Director of AI Transformation Job at Tripleseat

Job 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 Director of AI Transformation, 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.

Job Responsibility

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
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: what changes, what new behaviors are expected, and what success looks like
Drive the transition toward continuous delivery: prototypes reach production without sacrificing quality, stability, or scalability
Define and govern the R&D tooling stack: vendors must meet API accessibility, MCP support, and AI-workflow integration requirements
When needed, getting hands-on to prototype or pressure-test new ways of working so the R&D teams can see and learn from concrete examples
Own R&D Metrics and Visability
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
Track not just output metrics but adoption and behavior change, the leading indicators that predict whether the new operating model is sticking
Evolve the framework as the transformation matures
what matters in Month 3 is different from Month 12
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
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
Run the R&D Executive Operating Cadence
Own the operating rhythm across the SVP of Technology and CPO: joint planning sessions, shared OKR tracking, and cross-functional alignment
Prepare leadership for ELT readouts, board meetings, offsites, and major stakeholder interactions
Drive the agenda for R&D leadership forums so meetings produce decisions, not just discussion
Ensure follow-through: decisions made in meetings get captured, owned, and executed
Serve as a connective layer between Tech and Product when priorities need to be reconciled
Build reporting infrastructure that keeps Jellyfish and other tooling surfacing decision-ready signal, not raw data
Automate status reporting and executive rollups: what changed, what is at risk, what decisions are needed
Drive the R&D Strategic Initiatives
Identify and take ownership of R&D initiatives that lack a clear home but have a material impact on the transformation or on product delivery
Stand up the operating model for net-new R&D motions, such as the AI products development workflow, and ensure they are embedded and self-sustaining
Coordinate cross-functional technical workstreams that span Engineering, Product, and Design and require a dedicated driver
Work with the SVP of Technology and CPO to scope, launch, and close out high-priority special projects on behalf of R&D leadership
Pressure-test new initiatives before they become standing programs
distinguish between what needs dedicated ownership and what can be absorbed by existing teams
Drive Adoption and Capability Building Across R&D
Lead the change management work for the AI-native R&D transformation, including the AI Accelerator Sprint and ongoing enablement
Build lightweight playbooks, coaching materials, and guardrails that help engineers, PMs, and designers adopt new workflows with confidence
Define guardrails for secure, responsible AI use across the R&D lifecycle in partnership with Security, IT, and Engineering leadership
Partner with Engineering Managers and Product leadership to ensure transformation capabilities are embedded in their teams, not dependent on this role
Measure adoption, confidence, and sustained behavior change. Success means the organization has internalized a new way of working, not just completed a training

Requirements

10+ years in software engineering, engineering operations, product operations, or R&D leadership
you have mapped, measured, and improved how R&D organizations operate
Program leadership experience at the R&D or platform level: you have owned complex, multi-workstream roadmaps with real accountability for outcomes
Change leader, not just process designer: You understand that new tools and workflows only matter if people adopt them. You can bring skeptical, busy, high-performing teams along without creating unnecessary bureaucracy
Chief of Staff instincts: you know how to make senior leaders more effective, prepare them well, and ensure the organization moves on decisions rather than deferring them
Metrics fluency: you have owned engineering and product KPIs and used data to drive behavior change, not just produce dashboards
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
Customer-centered operator: You connect internal R&D improvements to customer outcomes: faster learning, better releases, more reliable delivery, and stronger product-market execution
Experience with brownfield codebases: you understand the challenges of driving transformation in a large, long-standing monolith alongside newer services
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

What we offer

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

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Director of AI Transformation

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