Role 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. You will partner closely with the SVP of Technology to ensure that the AI-native development practices you define are aligned with technical strategy and that the standards you set enable engineering managers to grow themselves and their teams. 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 - Transform the End-to-End Development Lifecycle - Map the journey from idea to production across R&D. - Measure time, cost, and friction at every stage. - Build and execute a roadmap for optimizing each step, with AI as the primary lever. - 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 vendor and tooling requirements for the R&D stack. - 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 bridges for cross-functional contributions. - Partner with sales, customer success, and support to ensure feedback is structured and actionable. - Drive Adoption, Capability Building, and Trust - Lead the change management for new AI-native ways of working. - Build lightweight playbooks and enablement materials. - Partner with leadership across each function to embed transformation capability. - Define guardrails for secure, responsible AI use. - Measure adoption, confidence, and sustained behavior change. Qualifications - 10+ years of experience in software engineering, engineering operations, product operations, or R&D leadership. - Humble, hungry, and smart with high standards and strong opinions. - Ability to think in process maps, cycle times, bottleneck analysis, and continuous improvement. - Bleeding-edge AI practitioner with hands-on experience using AI coding tools. - Experience defining and operating metrics frameworks for R&D organizations. - Experience with brownfield codebases and the challenges of transformation. Requirements - This position is open to remote candidates eligible to work in the United States. - Week 1 of onboarding is in-person, based out of our Concord, MA office. - A hybrid work schedule will be offered if the ideal candidate is based near our Concord, MA office. - Additional travel may be required for meetings, company events, and training. Benefits - 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. Base Compensation Range $180,000-$220,000 annually. Base salary is one component of total compensation. Employees may also be eligible for an annual bonus or commission.