Fractional COO & Strategic Operations Partner for mission-driven and founder-led organizations.

Paige Dempsey, Fractional COO and Strategic Operations Partner, Omaha Nebraska

You need help.

Most leaders don't need more advice.

They need someone who can look at the big picture objectively, identify what’s not working, and help fix it — without creating chaos in the process.

That is where I come in.

I work with small businesses, nonprofits, and growing organizations who are at the point where things have gotten complicated. Maybe you've outgrown your current structure but haven't figured out what comes next. Maybe the team is talented but scattered. Maybe everyone is working incredibly hard, but the numbers still don't work. Maybe finance and marketing and operations are working but not working together.

You bring the problems. I bring the solutions.

What I do

There aren't many people who can sit with your QuickBooks in the morning, facilitate a board conversation in the afternoon, manage your marketing messaging, and coach your executive director through hard conversations all while helping set the strategic vision and actually bring it to life. I can.

As a J.D. with three coaching certifications and extensive training in multiple facilitation methodologies, I have worked across industries including nonprofits, education, law, health care, small business, workforce development, banking, and more.

That combination is uncommon and what creates better results for you: clearer decisions, stronger operations, and an organization that spends less and earns more.

A green leafy plant with oval-shaped leaves on a thin vertical stem.

Fractional COO Engagement

3 to 12 months

You need senior operational thinking and hands-on support, but not a full-time executive. I embed with your leadership team, help stabilize what's broken, rationalize what's scattered, and build the capacity to sustain the work after I'm gone. This is where I do my deepest work.

Best for organizations at an inflection point — outgrowing their current structure, facing a financial challenge, or doing too many things to do any of them well.


Strategic Operations Partner

Project Based

A defined engagement around a specific operational challenge — building a process, fixing a system, consolidating programs, preparing for a board conversation, or creating the operational infrastructure a growing organization needs. We scope it, build it, and close it.

Best for organizations that have one clear thing they need to get right.


Founder Support

Early Stage and Build Out

Starting something new and not sure what to build first? I work with founders at the beginning — before the systems exist, before the structure is clear, before you know what you don't know yet. We figure out what the business actually needs to function, build it in the right order, and make sure you're not three years in before you realize something foundational is missing.

Best for founders who are ready to build it right from the start, not fix it later.


Leadership Coaching

Ongoing, 1:1

Regular conversations for executive directors and founders navigating high-stakes decisions, board dynamics, hard conversations with staff, and their own role in leading change. I bring coaching certifications, operational experience, and the willingness to say the thing other people won't.

Best for leaders who want a thought partner who has actually done the work, not just coached it.


Team Coaching & Training

Custom engagements

Sometimes the team needs to learn something new — a process, a system, a new way of communicating or doing business. I design and deliver training that meets people where they are, whether that's walking a team through a new operational process, building skills around difficult conversations, or working through the interpersonal dynamics that are quietly slowing everything down.

This isn't off-the-shelf content. It's built around what your team actually needs, delivered in a way people can absorb and use immediately.

Best for teams navigating a transition, implementing something new, or stuck in a pattern that's getting in the way of the work.


Executive & Board Strategy Sessions

Custom engagements

A focused working session for your leadership team or board on mission vs. model, program portfolio decisions, financial sustainability, or major organizational tradeoffs. I design and facilitate the session, bring structure to the conversation, and help you leave with actual decisions — not just a list of things to think about.

Best for leadership teams that need to make a hard call and want a skilled outside facilitator in the room.


Strategic Facilitation

Half-day to two days

Customized facilitation for strategic planning, merger integration, consensus building, and community impact initiatives. I'm certified in the Technology of Participation methodology and trained in Results-Based Accountability, Strategic Doing, and Strategic Foresight. I've facilitated rooms from three to three hundred. The goal is always the same: real decisions, real buy-in, real next steps.

Best for organizations that need to get a group of people to build consensus and make a decision — together.

Two green leaves on a small stem isolated on black background

Not sure which fits? Tell me what's going on, and together we'll figure out what makes sense. I'll listen to what you think you want, ask the questions that help you clear on your goals, and tell you honestly what I think you need.

My goal isn't to sell you an engagement. It's to help you move forward in a way that actually works for you.

Schedule a call with me here to begin the conversation or send me a message with more details here.

How I work

After two decades of operational and organizational work I've developed a way of working that's deliberate, repeatable, and genuinely different from most consultants.

If you're ready for change, I'm ready to help.

Who I am

Based in Omaha, Nebraska, I work with organizations locally, regionally, and virtually.

Lawyer. Learning & Development Director. Strategic Facilitator. Coach.

I have had what I like to call a non-linear career path. While most consultants go deep in one industry I went wide across many — and that is good news for you. From law and small business to non-profits and education to entrepreneurship and coaching, I've learned how wildly different people and organizations think and operate. I take what works anywhere and apply it everywhere. I cross pollinate and it works.

I've spent twenty-plus years working across nonprofits, education, workforce development, health systems, large-scale community initiatives, and law. As a lawyer and coach who is also trained in multiple facilitation methodologies (Technology of Participation, Results Based Accountability, Strategic Foresight, and Strategic Doing), I don't just help organizations think differently, I know how to get a room full of people to move together in the same direction while anticipating the risks you might face along the way.

Throughout my career I have had the opportunity to leverage my skills in marketing, technology, analytical thinking, data analysis, and financial acuity. I am tech-savvy and actively learning how to apply AI technology in my own work and in my clients' operations I don't just see the parts — I see how they fit together, where they create friction, and what needs to shift to make the whole system work better. I move fluently between financial, operational, marketing, and human conversations — and can translate across all of them so the right people can make the right decisions.

I am also deeply resourceful. I figure things out. If the first approach doesn't work, I find another one. That applies to everything from building a website from scratch to untangling a financial mess to creating processes that didn't exist before I arrived. I always find the through line. I ask the questions that point to what's really going on. I translate the complicated into the clear. Where you might see two options, I see ten. And I help build what comes next — without losing the soul of the thing in the process.

This is what I love to do.

Let’s build the next right thing together.