Technical Leadership

I translate vision into technical reality.

I've been CTO multiple times. I've built global teams, made hard architectural decisions, and connected business strategy to technical execution. I'm not writing production code anymore—but I know how systems work, how they break, and how to build teams that make the right decisions. My superpower isn't code—it's translation. I sit between the CEO saying "we need this" and the engineering team saying "that's impossible."

Bob Penland with team

I started in the trenches.

I was a network engineer who built data centers, configured BIND and POP3 servers, and designed cloud hosting infrastructure before "cloud" was a buzzword. I have certifications that don't matter anymore: CCNP, CCDP, CCIPTD, Network+, A+. I've written code in C++, Python, Pascal, Basic, HTML, and JavaScript.

I'm not hands-on technical anymore. I don't write production code. But I know how systems work, how they break, and how to build teams that make the right decisions. That's what matters at the CTO level.

Infrastructure

Data centers, BIND, POP3, cloud hosting, network architecture

Languages

C++, Python, Pascal, Basic, HTML, JavaScript

Certifications

CCNP, CCDP, CCIPTD, Network+, A+

Current Focus

Strategic architecture, team building, technical translation

I've built and led 25-person technical teams across six countries.

I've hired, managed, and led engineers in Minsk, Nairobi, Philadelphia, Bangalore, Pune, and Hyderabad. Building distributed teams isn't just about Zoom calls and Slack channels—it's about trust, clarity, and making people feel like they're part of something that matters.

My leadership philosophy: Hire the best engineers, give them space and cover, help them see the business needs, build accountability, then stay out of their way. Micromanagement kills talent. Clarity and autonomy build it.

Minsk
Nairobi
Philadelphia
Bangalore
Pune
Hyderabad
"Testimonial from engineer or technical leader. Something about leadership style, technical vision, or team building."
— Name, Title, Company
The $1.5M Question

Monolith to Microservices

The hardest technical decision I've made: spending $1.5 million to transform a monolith application into microservices with zero new customer features. Pure infrastructure play for long-term scalability.

The business didn't want to hear it. Investors didn't like it. But the monolith was going to break, and when it did, we wouldn't be able to scale. I made the call. We did it.

That's the CTO job—making decisions that hurt today but save you tomorrow. Not everyone gets it, but that's why you need someone who does.

My technical superpower isn't code—it's translation.

I'm the person who sits between the CEO saying "we need this feature yesterday" and the engineering team saying "that's technically impossible." I translate business needs into technical reality and technical constraints into business language.

I'm a visionary who sees how systems need to be built for the long run. I bring product knowledge and experience to technical teams. I help engineers understand why their work matters and help business leaders understand why things take time.

That's the role. Connector. Translator. Strategic thinker who knows enough about the details to make the right calls.

Kosa AI

CTO role focused on responsible AI governance. Built the dev and product teams. Ran operations. Led two pilots—one internal for enterprise development, another with British Standards Institution and GE Health for explainability in medical imaging applications.

We were building AI governance infrastructure before regulations made it mandatory. The technical challenge wasn't just building the analysis tools—it was creating frameworks that worked across industries and use cases.

TruMethods (2009-2022)

I was titled CTO at TruMethods for 13 years, but the role was really COO. I built and ran operations for three products at once: myITprocess, FormulaWon, and Winners Circle. Each served a different need, but they all had the same problem—they needed someone who could translate what business owners actually needed into working software.

I built myITprocess from scratch—the first compliance and vCIO tool for MSPs. I ran FormulaWon's technical operations for 13 years, delivering training content to thousands of companies globally. I co-created Winners Circle, a peer group that changed lives, not just businesses.

We grew the company from zero to acquisition by Kaseya. I stayed three years post-acquisition to integrate four product lines. After 13 years, it was time to see if what I learned applied elsewhere. It did.

Multiple CTO Roles

I've been CTO at multiple startups. Every time, the job was the same: build the team, make the hard architectural decisions, and connect technical strategy to business outcomes. I don't build features—I build systems that let teams build features at scale.

"There's an incredible amount of preparation that goes into my spontaneity."

I teach executive leadership at RIT.

Since 2024, I've been teaching Executive Leadership in the EMBA program at Rochester Institute of Technology. One semester a year. It's not about theory—it's about what actually works when you're leading people through uncertainty.

rit-teaching-screenshot.jpg

I coach youth hockey.

Since 2021, I've been a volunteer coach at Northampton Recreation Center. It's a reminder that leadership is the same everywhere—whether you're building software teams or teaching kids to skate. Show up. Be clear. Care about people.

hockey-coaching.jpg

Need a CTO who connects the dots?

Let's Talk