AI Strategist

AI Strategist
Big Timber AI · Remote (US) · Full-time · $100,000+ base
About Big Timber
We put AI where work already happens. No consoles nobody opens, no licenses nobody uses — we deploy AI agents inside the chat tools and systems our clients already live in, and we stay until the work is actually moving through them. We're small, senior, and allergic to hype. Everything we sell, we've run ourselves first.
The Role
You're the person our client sees. From the first discovery call through a live, humming deployment, you own the relationship and the plan: what gets automated, in what order, and why. You'll work beside a technical build team (human and AI), but the roadmap is yours — which means you need to be technical enough to design it, defend it, and know when something's harder than it looks.
This isn't a pure account-management seat and it isn't a pure engineering seat. It's the seat in the middle, with lead responsibility for making engagements succeed.
What You'll Do
• Own client engagements end-to-end — you're the point person with lead responsibility, from kickoff through implementation through the ongoing relationship
• Sit with the customer — understand how their business actually runs, find where AI genuinely fits (and say so when it doesn't)
• Plan the roadmap — sequence the work into milestones the client can see and feel: what ships in week one, what compounds by month three
• Direct the implementation — translate business reality into briefs the build side can execute, review what comes back, hold the quality bar
• Deliver our off-the-shelf projects — run our productized offerings (site builds, reporting automations, agent deployments) repeatably and profitably
• Feed what you learn back into the product — every engagement should make the next one faster
Who You Are
• You've led client-facing technical work — consulting, solutions, implementation, agency account leadership with real technical depth, or you've been the \"figures it out\" operator inside a business
• Technical enough to be dangerous: you can read an integration doc, understand APIs, CRMs, ad platforms, and reporting pipelines, and call a realistic build order — even if you don't write the code yourself
• You've actually used modern AI tools to do real work, not just watched demos
• You run toward ownership: when something's ambiguous, you make it concrete; when something slips, the client hears it from you first
• You explain technical things to non-technical people without dumbing them down or snowing them
Nice to Have
• Experience deploying or managing AI agents or automation in a real business
• Marketing, ecommerce, or B2B operations background (where our clients live)
• You've sold or scoped professional services work
The Honest Pitch
You'll be inside a working AI operation, not a slide deck about one. The tooling is real, the clients are real, and you'll have more leverage per hour than any job you had before — because half your team doesn't sleep. If you want a lane, this isn't it. If you want the whole road, let's talk.
Compensation: $100,000+ base, commensurate with experience.
Location: Fully remote.