A Letter to Anyone Wondering… Huh?

Aug 29

A friend in business retorted to me, “I’ve never known anyone to actively demote themselves and bring in their replacement while smiling.” - Carraig Stannwyck and Eric Skeens

Thanks to Bob Kingery, I’ve been given the privilege to build something beautiful over the last 8 years – a company that solves a real problem, a small but loyal customer base, and late nights that remind me why Bob and I started. With the company growing and scaling to empower more leaders across the country, we needed to level up. Enter in a new CEO, a fresh perspective, a professional leader. This leader is taller, younger (only by months), held C-suite roles, built successful teams in Fortune 500 and Fortune 1000 companies, and being neurodivergent, he is arguably much more intelligent. I hand over the keys and jump in the passenger seat. Will I get car sick riding in the passenger seat? 100% (some of you know about my control issues). Oddly this move is practical, a little bit calming, and quietly brilliant.

But isn’t it the goal in industry to be the “Man” or to be a “Thought Leader” or to be the one person that everybody looks to for guidance and wisdom? You would think so, especially with many of the examples across the globe today. I say, “Step aside and let a professional.”

Why I brought in a Professional Cyber Security Leader

Technology Choices that Protect Revenue

Cyber security leaders think in terms of impact. They don’t ask “Is this cool?” — they ask “If this fails, what breaks for customers and the business?” That mindset promotes growth while reducing friction in business.

Calm, Practiced Responses When Things Go Sideways

If you ever need it, having a CEO who has run incident response at scale is huge. They bring tested playbooks, composure with stakeholders and media, and the kind of discipline that keeps an incident from becoming a headline. That saves money and reputation — two areas 3 Tree Tech can’t afford to gamble with.

Investors Sleep Better

Fundraising and startups are part emotional, part math. A CEO who can credibly explain security posture, compliance readiness, and enterprise adoption risk lowers the “what if” in investor conversations. That often means better terms and smoother due diligence.

A Magnet for High-Quality Talent

When security is baked into leadership, people know you value craftsmanship and longevity. That engrained trait attracts people who care about building things that last, and it nudges the whole team toward being better.

Instant Trust for Enterprise Organizations

Big companies move slowly for a reason: they’re protecting billions of dollars and reputations. A former global CISO of a $20+Billion company brings credibility and can walk into board rooms speaking the same language as the board members and other c-suite.

Why Neurodiversity Adds an Edge (Carraig’s Superpower)

Let’s talk about it, as it has at times been tough to read Carraig Stanwyck over the years I’ve known him. I feel like I’m pretty decent at reading a person’s body language and measuring vocal responses along with situational context, but when it comes to neurodivergent individuals,such as Carraig, my read is less accurate, as the baseline that my “people-reading” power works off of becomes unusable. So I do what I do best – adapt. Being neurodivergent isn’t a label that limits — it often brings different superpowers.

In a CEO who’s also a former human intelligence officer in the US military, neurodivergent strengths tend to show up in some of the best ways possible:

Deep Pattern Recognition: noticing weird, subtle signals that others gloss over — exactly what you want when hunting for systemic risks.
Hyperfocus on Thorny Problems: that stubborn attention can move through a gnarly business puzzle faster than you expect.
Rigorous Clarity and Consistency: processes and procedures that are clear, repeatable, and reduce chaos.
Unconventional Problem-Solving: creative ways to simplify complexity, which is invaluable when scaling.

Making the Dynamic Work (the very practical stuff)

I’d like to mention again – I have control issues. So this hire only shines when you set them up to win. Small choices upfront make a big difference:

Define Clear Role Boundaries: founders keep vision and mission in mind; the CEO owns scaling, enterprise go-to-market (GTM), and ops. Clarity avoids turf wars.
Use Strengths-based Onboarding: ask about communication and meeting preferences, and adjust. Quiet prep time, written agendas, and asynchronous options are simple, high-ROI tweaks. CliftonStrengths is an effective assessment tool that we use. My top-five are Context, Belief, Relator, Learner, and Strategic.
Set Measurable Success Metrics that Blend Growth and Resilience: time-to-enterprise-adoption, mean-time-to-detect/repair, number of security-driven deliverables, and customer trust indicators.

Normalize Accommodations: they cost little but improve performance — think flexible schedules, structured meetings, and written follow-ups after conversations.

A Short Checklist for Founders

Identify three enterprise blockers where professional leader experience would shorten business development cycles (e.g., board committees, procurement partnership, organizing people).
Draft a one-paragraph division of responsibilities: who owns strategy vs. enterprise sales vs. operations.
Prepare a short onboarding plan that includes communication preferences and a 30/60/90 for company and GTM milestones.
Line up investor and advisor messaging that frames this company addition as risk reduction and enterprise acceleration.

Why this Mix is Special (and a little poetic)

Founders often bring the fire — vision, speed, intuition. As a former global CISO, Carraig brings structure, credibility, and a muscle for protecting that vision as it scales. Add neurodivergent strengths, and you get focused, unconventional thinking that spots problems before they bloom and creates order without killing creativity. It’s the rare combination of boldness and guardrails — the kind of leadership that helps a scrappy startup grow into a dependable company.

If you’re in the founder’s seat, think of demoting yourself as both an accelerator and an insurance policy: it speeds your access to enterprise markets while lowering the chance of the kinds of problems that derail companies. That’s a win you can measure! It all begins with an idea. Maybe you want to launch a business. Maybe you want to turn a hobby into something more. Or maybe you have a creative project to share with the world. Whatever it is, the way you tell your story online can make all the difference.

Don’t worry about sounding professional. Sound like you. There are over 1.5 billion websites out there, but your story is what’s going to separate this one from the rest. If you read the words back and don’t hear your own voice in your head, that’s a good sign you still have more work to do.

Be clear, be confident and don’t overthink it. The beauty of your story is that it’s going to continue to evolve and your site can evolve with it. Your goal should be to make it feel right for right now. Later will take care of itself. It always does.

Eric Skeens is the co-founder of 3 Tree Tech in Portland. He is a platform-agnostic tech researcher that transitions siloed organizations into automated DevOps centric businesses. Message him right here.