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STRATEGIC ADVISORY & EXECUTIVE COACHING

The advisor for decisions that define your company

I work with founders and CEOs of established companies who need a trusted thinking partner — for growth, leadership challenges, acquisitions, and successful exits.

Many of the leaders I work with are also navigating the unique opportunities and challenges that come with ADHD.
Dan Henderson, Gravity Insights

30

YEARS OF EXPERIENCE

24

M&A PROJECTS LED

7

SUCCESSFUL EXITS

Dan Henderson
Founder • M&A Executive • Venture Capital Investor • Executive Coach

HOW I WORK

Three ways I work with leaders

01
Strategic Advisory

A trusted sounding board for founders navigating growth, acquisitions, leadership transitions, major decisions, and the sale of their company.

02
Executive Coaching

Confidential coaching relationships that help founders and CEOs lead more effectively and think more clearly about the challenges they face.

03
ADHD & Leadership

Coaching for executives navigating ADHD — helping you understand how your brain works, harness your strengths, and lead at your best.

BEYOND THE INDIVIDUAL

Sometimes the work
expands to the

whole team

LEADERSHIP TEAM DEVELOPMENT

Individual coaching and advisory work often reveals something the founder already suspects — that the challenge isn't theirs alone to solve. The team that got the company to where it is may be struggling to communicate clearly, pulling in different directions, or hitting a ceiling that no amount of individual effort will break through. These are the moments when working with the leadership team as a whole — not just the person at the top — makes the difference.

​

When I see those patterns in my work with a founder or CEO, I'll say so. And when it makes sense, I'm equipped to take the work further — facilitating leadership discussions, team workshops, or offsite sessions that build on the deep context I already have from working inside the organization.

This kind of engagement typically grows out of an existing coaching or advisory relationship — which changes everything about what's possible in the room.

30

YEARS OF EXPERIENCE

24

M&A PROJECTS LED

7

SUCCESSFUL EXITS

14

BOARD POSITIONS HELD

22

INVESTMENTS AS LEAD INVESTOR

$300M+

COMBINED INVESTMENT VALUE

Testimonials

WHAT LEADERS SAY

Trusted by founders who've been through it

"Dan was invaluable in helping me figure out the early funding strategy that set us up for a successful exit three years later. After securing funding, I greatly appreciated Dan's ability to serve as a sounding board for growth strategies. One of his noteworthy skills is his knack for asking the right questions. Dan possesses a natural talent for identifying potential obstacles and encouraging us to consider different perspectives, which significantly enhanced our decision-making process."

JIGNESH SHAH

FOUNDER/CEO OF RYBBON, ACQUIRED BY BLACKHAWK

WHERE I FOCUS

Areas where I often help

Buying or selling a company is one of the most consequential decisions a founder will ever make. I help you understand the players, the incentives, and the deal terms that truly matter.

Navigating Business Growth

As companies grow, decisions become more complex. I serve as a strategic sounding board, helping founders clarify priorities and work through the issues that matter most.

Leadership can be isolating. My coaching provides a confidential space to think clearly, challenge assumptions, and lead with greater confidence.

Many entrepreneurs have ADHD — and many discover it only after years of pushing through challenges they didn't fully understand. I help leaders harness their strengths and perform at their best.

HOW I WORK

How engagements typically work

Most of my work involves ongoing advisory or coaching relationships with founders and CEOs. Every engagement is different — here's what they typically look like.

01 — Structure
Monthly retainers

Engagements are structured as monthly retainers and begin with a minimum commitment of several months — enough time to build trust and make meaningful progress together.

02 — Cadence
Every two to three weeks

We typically meet every two to three weeks. Between sessions, I'm available for brief calls or messages when a quick sounding board is helpful — decisions don't always wait for scheduled calls.

03 — Transaction Mode
When things move fast

When a deal is live — an acquisition in process, a term sheet on the table, a high-stakes negotiation underway — the engagement shifts. I'm available more intensively, move quickly alongside you, and the retainer reflects that.

04 — Focus
Advisory, coaching, or both

Some leaders engage me primarily for executive coaching. Others work with me as a strategic advisor on major business decisions. Many find that the line between the two is blurrier than they expected.

Start a Conversation

I look forward to connecting.

Email

Call

Follow

‪(703) 665-9337

  • LinkedIn

If you want a trusted advisor

who has been in your shoes,

we should talk.

© 2026 Gravity Insights LLC

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