Latest Episode

Episode 37 | Creating Alignment in Superstar Engineering Teams with Phil Calçado

Last Episode

Phil Calçado is the Global CTO at PicPay, one the largest engineering orgs in Latin America. He joins the podcast to re-tell his war stories as an engineering leader at SoundCloud, Digital Ocean, SeatGeek, MeetUp, and more celebrity-tier tech companies.

Latest Episodes

We release new episodes every two weeks. They come with accompanying show notes with our favorite moments from the conversation and topic explainers for some of each episode's more insightful & technical tidbits.

January 24, 2023
48
 MIN

Phil Calçado is the Global CTO at PicPay, one the largest engineering orgs in Latin America. He joins the podcast to re-tell his war stories as an engineering leader at SoundCloud, Digital Ocean, SeatGeek, MeetUp, and more celebrity-tier tech companies.

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January 10, 2023
44
 MIN

Happy 2023! or is it?… Jason and Eiso talk about the economic recession and share their predictions for the year ahead. They chat about what happened in 2022 that set the stage for 2023, what the hiring halt means for software engineers, what will happen to those that didn't prepare, and more!

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December 27, 2022
43
 MIN

Allison McMillan, VP of Engineering at Quota Path, joins us to talk about the transformation engineering leaders go through when they become parents and the lessons we can take parenting to our day-to-day as managers. From communication to rewards vs. consequences to dealing with other humans and their unique challenges.

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December 13, 2022
43
 MIN

Alexandra is a Senior Engineering Manager at Fellow.app and the author of Remote Engineering Management: Managing an Engineering Team in a Remote-First World. She joins us to discuss creating an excellent remote work foundation and the challenges of jumping back into in-person interactions when needed. We also chatted about how remote emotions translate to in-person ones, segmenting emotional reactions, wearing different masks, and more.

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November 29, 2022
41
 MIN

Bethany Foote is the Head of Infrastructure Engineering at Outschool and has had a hell of a journey as a software engineer. She joins us to talk about how diversity makes companies better, share the stories she's heard from women in tech over the years, and how they taught her how to be a better leader, mentor, and coach.

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November 15, 2022
51
 MIN

Shannon Vettes is a Transversal Product & Engineering Leader and self-proclaimed "process nerd" with a knack for reorgs (as long as you reaally need them!) and for making engineering leaders' lives easier. She joins the podcast for a deep dive into the PMOs and Program Manager's roles and when's the right time to introduce these roles and processes in your organization.

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November 1, 2022
39
 MIN

Adrienne Lowe shares her journey as an empathetic leader and how her goal to give people energy (rather than take it away) paved her way through a success engineering leadership career.

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October 18, 2022
39
 MIN

Jason & Eiso talk about Velocity in Software Engineering, what it means, how to measure it, why data and metrics won’t magically solve all your problems, and what engineering leaders can do for their teams to go faster.

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October 4, 2022
35
 MIN

Kohsuke Kawaguchi, the creator of Jenkins, pulls back the curtain on building tech companies in Japan. He shares his lessons from Cloudbees and how building two very different engineering organizations from the ground up showed him the importance of diversity in engineering teams.

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September 20, 2022
40
 MIN

Join Chad Fowler, Jason Warner, and Eiso Kant in a heartfelt existential episode on what it means to be an engineering leader that will have you question if the manager path is the right one for you. An essential listen for anyone trying to find meaning in their role.

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September 6, 2022
43
 MIN

Cesar Lugo, Software Engineer and founding member of the Engineering Intelligence team at Typeform, joins us to talk about the power of engineering metrics and how data can help influence how organizations behave.

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August 23, 2022
36
 MIN

Jason and Eiso ad lib on a variety of topics. From consensus-driver cultures, the trouble with software engineering endorsements and capacity planning best practices.

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August 9, 2022
42
 MIN

Craig Kerstiens joins us for a chat on decalcifying engineering teams, why you need to get your teams to ship more, and finding A-Players. Craig runs product and engineering at Crunchy Data and has been incredibly influential in the Postgres community.

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July 26, 2022
40
 MIN

Meri Williams, one of the most inspiring engineering leaders in the world, joins us for a discussion on managers vs. leaders, coaching vs. mentoring, how leaders can advise team members from different backgrounds, and the power of sponsorship.

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July 12, 2022
33
 MIN

Jason and Eiso explore what motivates engineering leaders. They chat about how engineering value creation differs from other functions, what role ego plays as a motivating factor, engineering leadership role models, and more.

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June 28, 2022
36
 MIN

Charity Majors, co-founder, and CTO of honeycomb.io, joins us to talk about everything that's wrong with engineering cycles, how throwing money at the problem by hiring more people is making it worse, and what we can do about it.

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April 19, 2022
46
 MIN

Dana Lawson, SVP of Engineering at Netlify and the human incarnation of sunshine, joins us on the podcast to share her lessons on hiring engineers and the interview process. We also spoke about the tech industry's changes in the last decade and how you can build inclusive software engineering teams.

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April 5, 2022
37
 MIN

Andrew Conner, Co-Founder and Engineering Leader at Levels, joins us to share his journey of leading an engineering team at a company with a strong hardware component. We spoke about building remote asynchronous companies, the importance of feedback loops, deep work, and transparency as you collectively build software and hardware.

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March 22, 2022
42
 MIN

Katie Wilde, the VP of Engineering at Ambassador Labs, joins us to spill the tea on Holacracy and decentralized management systems. Find out why these organizational structures don’t work for companies building software and how they can drive your best people away. Katie also shared how her previous company, Buffer, transitioned from a Holacracy into a strong engineering leadership culture, through goal-oriented 1:1s, effective feedback, and creating a strong sense of responsibility among its leaders.

