About the role
The Opportunity Freehand is building the future of enterprise operations—AI-native teams that replace traditional software and staff at the world’s largest brands. Our agentic platform automates complex spend management workflows for global leaders like Unilever, Apple, Cardinal Health, J&J, Dunkin’ and Meta. Weare now scaling our AI Teams for Spend Management—to autonomously manage the procure-to-pay lifecycle, including PO validation, contract compliance, invoice approvals, dispute resolution, and cross-border payments. What You’ll Do • Lead Fortune 100 enterprise customers through end-to-end platform migrations and implementations, managing complex multi-stakeholder programs with precision and composure. • Serve as the primary strategic point of contact for a portfolio of named enterprise accounts, building relationships that span the C-suite, operations teams, and IT organizations. • Develop and communicate a clear point of view on freight spend strategy — helping customers see patterns in their data they couldn’t see before. • Pull, synthesize, and present data-driven insights directly to customers with no analyst dependency required. • Partner closely with Freehand’s product and engineering teams to surface customer patterns, escalate friction points, and influence the product roadmap. • Define success at go-live and at 90 days post go-live, and hold yourself and the customer accountable to it. • Proactively identify risk, push back on customers when the situation calls for it, and resolve issues before they compound. • Help build the delivery playbook — document what works, improve what doesn’t, and raise the standard for the entire team. What We’re Looking For • Demonstrated track record of successfully delivering software solutions to enterprise customers — not just managing relationships but driving outcomes. • Experience leading complex, multi-stakeholder implementations or onboarding engagements where ambiguity was high and the stakes were real. • Fully self-sufficient with data: you find the insight, build the narrative, and present it without needing analyst support. Strongly preferred: • Supply chain or logistics domain experience — reduces ramp time and gives customers immediate confidence. • Payments domain familiarity: payment rails, reconciliation, fraud or compliance workflows are core to the Freehand platform. • Experience at or with high-growth B2B SaaS/AI companies where the delivery playbook was still being written.
