AI Deployment Strategist

About Freehand

Most AI companies are building tools. We're building the worker.

Freehand's AI agents replace the human decision-making and coordination layer that sits above enterprise software — handling the analysis, negotiation, prioritization, and execution that previously required armies of logisticians / supply chain professionals.

Our customers include Apple, Meta, GE, Pfizer, J&J, Schlumberger, Cardinal Health, and Unilever. They chose us because we have a fundamentally different answer to what enterprise software looks like when AI can do the job.

If you want to work on something that matters, with people who will push you to be sharper than you thought you could be, this is the place.

The Role & The Team

The AI Deployment Strategist role combines solution architecture, enterprise delivery, and strategic customer partnership. This role acts as the bridge between customers, product, engineering, and delivery teams to design, implement, and scale enterprise technology solutions. It requires both strategic thinking and execution capability, ensuring successful enterprise implementations while shaping product and solution direction.

What You'll Do

Customer Partnership & Strategy

• Act as a strategic advisor to enterprise customers across operations, finance, supply chain, and IT teams.
• Partner with customers to define business objectives, requirements, priorities, and transformation roadmap.
• Build strong relationships with customer stakeholders from operational teams to executive leadership.
• Help customers rethink workflows, freight operations, payments, and enterprise processes through technology.

Solution Architecture & Design

• Design end-to-end enterprise solutions integrating ERP, TMS, Spend management, and other enterprise systems.
• Create solution architecture, design documents, process flows, and implementation blueprints.
• Translate business requirements into scalable technical and functional solutions.
• Ensure solutions align with enterprise architecture, security, governance, and scalability requirements.

Enterprise Delivery & Implementation

• Lead end-to-end implementation and migration of enterprise customers onto the platform.
• Drive execution across integrations, data migration, testing, and go-live.
• Manage complex, multi-stakeholder enterprise implementations.
• Ensure successful adoption, delivery excellence, and business value realization.

Product & Engineering Collaboration

• Partner with product and engineering teams for integrations, feature adoption, and product improvements.
• Provide customer insights and feedback to influence product roadmap and platform capabilities.
• Act as the bridge between business stakeholders and technical teams.

Business Analysis & Process Improvement

• Analyze customer data, workflows, and operations to identify improvement opportunities.
• Recommend process optimization, automation, and cost reduction opportunities.
• Define business outcomes and measure success metrics post-implementation.

Delivery Excellence & Playbooks

• Establish implementation best practices, frameworks, and delivery playbooks.
• Continuously improve delivery processes and implementation methodology.
• Help define and scale enterprise delivery organization standards.

Who You Are

• 6–10 years of experience in enterprise software implementation, solution architecture, consulting, or enterprise delivery roles.
• Experience in supply chain, logistics, freight audit payments, finance operations, or enterprise SaaS platforms preferred.
• Experience working with enterprise systems such as ERP, TMS, Spend management, or payment platforms.
• Proven track record of delivering complex enterprise implementations successfully.
• Bachelor's degree required; MBA or Operations/Supply Chain specialization preferred.

Working at Freehand

Series B, ~100 people across the US and India. Big enough to have infrastructure, small enough that your work is visible. We run on five core operating principles; these are not values-on-a-wall, this is the exact philosophy we built our AI agents on :

• Context Before Confidence. We get in, ask (a ton of) questions, connect the dots ourselves and move fast. No passengers, no hand-holding. The amount of confidence you'll have in Week 1 is directly proportional to the context strive to gain.
• Decisions, not Recommendations. Freehand folks decide, they don't present options. You'll have real autonomy, and real accountability to match.
• High Agency, High Trust. We won't manage you closely or ask you to escalate every call. Act, share your reasoning, and course-correct when needed. That's the contract.
• Accountability is the Product. When something goes wrong — and it will — we name it, learn from it, and move on. No politics, no cover. Just fix it.
• The Work That Remains is the Work That Matters. We actively cut low-value work. What lands on your plate is there because it matters — and can only be done by you.

We proudly offer the following Benefits to all our full-time employees:

• Take what you need Vacation Policy
• Monthly home-internet costs
• Full health coverage (with multiple gold-standard carriers across medical, dental & vision)
• Life Insurance and Disability benefits
• HSA/FSA Access
• 401(k) with a 4% Employer Match
• Fully-paid Parental Leave

Equal Opportunity

Freehand hires on merit — your thinking, your track record, your potential — without regard to race, gender, age, religion, sexual orientation, national origin, disability, or any other protected characteristic. If you meet most of the criteria above but not all of it, apply anyway. We care more about your willingness to learn & take initiative than whether your resume maps perfectly to every line.

Compensation Range: $200K - $250K