Operating Leadership

I build the operating systems that scale companies.

Operating systems turn startups into sustainable businesses. They're not sexy. They're not what founders want to talk about. But they're what separates companies that scale from companies that stall. This is what I do. This is where I add value.

Bob Penland working

Operating Systems That Enable Scale

I've built operating systems at multiple companies. These aren't theoretical frameworks—they're the actual systems that made companies run:

OKRs with teeth: Clear objectives, measurable key results, designated owners (DRIs), weekly scorecards. Improved forecast accuracy to within ±5%.

Delivery discipline: Release trains, feature flags, retrospectives. Lifted on-time delivery from low 60s% to 90%+ consistently.

Customer success playbooks: Activation checklists, health scoring, expansion motions, quarterly business reviews. Achieved mid-90s% gross retention, low-100s% net retention.

Compliance programs: SOC 2 Type II with zero exceptions, ISO 27001 controls. Unlocked enterprise deals that required security certifications.

Incident response: Command structure, runbooks, on-call rotations. Reduced Sev-1 MTTR by ~40%.

TruMethods

2009–2022
Employee #1 & Founding Operator (titled CTO)

In 2009, Gary Pica had a vision for transforming how IT service companies operated. He needed someone to build the company while he built the market. I joined as employee #1.

Gary focused on vision, sales, and market positioning. I built and ran everything else—product development, engineering, customer success, compliance, finance, team building. We had complementary skills and trusted each other completely.

We grew the company from zero to acquisition by Kaseya. Thousands of customers across 9 countries. Scaled the team from 1 person to over 40. I stayed for three years post-acquisition to integrate four product lines into Kaseya's global portfolio.

My title was CTO, though the role was really COO. We were a small company and titles were flexible. I built operating systems, not just technology.

After 13 years, I moved on. I wanted to learn new things, work with new people, and see if the patterns I learned at TruMethods applied elsewhere. They did.

13 Years
Employee #1 Partnership
Zero→Exit
Acquired by Kaseya
1→40
Team Growth

Apex IT Group

2012–2018
20% Owner, Board Member, Service & Product

In 2012, my partner and I bought into a 15-person IT services company with a problem: growth had stalled, service delivery was inconsistent, and 40% of revenue tied to one client on a declining contract. The company was stuck at $100k MRR and going sideways.

We rebuilt the business planning process, focused the team on clients worth keeping, and cut the ones that weren't. We stopped chasing revenue and started building relationships with the right clients. It worked.

We grew MRR from $100k to $250k and sold in 2018. It wasn't glamorous. It was hard work, tough conversations, and a lot of saying no to things that looked good but weren't.

150%
MRR Growth
Turnaround
Stalled→Acquired
2018
Successful Exit

Salty Dudes Ventures

2021–Present
25% Owner, Co-Founder

In 2021, I co-founded an investment company with a simple thesis: bet on passionate founders in markets where our skills, contacts, and experience actually matter. No spray-and-pray. No trend-chasing.

We deployed capital in five investments. Our best decision was a seed investment in Rewst—a company that's now raised significant venture capital. But the real work isn't writing checks. It's identifying the right targets, advising when it matters, making connections, and being hands-on when founders need it.

I'm not a passive investor. I help founders see problems they're not solving and make introductions that change trajectories. That's where I add value.

5
Portfolio Companies
Rewst
Raised Significant VC
Active
Strategic Advisor

ServicePulse

2019–2022
37.5% Owner, Co-Founder, Product Leader

We built the first AI-powered sentiment analysis tool for IT service companies. The insight was simple: surveys are broken. They're skewed, unrepresentative, and people lie on them anyway.

We used NLP to analyze email and chat interactions to find signals of unhappy clients before they churned. We got to 30 customers and $10k revenue. Then LLMs commoditized our core tech overnight.

We shut it down. Not every company works, but the lessons do. I learned how to build in an emerging market and when to walk away.

Techist Company

Founder, 2025–Present

Product and business consulting for MSP and SaaS companies. I help founders figure out what they're actually building, how to prioritize, and how to think differently about problems everyone else sees the same way.

If you're stuck, spinning, or building the wrong thing, let's talk.

Let's talk about what you're building.

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