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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