Fractional COO & Strategic Operations Partner services for mission-driven and founder-led organizations.
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.
Done.
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 it is exactly what makes the difference for you.
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 running too many things to run 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.
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.
Executive & Board Strategy Sessions
Custom engagements
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.
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 to get clear on your goals, and tell you honestly what I think you need.
My goal isn’t to sell you an engagement package — it's to support you in making a meaningful impact at both the individual and organizational level.
Schedule a call with me here to begin the conversation or email me directly at paige.m.dempsey@gmail.com.
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.
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We might be thinking about the big issues, but I start with data and mechanics — who's doing what, how often, what the numbers actually show.
Then I move to defining the patterns.
By the time we get to the hard question, you've already seen the evidence.
That sequencing matters.
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Most organizations are stuck not because they lack solutions, but because they haven't yet gotten honest about what the real problem is.
I move the conversation toward specifics: unpredictable revenue generation, misaligned programs and services, mission scope creep, outdated operations systems, lack of standard processes and procedures, human resource issues, and more.
We don't touch solutions until we're clear about what we’re solving for.
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I'm not a CPA and I don't replace your accountant. But I see things that others miss.
I can read your financials, spot what the numbers are actually telling you, see how they are working for or against you, and translate those findings into decisions your leadership team and board can act on.
Most leaders need an objective third-party who can plainly say: here's what this means across the organization, here's what needs to change, and this is why.
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Financial and operational complexity shuts people down. I translate it into everyday language people can understand and act on — without emotion taking over — so leadership teams, staff, and boards can think together instead of reacting separately. That's what moves a room from stuck to decided.
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Most people know that something needs to change before they're ready to say it out loud. I ask the questions that close that gap — directly, without blame, and without letting "I know" substitute for actually doing something different.
Getting people across that line is some of the most important work I do.
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It's almost never just keep it or kill it. I separate mission — why you exist — from model — how you sustain it — from assets — what you currently own or operate. I look for what's actually in play: what you're trying to protect, how you're currently operating, and what you own or carry that might need to change.
That separation opens options nobody had considered. Repurpose, redesign, spin off, sunset, sell, or hand off — another path always exists. Finding it is the work.
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Fault looks backward and paralyzes. Responsibility looks at the present and creates options. I distinguish between the two deliberately and consistently.
Leaders don't need another source of blame. They need someone who will tell the truth, stay in the room, and help them figure out what to do next — with enough care that people can actually hear it.
I am that person.
If you're ready to think about your work differently, I'm ready to help you do that.
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. Often the solution to one company’s problem is something I’ve already seen somewhere else. 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 three-time certified 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 and anticipate 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 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 can move fluently between the financial conversation, the operational one, the marketing one, and the human one — and translate across all of them. That is what I love to do.
This is where I come in. I 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 see two options, I see ten. And I help build what comes next — without losing the soul of the thing in the process.
Let’s build the next right thing together.
