Engineering Unblocked

In this episode, Tara Hernandez shares what 18 months of rigorous AI experimentation taught her at MongoDB — including why the initial results showed negative ROI, and where her team eventually found the real productivity wins. Tara explains how AI saved developers an hour a week on coding but had zero impact on product velocity, why the unglamorous outer loop improvements (Slack bots, log analysi...

In this episode, Lada Kesseler shares what she’s learned from a year of hands-on experience building with AI coding tools — including the three fundamental challenges that define how these tools work, and why understanding limitations is what makes you better at using them. Lada explains why “focus” is the critical concept most developers miss, how a dedicated committer agent will catch issues tha...

In this episode, Rob Zuber shares what he’s learned from over a decade as CTO at CircleCI — including why the current market requires CTOs to be more hands-on than ever, and why he doesn’t even know who his competitors are anymore. Rob explains how his team deliberately encourages AI tool sprawl to find the gaps, how CircleCI went from instant product-market fit to navigating constant transformati...

In this episode, Michael Lopp shares what he's learned leading engineering teams at Slack, Pinterest, and Palantir — including why AI is delivering real but modest productivity gains, and why junior engineers churning out AI-generated code is probably slowing teams down. Michael Lopp (Rands) brings three decades of engineering leadership experience to the AI conversation — revealing why he thinks...

In this episode, Titus Winters discusses his framework for optimizing software’s commercial value, why having humans in the deploy phase is pure toil, and how to think about engineering productivity investments. Titus Winters brings infrastructure thinking to software economics — revealing why manual deployment processes are pure overhead and how to quantify the true cost of defects with a (someti...

In this episode of Engineering Unblocked, Rebecca talks with Charity Majors, CTO of Honeycomb, to explore the myths of engineering productivity and the importance of building systems that enable “normal” engineers to succeed. Charity Majors tears down the myths of engineering exceptionalism — challenging the tech industry's worship of “10x developers” and advocating for systems that empower everyd...

In this episode of Engineering Unblocked, Rebecca sits down with Allan Leinwand, Chief Technology Officer at Webflow and serial engineering leader who has scaled teams at Slack, ServiceNow, and Shopify. Allan shares his unique perspective on what it takes to be a successful “scaling CTO” — the type of leader who comes in at inflection points to help companies hockey-stick their growth. Allan also...

In this episode of Engineering Unblocked, Rebecca sits down with Kathryn Koehler, Director of Developer Productivity at Netflix, to explore the unique challenges of scaling engineering at a 20-year-old company. The conversation dives deep into the complexities of building versus buying solutions, managing migrations across a multi-repo environment, and maintaining Netflix’s culture of freedom and...

In this episode of Engineering Unblocked, Rebecca sits down with Julianna Lamb, co-founder and CTO of Stytch, to explore the challenges of building and scaling engineering culture at a fast-growing startup. Julianna shares her journey from Plaid to founding an authentication and fraud prevention platform, and dives deep into the cultural decisions that shaped Stytch's 30-person engineering team. F...

In this episode, Rebecca sits down with Max Kanat-Alexander, Executive Distinguished Engineer for Developer Experience at Capital One, to explore the nuances of developer productivity and experience. The conversation dives deep into what actually drives — and what kills — productivity in engineering organizations. Max shares hard-won insights about why most developer experience initiatives fail (h...

In today’s episode, Rebecca chats with Kristen Foster-Marks, Head of Developer Experience at Depot. They discuss questionable “ghost engineer” research, why ethical, rigorous studies matter, and how developer experience makes a difference—even in a tough economy. Find the transcript at: https://www.unblocked.fm/episodes/kristen-foster-marks-depot/ Timestamps (0:00) Introductions (0:56) Kristen’s r...

In today’s episode, Rebecca talks with Nathen Harvey who leads the DORA group at Google Cloud. Nathen shares insights from the 10th annual DORA report, covering topics like the relationship between AI adoption and software stability, the importance of transformational leadership, and the role of quality documentation. Find the transcript at: https://www.unblocked.fm/episodes/nathen-harvey-google-c...

In today’s episode, Rebecca talks with Iccha Sethi, the new VP of Engineering at Vanta. They discuss taking stock of an engineering organization as a new VP, how technical engineering managers need to be, and her work at Github, Atlassian, Invision, and now Vanta around operational health. Find the transcript at: https://www.unblocked.fm/episodes/iccha-sethi-vanta Timestamps (0:00) Introductions (...

