AI Deployment Strategist
About this role
We are looking for an AI Deployment Strategist with 5–10 years of experience to own the end-to-end implementation and success of Freehand's AI agents at Fortune 100 enterprises like Apple, Meta, Pfizer, and Unilever. You'll be the strategic bridge between customers, product, and engineering — a sharp, high-agency operator who can hold their own in a room of C-suite executives and push back when needed. This is not a hand-holding role; it's a seat at the table where your decisions shape both customer outcomes and the product itself.
What will you be doing?
Lead end-to-end enterprise onboarding — from pre-sales kickoff and blueprinting through integration setup and go-live — managing 5–6 accounts simultaneously
Own executive stakeholder relationships (Chief Supply Chain Officers, CFOs, 10–15 person steering committees) at Fortune 100 clients, presenting early wins and driving adoption
Act as a strategic advisor who pushes customers toward best practices rather than just fulfilling requests — you bring a strong point of view and defend it
Partner closely with product and engineering teams to translate customer insights into roadmap decisions and shape the product's direction
Work cross-functionally with pre-sales on PoCs and demos, and with junior analysts on integration and data ingestion work
Company at a glance
Freehand builds agentic AI infrastructure to automate supply chain spend management and procure-to-pay operations for Fortune 100 enterprises like Apple and Meta. The company achieved $15M ARR and targets $50M with $75M in funding.
Top Benefits
- Quarterly fully-paid trips for cross-functional teams
What happens next
Skip the application pile. I get you in front of the people who decide.
Confirm the fit
A few questions to make sure this role is the right shape for you. Two minutes.
I pitch you to the company
I write the intro, send it to the founder, and handle the back-and-forth.
A meeting lands on your calendar
When the company wants to meet, I get the call on your calendar. You just show up.
Culture & values
Context Before Confidence — get in, ask questions, connect the dots, and move fast with no passengers or hand-holding
Decisions, not Recommendations — employees have real autonomy with real accountability
High Agency, High Trust culture with no micromanagement; act, share reasoning, and course-correct as needed
Accountability is the Product — when something goes wrong, name it, learn from it, and move on with no politics
The Work That Remains is the Work That Matters — low-value work is actively cut and what lands on your plate matters
Remote-first, travel-first company with office hubs in San Francisco and Chicago serving as collaboration centers rather than mandatory workplaces
Teams are intentionally kept lean with every person's work visible and impactful
Work directly with founders and senior leadership; CEO is hands-on in hiring and strategy
GTM team meets monthly in a US location for collaboration
Fast-paced environment with complex problems requiring sharp, resourceful people who thrive in ambiguity
Promotions from within are valued as a signal of excellence
Company invests in people who prove themselves
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