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 • 6–15 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 C, ~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