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Geeks Who Lead Podcast — Software How-To
Geeks Who Lead Podcast

Hear the inside stories of the “geeks who lead at scale” – Directors, VPs and CTOs running software engineering orgs at larger companies with 100+ engineers, and interviews with domain experts who can help those leaders to manage their engineering orgs more effectively.

I’m your host – Peter Bell, I’ve been helping senior engineering leaders to connect with and learn from their peers since 2010!

This podcast is designed for engineering leaders who want to learn the latest good practices from their peers who are way too busy operating to write an article or publish a book!

Running a software engineering org at scale is hard! You need to manage stakeholder expectations, attract and retain top talent, align and structure your org effectively and keep up with the latest processes and tooling. And that’s before we even try to make sense of the potential impact of LLMs and GenAI on managing technical teams.

Our podcast and weekly newsletter provide you with access to hard-won wisdom from top engineering leaders and relevant domain experts. Learn more at https://geekswholead.com/

Copyright: © 2020 CTO Connection, LLC

Latest Episodes:

Breaking Codes, Designing Jets, and Building Teams with Randy Shoup Feb 13, 2020

Show notes

Randy Shoup has led engineering teams at a range of top companies including Oracle, eBay, and Google, as well as newer startups like Stitch fix and WeWork.

Randy talks to Peter about how the history of engineering – from Bletchley Park to Xerox PARC can provide lessons that are still applicable to building and managing high performance engineering teams.

If you’d like to see Randy sharing more about this topic, check out this video from the 2018 NY CTO Summit at the Nasdaq!

[00:23] - How Randy started his career

[01:08] - Training for management at eBay
[04:46] - Learning from the best
[06:13] - Building and managing high-performing teams at Google
[08:00] - Moving to VPE at Stitchfix
[10:19] - Adding a career ladder
[12:16] - The Bletchley Park experience
[17:53] - Modern approaches to an organization at Lockheed Skunkworks
[21:30] - Innovations at Xerox PARC
[24:09] - Purpose, culture, diversity, & excellence

CTO Connection is where you can learn from the experiences of successful engineering leaders at fast-growth tech startups. Whether you want to learn more about hiring, motivating or managing an engineering team, if you're technical and manage engineers, the CTO Connection podcast is a great resource for learning from your peers!

If you'd like to receive new episodes as they're published, please subscribe to CTO Connection in Apple Podcasts, Google Podcasts, Spotify or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.

Creating a Better Product using Tactical Empathy with Andrea Goulet Feb 06, 2020

Show notes

There are many routes to c-suite but Andrea Goulet has taken one of the most non-traditional paths we’ve seen on CTO Connection. As the Co-Founder and CEO of Corgibytes, Andrea leveraged her experience in content and strategic communications to help a software remodeling company scale its business.

Andrea is a big believer in the power of empathy – a word that’s not often prioritized in engineering. In this week’s edition of CTO Connection, Andrea explains how she makes empathy accessible to analytical audiences and the role empathy plays in creating a better experience and product.

[00:24] - Andrea's path to CEO
[03:25] - Communication debt
[06:28] - Domain-Driven Design
[08:06] - Keeping the knowledge close to the code
[08:22] - Working Effectively with Legacy Code
[11:43] - Continuous improvement
[15:12] - Definition of done
[18:05] - Experimentation and prototyping
[20:53] - Slack at scale
[24:05] - Teaching empathy

CTO Connection is where you can learn from the experiences of successful engineering leaders at fast-growth tech startups. Whether you want to learn more about hiring, motivating or managing an engineering team, if you're technical and manage engineers, the CTO Connection podcast is a great resource for learning from your peers!

If you'd like to receive new episodes as they're published, please subscribe to CTO Connection in Apple Podcasts, Google Podcasts, Spotify or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.

Cultivating Cross-Functional Teams with Cai GoGwilt Jan 30, 2020

Show notes

Cai GoGwilt took a fast-tracked, non-traditional road to becoming a CTO at Ironclad. As a non-traditional CTO, Cai sees his role as helping others on the team get unblocked from any issues in their way. This approach has required a bit of humility on Cai’s part as he’s helped cultivate a culture in which engineers have felt comfortable calling him out when he was wrong.

