Kit Colbert - From intern to CTO - lessons learned

Performance management has been a hot topic during this “year of efficiency”. In this Interview RC Johnson shares his experiences of building out, scaling and refining the performance management process at Indeed.

In a world where getting everyone into the same office five days a week is increasingly difficult, offsites are becoming an essential tool for aligning and connecting teams, departments and companies. But all too often, the planning falls to someone with limited events or facilitation experience - on top of their day job - and substantial value is left on the table.Allison - (currently an engineering leadership consultant - previously VPE at QuotaPath and Head of Engineering at Forem) has been planning offsites for 25 years and in this thoughtful interview she shares advice on setting meaningful goals for offsites, how to think about size, location and frequency and some best practices for making them more targeted and engaging to maximize their value.If you’d like to learn more about Allison, check out her website - https://daydreamsinruby.com/

Over the last decade as Avant has scaled to an 800+ person company, town halls have been a consistent pillar of their interval communications strategy to support and reinforce culture.This week Paul Zhang shares his experience and approach to running both company wide and department specific town halls and demo days to better align his team.

Hiring junior developers is always a concern. They’re easier to find and cost less than experienced engineers, but in addition to being less productive, they can easily become a drag on the performance of the senior devs you depend upon to ship mission critical features. Drawing on his experience in the Israeli Military (think the Israeli NSA), Aviv shares concrete advice that can allow you to accelerate the growth of your junior engineers so that they can become productive, mid-level developers in just 6-12 months, allowing for a more cost-effective blended team rate, more satisfaction and growth for the engineers, and the ability to invest effectively in growing the next generation of software engineering talent.

As engineering leaders, we have a responsibility to our organizations and their bottom line. At the same time, we’re leading humans, not automatons, and understanding and supporting the people in our org is both the right thing to do as a person and the most effective way to deliver business value. In this wide-ranging discussion Rukmini Reddit, SVP of Engineering, Platform at Slack shares five questions she asks throughout her org to support herself and her team when dealing with change and how she leverages models like Elisabeth Kubler-Ross’ famous change model to better understand and support her organization through difficult transitions.

Kit Colbert has taken an atypical route to becoming the CTO of a large, publicly traded corporation. He started at VMWare 20 years ago as an individual contributor and worked his way up to CTO leading a 2,300 person engineering org. In this fascinating interview, we walk through Kit’s progression from junior IC to senior engineering leadership and reflect on some of the lessons learned.

Naturally, as CTOs, we often think about our job as to work with developers to ship software. But what does that mean in a world of frameworks, low code, no code, and even GenAI solutions? In this fascinating interview, I got to chat with Jeremiah Stone, CTO of SnapLogic about heuristics for finding the right level of abstraction for delivering business value, how to engage with and support citizen development, and how to deal with shadow IT in a world where even the new marketing intern is writing code.

Over the last decade Josh Builder has led engineering at The Orchard (music), SoulCycle (fitness), Rent the Runway (fashion), and now Signify Health (healthcare). None of these were deep tech companies, but in each case, he found a core of engineering excellence and used that to entice and retain top talent to join his team - despite not being able to match big tech salaries. In this interview, Josh takes us through his process for selecting the right CTO opportunities to accept, then building a compelling engineering brand, and using it first to retain and then attract top talent.

In this week's interview with Albert Wenger, Managing Partner at Union Square Ventures, we discussed the changes that LLMs might bring - to our engineering teams, our products, and our society. We looked at the potential impact on how we write software, what software we need, opportunities for both incumbents and AI native startups, and the broader impact on the workforce and society as we deeply adopt Generative AI over the next 5-10 years. According to Albert, right now we’re both in the middle of an unprecedented hype cycle for LLMs and starting to witness a transformation as profound as that from an agrarian to an industrial society

Raji Subramanian brings a wide range of experience to the role of CTO at Opendoor (Nasdaq OPEN). She honed her technical chops culminating in a Principal Engineer role at Amazon and then ran engineering orgs at Yahoo and Amazon and cofounded Pro.com which was acquired by Opendoor.In this wide ranging interview, we discuss everything from the trend towards single threaded leadership within technical orgs, sustaining innovation in larger technical orgs, the importance of respecting failure, and the three stages of value creation.