Senior Director of Sales and Customer Success

At Hayden AI, we are on a mission to harness the power of computer vision to transform the way transit systems and other government agencies address real-world challenges.

From bus lane and bus stop enforcement to transportation optimization technologies and beyond, our innovative mobile perception system empowers our clients to accelerate transit, enhance street safety, and drive toward a sustainable future.

We are seeking a seasoned and strategic Sr. Director of Sales & Customer Partnerships to lead and expand Hayden AI’s presence across state and local government agencies throughout the eastern United States. This senior, field-facing leadership role is responsible for driving new logo acquisition, long-term revenue growth, and full customer lifecycle success across public sector transportation, transit, and municipal parking agencies.

This leader will own territory strategy while also overseeing end-to-end revenue performance — from prospecting and pilot to contract execution, expansion, renewal, and long-term partnership growth. The role combines enterprise sales execution with executive relationship management and customer success leadership to ensure durable, multi-year programs.

Success requires deep knowledge of transportation ecosystems, public sector procurement, and complex sales cycles, along with the ability to translate advanced technology into measurable operational and community outcomes.

• Strategic Revenue Leadership

  • Own East Coast territory strategy and execution, delivering on annual revenue targets through new logo acquisition, expansion, renewal, and lifecycle growth.

  • Develop and execute a multi-year territory plan aligned to Hayden AI’s broader strategic growth objectives.

  • Partner with the CGO to develop and execute overall revenue goals, market prioritization, pricing strategy, and strategic growth initiatives.

  • Own top-line KPIs including revenue forecasting, pipeline health, net new revenue, and churn performance.

  • Provide structured weekly and monthly revenue insights to executive leadership.

  • Lead disciplined pipeline management across long government sales cycles.

• End to End Customer Lifecycle Management

  • Own the customer lifecycle from prospect through long-term partnership.

  • Ensure successful transition from pilot to contract, and from initial deployment to expansion.

  • Drive renewals and alignment on contracting and payment terms.

  • Oversee customer health metrics including NPS and account performance indicators.

  • Lead account planning strategy, including executive relationship mapping and long-term expansion pathways.

  • Identify strategic growth opportunities within existing accounts, including ARR growth and deployment scale.

• Government and Transportation Expertise

  • Serve as a subject matter expert on transit operations, bus lane enforcement, curb management, and municipal parking ecosystems.

  • Navigate complex public sector procurement processes including RFPs, regulatory compliance, and legal review.

  • Stay informed on federal, state, and municipal transportation funding mechanisms.

  • Translate industry knowledge into actionable go-to-market and expansion strategies.

• Executive Relationship Management

  • Engage C-level and senior agency leadership in consultative discussions focused on safety, operational efficiency, and community impact.

  • Position Hayden AI’s integrated hardware and AI software platform as mission-critical infrastructure.

  • Represent Hayden AI at industry events, transit conferences, and public sector forums.

  • Cultivate long-term executive partnerships that extend beyond initial deployment into multi-year programs.

• Sales Strategy & Market Development

  • Develop and execute strategies to land new accounts across priority markets.

  • Identify new market opportunities and strategic use cases.

  • Lead involvement in key RFPs, expansion negotiations, QBRs, and launch meetings.

  • Partner cross-functionally to optimize competitive positioning and market placement.

  • Provide structured market feedback to inform product roadmap and strategic direction.

• Customer Success Leadership

  • Lead, mentor, and scale high-performing Sales and Customer Success teams, fostering a culture of accountability, collaboration, and continuous improvement.

  • Oversee overarching customer ownership and client relationship strategy.

  • Drive strategic insights that enable account expansion and program optimization.

  • Track and improve key lifecycle metrics including net new revenue, net new logos, churn rate, ARR growth, customer health score, sales cycle length, pilot-to-contract timeline, contract-to-expansion timing, and win rate.

• Cross-Functional Collaboration

  • Partner closely with Product, Operations, Engineering, Legal, and Marketing to ensure smooth implementation and strong customer outcomes.

  • Determine events, campaigns, and marketing initiatives that support revenue growth.

  • Provide structured feedback to influence pricing, contract structures, and go-to-market evolution.

  • Manage, mentor, and develop Sales and Customer Success team members.

  • Promote professional development through training, process optimization, and growth opportunities.

  • Build scalable processes that enable sustainable revenue performance.

• Travel Requirements

  • Position requires up to 25% travel. Ability to travel extensively with overnight travel throughout the East Coast region. Travel may include local, regional, and national trips for customer meetings.

• Bachelor’s degree in Business, Marketing, or related field.

• 10+ years of enterprise sales experience with significant focus on state and local government customers.

• Demonstrated success closing complex multi-million-dollar deals with long procurement cycles.

• Experience owning a full customer lifecycle including expansion and renewals.

• Deep familiarity with transportation agencies, transit operations, or municipal parking systems.

• Experience selling integrated hardware and software solutions in regulated or infrastructure-focused industries.

• Proven track record of exceeding revenue targets.

• Strong executive presence and ability to engage senior agency leadership.

• Experience managing or mentoring high-performing sales or revenue teams.

• Background in transportation technology, mobility, intelligent transportation systems, or smart city solutions.

• Established network within East Coast transit authorities and municipal Departments of Transportation.

• Experience within high-growth or venture-backed technology companies.

• Experience building or leading integrated Sales + Customer Success organizations

• Understanding of enforcement programs, camera-based systems, or data-driven urban infrastructure solutions.

• Experience mentoring or leading regional sales teams.