On today’s episode of CTO Connection, Peter and Cai discuss Ironclad’s process for annual planning as well as building cross-functional teams in a rapidly scaling company.

[00:20] - How Cai became a CTO
[01:47] - Leveling up product engineering at Ironclad
[06:03] - Core elements of the CTO role
[08:54] - Jack of all trades, master of none
[12:20] - Creating and sustaining culture
[14:12] - Annual planning cycle
[18:17] - Hiring a team that cares about the end-user
[21:27] - Bringing technology to the law
[22:58] - Cross-functional empathy
[30:31] - Selecting engineers to thrive in an empathetic culture
[34:31] - Finding the right applicants in the Bay area

CTO Connection is where you can learn from the experiences of successful engineering leaders at fast-growth tech startups. Whether you want to learn more about hiring, motivating or managing an engineering team, if you're technical and manage engineers, the CTO Connection podcast is a great resource for learning from your peers!

If you'd like to receive new episodes as they're published, please subscribe to CTO Connection in Apple Podcasts, Google Podcasts, Spotify or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.

Balancing Coding and Management with Dhruba Borthakur Jan 23, 2020

Show notes

Dhruba Borthakur is the Co-founder and CTO at Rockset but still manages to write code, on a good week, 50% of the time. In today's interview, Dhruba explained his ethos, namely that he likes to code to add value to other developers’ lives, and discussed how it is essential to create a culture where every person on the team feels empowered to make decisions that bring the organization to the next level.

As one of the founding architects of Hadoop software, Dhruba also shares his insights on how and why Hadoop was created as well as the difference between putting together teams for shipping software externally versus SaaS (software as a service) products. Tune in!

[00:25] - How Dhruba became a CTO
[02:06] - Transitioning to team management
[04:59] - Building a supportive culture
[07:50] - Solving tomorrow's problems
[10:34] - Creation of the Hadoop file system
[16:21] - Recruiting for an open-source project
[19:34] - Finding rock star engineers at Rockset
[27:36] - Team geography
[30:15] - Fail fast and learn quickly
[32:12] - Pulling the plug
[36:17] - Fast-moving teams
[41:25] - Finding time to write code

CTO Connection is where you can learn from the experiences of successful engineering leaders at fast-growth tech startups. Whether you want to learn more about hiring, motivating or managing an engineering team, if you're technical and manage engineers, the CTO Connection podcast is a great resource for learning from your peers!

If you'd like to receive new episodes as they're published, please subscribe to CTO Connection in Apple Podcasts, Google Podcasts, Spotify or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.

Trust, Delegation and Managing Managers with Raghavendra Prabhu Jan 16, 2020

Show notes

According to Raghavendra Prabhu, CTO of Thumbtack, making the transition from programmer to manager isn’t too much of a stretch since you already understand the issues and stakes of your project. When you take it a step further and begin managing other managers, you’re getting further from the work and making a more indirect impact.
On today’s episode of CTO Connection, Raghavendra discusses what it’s like making the transition to higher levels of leadership and how to balance his desire for control with the need for delegation. Tune in for insights on how to successfully climb the leadership ladder.

[00:20] - How Raghavendra started his career at Microsoft
[02:09] - Why search is compelling
[03:23] - The culture shift moving to Google
[05:29] - Moving from Google to Twitter
[08:40] - Scaling teams at Pinterest
[13:22] - Hiring managers as engineers
[16:56] - Transitioning from manager to director
[20:52] - Implementing the mentorship program
[23:28] - Anticipating and planning
[26:17] - Fixing the hiring process
[29:06] - What kind of CTO is Raghavendra?

Raghavendra Prabhu (RVP) is the CTO of Thumbtack and was previously the head of infrastructure at Pinterest and a senior software engineer at Twitter, Google, and Microsoft. Thumbtack is an online services marketplace enabling hundreds of thousands of local professionals from plumbers to DJs to build sustainable businesses by connecting them to millions of customers nationwide.
CTO Connection is where you can learn from the experiences of successful engineering leaders at fast-growth tech startups. Whether you want to learn more about hiring, motivating or managing an engineering team, if you're technical and manage engineers, the CTO Connection podcast is a great resource for learning from your peers!
If you'd like to receive new episodes as they're published, please subscribe to CTO Connection in Apple Podcasts, Google Podcasts, Spotify or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.
Podcast episode production by Dante32.