Emily Nakashima, VPE at Honeycomb, shares her experience about the hard choices an engineering leader has to make about how to structure — and sometimes restructure — their engineering org. Emily and Rebecca talk cross-team collaboration, emphasizing eng as an equal partner to other functions, and mistakes that seemed like such a good idea at the time. Find the transcript at: https://www.unblocked...

Mason Jones recently started a new role at Zapier, where he’s bringing his platform leadership experience from Lattice and Credit Karma. In this episode, Mason shares his thoughts on what makes a platform team work, common tradeoffs in platform development, and the challenges of making your team’s work visible and understandable to the whole organization. Find the transcript at: https://www.unbloc...

Alice Bartlett, Tech Director for Customer Products at the Financial Times, shares what it takes to introduce modern technology to a 136-year-old company and how to successfully lead significant efforts to re-architect understandable but unfortunate decisions of the past. In this episode, Rebecca and Alice dig deep on one of those decisions and how she got the work funded and how she got the work...

Colleen Tartow, Field CTO and Head of Strategy at VAST Data, shares her experience from years in data engineering leadership roles. In this episode, Rebecca and Colleen talk about how “data” has evolved over the years, how AI is turning everything we know about data upside down, and how a PhD in Astrophysics got her started on this path. Find the transcript at: https://www.unblocked.fm/episodes/co...

Andrea Corey is a VP of Engineering for platform engineering at Homebase. In today’s episode, Rebecca and Andrea talk about Andrea’s experience in working at scaleups, the lessons she’s learned, the pitfalls she’s trained herself to avoid, and some of the biggest problems leaders need to solve as their organization grows. Find the transcript at: https://www.unblocked.fm/episodes/andrea-corey-homeb...

Liz Hustedt is a Senior Engineering Manager at ActBlue, an American political action committee and fundraising platform established serving left-leaning and Democratic nonprofits and politicians. In today’s episode, Rebecca and Liz talk about how Liz’s early experience as an ICU nurse shaped her leadership skills and style, and about managing change in a way that’s empathetic to where the organiza...

Scott Bonneau is the EVP of Product and Operations at Karat, the end-to-end solution for technical hiring. Before Karat, Scott has worked in various engineering and HR roles at Google and Indeed. In today’s episode, Rebecca and Scott discuss Scott’s career at the intersection of technology and people, how leaders can win the trust of a team that they’ve inherited, and how the tech industry has cha...

Lena Reinhard has been a software engineer, a cofounder, and a vice president of engineering, including leadership stints at Travis CI and CircleCI. These days, she’s an engineering leadership coach and consultant. On today’s episode, Rebecca and Lena talk about those experiences, and how they’ve shaped Lena’s perspective of engineering management and managing with metrics. Find the transcript at:...

Grant Jenks is a Senior Staff Software Engineer at LinkedIn. In this episode of Engineering Unblocked, Rebecca and Grant discuss how LinkedIn approaches the challenges of keeping its software engineers (and others) happy and productive, and how the Engineering Insights organization informs its work and the work of teams across LinkedIn. Find the transcript at: https://www.unblocked.fm/episodes/gra...

Ben Vinegar has spent the last 8 years at Sentry in a variety of roles, from Software Engineer to VP of Engineering. Today, Rebecca and Ben discuss non-linear careers, engineering career ladders, acquisitions, and more. Find the transcript at: https://www.unblocked.fm/episodes/ben-vinegar-sentry-reflecting-on-ladders-acquisitions-and-personal-trajectory Timestamps (00:00) Introduction (01:26) Thir...

David Demaree is a Principal Product Manager at Webflow, where he helps lead the designer experience effort. Before Webflow, David was at Stripe, where he worked on their design system Sail; and at Google, where he worked on Google Fonts and Material Design. In this episode, David and Rebecca discuss the power of platforms to accelerate engineering efforts, and the power of involving a product man...

Alex Plugaru is co-founder and CTO at Gorgias, a platform that helps ecommerce businesses provide top-tier customer support. In this episode, Alex talks about the challenges of building a business in an unfamiliar realm, learning from low-risk experiments, and how headcount isn’t an indicator of success. Find the transcript at: https://www.unblocked.fm/episodes/alex-plugaru-gorgias-success-is-more...