AI Deployment Strategist - Enterprise (Founding Team)

Fractional AI builds bespoke software to help organizations solve complex, high-impact problems.

Every C-suite in the country is trying to bridge the gap between AI in theory and AI in practice. We close this gap with exceptional engineering talent and custom end-to-end AI builds (see some of our case studies to learn more).

By joining Fractional AI, you’re stepping onto a San Francisco, NYC, NC, and Dubai-based team working on AI projects for top companies from the comfort of an engineering-first startup.

Fractional AI is launching a new enterprise division, which is physically headquartered in the Triangle of North Carolina. The enterprise division is initially focused on healthcare and life sciences (an area where our leadership team has deep experience), with plans to expand into other industries as we grow. This unique opportunity allows you to be a part of the founding team to help build the division from scratch, but with the stability and resources of an established and profitable startup.

Our clients come to us with ambitious, often fuzzy goals—make content moderation faster, customer service cheaper and better, unlock new integrations, automate the workflows no one else can touch.

Your job is to turn those goals into AI-powered solutions that actually work in the real world—and to own the journey from first conversation → live system → real business impact.

This is a forward-deployed, full-stack client role:

• Part engagement manager (you’re the primary face of Fractional to the client)

• Part product manager (you decide what we build and why)

• Part delivery/program manager (you run the execution motion end-to-end)

• Part “do whatever it takes” operator (you jump into the gaps to keep things moving)

Own the client relationship end-to-end

• Act as the client’s day-to-day strategic partner and primary point of contact.

• Join early-stage calls, run discovery, synthesize feedback, and keep clients aligned on what we’re building and why.

• Build trusted relationships across all levels of an organization, setting clear expectations and being candid about tradeoffs.

Shape what we build and why

• Define product builds, refine and sequence scope, and identify the highest-leverage use cases.

• Translate ambiguous business problems into crisp problem statements, user journeys, and success metrics.

• Work with clients to define what “success” actually means—then design experiments, KPIs, and dashboards to prove it.

Turn messy problems into shipped solutions

• Translate ambiguous client needs into clear requirements, PRDs, and plans for engineers.

• Shape workflows, edge cases, evaluation criteria, and deployment success metrics for AI-powered systems.

• Sit in the loop with engineering: prioritization, tradeoffs, testing, evals, and launches.

Drive execution across multiple AI builds

• Run the day-to-day execution rhythm: stand-ups, planning, check-ins, risk/issue tracking, and runway management.

• Coordinate between clients, engineers, designers, and other Fractional teammates to keep projects unblocked and moving.

• Own timelines and delivery quality—getting projects across the finish line consistently and calmly, even when things change late.

Help create demand, not just fulfill it

• Jump on early, messy conversations where the “project” is still a vague idea.

• Help founders and sales tease out real pain, sketch solution approaches live, and scope engagements that we can actually deliver.

• Spot expansion opportunities and help turn successful deployments into broader, long-term partnerships.

Drive adoption and long-term impact

• Work with client teams on rollout, enablement, and change management—so the systems you build actually get used.

• Monitor performance, gather qualitative and quantitative feedback, and push for improvements where they matter most.

• Bring back insights and patterns that inform Fractional’s internal playbooks, tooling, and product direction.

Bring judgment and clarity

• When requirements are fuzzy, data is messy, or clients change course, you’ll break the problem down and guide everyone toward the highest-impact solution.

• Be the person in the room who can say, “Here’s what we’re actually trying to do, here’s what we know, here’s the plan.”

Client-facing, high-stakes experience

• You’ve led projects where clients were under pressure, stakeholders weren’t aligned, and the path wasn’t obvious.

• You’re comfortable pushing back, reframing the problem, and holding the line on quality.

Real product & delivery experience

• You’ve built and shipped products or services in partnership with engineers and designers—ideally across multiple cycles.

• You know how to run an execution rhythm (stand-ups, planning, tracking, retros) without turning it into process theater.

Structured problem-solving and communication

• You ask good questions, structure chaos, and turn ambiguity into a plan.

• You can go from whiteboarding with execs to writing a crisp doc for engineers without losing the plot.

Bias for action and ownership

• You roll up your sleeves and make things happen, whether that’s writing a scrappy SQL query, drafting a support playbook, or jumping into a last-minute exec demo.

Experience range

• Typically 4–8 years in product, consulting, implementations, or any role where execution and client trust mattered more than your job title. (We care more about what you’ve done than the exact label on your resume.)

Comfort with ambiguity and intensity

• You like high-energy environments, messy problems, and “we haven’t done this before” projects.

• You can juggle multiple clients, keep priorities straight, and make good calls with incomplete information.

AI curiosity, not AI dogma

• You don’t need deep AI expertise on day one. You do need curiosity, strong reasoning, and a desire to learn fast—and to overuse AI in your own workflow.

• Take full ownership of a live client project and become their primary point of contact.

• Run discovery sessions and turn a fuzzy problem into a clear plan for engineers, complete with success metrics and a first milestone.

• Lead regular client meetings, track progress, and keep delivery smooth—flagging risks early and offering options instead of surprises.

• Guide high-stakes moments—like demoing a prototype to a CTO or VP, handling sharp questions, and steering the conversation toward outcomes.

• Kick off a second project in a totally different industry, learning new workflows on the fly.

• Overuse AI: from note-taking and research to drafting docs and testing prototypes.

• Plug into Fractional’s rhythm—from Project Lunch & Learns to our monthly Happy Hour—and start shaping how we deliver applied AI, not just what we deliver.

We believe in transparency and know joining a company is a big decision. We’re not the best fit for everyone and try to be clear on what we are and what we’re not so you make the choice that’s right for you.

Why join Fractional?

• A front-row seat to the AI revolution: In one year at Fractional AI, you will have led many 0-to-1 gen AI builds for leading companies, quickly becoming an expert in applied AI.

• A huge and growing problem space: Getting gen AI into production is the challenge of our time – with legacy consulting firms already driving several billion dollars per year on gen AI advising revenue. Most offerings on the market don’t meet the need – they are one size fits all product solutions or advising services without the engineering team to deliver. We offer the engineering talent to meet the need.

• A team of veteran founders: The team is built from multi-time founders and co-founded by Travis May, former CEO of LiveRamp and founder + former CEO of Datavant.

Why you shouldn't join?

• We are unapologetically building an engineering-first culture. This is how we build the team to meet the moment. We overdeliver for our clients by crafting a culture that enables the best engineers to thrive.

• We are a professional services business. Building for clients and their customers is distinctly different from building for your own product’s customer or users. It’s not for everyone.

• We are in-person. We’re committed to building an in-person team in North Carolina. This enables us to learn faster together. For the right person, this is a pro, not a con, but it’s non-negotiable.

We overdeliver.

We overuse AI.

We “over engineer” the culture.

Raleigh-Durham-Chapel Hill, NC

Work Arrangement: 4 days in-person, Fridays remote

🏦 Competitive Compensation Package: Attractive salary and meaningful equity aligned with your experience and skills.

📈 401k with Matching: Invest in your future with our company-matched retirement plan.

🌴 Unlimited PTO: Take the time you need to relax and rejuvenate.

🏥 Exceptional Medical, Dental, and Vision Coverage: Comprehensive health benefits to keep you and your family healthy.

🚑 Health FSA: Manage out-of-pocket health expenses effectively.

🚌 Commuter Benefits: Make your travel to work easier and more affordable.

🏥 Life Insurance: Providing peace of mind for you and your loved ones.

🎉 Team Events and Activities: Regular events to build camaraderie and a strong team spirit.