Head of Sales (North America) - San Francisco Bay Area

About the role

Flagright is an AI operating system for financial crime compliance used globally by Fortune 500 companies, large banks, fintechs, and fast-growing startups. We enable real-time risk detection, automated investigations, and intelligent decisioning, helping compliance teams operate at their full potential in the fight against financial crime. As the Head of Sales in the Bay Area, you will lead and scale Flagright’s presence across North America, driving revenue generation and quota attainment for complex enterprise deals.

This is a leadership role with full responsibility for the North American sales team, pipeline health, and strategic deal execution. You will be required to travel and attend conferences/events across North America.

Culture fit

People who thrive at Flagright:

• Have been knocked down before and gotten back up
• Are resourceful—they figure things out with whatever tools are available
• Have strong opinions and can defend them
• Are hungry to learn and contribute
• Want to work with no-BS people

People who struggle here:

• Need extensive hand-holding
• View high expectations as “unreasonable”
• Expect strict 9-to-6 boundaries
• Can’t handle ambiguity or rejection
• Prefer consistent routine over fast-changing priorities

Responsibilities

• Responsible for all new revenue generation and quota attainment across North America
• Build, lead, and scale a high-performing sales team to consistently win complex enterprise opportunities
• Maintain full ownership of pipeline health, including pipeline coverage, deal progression, and conversion to closed revenue
• Drive disciplined pipeline creation across outbound and inbound channels, collaborating with the BDR and marketing teams
• Lead and influence strategic, high-value deals, including executive engagement and complex negotiations when needed
• Maintain rigorous forecasting practices and provide clear visibility into regional sales performance
• Establish and enforce strong qualification standards and deal strategy discipline
• Recruit, hire, and develop top-performing sales talent
• Ensure the team consistently executes with clear positioning and messaging
• Build and maintain executive relationships with senior stakeholders at target institutions
• Work closely with marketing and partnerships teams to generate high-quality pipeline
• Continuously raise the performance bar across the North American sales team

Requirements

• 5+ years of B2B SaaS sales experience, with mandatory experience selling to enterprise customers, ideally in fintech, compliance technology, fraud prevention, or data infrastructure
• 2+ years of experience building and leading sales teams with a demonstrated track record of exceeding revenue targets
• Strong ownership mindset with the ability to drive outcomes and hold yourself and your team accountable to targets
• Excellent communication, negotiation, and executive presence
• Ability to coach and develop sales talent and build high-performing teams
• Thrive in a fast-paced, high-performance environment
• Strong written and verbal communication skills
• Based in the Bay Area with the right to work in the USA (no visa sponsorship available)
• Hybrid role: 3 days per week from our Santa Clara office
• Willing and able to travel up to 60% of the time

Benefits

• Housing subsidy for those living within 1 mile of the office
• Leadership position with direct influence on Flagright’s North America sales strategy and direction
• Reports directly to the CEO
• Product with clear, real-world differentiation
• High-bar environment focused on execution, learning, and continuous improvement
• Equity from day 1 at a Y Combinator startup
• Work alongside a highly competent, top-tier team, including professionals from Y Combinator, ex-AWS, and Palantir
• Low-bureaucracy environment, minimal meetings, and an asynchronous communications culture