Balancing Engineering Craft with Customer and Company Needs with Ryan Graciano Jan 09, 2020

Show notes

Ryan Graciano got his start working for a small company that was acquired by IBM. Having been on the employee side of a large merger, Ryan has been able to take what he learned to his role as CTO at Credit Karma. On today’s episode of CTO Connection, Ryan talks to Peter about his distaste for terms like microservices and technical debt as well as how to craft an environment that values both craft and customer.
Listen in as Ryan discusses managing large teams of engineers while stressing a culture of agility and experimentation.

[00:21] - How Ryan started his career in software development
[01:40] - Transitioning to Credit Karma
[02:50] - Building an engineering team
[05:26] - Staying connected to the code
[06:36] - Recruiting talent
[11:13] - Moving from IC to manager
[15:19] - Drawing the line at microservices
[17:32] - Technical debt
[22:31] - Communicating with business stakeholders
[24:19] - Company, customer, craft
[27:18] - What to look for in a great engineer
[29:37] - What to look for in upper management

CTO Connection is where you can learn from the experiences of successful engineering leaders at fast-growth tech startups. Whether you want to learn more about hiring, motivating or managing an engineering team, if you're technical and manage engineers, the CTO Connection podcast is a great resource for learning from your peers!
If you'd like to receive new episodes as they're published, please subscribe to CTO Connection in Apple Podcasts, Google Podcasts, Spotify or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.

Challenges Facing CTOs of Large Organizations with David Schwartz of Ripple Jan 02, 2020

Show notes

Tech organizations with more than 100 employees have a unique set of challenges. When you’re in the business of innovation, it can be hard to say no to exciting new opportunities. In this week’s episode of CTO Connection, David Schwartz, CTO of Ripple stopped by to discuss why companies need to stick to their core competencies.
Tune in as Peter and David talk about the challenges of blockchain, managing the expectations of so many different stakeholders, and why hiring people who are strong in areas where the company has been weak has paid off for Ripple. Listen in!

[00:20] - How David became a CTO
[02:14] - Changing international payments
[02:47] - Banking integration
[03:57] - Scaling the organization
[05:54] - Roles and responsibilities at Ripple
[11:46] - Integration engineering vs. product
[17:20] - Hiring for the integration engineering world
[18:34] - Surprises and challenges in a CTO role
[21:02] - Balancing management
[24:04] - Attracting and retaining talent

CTO Connection is where you can learn from the experiences of successful engineering leaders at fast-growth tech startups. Whether you want to learn more about hiring, motivating or managing an engineering team, if you're technical and manage engineers, the CTO Connection podcast is a great resource for learning from your peers!
If you'd like to receive new episodes as they're published, please subscribe to CTO Connection in Apple Podcasts, Google Podcasts, Spotify or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.
Podcast episode production by Dante32.

How to Build a Culture of Security with Nick Streaker Dec 26, 2019

Show notes

Whether it’s private communications or a product that handles sensitive information, every company needs to foster a culture of security. Our guest this week, Nick Streaker, is the CTO of ID Agent, a Kaseya company, and was an intelligence officer in the military. Nick talks to Peter about how to make security a part of your company’s overall strategic plan from hiring to product launch.
Tune in to learn why it’s hard to find cybersecurity professionals, what Nick considers the bare minimum security features, and why he turns to bootcamps to find new hires.

