Senior Enterprise Account Executive - US

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 Senior Enterprise Account Executive to drive revenue growth and help scale Flagright’s presence across North America. This is a high-ownership role with full responsibility across the enterprise sales cycle. You will win complex deals with fintechs, banks, and financial institutions, develop deep product and industry expertise, and contribute directly to how Flagright scales in the region.

You will manage deals from discovery through to close, build pipeline proactively, and operate with minimal hand-holding in a fast-moving environment. You will be required to travel frequently, 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:

Revenue Ownership

• Own the full sales cycle from discovery through close

• Close complex, multi-stakeholder deals with financial institutions and fintech companies

• Maintain a disciplined, high-quality, conversion-focused pipeline aligned to revenue targets

• Drive expansions, upsells, and long-term account growth

Pipeline & Market Development

• Build pipeline through inbound, outbound, and proactive market engagement

• Represent Flagright at industry events, and customer meetings across North America

• Develop relationships within the fintech, banking, and compliance ecosystem

Product & Industry Mastery

• Develop deep expertise in Flagright’s platform and core FCC use cases

• Understand operational needs of AML and compliance teams across institution types

• Deliver high-credibility product demos and value-driven sales conversations on your own

• Position Flagright clearly against incumbents and competitors

Player / Coach Responsibilities

• Set the standard for enterprise deal quality, discovery depth, and demo execution

• Coach and elevate junior AEs and SDRs through deal reviews and direct feedback

• Contribute to improving sales messaging, objection handling, and internal playbooks

Cross-Functional Collaboration

• Partner with Product, Engineering, and Customer teams during evaluations and POCs

• Provide structured market feedback to inform product and go-to-market strategy

Who we are looking for:

• 4+ years of B2B enterprise SaaS sales experience with direct closing responsibility

• Startup or scale-up experience required

• Experience in fintech, payments, banking, compliance, risk, or financial infrastructure

• Proven success selling complex solutions and AI solutions to enterprise customers

• Data-driven and experimental approach to optimizing customer engagement and conversion

• Strong ability to own deals end-to-end across varying sales cycles

• Track record of building pipeline and winning competitive deals

• Clear communicator with a structured, consultative sales approach

• Willing and able to travel up to 60% of the time

What we offer:

• Competitive compensation

• One number, real ownership, no artificial segmentation

• Direct exposure to leadership and influence on sales and product direction

• 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