Geeks Who Lead Podcast

We’re going to take a breath on the CTO Connection podcast for the next 3-4 weeks. When we first started the podcast, it was a “startup CTO podcast”. We’ve really enjoyed sharing the wisdom and experience of our guests on building and managing engineering teams at startups. However, we’ve seen over time that the challenges of running (say) a 5-20 person engineering team are very different from those involved when running a 200+ person org. And as many of our original startup CTOs have scaled their orgs to 200 people and beyond, we’ve decided to follow them.
Because of that, we’re going to refocus the podcast, the content, the summits, and the community on “geeks who lead at scale” - senior engineering leaders in larger companies with 200+ full-time employees in product/engineering. In that way, we’ll be able to provide information that is more consistently tuned to one of the most challenging tasks out there - leading engineering orgs at scale.
At the same time as we make the community more exclusive, we’re also going to make it more inclusive. Whether you’re running data, security, IT, or software development, there are many similarities when you’re working within a company of around 500 - 10,000 employees. I’ve been involved with a number of “CTO” clubs across the US and in each case, I’ve seen the benefits of having a range of roles (from CIO and CISO to CDO and CTO - as well as directors and VPs of Software, Platform, Data/Analytics, and Security), as many of the challenges are the same, and it means the community has deeper expertise in a number of key topics if a CDO wants to learn more about engineering best practices for their data team or a CTO needs a hot take on an AppSec challenge they’re facing.
I am disappointed that - given our limited resources - we won’t be able to continue the focus on content specifically tailored to startup CTOs, but I look forward to refining our focus so we can scale our ability to share experiences and insights from and between geeks who lead at scale.

Raffi Krikorian (CTO, Emerson Collective) talks with Laura Edelson (Postdoctoral Researcher at NYU, and Co-Founder of Cyber Security for Democracy Project) about what it looks like to be mission driven in her work.

In part two of my interview with Jason Wodicka, Staff Software Engineer at Karat, we dig deeper into the process of creating predictive, fair, and efficient interview loops. In this episode we start with culture - how do you identify the cultural attributes important to help someone thrive in your environment and how do you interview for culture fit/culture add. We then discuss approaches to blending cultural and functional tests into an interview loop. We then take a little time to discuss how and when to provide hints for candidates during an interview and the surprising value of allowing candidates a redo. 

PARTNER
Thanks to our partner CloudZero — Cloud Cost Intelligence Platform. Control cost and drive better decisions with CloudZero cloud cost intelligence. The CloudZero platform provides visibility into cloud spend without the typical pitfalls of legacy cloud cost management tools, like endless tagging or clunky Kubernetes support. Optimize unit economics, decentralize cost data to engineering, and create a shared language between finance and technical teams. CloudZero helps you organize cloud spending better than anyone else. Join companies like Drift, Rapid7, and SeatGeek by visiting cloudzero.com/ctoconnection to get started.

Raffi Krikorian (CTO, Emerson Collective) talks with Fred Diego (Co-Founder & CTO, Streetwide) about what it looks like to be mission driven in his work.

Especially in the early days, too many companies still have ad-hoc interview processes or over index on things like resumes which aren’t super predictive of likely performance and tend to exclude many great candidates. In this episode, I get to chat with Jason Wodicka, Staff Software Engineer at Karat about their experiences in structured interviewing for engineering roles. We talk about ways to do an inexpensive but predictive initial technical screen, avoiding “pedigree bias”, structuring tests for functional competence and how best to build a lightweight, quick but predictive loop with independent assessments and clear rubrics for everyone involved.

PARTNER
Thanks to our partner CloudZero — Cloud Cost Intelligence Platform. Control cost and drive better decisions with CloudZero cloud cost intelligence. The CloudZero platform provides visibility into cloud spend without the typical pitfalls of legacy cloud cost management tools, like endless tagging or clunky Kubernetes support. Optimize unit economics, decentralize cost data to engineering, and create a shared language between finance and technical teams. CloudZero helps you organize cloud spending better than anyone else. Join companies like Drift, Rapid7, and SeatGeek by visiting cloudzero.com/ctoconnection to get started.

Raffi Krikorian (CTO, Emerson Collective) talks with Adam Kircher (Co-Founder, Sirum) about what it looks like to be mission driven in his work.

I was lucky enough to attend a dinner during which Hilary Mason dropped more wisdom about hiring in one course than many people do in a 90-minute talk. In this week's episode, I get to chat with Hilary, learning how she thinks about screening for judgment, identifying the requirements for a role, the value of creating a humane, fun, structured interviewing process, and the importance of valuing a mix of talents and perspectives on the team (hackers and scalable systems builders, optimists and pragmatists, etc).

PARTNER
Thanks to our partner CloudZero — Cloud Cost Intelligence Platform. Control cost and drive better decisions with CloudZero cloud cost intelligence. The CloudZero platform provides visibility into cloud spend without the typical pitfalls of legacy cloud cost management tools, like endless tagging or clunky Kubernetes support. Optimize unit economics, decentralize cost data to engineering, and create a shared language between finance and technical teams. CloudZero helps you organize cloud spending better than anyone else. Join companies like Drift, Rapid7, and SeatGeek by visiting cloudzero.com/ctoconnection to get started.

Raffi Krikorian (CTO, Emerson Collective) talks with Ariel Ekblaw (CEO, Aurelia) about what it looks like to be mission driven in her work. 

Jesse White grew with the company over at OpenNMS, from developer through to hands on CTO. He started with a team of just five, but as the company and the team grew, he founds himself working longer and longer hours until he finally burned out. After taking time to get back in balance, he returned to continue running the org. In this interview, we discuss the journey and the lessons learned.

PARTNER
Thanks to our partner CloudZero — Cloud Cost Intelligence Platform. Control cost and drive better decisions with CloudZero cloud cost intelligence. The CloudZero platform provides visibility into cloud spend without the typical pitfalls of legacy cloud cost management tools, like endless tagging or clunky Kubernetes support. Optimize unit economics, decentralize cost data to engineering, and create a shared language between finance and technical teams. CloudZero helps you organize cloud spending better than anyone else. Join companies like Drift, Rapid7, and SeatGeek by visiting cloudzero.com/ctoconnection to get started.

Raffi Krikorian (CTO, Emerson Collective) talks with Nellwyn Thomas (CTO, Democratic National Committee) about what it looks like to be mission driven in her work.