- Zero to $50M: 5 Hard-Won Lessons Scaling a Global Development TeamIn 2018, I faced a familiar challenge that many technical leaders encounter - Amazon and Microsoft had recruited away my best developers, and another key team member received an offer I couldn't ma…
- Demo Days Bridge the Gap Between Engineers and ExecutivesSoftware engineers often operate in their own world, heads down writing code, while executives are focused on business metrics and market opportunities.
- How to Run Effective Quarterly Developer ReviewsBuilding and maintaining a high-performing development team requires more than just hiring great talent. One of the most crucial aspects is having a structured approach to developer growth and perf…
- The Hidden Costs of AI Development Tools: What CTOs Need to KnowAs a CTO who has spent decades in the trenches, I've seen countless "revolutionary" tools promise to transform how we build software. Today, AI coding tools like GitHub Copilot and Cursor are makin…
- The Three Faces of Technical Leadership: Understanding the Critical Roles That Drive Engineering SuccessAs a CTO and startup founder for over 20 years, I've experienced firsthand how technical leadership evolves as organizations grow.
- The Cultural Guide to Global Software TeamsBuilding global software teams is more complex than just finding talented developers - it's about understanding and embracing cultural differences.
- From Coder to Leader: The Challenging Transition Technical Founders Must MakeBuilding great software is about solving complex technical problems, but scaling a successful software company requires solving an even more complex challenge: people management.
- Your Customers Are Bad at Explaining Their Problems (And That's OK)Building great software products is a lot like being a doctor.
- Your Users Hate Extra StepsLet me share a brutal truth I've learned after decades of building software products:
- The Art of Saying No to Feature Requests: A Guide to Making Better Product DecisionsOne of the most challenging aspects of building software products is learning when to say no.
- Building Features in Silence: Why Product Marketing Needs to Be Part of Your Development CycleIf a development team ships a new product feature and no one tells the customers about it, did it really ship?
- Why Industry Knowledge Trumps Technical Expertise in 20252025 is the year CTOs must evolve or risk becoming obsolete.
- The 5-Minute vs 5-Day Rule: Finding the Sweet Spot for Developer SupportOne of the hardest challenges in managing software teams is knowing when to step in and when to step back.
- The Asynchronous Myth: Why Some Development Teams Need Face Time to SucceedThe push for fully asynchronous development teams is hurting product quality.
- The Hidden Cost of Not Having Technical LeadershipI recently spoke with a founder who spent $350,000 on development agencies before realizing her life partner was the CTO she needed all along.
- Stop Polishing the Floor: When Perfect Becomes the Enemy of LaunchRecently, I spoke with a first-time founder who perfectly illustrated a challenge I see repeatedly: the endless pursuit of perfection preventing product launch.
- When Your Tech Stack Dies: Lessons in Product EvolutionEvery tech leader's nightmare came true for Todd Watson when Apple effectively killed Flash, forcing him to completely rebuild his website builder platform, Showit.
- Breaking Free from the Request Ticket TrapI've noticed a dangerous pattern that's killing engineering productivity.
- When to Use Project-Based vs. Staff Augmentation Models: A Decision Framework for Technical LeadersAfter 20+ years as a CTO and founder, I've learned there's no one-size-fits-all approach to offshore development. The key is matching your engagement model to your specific needs.
- The Art of Scaling: Why Growth Stage is Easier Than Startup PhaseGetting to your first million in revenue is infinitely harder than growing from one million to ten million. After founding multiple companies and investing in dozens more, I've learned this truth t…
