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.

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.

Clipboard Health is looking for the next generation of exceptional software engineering leaders, not just managers. They’re a profitable unicorn, backed by top-tier investors, and they take the craft of engineering management seriously.

Clipboard Health matches highly qualified healthcare workers with nearby facilities to fulfill millions of shifts a year - revolutionizing healthcare staffing with a fast, flexible, and user-friendly platform.

Learn more & browse their open roles at clipboardhealth.com/engineering

• 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)

• 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.

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/

Michael is the founder and CEO of WorkOS, a developer platform that enables companies to become Enterprise Ready through features like Single Sign-On (SAML). Their customers include many of the fastest-growing startups including Webflow, Drata, Loom, and +200 others. Before WorkOS, Michael co-founded Nylas and studied CS at MIT.

Clipboard Health is looking for the next generation of exceptional software engineering leaders, not just managers. They’re a profitable unicorn, backed by top-tier investors, and they take the craft of engineering management seriously.

Clipboard Health matches highly qualified healthcare workers with nearby facilities to fulfill millions of shifts a year - revolutionizing healthcare staffing with a fast, flexible, and user-friendly platform.

Learn more & browse their open roles at clipboardhealth.com/engineering

• Michael’s first journey as a founder @ Nylas (2:21)
• Great product experience happens in the margins (6:09)
• Why prioritizing the details of the last 3% of your product is key (7:17)
• How obsession, taste, care, and the intangible wow factor impact your product experience (9:24)
• Study and design the business model like you would the product experience / system architecture (12:59)
• Designing WorkOS’s early business model & prioritizing early product decisions (16:39)
• The Philosophy of 'You Pay When We Create Value For Your Business' and Why It Works (20:04)
• ”Pricing is the API between your business model and your customer” (22:10)
• Why you should iterate on pricing the same way you iterate your product (24:18)
• How to navigate making a pricing decision - and think through options like public pricing, tiers, usage, etc. (27:21)
• Questions Michael asks to determine pricing of different WorkOS products (30:54)
• Pricing is all about considering trade-offs - start with “what’s the ideal buying experience and pricing structure for your consumer?” (32:53)
• Factors to consider when changing prices or revisiting pricing assumptions (34:00)
• Rapid fire questions (36:28)

• ACQUIRED - Every company has a story. Learn the playbooks that built the world’s greatest companies — and how you can apply them as a founder, operator, or investor.
• The Challenger Sale: Taking Control of the Customer Conversation - The need to understand what top-performing reps are doing that their average performing colleagues are not drove Matthew Dixon, Brent Adamson, and their colleagues at Corporate Executive Board to investigate the skills, behaviors, knowledge, and attitudes that matter most for high performance. And what they discovered may be the biggest shock to conventional sales wisdom in decades.
• Founder-Led Sales: Sales Simplified for Startup Founders - Founder-led sales can be challenging, as it requires expertise and charisma to sell a product or service. Potential customers may be skeptical of the founder's intentions. However, founder-led sales can also be rewarding, providing valuable feedback and insights to improve the product or service, building strong customer relationships, and leading to repeat business and positive recommendations. It's a powerful tool for business growth.

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/

Jake Schwartz (Co-Founder @ Endorsed) joins us to talk about de-risking the co-founder relationship! We cover how they built in stress-tests to validate co-founder fit, how to host a hackathon to stress-test your partnership, and why reference calls are an important component of finding a co-founder. Plus the story behind Jakes's transition from Life360 to co-founding Endorsed, prioritizing which projects to focus on, early-stage product strategy considerations around AI, and why you need to approach your customers with a genuine sense of curiosity.

Jake is an engineering leader, entrepreneur, and technology investor based in San Francisco. From building his first website at age 8 to shipping large-scale software at Apple and overseeing the development of the flagship Life360 app, Jake has tackled engineering challenges at every scale. At Life360, he jump-started the European engineering office, helping scale the company from 50 to 500 people and reaching an audience of 70M users worldwide. He is now the co-founder of Endorsed.com, an AI recruiting platform that helps teams hire better and faster.

• The origin story behind Endorsed (1:59)
• What inspired Jake to dive into the world of hiring (6:05)
• The whiteboarding conversation between Jake & his co-founder (7:12)
• Jake’s transition from Life360 to starting Endorsed (9:24)
• Insights on experimentation & stress-testing the co-founder relationship (11:23)
• Deciding what experiments to pursue further or toss (13:16)
• Strategies for de-risking the co-founder relationship & transition to a startup (14:30)
• Organizing a hackathon to test the co-founder relationship (16:50)
• What Jake learned from the co-founder hackathon & tips for trying your own (18:07)
• Main objectives for co-founder reference calls (19:59)
• Dissecting Jake’s decision-making process behind the different pivots (21:27)
• Why they decided to commit to selling direct vs. building an API layer (24:38)
• Recommendations for sorting through problems & deciding which to solve (25:57)
• Approach your customers with curiosity (29:31)
• Early-stage considerations for AI in terms of product strategy (30:33)
• Rapid fire questions (33:34)

• Steve Jobs “Keeper of the Vision” quote
• The Three-Body Problem - Set against the backdrop of China's Cultural Revolution, a secret military project sends signals into space to establish contact with aliens. An alien civilization on the brink of destruction captures the signal and plans to invade Earth. Meanwhile, on Earth, different camps start forming, planning to either welcome the superior beings and help them take over a world seen as corrupt, or to fight against the invasion.

