROWITZEliot Horowitz is the Founder and CEO of Viam, an engineering platform unlocking AI, automation, and data for devices in the physical world. With a deep commitment to advancing technology, Eliot leads Viam in helping companies build solutions across robotics, food and beverage, climate, marine, industrial manufacturing, and more.A career software developer and technology leader, Eliot co-founded MongoDB in 2007, writing the core code base for the pioneering database and leading the engineering and product teams for 13 years as CTO. MongoDB, which went public in 2017, has since reached a market cap of over $20 billion. Before MongoDB, he co-founded the ecommerce company ShopWiki and served as CTO, and he began his career in software development in the R&D group of adtech firm DoubleClick.Eliot is passionate about using technology to address pressing societal issues, including working with WAVS to protect marine life in the North Atlantic and supporting Billion Oyster Project’s work to help restore New York Harbor’s ecosystem.Join us at ELC Annual 2025ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections!🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES:The origin story of founding Viam (2:07)How Viam can be a game-changing platform, accelerating robotics software & hardware 10x to 100x (3:43)The ideation journey behind Viam: Building a platform that simplifies the integration of hardware and software development (5:22)Solving challenges with seamless APIs, a modular system, the right abstraction layers, and a comprehensive platform (9:04)Key questions for identifying the right abstraction layers at Viam (10:42)Optimizing your platform for flexibility and ease of use (12:42)The evolution of product building, from first-hand experience to customer-driven (15:43)How Eliot’s MongoDB Experience shaped Viam’s user-centric approach, open-source strategy, business model & ecosystem approach (17:58)Cultivating developer communities & leveraging community insights at MongoDB & Viam (22:11)Frameworks for deciding on your business model & pricing (24:02)Eliot’s approach to building developer tools & products used by engineers (25:34)Aligning your eng team & stakeholders on the product vision (29:01)What it means to deeply understand engineers and how they interact with your product (30:20)Strategies for eng leaders to better connect with customers (33:48)Viam’s real-world applications & what’s next (35:41)Rapid fire questions (38:31)LINKS AND RESOURCESViam - At Viam, we believe in the power of technology to make our world smarter, happier, and more sustainable. We're building a revolutionary engineering platform for problem-solving in the physical world, so that innovators from all disciplines can address humanity's most complex challenges with practical solutions. Together with our partners, we're committed to making a lasting positive impact on industries, communities, and the planet.This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/
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    42 mins
  • From early days to IPO: Scaling leadership, enterprise growth, product ownership, & outgrowing your failure modes w/ Jon Hyman @ Braze

    From early days to IPO: Scaling leadership, enterprise growth, product ownership, & outgrowing your failure modes w/ Jon Hyman @ Braze
    Mar 13 2025
    Jon Hyman (Co-Founder and CTO @ Braze) shares the pivotal moments that shaped the company - from being the only person on call in the early years to identifying (and pivoting) product-market fit. Jon discusses how they navigated early-stage failure modes, carved out areas of product ownership, and made the shift to enterprise customers. Plus how leadership priorities evolve pre- vs. post-IPO and the next evolution of Jon’s leadership growth after almost 14 years at Braze.ABOUT JON HYMANJon Hyman is the co-founder and chief technology officer of Braze, the customer engagement platform that delivers messaging experiences across push, email, in-app, and more. He leads the charge for building the platform’s technical systems and infrastructure as well as overseeing the company’s technical operations and engineering team.Prior to Braze, Jon served as lead engineer for the Core Technology group at Bridgewater Associates, the world’s largest hedge fund. There, he managed a team that maintained 80+ software assets and was responsible for the security and stability of critical trading systems. Jon met cofounder Bill Magnuson during his time at Bridgewater, and together they won the 2011 TechCrunch Disrupt Hackathon. Jon is a recipient of the SmartCEO Executive Management Award in the CIO/CTO Category for New York. Jon holds a B.A. from Harvard University in Computer Science.ABOUT BRAZEBraze is the leading customer engagement platform that empowers brands to Be Absolutely Engaging.™ Braze allows any marketer to collect and take action on any amount of data from any source, so they can creatively engage with customers in real time, across channels from one platform. From cross-channel messaging and journey orchestration to Al-powered experimentation and optimization, Braze enables companies to build and maintain absolutely engaging relationships with their customers that foster growth and loyalty. The company has been recognized as a 2024 U.S. News & World Report Best Companies to Work For, 2024 Best Small & Medium Workplaces in Europe by Great Place to Work®, 2024 Fortune Best Workplaces for Women™ by Great Place to Work® and was named a Leader by Gartner® in the 2024 Magic Quadrant™ for Multichannel Marketing Hubs and a Strong Performer in The Forrester Wave™: Email Marketing Service Providers, Q3 2024. Braze is headquartered in New York with 15 offices across North America, Europe, and APAC. Learn more at braze.com.Join us at ELC Annual 2025ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections!🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES:What Jon learned from being the only person on call for his company’s first four years (2:18)Knowing when it’s time to get help managing your servers, ops, scaling, etc. (5:05)Establishing areas of product ownership & other scaling lessons from the early days (8:48)Frameworks for conversations on splitting of products across teams (11:22)The challenges, complexities & strategies behind assigning ownership in the early days (14:02)Founding Braze (17:23)Why Braze? The story & insights behind the original vision for Braze (19:30)Identifying Braze’s product market fit (21:56)Early-stage PMF challenges faced by Jon & his co-founders (25:03)Pivoting to focus on enterprise customers (27:10)“Let’s integrate the SDK right now” - founder-led sales ideas to validate your product (28:45)Behind the decision to hire a chief revenue officer for the first time (33:25)The evolution of enterprise & its impact on Braze’s product offering (36:04)Growing out of your early-stage failure modes (38:22)Why it’s important to make personnel decisions quickly (40:44)Setting & maintaining a vision pre IPO vs. post IPO (43:43)Jon’s next leadership evolution & growth areas he is focusing on (49:13)Rapid fire questions (50:44)LINKS AND RESOURCESWhen We Cease to Understand the World - Benjamín Labatut’s fictional examination of the lives of real-life scientists and thinkers whose discoveries resulted in moral consequences beyond their imagining. At a breakneck pace and with a wealth of disturbing detail, Labatut uses the imaginative resources of fiction to tell the stories of Fritz Haber, Alexander Grothendieck, Werner Heisenberg, and Erwin Schrödinger, the scientists and mathematicians who expanded our notions of the possible.This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/
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    57 mins
  • Shifting from founder-led sales to repeatable GTM, differentiating on responsiveness/customer support & the art vs. science of product building w/ Stephen Whitworth @ incident.io

