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Scaling Software Teams

48 episodes - English - Latest episode: over 4 years ago -

Scaling Software Teams is a weekly podcast to help software leaders navigate fast growth without losing the magic that made that growth possible. Every week, we bring you stories of trials, tribulations, and keys to success from high-growth engineering leaders all around the world.
We will learn together about how to scale a world-class engineering organization through hard-won stories about hiring developers, structuring teams, scaling collaboration, and managing managers.

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Episodes

On Startups and Escape Rooms, with Gregory Koberger

November 19, 2019 15:56 - 39 minutes - 27.2 MB

Gregory Koberger is the founder of ReadMe, a company that helps dev teams create and manage documentation and monitor APIs. He founded ReadMe after working at several startups in Silicon Valley, including Mozilla, and finding himself writing documentation for all of them. In this episode, we talk about how he uses Challenge Coins to build community, human connection to drive out toxicity, and builds a technical interview that doesn’t feel like a pop quiz.

GregKobergerPodcast.mp3

November 19, 2019 15:56 - 39 minutes - 27.2 MB

How Zapier Scales Past 100 Engineers, Part One With Doug Gaff

November 18, 2019 18:45 - 31 minutes - 21.9 MB

Doug Gaff is the VP of Engineering at Zapier, the software solution that helps your other software work together more effectively. His team recently crossed the 100 engineer threshold and they’re currently going through some exciting transitions as an organization. Their current inflection point has them moving from a functional focus to a vertical product focus. We’re excited to share what Doug has learned through this transition. In this episode, we’re going to dive into Zapier’s organiza...

Launching a Coding School Without Writing a Single Line of Code, with Ariel Camus

November 12, 2019 20:20 - 47 minutes - 32.7 MB

Ariel Camus is the Founder and CEO at Microverse, a YC-backed distributed school for software engineers. They are available anywhere in the world, and they don’t charge students anything until they get hired. In this episode, we talk about why remote workers are so much better at documentation than co-located workers, the practices that help hiring managers hire remote junior developers, and how Ariel launched a coding school without writing a single line of code.

The Three Questions To Ask Every New Manager, Part Two With Doug Gaff

November 05, 2019 18:45 - 37 minutes - 25.8 MB

This week, we bring you part two of our conversation with Doug Gaff. Doug is the VP of Engineering at Zapier, the software solution that helps your other software work together more effectively. As the leader of an organization with over 100 engineers, he has learned a lot about effective management and leadership. In this episode, we talk about Doug’s management style and what questions he asks everyone who says they want to get into management. For notes and a full transcription of the ep...

Building a World-Class Onboarding Process For Your Software Engineering Team

October 22, 2019 17:45 - 18 minutes - 12.6 MB

This is the final week of our community questions series, and we saved the best for last. We're not talking about hiring...we're talking about what comes next. How can we build a world-class onboarding process that keeps our new teammates engaged from day number one? In this episode, we chat with folks from large companies who have learned a lot about effective onboarding to find out what makes their process different.

What Do The Best Technical Assessments Have In Common?

October 15, 2019 17:45 - 21 minutes - 15.2 MB

The most common questions we get are about technical assessments. It's an area of concern for a lot of engineering leaders. Some believe their technical assessment is costing them great-fit candidates. Others believe they're not getting good enough information from their technical screening process. In this episode, we dive deep into actionable insights that we can use to build effective, information-dense technical assessments. We talk to engineering leaders across the country who have gott...

How Can I Speed Up My Hiring Process Without Sacrificing End Results?

October 08, 2019 17:45 - 15 minutes - 10.8 MB

There's a tension in hiring, especially with software developers. If I hire too slow, candidates withdraw. If I hire too fast, I may hire the wrong person. In this episode, we talk to engineering leaders who have threaded that needle to figure out what makes their process work. We'll discover the simple process changes that had the biggest impact on reducing their time-to-hire. We'll also learn about the importance of information density, and how we can build information-dense technical scr...

Hunting Hidden Gems - Tricks to Find Great-fit Developers That Other Hiring Managers Miss

October 01, 2019 17:55 - 34 minutes - 23.9 MB

Some hiring managers are elite at finding diamonds in the rough. In this episode, we're going to learn why. This week, we talked to hiring managers across the country to learn what they do differently in their hiring process to find great-fit engineers that other leaders miss. We'll also find actionable steps you can take today to find more hidden gems in your hiring pool, so you can spend less time and money on headhunters and more time building great software.

Hiring Faster By Identifying Our Best-Performing Candidate Sources

September 24, 2019 17:55 - 17 minutes - 12 MB

On this week's episode, we're talking about hiring. More specifically, how do we find the candidate sources that are bringing us the best candidates? If our methodology is flawed here, it could bias our entire hiring process, leading to worse outcomes and more homogeneous teams. In this episode, we're learning the best practices from hiring managers across the country so we can find better candidates and hire faster.

