Chief of Staff

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.

The Chief of Staff partners closely with the CEO and executive leadership team to help drive and shape corporate strategy, then operationalize it so it translates into real execution across the company. This role acts as connective tissue across the organization, catching what falls between functions, managing information flow to leadership, and taking on the ambiguous or cross-functional initiatives that don't have a natural home elsewhere.

The role combines strategic thinking with hands-on execution. The Chief of Staff identifies new market opportunities, analyzes competitive and industry dynamics, supports board and investor preparation, and ensures alignment against key company objectives, while also driving the follow-through that turns strategy into results.

This leader works across Product, Growth (Sales), Engineering, Operations, Government Affairs, and Finance to improve decision-making, drive strategic initiatives, monitor key performance indicators, and ensure organizational alignment as the company scales. Success in this role requires analytical rigor, sound business judgment, strong operational execution, and the ability to communicate clearly with both executives and cross-functional teams. As Hayden scales, this role is expected to evolve. In year one, the priority will be developing the strategy and then operationalizing it; the remaining responsibilities below will be layered in as capacity allows once that foundational work is underway.

Responsibilities:

• Strategic Partnership & Thought Leadership

  • Serve as an active thought partner to the CEO and executive leadership team, offering perspective and pressure-testing ideas before decisions are finalized.

  • Assess market opportunities for potential new investments and growth initiatives, including market size, competitive dynamics, and fit with the current Hayden roadmap.

  • Pull data from a variety of sources, including current customers or partners, investors, industry analysts, and other primary and secondary sources, to support key insights, conclusions, and recommendations.

  • Become deeply familiar with the Hayden system, roadmap, and market dynamics to quickly support other teams' market and product investigations, becoming the go-to source for this type of information.

  • Lead the annual strategy process

• Operationalizing Strategy & Cross-Functional Alignment

  • Translate strategic priorities into clear, actionable plans, and own the follow-through that keeps workstreams moving across functions.

  • Gather and synthesize operational data and performance metrics across departments, ensuring insights are communicated clearly to drive action.

  • Contribute to Finance's Monthly Operating Review by tracking metrics in real time through the goal-setting process and monitoring progress against key strategic objectives

  • Serve as connective tissue across Product, Growth, Engineering, Operations, Government Affairs, and Finance, identifying gaps and misalignment before they become problems.

• Executive Cadence & Meeting Rhythm

  • Own the ELT meeting cadence, including agenda setting, pre-reads, and follow-up tracking to ensure decisions and action items move forward.

  • Partner with the CEO to structure recurring leadership rhythms, such as weekly staff meetings, monthly business reviews, and quarterly offsites, that keep the organization focused on priorities.

• Executive Support & Board Engagement

  • Serve as a trusted partner to the executive team, managing the flow of information and priorities so leadership's time and attention go to what matters most.

  • Prepare for strategic reviews, Board meetings, and other key engagements, providing insights, analysis, and recommendations that support informed decision-making.

  • Take on ambiguous, sensitive, or cross-functional special projects that don't have a natural owner elsewhere.

• Market Monitoring & Intelligence

  • Proactively track and analyze data relevant to Board inquiries, ensuring accurate and timely business intelligence to support informed decision-making.

  • Maintain an ongoing, deep understanding of market trends and competitive dynamics to support strategic discussions at the ELT and Board level.

Qualifications:

• Bachelor's degree in business, engineering, or a related field; graduate degree a plus

• 7+ years of experience in strategy consulting, business operations, or product management, in technology companies of comparable size and complexity

• Experience working with and presenting to C-level executives and Boards of Directors

• Excellent communication and presentation skills, both one-on-one and with groups

• Demonstrated experience applying AI tools (e.g., Claude, Claude Code) to data analytics, reporting, and productivity, beyond general familiarity

• Demonstrated ability to move fluidly between strategic thinking and hands-on execution

• High degree of discretion and sound judgment in handling confidential and sensitive information