Director, North America Enterprise Sales

About Oversight

Oversight is the world's leading provider of AI-based spend management and risk mitigation solutions for large enterprises. Based in Atlanta, GA, Oversight works with many of the world's most innovative companies and government agencies to digitally transform their spend audit and financial control processes. Learn More.

Oversight's AI-powered platform works across our customers' financial systems to continuously monitor and analyze all spend transactions for fraud, waste, and misuse. With a consolidated, consistent view of risk across their enterprise, customers can prevent financial loss and optimize spend while strengthening the controls that improve compliance.

Position Overview : Job Purpose

Oversight helps CFO organizations leverage AI-driven solutions to continuously monitor spend, identify risk, and drive savings across AP, T&E, and procurement. As Director, North America Enterprise Sales, you'll lead our enterprise new-logo and expansion motion across the U.S. and Canada, maximizing productivity of our field AEs and scaling revenue through both direct enterprise selling and indirect channels.

Responsibilities and Expectations

Lead and Coach High-Performance Team

Hire, onboard, and develop a winning team of Enterprise AEs; set clear territories, goals, and scorecards.

• Run weekly 1 : 1s and deal reviews; institute effective processes, exec mapping, and value hypothesis discipline.
• Establish a repeatable operating cadence (QBRs, monthly forecast, pipeline councils, partner councils).
• Create a winning atmosphere that allows Oversight to position, compete and win with integrity while adding to its world-class client base.

Drive Enterprise Revenue (Direct)

Own regional new-logo and expansion number across ICP-targeted accounts; personally engaging in deals where needed to support the team and outcomes.

Scale Through Partners (Indirect)

Build and execute joint go-to-market with Oversight partners and strategic resellers.

Operational Excellence

Own forecasting in Salesforce with data-driven stage definitions, exit criteria, and inspection; enforce activity / productivity standards.

Market and Product Leadership

Provide field feedback to Product on buyer pain (AP audit, duplicate / fraud risk, policy leakage), integrations (ERP / T&E / Procurement), and competitive intelligence.

Qualifications

8-12+ years in enterprise SaaS with 4-6+ years leading enterprise AEs; consistent over-achievement against multi-million-dollar new business targets.

How we'll measure success

New and expansion ACV vs. plan

Compensation and Travel

Competitive base + accelerators with uncapped commission. Travel may vary, but approx. 25% for customer, partner, and team engagements.