Scaling Software Teams

Usually, we feature interviews with engineering leaders who have experienced high-growth. For the next few weeks, we're changing things up a bit. Our team has talked to hundreds of engineering, HR, and recruiting leaders in the past year. As a result, we’ve heard a lot of the same questions over and over again. We wanted to pose those questions to our guests and provide insights from across the country.

In this series, we sit down with engineering leaders from large companies like Stripe, AngelList, and Drift. We also talk to smaller companies that are growing fast with (and without) venture funding. Here are some of the key questions we’ll answer over the next few weeks:


What hiring and management practices break on our team after a major round of funding?
How can we tell if a recruiting source is actually bringing in the wrong candidates?
What tricks do hiring managers use to uncover developers that other hiring managers may miss?
How can we speed up our hiring process without sacrificing quality?
What do top hiring managers look for in an A+ technical screening process?

Ryan Carroll is the VP of Engineering at Zylo, a SaaS company that helps you manage your SaaS spend. Last year, Zylo raised a $9M Series A round of funding, and they’ve been on a high-growth path ever since. Ryan has already hired 20 engineers to-date, and has plan of hiring ten more in the next year.

In this episode, we discuss why the best teams don’t take agile directly off-the-shelf, and how a big round of funding changed his team structure and hiring process.

For notes and a full transcription of the episode, visit woventeams.com/35. Special Guest: Ryan Carroll.

David Odmark is the Co-Founder and CTO of Greenlight Guru, a quality management software platform designed for medical devices companies that has undergone a ton of growth in the past year. Today, David oversees an engineering team of about 20, and is planning on ramping up hiring in the year to come.

In this episode, we discuss the difference between being a valuable company and being a good company, how quality systems can help us move faster, and whether or not there’s truly an answer for work/life balance.

For notes and a full transcription of the episode, visit woventeams.com/34.Special Guest: David Odmark.

Rukmini Reddy is the VP of Engineering at Abstract, a design management system that centralizes design decisions, feedback, Sketch files, and specs for your team. It’s kind of like Github for design. Abstract has raised over $50M in VC dollars since their founding in 2015. Today, Rukmini oversees their engineering team of about 45, and will be expanding to 60 within the next 18 months.

In this episode, we discuss how she’s used feedback to get better, how she attracts less traditional candidates to engineering roles on her team, and why the “10x engineer” trope is harmful to women in the engineering field.

Link to Rukmini's blog about engineering leadership as a woman of color: https://www.abstract.com/blog/engineering-leader-lessons/

For notes and a full transcription of the episode, visit woventeams.com/33. Special Guest: Rukmini Reddy.

Radoslav Stankov is the Head of Engineering at Product Hunt. He actually took over the post from our last guest, Andreas Klinger, and Andreas wanted us to follow up with Rado to learn about some of the changes he’s made.

In this episode, we dive into the impact that “single-player mode” has on remote work and how Rado uses checklists and clear expectations to ensure his team gets onboarded effectively.

For notes and a full transcription of the episode, visit woventeams.com/32. Special Guest: Radoslav Stankov.

Andreas Klinger is the Head of Remote at AngelList, the largest remote hiring job board in the world. After building multiple remote teams at companies like CoinList and Product Hunt, Andreas has become one of the preeminent voices in the remote work movement.

In this episode, we discuss how Andreas uses metrics for de-risking instead of politics and how he builds an onboarding process that makes it easy to scale remote engineering teams.

For notes and a full transcription of the episode, visit woventeams.com/31.Special Guest: Andreas Klinger.

Melissa Leffler is the VP of Engineering at Drift, a chat software and conversational marketing platform based out of Boston that has grown a ton over the past few years. In the past 5 years, they’ve raised $107M in funding. They have 75 developer on staff and are showing no signs of slowing down in the next few years.

In this episode, we discuss how Drift changed Melissa’s mind on the power of small teams, how she uses incident response to guide her team, and the one question she asks to unlock the biggest problems in her department.

For notes and a full transcription of the episode, visit woventeams.com/30.Special Guest: Melissa Leffler.

Will Larson is the author of my new favorite engineering management book, An Elegant Puzzle: Systems of Engineering Management, and this week, we’re answering listener questions about real-life situations with him.

Will has been an engineering leader and software engineer at technology companies of many shapes and sizes including Digg, Uber, and Stripe. He currently leads foundation engineering at Stripe, where he is responsible for the infrastructure and platform organization. If you haven’t heard of Stripe, they’re a huge player in the online payment space, building the economic infrastructure for the internet. They’ve raised over $700M to date and show no signs of slowing their growth any time soon.

For notes and a full transcription of the episode, visit woventeams.com/29. Special Guest: Will Larson.

Will Larson is the author of my new favorite engineering management book, An Elegant Puzzle: Systems of Engineering Management. Will has been an engineering leader and software engineer at technology companies of many shapes and sizes including Digg, Uber, and Stripe. He currently leads foundation engineering at Stripe, where he is responsible for the infrastructure and platform organization. If you haven’t heard of Stripe, they’re a huge player in the online payment space, building the economic infrastructure for the internet. They’ve raised over $700M to date and show no signs of slowing their growth any time soon.

In this episode, we talk about the importance of increasing your offer acceptance rate, how Stripe defines developer productivity, and why sometimes, the best policy is to throw away your policies.

For notes and a full transcription of the episode, visit woventeams.com/28.Special Guest: Will Larson.

Peter Cullen is the Product Architect at Dispatch, a software company that enables businesses to order a courier directly from the driver. Based out of Bloomington, Minnesota, they’re fresh off of a nearly $8M Series A and are looking to grow their engineering team substantially in the next year.

In this episode, we talk about why it’s important to keep the wheels greased for remote communication, even if your team is all local. We also talk about why Peter hired someone else to manage the people side of the engineering department, and how to decide whether that decision is right for your team.

For notes and a full transcription of the episode, visit woventeams.com/27.Special Guest: Peter Cullen.