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Head of Sales, Direct

What You’ll Do

  • Own the full enterprise sales cycle — from prospecting and discovery to negotiation and closing.
  • Build and manage a pipeline of enterprise fintech accounts, ensuring consistent quota attainment.
  • Develop account strategies to land and expand relationships with key stakeholders (C-level, Product, Compliance, and Legal).
  • Collaborate closely with Marketing, Product, and Customer Success to align sales strategy with customer needs.
  • Provide input to leadership on pricing, positioning, and competitive landscape.
  • Represent the company at industry events and conferences to build brand presence.
  • Lay the foundation for building and leading a high-performing direct sales team as the company grows.

What We’re Looking For

  • 5+ years of experience in enterprise fintech sales with a strong closing track record.
  • Proven ability to manage long sales cycles and complex stakeholder relationships.
  • Deep understanding of fintech ecosystems (banks, processors, SaaS, payment platforms, etc.).
  • Experience with compliance/regulatory technology is a strong plus.
  • Exceptional communication, negotiation, and relationship-building skills.
  • Self-starter mindset — able to thrive in a fast-paced, high-growth startup environment.

Why Join Us

  • Chance to define and own the direct sales channel at a high-growth fintech startup.
  • Hybrid setup with a collaborative Brooklyn HQ.
  • Competitive base + commission structure with strong upside potential.
  • Direct impact on revenue growth and company trajectory.
  • Work closely with leadership to shape sales strategy, culture, and team.
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