What Changes Our Engineering Team Should Expect After a Major Round of Funding

September 17, 2019 17:45 - 20 minutes - 14.5 MB

This week, we're talking about the scary side of a really exciting day...the day our startup raises a major round of funding. Unfortunately, more money can mean more problems. The act of raising Venture Capital looks less like receiving a cardboard check from Publisher's Clearing House and more like hiring a new boss. In this episode, we talk to engineering leaders across the United States who have gone through a big fundraise and learn from their experience. We'll discuss what processes br...

Answering Your Best Questions With Engineering Leaders Across The World

September 10, 2019 17:45 - 2 minutes - 1.96 MB

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, An...

Changing Your Hiring Process After a Big Round of Funding, with Ryan Carroll

September 03, 2019 17:45 - 34 minutes - 24 MB

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 trans...

Building Companies That Are Both Good & Valuable, with David Odmark

August 27, 2019 17:45 - 37 minutes - 26.2 MB

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...

Are All Women Engineers Like You?, with Rukmini Reddy

August 20, 2019 17:45 - 36 minutes - 25 MB

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 candi...

Using Checklists For Onboarding Success, with Radoslav Stankov

August 13, 2019 17:45 - 34 minutes - 24.2 MB

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 Gue...

Hiring and Managing World-Class Remote Teams, with Andreas Klinger

August 06, 2019 17:45 - 47 minutes - 32.6 MB

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, v...

Achieving Operational Excellence Through Small Teams, with Melissa Leffler

July 30, 2019 17:56 - 39 minutes - 54.9 MB

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 un...

Solving Your Elegant Puzzles, Part 2 with Will Larson

July 23, 2019 17:45 - 25 minutes - 35.2 MB

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’...

An Elegant Puzzle, Part 1 with Will Larson

July 16, 2019 17:45 - 27 minutes - 37.8 MB

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 econo...

Why You May Want To Delegate Management, with Peter Cullen

July 09, 2019 17:45 - 32 minutes - 45 MB

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 p...

We’re Not Google… And That’s a Good Thing, With Skyler Nesheim

July 02, 2019 17:45 - 35 minutes - 48.4 MB

Skyler Nesheim is the VP of Engineering at Dwolla, a fast-growth FinTech scale-up. They’ve raised over $50M in venture dollars to connect enterprises to the US banking system. The Dwolla team has built one of the most disruptive products in the enterprise FinTech space, all from Des Moines, Iowa. In this episode, we talk about how to build a microservice architecture as we scale, how to incorporate customer feedback into our product vision, and why we’re not Google… and that’s a good thing. ...

Being Thoughtful About The Algorithms In Our Lives, With Jake Miller

June 25, 2019 17:45 - 40 minutes - 56 MB

Jake Miller is the CTO and Co-Founder of MetaCX, an Indianapolis-based startup that raised a $14 Million dollar initial round to revolutionize the Customer Success industry. Before starting MetaCX, he was an engineering leader at ExactTarget and Salesforce. In this episode, we talk about why we should never say no to PTO, how algorithms make diversity worse, and how he focuses on building a balanced team instead of a senior team. For notes and a full transcription of the episode, visit wov...

Hard Decisions on Fast-Growing Teams, With Ron Lancaster

June 18, 2019 17:55 - 29 minutes - 40.1 MB

Ron Lancaster is the CTO of Structural, a Minneapolis-based platform that allows clients to create an internal people network powered by both data science and people science. In this episode, we talk about making hard decisions as a leader, building a hiring plan that adapts as you grow, and hiring the best available player instead of a less talented specialist. For notes and a full transcription of the episode, visit woventeams.com/24. Special Guest: Ron Lancaster.

Getting Diversity and Inclusion Right, With Jason Wong

June 10, 2019 17:45 - 33 minutes - 46.2 MB

Jason Wong is an engineering leadership consultant who focuses on Diversity and Inclusion. His past lives include engineering roles with Yahoo! Sports, Etsy, and Blink Health. In this episode, we talk about the difference between diversity and inclusion, and why that difference is important. We also touch on some of Jason’s favorite management and hiring practices. For notes and a full transcription of the episode, visit woventeams.com/23. Special Guest: Jason Wong.

Why Remote Teams Don’t Always Work, With Kyle Gunderson

June 03, 2019 17:55 - 31 minutes - 43.3 MB

Kyle Gunderson is the President and CTO at Revel Health, a Minneapolis-based software company that uses advanced analytics and AI to create health action programs that improve the health of people on an individual-basis. He’s a tech veteran, with over 20 years of leadership experience and multiple high-growth teams under his belt. In this episode, we talk about how he uses data to navigate tough conversations about his product roadmap. We also learn about how he attracts top-talent without ...

