[Remote] Director of AI Transformation and R&D Operations

Note: The job is a remote job and is open to candidates in USA. Tripleseat is the leader in Event Management for Venues, providing innovative software solutions to streamline operations for over 19,000 venues. The R&D Operations & AI Transformation Director will drive the transformation of R&D processes to leverage AI capabilities, ensuring efficient product development and collaboration across engineering, product, and design teams.

Responsibilities

• 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 Visibility
• 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 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

Skills

• 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

Benefits

• Competitive Medical, Dental, and Vision Insurance: Tripleseat provides its employees with comprehensive medical, dental, and vision insurance coverage, ensuring that their health and well-being are taken care of.
• Company Paid Life Insurance, Short- and Long-Term Disability Plans: Tripleseat takes care of its employees by providing them with life insurance coverage, as well as short and long-term disability plans to protect them in case of unforeseen circumstances.
• 401(k) with Company Match: Tripleseat offers a 401(k) retirement plan to its employees, and also provides a company match, helping employees save for their future and plan for retirement.
• Parental Leave: Tripleseat understands the importance of work-life balance and offers parental leave to employees who become parents through birth, adoption, or foster care, allowing them to bond with their new family members without worrying about their job security.
• Flexible Paid Time Off: Tripleseat believes in the importance of work-life harmony and offers flexible paid time off to its employees, giving them the flexibility to take time off when needed and maintain a healthy work-life balance.
• Pet Insurance: Tripleseat recognizes the importance of pets in employees' lives and offers pet insurance to help them take care of their furry friends and ensure their well-being.

Company Overview