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March 8, 2022
45
 MIN

Co-Founder and CEO of Moov Financial, Wade Arnold, has had a hell of a journey as a software engineering leader. He joins us on the podcast to chat about building companies, attracting great software engineering talent, and increasing velocity as you scale.

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February 22, 2022
37
 MIN

We welcome Jonathan Nolen, Senior VP of Engineering and Product at LaunchDarkly, to talk about his 100+ people Product Delivery team - a term coined by the company, where Engineering, Product, and Design come together. We spoke about what this three-function team means for engineering organizations, how you can build a culture of shared responsibility, and much more!

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February 8, 2022
39
 MIN

Eiso and Jason step up to the mic and make their wild guess on how the state of software engineering will evolve, given what we know now. The tech industry will look a lot different in 20 and 30 years. From autonomous coding to self-driving cars to automatically powered engineering leadership. We might not be ready for that yet, but our kids are gonna love it.

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January 25, 2022
38
 MIN

In an episode dedicated to what we think the next generation of engineering leaders should avoid, Jason and Eiso talk about the books every engineering leader reads, the over-glorification of 80’s maniacal leaders, OKRs, and other tech industry things we love to hate.

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January 11, 2022
38
 MIN

Senior Director of Engineering at Datadog, Nuno Antunes, joins us to talk about a highly requested topic: Transitioning from Software Engineer to Engineering Leader. From striking the right balance between being a people vs. process-oriented leader to the challenges of building teams in fast-growing companies, this episode is jam-packed with teachable moments, workshop approaches, and the organizational shifts we've witnessed through the years.

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December 28, 2021
43
 MIN

Dagger Co-Founder and Docker’s former VP of Engineering, Sam Alba, joins us for a retrospective on company culture and how early-stage teams should develop it as their companies evolve. As Dagger grows from a founding team of three to ten and so forth, Sam, Jason, and Eiso, share their views on building companies, leading by example, and the importance of embracing culture in a genuine way.

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December 14, 2021
44
 MIN

Erik Bernhardsson joins us on the podcast to chat about building engineering teams and the delicate balance between innovation and productivity as organizations grow. We also shared our views on team mentalities, skunkworks projects, and more as we tried to answer the question: "what is success in engineering?"

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November 30, 2021
41
 MIN

Community creator and engineering leader at Apple, Michael Lopp (aka rands), joins Jason and Eiso to chat about the power of storytelling for engineering and the state of content for engineering leaders. The author of "Small Things Done Well" shares his opinions on video conferencing, distributed work, and how managers can create more authentic connections with remote teams.

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November 16, 2021
39
 MIN

On our 10th episode, Eiso and Jason present a conversation dedicated to CEOs and everything they need to know about their engineering organization and leadership. From tech debt to dependency management and communication styles, understand engineering team's infrastructures, the timings and expectations of building product, and much more.

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November 2, 2021
42
 MIN

Sam Lambert, CEO of PlanetScale and previously VP of Engineering at GitHub, joins us to talk about building high-performance teams. We chatted about leading with influence, advocating for your team, creating delightful hiring experiences, knowing when to fire people and how to keep your software engineers close to your end-users to build great products.

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October 19, 2021
38
 MIN

Jason and Eiso wrap up their three-part series on Engineering Leadership roles by taking a deep dive into Engineering Managers and Tech Leads. Learn how to hire your first engineering manager, whether to hire your engineering leaders from inside the company, and how the roles of tech leads change as your company grows. We also covered communication techniques and how to design your teams as the company scales and communication lines increase.

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October 5, 2021
41
 MIN

Jason and Eiso continue their deep dive on different engineering leadership roles, sharing their thoughts on CTOs, VPs, and Managers, how to hire for these roles, and adopting organizational structures that promote transparency and trust in the decision-making processes that shape your business.

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September 21, 2021
48
 MIN

In this episode of Developing Leadership, we kick off our deep-dive series on different Engineering Leadership roles. Jason and Eiso discuss how CTOs, VPs of Engineering, and Engineering Managers should navigate through the various stages of their company. From prioritizing at different seed rounds to developing a go-to-market strategy, building their company’s architecture, and the day-to-day of each of these roles.

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September 7, 2021
44
 MIN

Former GM of Snyk, Anton Drukh, recently became a mentor for VPs of Engineering and joined us on this week's episode to discuss his experiences leading a team split between two very different cultures. His journey as a leader working with teams in Israel and the UK is a lens into how diversity of mentalities can be an essential asset for tech companies and how it played a role in Snyk's success.

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August 24, 2021
58
 MIN

Neo4j just raised the biggest round in database history and their CEO, Emil Eifrem, joins us on the podcast to tell us about his experience transitioning from a day one CEO to running a company with more than 500 employees.

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August 10, 2021
39
 MIN

Jason and Eiso share the frameworks that have helped them navigate big and small decisions through the years and look back at how key decision-making moments shaped how they operate as leaders today.

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July 27, 2021
43
 MIN

How do we make sure that we are deliberate about the culture of our organization and not find ourselves pushing for outcomes without care of how we achieve them? Jason and Eiso go through the building blocks of positive company culture and explore how companies and leaders can adapt as their teams grow from two people in a garage to thousands of employees.

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July 6, 2021
36
 MIN

In the first episode of Developing Leadership, Jason and Eiso talk about how the roles and perceptions of engineers and engineering leaders have changed over the decades. From the catastrophic offshoring trend of the early 2000s to the golden age of development, the tools, the processes and the culture shifts.

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