[00:46] - Nick's path to becoming a CTO
[03:39] - Recruiting for cyber skills
[08:31] - Insight from outside the models
[10:46] - Diversity of opinion
[11:54] - Creating an innovative culture
[13:58] - Empowering end-users with ID Agent
[14:38] - When to build a culture of security
[20:14] - Baseline security requirements
[22:25] - Two-factor authentication
[26:03] - Cybersecurity trends
[32:01] - Filling the security role
[36:00] - Relating the need for security

This episode is sponsored by Clubhouse.io. Clubhouse lets you manage software projects with the perfect balance of simplicity and structure, so you and your team can be happier, less stressed, and hyper-focused on building products that customers love. It’s free for up to 10 users, plus you can get two free months on any paid plan at https://clubhouse.io/CTO.
CTO Connection is where you can learn from the experiences of successful engineering leaders at fast-growth tech startups. Whether you want to learn more about hiring, motivating or managing an engineering team, if you're technical and manage engineers, the CTO Connection podcast is a great resource for learning from your peers!
If you'd like to receive new episodes as they're published, please subscribe to CTO Connection in Apple Podcasts, Google Podcasts, Spotify or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.
Podcast episode production by Dante32.

From Engineer to General Manager with Mike Reust Dec 19, 2019

Show notes

Mike Reust never pictured himself in management. But after several years at Betterment, the opportunity presented itself. Mike joins us this week on CTO Connection to discuss what it’s like to transition from engineering to a management role.
Listen in as Mike and Peter talk about the growing pains of transitioning roles as well as advice for those thinking of going into management.

[00:54] - Making moves at Betterment
[02:15] - Inflection point in accountability
[04:11] - The next dramatic change
[06:02] - Emotional weight
[08:26] - Boss duality
[08:57] - Change in responsibility
[10:11] - Betterment Everyday
[11:35] - Taking on a dual role
[14:14] - Pushback
[17:16] - Opportunity for impact
[19:16] - Surprises about management
[22:56] - Stepping back
[25:13] - CTO vs. General Manager
[27:03] - A greater level of empathy

This episode is sponsored by Clubhouse.io. Clubhouse lets you manage software projects with the perfect balance of simplicity and structure, so you and your team can be happier, less stressed, and hyper-focused on building products that customers love. It’s free for up to 10 users, plus you can get two free months on any paid plan at https://clubhouse.io/CTO.
CTO Connection is where you can learn from the experiences of successful engineering leaders at fast growth tech startups. Whether you want to learn more about hiring, motivating or managing an engineering team, if you're technical and manage engineers, the CTO Connection podcast is a great resource for learning from your peers!
If you'd like to receive new episodes as they're published, please subscribe to CTO Connection in Apple Podcasts, Google Podcasts, Spotify or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.
Podcast episode production by Dante32.

Engineering Apprenticeships and Ongoing Education with Andy Britcliffe Dec 12, 2019

Show notes

The customer service reps at Holiday Extras spend their days talking to customers on the phone. Andy Britcliffe, CTO of Holiday Extras, had a wild thought: what if we had an engineering apprenticeship program that enabled these reps to learn the other side of the business?
On this week’s episode of CTO Connection, Andy talks to Peter about the success of the internship and apprenticeship programs at Holiday Extras. He discusses why education programs for employees lead to better retention and higher engagement. Listen in for Andy’s tips on how to start a program like this at your company.

[00:46] - Holiday Extras
[01:44] - Learning to be a tech leader
[03:38] - Apprenticeship scheme
[08:24] - Preparation and infrastructure
[09:24] - Sandwich year
[10:48] - Matrix management structure
[11:57] - Dev coaches
[15:28] - Foundations teams
[19:53] - Team rotation
[22:19] - Pod composition
[23:17] - Optional participation
[25:08] - Distributed nearshoring teams

This episode is sponsored by Clubhouse.io. Clubhouse lets you manage software projects with the perfect balance of simplicity and structure, so you and your team can be happier, less stressed, and hyper-focused on building products that customers love. It’s free for up to 10 users, plus you can get two free months on any paid plan at https://clubhouse.io/CTO.
CTO Connection is where you can learn from the experiences of successful engineering leaders at fast-growth tech startups. Whether you want to learn more about hiring, motivating or managing an engineering team, if you're technical and manage engineers, the CTO Connection podcast is a great resource for learning from your peers!
If you'd like to receive new episodes as they're published, please subscribe to CTO Connection in Apple Podcasts, Google Podcasts, Spotify or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.
Podcast episode production by Dante32.

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