    Shifting from founder-led sales to repeatable GTM, differentiating on responsiveness/customer support & the art vs. science of product building w/ Stephen Whitworth @ incident.io
    Feb 13 2025

    Stephen Whitworth (Co-Founder & CEO @ incident.io) joins us to discuss strategically differentiating your product based on responsiveness / customer support and the shift from founder-led sales to repeatable / scaleable GTM. You’ll learn how they landed major logo companies like Netflix, Airbnb & Etsy and how you can apply that to your early enterprise customers. Plus the story behind their co-founder team transition from part-time to full-time, a product-market-fit “cheat code” that helped them decide on incident.io, how they generated 750 demo requests on launch, key qualities when hiring your first AEs to help scale yourself out of sales activities, and Stephen’s perspectives on the art vs. science of product building.

    ABOUT STEPHEN WHITWORTH

    Stephen is the co-founder and CEO of incident.io, where they're building incident management tooling that's so good, people will break things on purpose. A software engineer by training, he previously led engineering teams at Monzo, and co-founded Ravelin, a fraud detection startup.

    ABOUT INCIDENT.IO

    Incident.io provides a platform to help you better respond to and learn from incidents. Helping you seamlessly orchestrate incident response from start to finish.

    Join us at ELC Annual 2025

    ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections!

    🔗 Get your ticket now → https://sfelc.com/annual2025

    SHOW NOTES:
    • The early days of incident.io (2:45)
    • Transitioning from working on incident.io part-time to full-time (5:32)
    • Tactics that helped the co-founder team decide on incident.io over other ideas (8:21)
    • How incident.io received 750 demo requests right away (11:07)
    • incident.io’s product-market fit cheat code & identifying internal PMF (12:24)
    • How incident.io landed major logo companies like Netflix, Airbnb & Etsy (14:32)
    • Strategies to differentiate yourself from competitors in the B2B space & why execution and responsiveness can beat technological advantage (17:30)
    • Stephen’s perspective on “inflicting software” on people & how that changes your product, org & GTM strategy downstream (21:14)
    • Enterprise sales insights that surprised Stephen (23:56)
    • Why GTM is infinitely harder than product & how founders can start to scale themselves out of sales activities (27:21)
    • What incident.io’s GTM team looks like now (32:12)
    • Differentiating in B2B enterprise on customer support & the strategic role of support at incident.io (34:20)
    • Why a culture of responsiveness and support can be your hidden advantage (37:03)
    • Rapid fire questions (39:26)
    LINKS AND RESOURCES
    • Billion Dollar Whale - Tom Wright and Bradley Hope’s epic tale of white-collar crime on a global scale revealing how a young social climber from Malaysia pulled off one of the biggest heists in history.
    This episode wouldn’t have been possible without the help of our incredible production team:

    Patrick Gallagher - Producer & Co-Host

    Jerry Li - Co-Host

    Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

    Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

    Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/
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    46 mins