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/

Nancy Wang, Venture Partner @ Felicis and Former GM @ AWS, joins us to discuss strategies & considerations for scaling costs, becoming enterprise ready on Day 1, maintaining business health, and more. We cover Nancy’s journey as a founding product manager at AWS and how those lessons have guided her throughout her career & how she coaches founders. We address why it’s paramount to prioritize scaling costs early on as a founder, how to make design decisions with cost considerations in mind, and what tools you can employ to identify the features that most benefit your customers. Finally, Nancy & Patrick talk about how to land on your V1 while being enterprise-ready from the get-go and trends / growth opportunities that founders should be aware of today.

Nancy is a product & engineering executive, advisor, and investor who is passionate about creating seats at the table for women, especially within engineering and technical roles. Most recently, as General Manager of Data Protection at AWS Nancy scaled her engineering teams from 18 to 100+, all while averaging over 45% female and delivering triple-digit YoY growth businesses that delivered over $1B+ ARR including its integration into Amazon’s suite of AI products.

Previously, Nancy launched Rubrik’s (NYSE: RBRK) first Cloud SaaS business, growing their company valuation to over $4B in less than 2 years. Rubrik IPO’ed in Q22024, as one of the fastest-growing enterprise SaaS businesses. As Founder and Board Chair of the non-profit Advancing Women in Tech since 2016, Nancy helps prepare women and underrepresented minorities for leadership roles. She is currently a Venture Partner at Felicis, looking after their infrastructure and cybersecurity investments.

• Nancy’s journey as the founding product manager for AWS (2:57)
• Why AWS was launched & how it scaled (5:31)
• How to build a successful business within the confines of your org (7:41)
• Insights into the people side of scaling your business (10:25)
• Understanding the cost component of scaling / founding (13:12)
• Ensure your processes aid the overall health & mission of the company (15:43)
• Why founders need to prioritize scaling costs early (17:15)
• Breaking down different cost scenarios founders may face (20:08)
• Avoiding design decisions that create exponential cost but linear revenue (22:51)
• Considerations for being enterprise-ready from Day 1 (28:10)
• Think of hyperscalers like a T-rex (32:31)
• Nancy’s lessons learned on landing your V1 while being enterprise-ready (34:05)
• Questions founders can ask to help identify their market & where to start (39:24)
• Current trends / growth opportunities for founders to consider (40:59)
• Rapid fire questions (43:31)

• CEO Excellence - McKinsey & Company led a research effort to identify those CEOs whose companies grew demonstrably healthier during their tenures, looking across more than 20 years’ worth of data on 7,800 CEOs from 3,500 public companies across 70 countries and 24 industries to further identify those whose actions have led to breakaway success.

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/

In this episode of Engineering Founders, we discuss something we’ve never covered before – why you SHOULDN’T be a founder! Travis McPeak (CEO & Co-Founder @ Resourcely) joins the pod to share his founder story and questions to ask yourself to truly validate if the founder lifestyle is right for you. We also address how to de-risk your org & understanding the two main kinds of risks; things to consider when raising capital, like going bootstrap vs. VC; balancing the wedge vs. long-term vision; and how to create a lifestyle that supports you as a founder.

Travis is currently Co-Founder and CEO of Resourcely which enables platform, security, and DevOps engineering teams to offer simple self-service to their developers. Prior to Resourcely, Travis served as the Head of Product Security at Databricks. With an extensive background in application and cloud security, Travis enjoys building automated solutions to hard and critical problems. Prior to joining Databricks, Travis led the team at Netflix that automates application security including vulnerability management, asset inventory, and security reviews. During his time at Netflix Travis also built Repokid, a tool that automates least privilege at scale. Previously Travis led large security initiatives at IBM, HPE, and Symantec.

Travis is an extrovert and enjoys sharing ideas and meeting new people. In his spare time, Travis leads the OWASP Bay Area chapter, mentors people getting started in security, and loves to help startups. He is an advisor for four companies including Ermetic and Appaegis. Travis is an angel investor in startups including Temporal, Truffle Security, and AuthZed.

" The stress is going to get you anyway, and your mindset about how you approach that stress is going to make the difference. So you're the one that's like, ‘All right, it's challenge time. Let's do this.’ Or are you like, ‘I'm overwhelmed right now. This feels too hard for me and then you go like hide in your shell.’”

- Travis McPeak

• The origins behind Resourcely & Travis’s founder journey (1:52)
• Questions to ask before starting a company (5:07)
• What it was like for Travis to answer these questions for himself (8:00)
• Processes for becoming more self aware (9:06)
• What you should do / think about before starting a company (11:12)
• Methods for de-risking the two main kinds of risks (14:28)
• Resources for better understanding de-risking business risk (16:30)
• Identifying when to go bootstrap vs. VC for funding (19:00)
• Frameworks for differentiating which investor path is the right fit (21:30)
• Presentation strategies & considerations when raising capital (22:48)
• Linking together the wedge vs. long-term vision (28:21)
• How Travis was able to have 45 conversations in the first 45 days (32:31)
• Adapting to the founder lifestyle & increasing your odds for success (34:25)
• Strategies for prioritization & developing discipline (35:39)
• Practice rigorous scheduling (40:23)
• Rapid fire questions (41:49)

• The Mom Test - Rob Fitzpatrick’s quick and easy handbook about how to get more learning and more sales out of your customer conversations. Even when everyone is lying to you.
• Tomorrow, and Tomorrow, and Tomorrow - Gabrielle Zevin's dazzling and intricately imagined novel that examines the multifarious nature of identity, disability, failure, the redemptive possibilities in play, and above all, our need to connect: to be loved and to love. Yes, it is a love story, but it is not one you have read before.

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/