Director of AI Enablement

You’ll lead a new, innovative service line that helps clients turn AI from buzzwords into measurable outcomes.

Unlocking the value of AI and automation may be the single biggest change management challenge our clients face this decade. For some, their survival depends on how they do it. For most, they have no idea where to even begin.

That’s where you come in.

The Opportunity

We’ve developed a scalable AI Enablement approach that can be tailored to small and mid-sized business everywhere.  We hold that AI Enablement requires unlocking leaders and organizations – not just technology.   We have a tremendous opportunity through our platform of MSPs and their thousands of clients. In serving them, we can deliver significant value and build a compelling service team.

Your mission is to make it real.

You’ll start hands-on: working directly with early clients to ship tangible wins within the first 30–45 days, and turn those successes into reusable playbooks. That builds into recruiting, training, and working with leaders throughout the platform for growth. 

You’ll partner closely with the Chief Innovation Officer and the Innovation Center to build it all. 

Long term, you’ll own the revenue performance, delivery excellence, and evolution of the AI Enablement business unit, building it into one of our most strategic offerings.

The first quarter’s focus is on building approach, testing it with clients, refining, and laying down the foundation for scale.  Within a year, we expect to have a strong team serving hundreds of clients.

You Will:

• Lead AI Enablement engagements on an ongoing basis, shepherding clients along their journey.
• Identify key strategic and operational areas at clients that can be elevated with AI.
• Develop enablement frameworks and training programs that can scale.
• Partner with client executives to define strategy, governance, and metrics.
• Build internal playbooks and artifacts that document what works, and why.
• Hire, train , and lead a small team of enablement specialists.
• Measure success through client adoption, ROI, and value realized.
• Use AI and automation extensively in your own work (and expect your team to do the same).

Who You Are

• A builder first. You can’t do things halfway. You move fast, iterate, and care deeply about the quality of what ships.
• A change agent. You’ve led organizations through mindset and behavior shifts, whether that’s adopting new tools, new workflows, or new cultures.
• A strategist who executes. You can zoom out to design a framework and zoom in to build a working prototype in a day.
• A leader and coach. You know how to attract, hire, and grow strong people.
• Fluent in AI. You already use AI tools to accelerate your own work and have a point of view on responsible, effective enablement.

Core Competencies

• Proven ability to lead and scale a service or business line.
• Deep skill in leading complex client engagements and facilitating executive conversations.
• Comfort with ambiguity, thrives in “build it while we scale it” environments.
• Experience with Microsoft 365, Copilot, or similar enterprise AI ecosystems.
• Facility with data, metrics, and outcomes-driven decision-making.

Compensation

Target range: $180,000–$230,000 base + performance bonus, with flexibility for exceptional candidates.

Why This Role Matters

You’ll be the integral leader of the team that helps hundreds (perhaps thousands) of our clients navigate the defining transformation of this decade: how humans and AI work together in ways that are meaningful, wise, and beneficial - for people and organizations everywhere.