R&D AI Transformation Director

Reports to: SVP of Technology

Department: Research and Development

Location: Remote, US.

Tripleseat is the leader in event management software for venues, trusted by over 19,000 hospitality operators. We are in the middle of an AI-native transformation that will define how we build and deliver products for the next decade. The companies that rewire their development processes around what AI makes possible will build better products, and create more value for customers with less friction. We intend to be one of them.

This is a Director-level program management role. You are not building product features. You are running the program that changes how R&D builds them: setting the roadmap, tracking progress, and holding the org accountable to it. This role reports to the SVP of Technology and works closely with Engineering, Product, and Design leaders to turn shared understanding into a practical, sequenced transformation plan. 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; synthesize input from the teams closest to the work, identify the biggest sources of friction and delay, and turn that shared understanding into a practical transformation roadmap. Convert the roadmaps and ideas into a cohesive plan that can be tracked.

• Define what AI-native means for every role in R&D: what changes, what new behaviors are expected, and what success looks like

• Define and govern the R&D tooling stack: vendors must meet API accessibility, MCP support, and AI-workflow integration requirements.

Own R&D Metric and Visability

What gets measured gets managed. This role owns the metrics layer that tells R&D leadership whether the transformation is working.

• Define and own the R&D metrics framework: business outcomes, project velocity, agentic velocity, delivery velocity, quality, and transformation progress

• Ensure R&D transformation is anchored in customer value, not internal efficiency alone; connect workflow changes to faster learning, faster delivery, higher-quality releases, and measurable customer impact.

• Establish evaluation and continuous improvement practices for every system and workflow you build: define success metrics, run phased rollouts, measure adoption and quality, and iterate.

• Close Customer and GTM Feedback Loops. Automate the ingestion and synthesis of customer and GTM feedback at scale. Cluster themes, map signal to roadmap areas, and produce decision-ready evidence that product teams can act on.

• Partner with sales, customer success, and support to ensure feedback is structured, traceable, and actionable, and that the loop closes by communicating what shipped and what changed back to the field.

Drive R&D Strategic Initiatives

Some of the highest-leverage work in R&D does not fit neatly into a product pod or an engineering team. This role provides the leadership capacity to drive those initiatives from inception to outcome. Examples include standing up the AI products development motion, coordinating cross-functional technical initiatives, and owning R&D-wide programs that require dedicated ownership to move.

• Work with the SVP of Technology and CPO to scope, launch, and close out high-priority special projects on behalf of R&D leadership

• Coordinate cross-functional technical workstreams that span Engineering, Product, and Design and require a dedicated driver

• Pressure-test new initiatives before they become standing programs; distinguish between what needs dedicated ownership and what can be absorbed by existing teams

What You Bring

• 5-7 years in software engineering, engineering operations, product operations, or R&D leadership

• Program leadership experience at the R&D or platform level: you have owned complex, multi-workstream roadmaps with real accountability for outcomes

• Bleeding-edge AI practitioner: you use Claude Code, Cursor, or equivalent AI coding tools daily and have hands-on experience transforming how development teams work

• Metrics fluency: you have owned engineering and product KPIs and used data to drive behavior change, not just produce dashboards

• Customer-centered operator: You connect internal R&D improvements to customer outcomes: faster learning, better releases, more reliable delivery, and stronger product-market execution.

• Humble, hungry, and smart: high standards and strong opinions, low ego; you build trust, push for better outcomes, and bring others along

• Excellent communicator and facilitator: you run tight meetings, write clear documents, and can move a leadership team to a decision

Salary Range: $180,000.00-$220,000.00

Compensation is based on relevant experience, skill set, geographic location, and alignment with our internal compensation framework. This role is also eligible for additional benefits and incentives.

• Competitive Medical, Dental, and Vision Insurance

• Company Paid Life Insurance, Short- and Long-Term Disability Plans

• 401(k) with Company Match

• Flexible Paid Time Off

• Parental Leave

• LinkedIn Learning Access

• Pet Insurance and Employee Discount Programs

This position is open to remote candidates eligible to work in the United States. Week 1 of onboarding is in-person at our Concord, MA office. A hybrid schedule is available for candidates based nearby.

At Tripleseat, we place a high value on our employees' well-being and happiness, recognizing that they are the driving force behind our success. We are committed to fostering a positive and supportive work environment. We take pride in our work and the collaborative spirit of our team.

We are proud to be an equal-opportunity employer and do not discriminate based on race, color, ethnicity, ancestry, religion, sex, national origin, sexual orientation, age, citizenship status, marital status, disability, gender identity, gender expression, veteran status, or genetic information. We are dedicated to fostering a culture of inclusion, diversity, and equity. Everyone Valued – Everyone Included.