Chief of Staff, R&D

Role Description

Tripleseat is in the middle of a major transformation: rewiring how R&D operates to take full advantage of what AI makes possible. This is not a tooling project. It is a fundamental shift in how engineering, product, and design work together, move from idea to production, and deliver customer value.

As the Chief of Staff, R&D, you will treat product development itself as a product. You will analyze the end-to-end software development lifecycle at Tripleseat, design the systems and workflows that make it radically more efficient, and transform it into an AI-native operation. You will own the R&D transformation roadmap, drive the Agentic SDLC across engineering, product, and design, run the executive program cadence, and serve as Chief of Staff across the Technology and Product organizations. You are not building product features. You are building the conditions under which R&D can build great products, faster, with higher quality, and with less friction.

This is a role that requires equal comfort operating at the leadership level and getting hands-on to define and demonstrate what good looks like. This role requires a low-ego builder and facilitator: someone who listens deeply to Engineering, Product, Design, CS, and GTM, synthesizes the best ideas from the people closest to the work, and turns that shared understanding into practical operating change. This role reports to the SVP of Technology with a dotted line to the CPO, operating at the intersection of Engineering, Product, and Design. You will deeply collaborate with our CS and GTM teams to ensure our transformation work is practical, trusted, and connected to the real needs of the business and our customers.

What You Will Do

• Drive the R&D Agentic SDLC Operating Model
  • Lead a collaborative discovery process with Engineering, Product and Design leaders to map the end-to-end R&D workflow from idea to production.
  • Conduct an AI readiness assessment across documentation quality, test coverage, repo structure, design system maturity, and tooling.
  • Define what AI-native means for every role in R&D.
  • Drive the transition toward continuous delivery.
  • Define and govern the R&D tooling stack.
  • Prototype or pressure-test new ways of working.
• Own R&D Metrics and Visibility
  • Define and own the R&D metrics framework.
  • Ensure R&D transformation is anchored in customer value.
  • Track output metrics, adoption, and behavior change.
  • Close Customer and GTM Feedback Loops.
  • Establish evaluation and continuous improvement practices.
• Run the R&D Executive Operating Cadence
  • Own the operating rhythm across the SVP of Technology and CPO.
  • Prepare leadership for ELT readouts, board meetings, offsites, and major stakeholder interactions.
  • Drive the agenda for R&D leadership forums.
  • Ensure follow-through on decisions made in meetings.
  • Build reporting infrastructure that keeps decision-ready signal.
  • Automate status reporting and executive rollups.
• Drive R&D Strategic Initiatives
  • Identify and take ownership of R&D initiatives.
  • Stand up the operating model for net-new R&D motions.
  • Coordinate cross-functional technical workstreams.
  • Work with the SVP of Technology and CPO on high-priority special projects.
  • Pressure-test new initiatives before they become standing programs.
• Drive Adoption and Capability Building Across R&D
  • Lead the change management work for the AI-native R&D transformation.
  • Build lightweight playbooks, coaching materials, and guardrails.
  • Define guardrails for secure, responsible AI use.
  • Partner with Engineering Managers and Product leadership.
  • Measure adoption, confidence, and sustained behavior change.

Qualifications

• 10+ years in software engineering, engineering operations, product operations, or R&D leadership.
• Program leadership experience at the R&D or platform level.
• Change leader, not just process designer.
• Chief of Staff instincts.
• Metrics fluency.
• Bleeding-edge AI practitioner.
• Customer-centered operator.
• Experience with brownfield codebases.
• Humble, hungry, and smart.
• Excellent communicator and facilitator.

Benefits

• Competitive Medical, Dental, and Vision Insurance.
• Company Paid Life Insurance, Short- and Long-Term Disability Plans.
• 401(k) with Company Match.
• Parental Leave.
• Flexible Paid Time Off.
• Pet Insurance.

Company Description

Tripleseat is the leader in Event Management for Venues, providing software built by hospitality professionals to support event teams. Trusted by over 19,000 venues, Tripleseat helps streamline operations, reduce complexity, and turn pressure into profit.