Scaling Software Teams

Jacob Kaplan-Moss is a veteran software leader and the co-creator of Django, the python web framework that powers Pinterest, Eventbrite, and Instagram. In addition to authoring the book, The Definitive Guide to Django, Jacob has also led teams at 18F and Heroku. Today, Jacob is considered one of the foremost experts on hiring for software teams that are in that “adolescent” phase between start-up and scale-up.

Today’s episode is the first of a two-part interview that we did with Jacob. In today’s interview, we discuss ways that we can reduce bias in our hiring process and how the Satir Change Model can help us navigate the challenges associated with rapid growth without losing our minds. Special Guest: Jacob Kaplan-Moss.

Randy Syring is the Chief Executive Developer at Level 12, a custom software development organization in the Louisville area. Randy’s story is a fun one. Growing up, he didn’t have any aspirations to get into software development at all, and today he runs his own software development shop.

Originally, Randy wanted to fly Apache helicopters in the Army. Eventually, he set his sights on becoming a pastor. Ultimately, neither of those career paths panned out, and he stumbled into software development and never looked back. Special Guest: Randy Syring.

Steve Caldwell is the VP of Data, Infrastructure, and Security at Springbuk where he leads a fast-growing team that has been hiring like crazy over the past year. Steve has become a widely-respected software leader who is able to grow and manage highly effective development teams. What often gets left out of that conversation, however, is the frequency with which those lessons are learned through trial and error.

In our conversation, Steve opens up about the lessons he’s learned about effective hiring and management, including lessons he learned the hard way. We talked about the hidden expenses of hiring, and ways that your scale-up can hire more effectively when you’re growing quickly. Special Guest: Steve Caldwell.

Micah Weaver is the CTO of Bloomerang, a donor management software company for nonprofits. In our conversation, Micah opens up about suffering a panic attack early in his role as CTO and the impact that experience had on his life, and I’m eager to share this powerful conversation with you.

Early in his career, Micah never thought he would be the type of person to suffer a panic attack. He had always considered himself a low-stress individual, great at rolling with the punches. Then, one day, driving home from work, it happened. That experience went on to shape his management style and ideology on work.Special Guest: Micah Weaver.

Raman Ohri is the President of SEP. He builds software teams that helps his clients build exceptional software and systems. SEP is different from many software development shops because their clients work directly with the software engineers themselves.

This adds tons of value for the client, but it also makes every new hire more risky. Every software engineer he brings on will be responsible for representing the SEP name to a client, so Raman needs to avoid making the wrong hire at all costs. This has led his team to adopt extremely thorough, risk-averse hiring practices that make it extremely hard to make the wrong hire. In this episode, we’ll explore those hiring practices and uncover how you can leverage these tactics in your organization. Special Guest: Raman Ohri.

Roger Deetz is the VP of Engineering at Springbuk, a fast-growing scale-up in our hometown of Indianapolis. Before that, he was the Vice President of Engineering at Angie’s Home Services where he led their software engineering modernization project. I got a lot out of this conversation with Roger and especially enjoyed the discussion of the juxtaposition of development work and management work.

The transition from what helps us feel productive as a software engineer compared to an engineering team leader is a transition that a lot of people struggle with, Roger’s story illustrates ways that you can help your new engineering managers overcome the psychological barriers to leadershipSpecial Guest: Roger Deetz.

My name is Wes Winham, and I want to help you scale your engineering team. Listen to this episode to understand why I'm passionate about helping your team scale, and what I hope you get out of our podcast.

This show is brought to you by Woven. At Woven, we help software teams hit ambitious hiring goals. We do that by improving the fuzziest step in the hiring process: candidate screening. By giving every candidate a fair chance to show what they can do, our customers find more great candidates and back their decisions with evidence to remove bias. If you want to learn more about how Woven could help you scale your development team, check us out at woventeams.com.