Jason Huntley

About Jason Huntley

I bring 20 years of B2B sales experience, including 17+ years in enterprise sales closing complex, multi-threaded deals across fintech, payments, treasury, financial data, and risk platforms—consistently delivering six- and seven-figure outcomes within global organizations. My background also includes 10+ years in sales leadership, building teams, designing go-to-market strategy, and developing outbound motion, sales playbooks, and sales development organizations.In my current role at Oversight, I partner with finance teams operating across ERP, expense (T&E), and broader financial ecosystems to identify gaps in visibility, auditability, and control across procure-to-pay (P2P), vendor, and transaction workflows—helping organizations detect risk, strengthen compliance, and improve financial integrity.I have held sales leadership roles at Western Union Business Solutions, Cintas, Worldwide Express and served as Chief Revenue Officer of SkyOne Air, scaling the go-to-market engine from zero to $10M+ ARR in 34 months, fully bootstrapped.Core Areas of Focus:• Enterprise Pipeline Creation & Outbound GTM Execution (BDR Alignment, Playbooks, Territory Build)• Executive Engagement & Complex Deal Orchestration (CFO, Treasury, Finance, Procurement)• Enterprise SaaS Sales Leadership & Net-New Pipeline Development• Large Deal Execution ($250K–$2M+ ARR, Multi-Threaded Sales Cycles)• Strategic Account Penetration & Expansion within Global Enterprises• Finance & Spend Operations Expertise (I2P / P2P / AP / Expense / Payments)• Workflow Automation, Audit & AI-Driven Finance Solutions• Financial Systems & Ecosystem Selling (ERP, T&E, Vendor, Payment Workflows)

Experience

1. Senior Enterprise Account Executive Western Us & Canada

   Oversight

   May 2023 — Present · Los Angeles, CA, US

   I lead enterprise sales across the Western U.S. and Western Canada, partnering with Fortune 50 and large global organizations.I work directly with CFOs and leaders across Audit, AP, Procurement, and Finance to improve real-time financial visibility, strengthen controls, and reduce risk across complex spend and transaction workflows.My focus is navigating multi-threaded, high-value enterprise sales cycles—building executive alignment across finance, operations, and IT within complex environments spanning ERP, expense (Concur/T&E), and vendor ecosystems.I help organizations uncover gaps in financial visibility, risk monitoring, and workflow efficiency that impact broader finance operations—then guide initiatives that improve governance, control, and operational performance at scale.I specialize in positioning AI-driven automation within core finance workflows, enabling companies to shift from reactive, point-in-time audits to continuous, proactive finance risk intelligence.

Education

• University of California, Riverside

  Bachelor's Degree