Lessons learned leading and building great products.
Hosted by Allen Pike. New episodes every 2 weeks.

Coaching New Managers, with Tiffany Conroy

Tiffany Conroy, former VP of Engineering at SoundCloud, shares what she’s learned about where new engineering managers stumble and how to support them, considering whether you want to be a manager at all, the value of explicitly asking those around you what success means, the power of having the confidence to say “I don’t know”, coaching managers through their first case of underperformance, how rigid role definitions hold back folks that preform both product and engineering work, the power of the Six Thinking Hats for making intense decisions, and the cultural responsibilities of senior leadership.

Ep 16

Sep 20, 2023 • 55 min

Telling Product Stories with Adam Lisagor of Sandwich

Adam Lisagor, Founder of Sandwich Video, shares what he’s learned about the nature of storytelling, about how to zoom out to tell the story of your product, understanding the emotional valence of our work, when pre-visualization and storyboarding does and doesn’t pay off, spotting great talent, the value of making pretty good decisions quickly, learning how to let go (a little bit) as a founder, execution-centric leadership vs. results-centric leadership, what kinds of products he likes to invest in, and making people glad to have worked with you.

Ep 15

Sep 06, 2023 • 56 min

Small But Mighty, with Ridwell Co-founder Aliya Marder

Aliya Marder, Co-Founder of Ridwell, joins us to share what she’s learned about the people-service mindset for product work, the demands of running a startup with a real-world footprint, the power of a higher mission for rallying a company, doing more with a smaller team, the pathologies of product backlogs, strategic communication past 150 employees, and the challenge of delegating for detail-oriented leaders.

Ep 14

Aug 23, 2023 • 40 min

Engineering Practices That Pay Off, with Later CTO Ian MacKinnon

Ian MacKinnon, CTO of Later and Mavrck, shares lessons learned building Later from founding to success to acquisition – and from the startups that weren’t so fortunate. We discuss early engineering practices that paid off, approaches for moving fast and tolerance for breaking (small) things in that pursuit, the pros and cons of PaaS platforms like Heroku, the insurmountability of building the wrong thing, the virtues of boring tech stacks, and Later’s successes using GPT-4 to migrate and modernize legacy codebases.

Ep 13

Aug 11, 2023 • 46 min

The Intersection of Business and Design, with former Shopify Product GM Lynsey Thornton

Lynsey Thornton shares what she learned helping Shopify grow almost 100x as GM of Core Product, VP of UX, and more. We review some common challenges companies hit as they scale, how to identify hires that have high growth potential, how different personalities contribute to team effectiveness, how to design an org for maximum impact, user research as a driver of strategic outcomes rather than checkbox-checking, and how to level up as a leader.

Ep 12

Jul 26, 2023 • 54 min

Product Management and Growing Up as an Organization, with Mailchimp’s Bruce Alderson

Bruce Alderson, Senior Product Manager at Mailchimp, shares what he’s learned in 20 years as a CTO, engineering leader, and product manager. We discuss the role of multi-disciplinarians in large orgs, engineering leadership vs. product leadership, the value of repeating yourself, finding the team members who can help share context across your company, what it means to stay focused as you scale, and being effective in the face of great uncertainty.

Ep 11

Jul 05, 2023 • 53 min

Building Developer Experiences at Slack, with Steve Gill

Steve Gill, Slack’s Director of DevRel Engineering, digs in to the craft of building great APIs for developers. We discuss the power of open source for informing platform work, building platforms that developers will actually use, the tricky issues around building and supporting SDKs, the concept of “raccooning” at Slack, how Slack’s new composable apps enable a whole new category of app, and the importance of saying “no” when a new feature isn’t working out.

Ep 10

Jun 13, 2023 • 48 min

Principal Engineering at AWS Scale, with Nik Pinski

Nik Pinski, Principal Engineer at AWS, shares how AWS is organized for autonomy and customer-centric product development, dealing with millions of events per second, and how Staff and Principal Engineer career tracks work across different software organizations.

Ep 9

May 17, 2023 • 47 min

Scaling a UX Org from 30 to 450, with Shopify’s former Head of Design Kyle Peatt

Kyle Peatt, former Head of Design at Shopify, shares lessons he learned helping rapidly scale Shopify’s UX team from 30 folks to 450. We talk about effective triads of product, design, and engineering leadership; building a UX organization without becoming a matrix org; the concept of UX Leads that manage folks from front-end engineering through design and content strategy; what makes a Staff Designer; and the importance of having an opinion in design leadership.

Ep 8

Apr 26, 2023 • 56 min

Effective and Scalable Machine Learning, with Opendoor Co-Founder Ian Wong

Ian Wong, co-founder of Opendoor, shares what he’s learned about machine learning and data science in his work as CTO of Opendoor and helping detect fraud at Square. We talk about the differences between descriptive and predictive ML, approaches to human-in-the-loop prediction, setting up a data science org to deliver real business impact, why so many internal tooling projects fail, and how leaders should be dividing their attention between top-level strategy and the details that really matter.

Ep 7

Apr 05, 2023 • 46 min

Architecting Apps at Netflix Scale, with Arik Devens

Netflix’s Arik Devens shares what he’s learned about architecting mobile apps with many millions of users, building from early adventures at Netscape and Palm up to architectural roles at Fitbit and Netflix. We talk about Netflix’s culture of small, high-trust teams; some of the pathologies of very large engineering teams; how to sell new architectural patterns to a team working on a large existing codebase; and the challenges of A/B testing hundreds of millions of users.

Ep 6

Mar 17, 2023 • 56 min

Making Billions with Ethical Onboarding, with Jaycee Day

Jaycee Day, a seasoned designer having worked at GitHub and Blinkist, shares what she learned designing a now world-famous app onboarding flow. We talk about onboarding flows, subscription and trial mechanics in apps, the tensions between ethics and short-term profiteering, the business model of mobile games, and A/B testing.

Ep 5

Feb 15, 2023 • 41 min

Solving Engineering Problems with DuckDuckGo’s Cate Huston

Cate Huston shares what she’s learned leading engineering teams at DuckDuckGo, Automattic, and Google. We talk about the challenges of hiring directors, what makes DuckDuckGo weird, supporting team happiness vs. team effectiveness, the quagmire of trying to measure team velocity, and the tradeoffs inherent in cross-platform app development.

Ep 4

Jan 20, 2023 • 39 min

Effectively Leading Technical Teams, with Khan Academy’s Shawn Jansepar

Shawn Jansepar, Director of Engineering at Khan Academy, shares what he’s learned about keeping product teams engaged, effective engineering practices and how to teach them, and building trust.

Ep 3

Dec 28, 2022 • 41 min

Lessons Learned Building Alexa, with Product Manager Polly Allen

Polly Allen, former Principal Product Manager on Amazon Alexa, shares what she’s learned about the challenging world of building products for voice and AI, as well the roles of data-driven decision-making and computing science education in product leadership.

Ep 2

Dec 07, 2022 • 43 min

How Not to Ship Your Org Chart, with veteran product designer Brad Ellis

Brad Ellis pulls from his experience designing for Square, Lyft, and many other products to share what he’s learned about the incredible value of user testing, scaling product design across a large org, and how to make great experiences instead of shipping your org chart.

Ep 1

Nov 16, 2022 • 58 min