Head of Sales (North America) - San Francisco Bay Area at Flagright.com

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 Head of Sales (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