On this episode of Tech Teams Today, I sat down with Logan Connors, VP of Technology and CISO at Healthyr, and we explored what it really takes to scale engineering organizations across SaaS, healthcare, finance, and venture capital.
The conversation centered on leading through hypergrowth, balancing speed with security, and redefining what makes a great engineer in the AI era.
The Problem with “Stay in Your Lane”
Early career advice often sounds simple: “Stay in your lane and you’ll get there.” But as this episode made clear, growth doesn’t happen by standing still. True leadership requires adaptability, knowing when to anticipate roadblocks, spot new opportunities, and pivot when the timing is right. Consistency has its value, but without flexibility, consistency turns into complacency.
Key takeaway: Great leaders know when to change lanes. Adaptability and timing are just as important as consistency.
Hungry ICs vs. Calm Leaders
High-performing individual contributors with something to prove can drive incredible results. They’re problem-solvers, relentless, and often the first ones to break through tough challenges. But that same intensity doesn’t always translate into management. Leading requires patience, emotional maturity, and the ability to build trust across a group of people with different personalities and motivations. Pairing ambitious ICs with calm, steady managers creates a balance that lets both thrive.
Key takeaway: Don’t rush your top ICs into management. Value their drive, but scale teams with calm leaders who can hold everything together.
Balancing Innovation and Security
In highly regulated industries like healthcare, building products quickly while protecting sensitive data is a constant balancing act. The framework here is practical: move fast when building toward a “lovable MVP,” but circle back to harden security before real customer data is at stake. Security inevitably introduces friction, from compliance frameworks to simple things like two-factor authentication, but if you plan for it early, you avoid backtracking later.
Key takeaway: Speed matters, but security must scale with you. Build with security in mind from the start, even before customer data comes into play.
How AI Is Changing Engineering
AI is redefining what it means to be a “great engineer.” Technical skills remain essential, but they’re no longer the only differentiator. Soft skills like communication, adaptability, and product sense are becoming just as critical. The engineers who will thrive in this new landscape are the ones who know how to manage AI tools, translate outputs into value, and bridge the gap between technology and human needs.
Key takeaway: Tomorrow’s best engineers will be “AI managers” blending technical fluency with adaptability and strong human skills.
Lessons from Scaling Globally
Scaling a 200+ person global team brings unique challenges that go beyond cost efficiency. Remote environments introduce issues with engagement, communication, and even infrastructure reliability. The solution wasn’t more oversight — it was more communication. Instead of lightweight standups, the team relied on working sessions that forced collaboration and kept silos from forming. Over-communication became the glue that held the organization together.
Key takeaway: Scaling globally means over-communicating. Structure collaboration intentionally or risk teams drifting into silos.
Final Takeaway
Leading high-performing teams isn’t about promoting the loudest voice or sticking to the safest path. It’s about balance — pairing ambitious ICs with calm leaders, moving fast while planning for security, and adapting quickly in an AI-driven world. The leaders who succeed are the ones who know when to push forward, when to step back, and when it’s time to change lanes.
🎧 Listen to the full episode:
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