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An interview series featuring product leaders in tech about the lessons they've learned building great products and teams. Hosted by Allen Pike of Steamclock, new episodes every 3 weeks.
27 Episodes
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Teresa Torres, author of Continuous Discovery Habits, joins to share lessons from her popular and acclaimed book. We talk about the benefits of constantly talking to customers, why it can be worth seeking delight rather than strictly building products in terms of problems, how to avoid choosing perverse outcomes and metrics, and how to get the truth from customers – despite their aspirational overconfidence.
Luke Hutscal, Principal Engineer at Clio – formerly of Shopify and Testflight – joins to talk about finding ways to learn rapidly, the downsides of a mercenary mindset, spending time with people who intimidate you, building a coaching village, making wrong things look wrong, choosing boring technology, resume-driven development, and putting in the reps to get great at hiring.
James Clift, Founder and CEO of Durable and VisualCV, joins us to talk about helping folks build great businesses, staying long-term optimistic yet short-term pessimistic, choosing between exciting ideas vs. clearly profitable ones, the distraction of “fake work”, getting good at rapidly trying and killing ideas, lessons learned from two years of building on LLMs, and the longevity of non-chat workflows.
Eric Amodio, creator of GitLens, GitKraken CTO, and former Principal Engineer on VS Code, joins us to talk about founding products by scratching your own itch, building GitLens from an idea to tens of millions of users, the audacity of charging for software, the origins of github.dev and Copilot at Microsoft, LLMs as a new layer of abstraction for developers, and how GitKraken is helping engineers understand large codebases faster.
Merci Grace, CEO and co-founder of Panobi, and former partner at Lightspeed Ventures and first Head of Growth at Slack, shares lessons about growth as a discipline, pitfalls of fundraising and her “Marauder’s Map” to raising capital, best practices for starting and scaling growth teams, and her vision for making metrics and growth tooling far better.
Ian Crosby, founding CEO of Bench and now Teal, talks building Bench from zero to hundreds, how vertical SaaS is transforming SMB startups, what it really takes to become highly profitable, why Teal hires for “boring competence”, paying highly for top talent, the psychology of firing, and the limits of culture docs.
Paul Lambert, CEO and founder of Quilt and former Director at Google’s Area 120, joins Allen to talk society-scale problems, why searching for product-market fit is overrated, the power of building a better mousetrap, why the “internal incubator” model usually fails, how modern hardware startups iterate rapidly, and why different cities lend themselves to different startups.
Dennis Pilarinos, founder of Buddybuild and now Unblocked (and former Director at Microsoft, Amazon, and Apple) shares what he’s learned about product leadership. We talk about why you should build a product that is hard, how providing support is key to product culture, staying deeply curious about what’s not working, cutting down recurring meetings, and how startups with distribution outcompete the giants.
Honeycomb.io co-founder and CTO Charity Majors joins Allen to share what she’s learned growing Honeycomb from idea to 170-person distributed company, including what goes into being a good manager beyond supporting your reports, how to build a team that feels supportive and safe while still keeping boundaries and limits, systems thinking for teams and cultures, the difference between generic company values and ones that take a stand, and why having a healthy culture is more important than having a novel one.
Ada co-founder David Hariri joins Allen to talk about an audacious product discovery process that kicked off a 250-employee startup, limitations of hand-scripted workflows, strengths and weaknesses of LLM techniques like code execution, RAG, and function calling, and how support automation may create whole new business models.
Michael Lopp, aka Rands, joins Allen to talk about the fundamental need for growth, finding your team’s core motivations, the value of writing for developing clear thinking, the joys and perils of writing a book, the art of a compelling presentation, habits for editing and refining writing, and fostering clarity of responsibility – and curiosity – on your team.
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 perform both product and engineering work, the power of the Six Thinking Hats for making intense decisions, and the cultural responsibilities of senior leadership.
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.
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.
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.
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.
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.
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.
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.
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.
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