What are the responsibilities and job description for the Director, North America Enterprise Sales position at Oversight Systems Inc?
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.
- Orchestrate multi-threaded cycles with Office of the CFO, CFO staff (Controller, CAE, CPO), and Finance Ops; align on business cases that drive decisions (savings, risk reduction, compliance).
Scale Through Partners (Indirect)
- Build and execute joint go-to-market with Oversight partners and strategic resellers.
- Support co-sell plays, partner enablement, and pipeline programs that maximize overall success in North America.
Operational Excellence
- Own forecasting in Salesforce with data-driven stage definitions, exit criteria, and inspection; enforce activity/productivity standards.
- Partner with Marketing on ABM, field events, and pipeline SLAs; with Sales Ops and Finance on territory design, comp plans, and capacity models.
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.
- Represent Oversight at industry events and executive briefings; elevate our brand with the Office of the CFO.
Qualifications
- 8–12 years in enterprise SaaS with 4–6 years leading enterprise AEs; consistent over-achievement against multi-million-dollar new business targets.
- Proven success selling to the Office of the CFO (finance transformation, spend risk/audit, CPM/FP&A, ERP/T&E/Source-to-Pay). Experience selling AI-based tools is a plus.
- Mastery of sales process methods, executive storytelling, business case creation, and complex deal orchestration.
- Demonstrated experience building both Direct and partner-led pipelines.
- Metrics-driven leader fluent in Salesforce reporting, forecast governance, territory planning, and capacity/quota models.
- Strong people leader: high integrity, recruits strong players, coaches for excellence, and builds a team-oriented and supportive culture.
- Bachelor’s degree required; MBA or equivalent experience a plus.
How we’ll measure success
- New and expansion ACV vs. plan
- AE productivity per head and ramp time
- Pipeline coverage/quality and stage hygiene
- Forecast accuracy and slip rate
- Win rate and cycle time
- Partner-sourced/influenced revenue %
- Team engagement/retention
Compensation and Travel
Competitive base accelerators with uncapped commission. Travel may vary, but approx. 25% for customer, partner, and team engagements.