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Tripleseat Logo Tripleseat · IT - Software Development

R&D Operations & AI Transformation Director

United States Employment contract 180000.00 - 220000.00 USD / Year · Job Posted May 05, 2026
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Job Description

As the R&D Operations & AI Transformation Director, 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 are not building product features. You are building the operating system that lets engineering, product, and design build features faster, with higher quality, and with less friction. You will map every step from idea to production, measure the time and cost at each stage, identify where AI eliminates bottlenecks, and set the standards and tooling that the entire R&D organization operates against. This is a hands-on leadership role that reports to the Chief Product Officer and works cross-functionally with software engineering and platform leadership. You will be a player/coach managing a small team of two to three people, and you will personally drive the first wave of transformation work.

Job Responsibility

  • Transform the End-to-End Development Lifecycle
  • Map the journey from idea to production across R&D
  • Conduct an AI readiness audit covering documentation, test coverage, repo structure, design system maturity, and observability
  • Drive the transition from legacy agile processes to a continuous delivery model
  • Define the vendor and tooling requirements that any tool in the R&D stack must meet
  • Personally prototype and stand up the first generation of workflows, automations, and operating mechanisms
  • Build the AI-Native EPD Operating System
  • Automate the ingestion and synthesis of customer feedback at scale
  • Define and own the R&D metrics framework
  • Automate status reporting and executive rollups
  • Align and cascade OKRs across engineering, product, and design
  • Build the bridges that make cross-functional contribution safe and productive
  • Partner with sales, customer success, and support to ensure feedback is structured, traceable, and actionable
  • Drive Adoption, Capability Building, and Trust
  • Lead the change management required to make new AI-native ways of working stick
  • Build lightweight playbooks, enablement materials, and coaching
  • Partner with leadership across each function to ensure transformation capability is embedded in their teams
  • Define guardrails for secure, responsible AI use across the R&D lifecycle
  • Measure also adoption, confidence, and sustained behavior change

Requirements

  • 10+ years of experience in software engineering, engineering operations, product operations, or R&D leadership
  • Humble, hungry, and smart
  • You think in process maps, cycle times, bottleneck analysis, and continuous improvement
  • Bleeding-edge AI practitioner
  • Experience defining and operating metrics frameworks for R&D organizations
  • Experience with brownfield codebases and the specific challenges of driving transformation in a large, long-standing monolith alongside newer services

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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