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 Head of Sales 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 — figure it out with whatever tools exist

• Have strong opinions, defend them, and drop them when proven wrong

• Would rather own targets than a task list

• Run toward ambiguity, not away from it

• Want to work with no-BS people

People who struggle here:

• Confuse ambitious goals with unreasonable ones

• Want 9-to-6 and a predictable week

• Need priorities to hold still for a quarter

• Take blunt feedback or lost deals personally

• Say — or think — “that’s not my job”

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 hybrid 3 days per week from 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