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

About Flagright: Flagright is an AI operating system for financial crime compliance used globally by Fortune 500 companies, large banks, fintechs, and fast growing startups. Flagright enables real-time risk detection, automated investigations, and intelligent decisioning, helping compliance teams operate at their full potential in the fight against financial crime. We operate as a lean, high-performance team with high individual ownership and direct access to leadership. Role overview: Our Sales team drives customer growth globally. They own their craft end-to-end, and help more financial institutions realize the value of Flagright. We are hiring a Sales Director (North America) in the Bay Area to lead and scale Flagright’s presence across North America. This is a leadership role with full responsibility for revenue generation and quota attainment across the region. You will lead and develop the sales team to win complex enterprise deals and play a critical role in how Flagright scales in North America. You will be required to travel, and attend conferences/events across North America. 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 Learn fast because they're hungry Want to work with no-BS people building something important People who struggle here: Need extensive hand-holding View high expectations as “unreasonable” Actually prioritize work-life balance Can’t handle ambiguity or rejection Prefer consistent routine over fast-changing priorities Key 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 team to generate high-quality pipeline Continuously raise the performance bar across the North American sales team Who we are looking for: 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 You have a 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 You 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), this is a fully in-person role at our Santa Clara office Willing and able to travel up to 60% of the time What we offer: 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 Get 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 Enjoy a low-bureaucracy environment, minimal meetings, and an asynchronous communications culture