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Watershed
Watershed
Charleston, SC · Est. 2007

FractionalCxO
Leadership

Senior leadership when you need it—without the full-time overhead.

Strategic executive partnership for companies at inflection points. Proudly Charleston-based. Wherever you need us.

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Trusted by 50+ organizations

Oracle
ConEdison
Kroger
Wendy's
Cars Commerce
Omilia
The Ideal Life
Rynoh
The Methodical Group
Odyssey Group
Bublish
Audiogon
First Tee Greater Charleston
Cancer Treatment Centers of America
Vidence
Mater Dei High School
HLTH.IT
DFND
Charleston Roofs + Windows
Charleston Heating + Air
AmmoReady
TE21
Porter-Gaud School
Bennett Chiropractic
Blackbaud
Brightly
Ashley Hall
Oracle
ConEdison
Kroger
Wendy's
Cars Commerce
Omilia
The Ideal Life
Rynoh
The Methodical Group
Odyssey Group
Bublish
Audiogon
First Tee Greater Charleston
Cancer Treatment Centers of America
Vidence
Mater Dei High School
HLTH.IT
DFND
Charleston Roofs + Windows
Charleston Heating + Air
AmmoReady
TE21
Porter-Gaud School
Bennett Chiropractic
Blackbaud
Brightly
Ashley Hall
What We Do

Three focused service pillars

Designed to meet you where you are and scale with your growth

Anchor Service

Fractional Executive Leadership

The executive layer your company needs before it can afford a full leadership team. CTO + CIO + COO under one roof.

Technology Strategy
Operations Excellence
Digital Transformation
Team Leadership
Project-Based

Strategic Accelerators

Discrete, time-boxed engagements with clear deliverables. Perfect entry points that often convert to retainers.

Technology Roadmap & Audit
Organizational Scaling Sprint
Product Ownership Sprint
Standalone + Add-on

Leadership Coaching

Strategic coaching specifically for founders and early executive teams navigating growth challenges.

Founder Coaching
Executive Team Development
Strategic Decision Making
Leadership Transition
Our Approach

A partnership rooted in trust

01

Listen

We start by understanding your business, your team, and the real challenges keeping you up at night. No assumptions, no templates.

02

Strategize

Together we build a clear, actionable roadmap tailored to your goals, resources, and timeline. Strategy that fits your reality.

03

Execute

We roll up our sleeves and work alongside your team—driving execution, measuring results, and adjusting as we go.

04

Scale

We build lasting capability within your organization so the impact scales and continues long after our engagement ends.

Nathan Holleman
Meet the Founder

Nathan Holleman

Founder & Principal Advisor

“The best leadership is the kind that makes itself unnecessary.”

With 18+ years of hands-on executive experience, Nathan partners with growing companies navigating critical inflection points. From healthcare startups to established enterprises, he brings the strategic clarity and operational rigor that turns ambitious goals into measurable outcomes.

Get Started

Ready for your next watershed moment?

Let's have a conversation about where you are, where you want to go, and how we can get there together.