Avoiding the All-Senior Trap, Part 2 With Charity Majors

May 20, 2019 17:45 - 18 minutes - 26 MB

Charity Majors is the CTO at Honeycomb, a startup that builds observability for distributed systems, and this week, we’re diving into part two of our conversation with her. Charity’s team is on a mission to make monitoring less cumbersome so that being on-call can suck less. In this episode, we talk about how to hire the right seniority mix for your team and ensure you see everyone at their best, both when they’re interviewing for a job and once they’ve started. For notes and a full trans...

Hiring for Strengths, Not Lack of Weaknesses, Part 1 With Charity Majors

May 13, 2019 17:45 - 27 minutes - 38.3 MB

Charity Majors is the CTO at Honeycomb, a startup that builds observability for distributed systems. Occasionally, we have a conversation that’s so much fun, we need to break it into two episodes. This is one of those weeks. We recently sat down with Charity, and the result is one of the most thoughtful discussions we’ve had on our show to-date. Charity’s team is on a mission to make monitoring less cumbersome so that being on-call can suck less. In this episode, we talk about when pain an...

How Speed Shaped Lambda School, With Bob Lauer

May 06, 2019 17:43 - 33 minutes - 45.5 MB

Bob Lauer is the VP of Engineering at Lambda School. Lambda School has been in the news a ton for the way they’re revolutionizing the financial model of education. Today, we get to talk with one of the architects of this revolution. For those of you who aren’t familiar, Lambda School is a coding academy that aims to help anyone, from any background, get a high-paying job in software development. In this episode, we talk about the importance of speed at an early-stage startup, why delibera...

Hiring and Mentoring Coding Bootcamp Grads, With John Harden

April 29, 2019 17:45 - 35 minutes - 49.3 MB

John Harden is the Principal Software Engineer at Kerauno. Kerauno is a workflow and communication software company that just raised a $25M Series A. When he’s not leading a high-growth development team, he’s mentoring for two coding academies, Eleven Fifty and Kenzie Academy. Hiring coding bootcamp alumni is a controversial subject in development circles, and I’m excited to dive into it. In this episode, we talk about his experience both hiring and mentoring coding bootcamp alumni, findin...

Doing Better Work, With Max Yoder

April 22, 2019 17:55 - 38 minutes - 52.9 MB

Max Yoder is the founder and CEO of Lessonly, a team learning and training software company that raised a $8M Series B in late 2017. Max’s team is dedicated to helping people “Do Better Work,” which is where he got the title of his new book, Do Better Work: Finding Clarity, Camaraderie, and Progress in Work and Life. In this episode, we talk about vulnerability, sharing work before you’re ready, and why leaders don’t always know the answer (and that’s a good thing). For notes and a full tr...

Communicating Feedback to Your Team, With Miles Sterrett

April 15, 2019 17:45 - 40 minutes - 55.4 MB

Miles Sterrett is a Partner at Fretless, a custom software development shop that helps software companies level-up their software chops. Miles’ team specializes in coming into high-growth teams and acting as an interim software leader. He has worked with startup and scale-ups to help them overcome technical debt and build the engineering team that can help them hit their future product goals. In this episode, we talk about ways he reduces stress, reasons to hire out of a coding bootcamp, and...

Getting the Technical Hiring Process Right

April 08, 2019 17:44 - 17 minutes - 23.8 MB

This week, we're doing something different. Instead of talking to one engineering leader about a broad range of topics, we talked with a collection of engineering leaders about one topic: How do you screen for technical talent? In this episode, we talk to: Jon Lavender, CTO at Dragos Adam Perelman, CTO at Affinity Ryan Carroll, VP of Engineering at Zylo Ryan Rusnak, CTO at Airspace Technologies Jeff Stickel, CTO at Kerauno For a full transcript of this episode, woventeams.com/15.

Announcement: Woven Acquires Headlight

April 01, 2019 17:45 - 16 minutes - 22.4 MB

Today’s a really exciting day for us. Our startup just acquired a New York City-based tech hiring platform called Headlight. We're sitting down with Wayne Gerard to talk about this transition. We wanted to know what they’ve learned while uncovering some of the best software engineers in New York City. Over the past two years, they’ve uncovered hidden gems and made the hiring process better for both developers and hiring managers. What’s more, they did it in one of the nation’s most competit...

