I Talk With People

I like to be held accountable. You should too. 

That means we’re going to chat. Regularly.

About targets, and how we get there, and what needs to change, and how we get better. And if the day ever comes when everything is in sync, the question becomes "can we duplicate this?" 

I get things done, the important things, and along the way I help make our Team (Caps) inclusive and strong and ready for the next challenge – to meet it and beat it.

If history predicts the future, look at my accomplishments. 

In most cases my numbers are above average. In others, my accomplishments are outstanding and top tier. But what they all have in common is…

I had zero experience when I began each tenure and still produced, sometimes exceptionally well. 

I am able to quickly grasp new concepts and technology, then I transfer that enthusiasm and knowledge to other people in a way that makes them act.

Other words used to describe me include, smart, funny, well rounded, professional, and more.

Once in a while humble and modest, but this isn’t that time; I mean c'mon, it’s LinkedIn.

Most business is about relationships and I attribute all my success, like below, on a simple formula… 

Act in ways that build trust, be genuine and be genuinely interested in people and do good things. If you do that, business will follow.

That's what happens to me, every time.

I wish I had some wild and crazy sales strategy, but I don’t, “be interested instead of interesting” opens a lot of doors.

I have led training seminars and done presentations 1 on 1 and to large groups, connecting the dots on technical and product details in a way that people ‘get it’ and act. 

As a hunter I am relentless; as a farmer I am attentive and thorough.

In summary I find, develop, maintain and grow the business. 

I create enduring revenue streams.

Derrick Swain

Chief of Staff | Strategy & Operations | Program Manager | Executive Business Partner | Project Management | Force Multiplier

I’m a 3x Chief of Staff and strategic operator who builds the systems, structure, and clarity that make growth scalable and sustainable. With over 15 years of experience across SaaS, finance, entertainment, and education, I specialize in turning vision into execution and chaos into momentum.

I’ve partnered directly with CEOs, founders, and boards to translate strategy into action through frameworks that align teams, drive accountability, and accelerate results. My work often lives at the intersection of operations, people, and strategy, whether that’s building OKR programs, standing up new operating cadences, or leading high-impact cross-functional initiatives that connect business goals to execution.

Across every role, my focus has been on operational clarity and adoption, diagnosing where friction lives, designing better systems, and helping teams embrace the change that comes with growth. I’ve led post-merger integrations, developed scalable enablement programs, and guided leadership teams through strategic realignments with empathy, transparency, and precision.

What drives me is the balance between people and process. Creating an infrastructure that supports scale while preserving culture. I’m most in my element when I’m untangling complexity, building trust across teams, and helping leaders and organizations operate at their best.

At my core, I’m a builder of systems, teams, and trust. I lead with curiosity, pull no punches, and have a relentless drive to make things better than I found them.

Builder. Operator. Integrator. Dog Mom.

taplio

The Battle

Derrick Swain

Stephanie Majors

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