Using Rubrics For More Objective Hiring, With Christine Spang

March 25, 2019 17:45 - 36 minutes - 49.7 MB

Christine Spang is the Co-Founder and CTO of Nylas. Nylas’ API powers communications in software applications, taking data from 4.5 billion inboxes worldwide and connecting it directly to productivity, sales and marketing apps. Nylas has raised $30M in funding and has 20 engineers across 4 teams. In this episode, we talk about her entrepreneurial journey, building a support network as a founder, and building a diverse team with less bias. For notes and a full transcription of the episod...

Empowering Our Teams With The Right Tools, With Amjad Masad

March 18, 2019 17:45 - 37 minutes - 51 MB

Amjad Masad is the founder and CEO of Repl.it. Repl.it is a Y Combinator-backed online development environment that helps developers learn, build, collaborate, and host all in one place. They’re on a mission to make programming more accessible. In this episode, Amjad shared why he believes that discovery great people is the key to great teams. He contrasts that with talent identification, which is about credentials and resumes. For more information, notes, and takeaways, visit woventeams....

Explaining the “Why” Behind Your Features, with Mitch Stewart

March 11, 2019 17:52 - 28 minutes - 38.9 MB

Mitch Stewart is the co-founder of Guru, a software company based out of Pennsylvania that is working with companies like Shopify, Square, and Spotify to unify their team’s collective knowledge and empower them with information when they need it most. In this episode, we talk about some of the management practices that have made Mitch successful at Guru. We dive into his transition from developer to manager, and the lessons he learned about building and motivating teams along the way. For m...

Increasing Your Offer Acceptance Rate With Sandwiches, With Austin Broyles

March 04, 2019 18:55 - 31 minutes - 42.8 MB

Austin Broyles is the Director of Engineering at Primer, a Bay Area company using AI to parse and collate a large number of documents across several languages. In this episode, we talk about Austin’s experience transitioning into a management role at Google and how he is splitting leadership between machine learning and pure software engineering teams in his current role. We also dive into the story of how he increased his offer acceptance rate by being smarter about sandwiches. For more i...

Trying to Replace Yourself, With Eric Tobias

February 25, 2019 18:50 - 40 minutes - 56.1 MB

Eric Tobias is a Partner at High Alpha, a Venture studio that conceives, launches, and scales next-generation enterprise cloud companies. In this episode, we chat about how he parlayed an early love of basketball and bootlegged music into a passion for the internet, how he grew his first team at batteries.com during the dot-com era, and the lessons he learned starting and scaling iGoDigital, which he sold to ExactTarget, which he helped sell to Salesforce. For more information, notes, and...

Being a Tortoise in a Hare's World, With Ade Olonoh

February 18, 2019 16:51 - 38 minutes - 53.1 MB

Ade Olonoh is the founder of two companies with similar names and very different stories. Formstack is an online form builder that has witnessed slow, steady growth since its founding in 2006. In their first month, they had $75 in Monthly Recurring Revenue and today, they’re clocking in at seven figures. Formspring was an anonymous social Q&A app that grew from zero users to over a million users in 45 days, making it at the time, the fastest growing social network in history Those two expe...

Treating Your Engineering Team Like Adults, Part 2 with Jacob Kaplan-Moss

February 11, 2019 18:55 - 25 minutes - 35.8 MB

Jacob Kaplan-Moss talks to us about managerial practices he believes in, as well as practices he’s sick of, in this week's part two of his interview. One central thesis: Our teams perform better when we treat them like adults. For those who missed part one, Jacob Kaplan-Moss is a veteran software leader and the co-creator of Django, the python web framework that powers Pinterest, Eventbrite, and Instagram. I built my last startup on Django, so speaking with him was a huge pleasure.Special G...

Managing Change In The Face Of Rapid Growth, Part 1 with Jacob Kaplan-Moss

February 04, 2019 18:43 - 34 minutes - 47.3 MB

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 to...

Learning The Hard Work Of Hiring, with Randy Syring

January 29, 2019 18:55 - 32 minutes - 45.2 MB

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 devel...

Managing Mental Health, With Micah Weaver

January 28, 2019 18:55 - 37 minutes - 51.5 MB

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,...

Embracing Your Inner “Latent Leader,” With Roger Deetz

January 28, 2019 18:55 - 31 minutes - 43.5 MB

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 engineeri...

Avoiding Mis-Hires Through Evidence, With Raman Ohri

January 28, 2019 18:55 - 34 minutes - 47.3 MB

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 cost...

Software Hiring Trial By Fire, With Steve Caldwell

January 28, 2019 16:52 - 47 minutes - 65.6 MB

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 effect...

Wes Winham | Scaling Software: What's this all about?

January 14, 2019 18:58 - 2 minutes - 3.01 MB

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 candidat...

Guests

Charity Majors
2 Episodes
Will Larson
2 Episodes
Radoslav Stankov
1 Episode