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Tripleseat is the leader in Event Management for Venues, providing software built by hospitality professionals to support event teams. Trusted by over 19,000 venues, Tripleseat helps streamline operations, reduce complexity, and turn pressure into profit. We believe the way software gets built is changing faster than most organizations can adapt. AI tools have compressed the cycle from idea to working software from months to hours. The companies that rewire their development processes around this reality will build better products, faster, with smaller teams.

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. Use findings to build a transformation roadmap.

• Drive the transition from legacy agile processes to a continuous delivery model where teams can move prototypes into production without sacrificing quality, stability, or scalability.

• Define the vendor and tooling requirements that any tool in the R&D stack must meet, including API accessibility, MCP support, and integration with AI-assisted workflows.

• Personally prototype and stand up the first generation of workflows, automations, and operating mechanisms, then scale what works through the R&D organization.

Build the AI-Native EPD Operating System

• Automate the ingestion and synthesis of customer feedback at scale. Cluster themes, map signal to roadmap areas, and produce decision-ready evidence that product teams can act on.

• Define and own the R&D metrics framework to ensure the team is measuring what matters, and create accountability through transparency.

• Automate status reporting and executive rollups focused on what changed, what is at risk, and what decisions are needed. Make transformation progress legible to the entire organization.

• Align and cascade OKRs across engineering, product, and design. Ensure every team is working toward shared goals and that progress is visible at every level.

• Build the bridges that make cross-functional contribution safe and productive, and ensure development environments accessible to PMs and designers using AI coding tools.

• Partner with sales, customer success, and support to ensure feedback is structured, traceable, and actionable, and that the loop closes by automatically communicating what shipped.

Drive Adoption, Capability Building, and Trust

• Lead the change management required to make new AI-native ways of working stick across product, design, and engineering.

• Build lightweight playbooks, enablement materials, and coaching that help teams adopt new workflows with confidence. Meet people where they are and move them forward.

• Partner with leadership across each function to ensure transformation capability is embedded in their teams. Success means the organization sustains the new operating model.

• Define guardrails for secure, responsible AI use across the R&D lifecycle, in partnership with security, IT, and engineering leadership.

• Measure also adoption, confidence, and sustained behavior change to ensure the organization has internalized a new way of working.

What You Bring

• 10+ years of experience in software engineering, engineering operations, product operations, or R&D leadership. You have mapped, measured, and improved how R&D teams operate.

• Humble, hungry, and smart. You have high standards and strong opinions, but low ego. You build trust, listen well, and know how to push for better outcomes while bringing others along.

• You think in process maps, cycle times, bottleneck analysis, and continuous improvement. You are energized by turning a messy, unmeasured workflow into an optimized system.

• Bleeding-edge AI practitioner. You are not theoretically interested in AI-assisted development. You use AI coding tools daily and have hands-on experience with Claude Code, Codex, etc.

• Experience defining and operating metrics frameworks for R&D organizations. You have owned engineering and product KPIs and used data to drive behavior change at scale.

• Experience with brownfield codebases and the specific challenges of driving transformation in a large, long-standing monolith alongside newer services.

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.

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. The above represents the expected base compensation range for this job requisition. Ultimately, in determining your pay, we’ll consider many factors including, but not limited to, skills, experience, qualifications, geographic location, and other job-related factors.

Tripleseat truly values its employees and places a high emphasis on their well-being and happiness. We understand that our people are the driving force behind its success and strive to create a positive and supportive work environment. We love what we do and who we get to do it with! Here are some of the awesome benefits that Tripleseat offers to its employees:

• 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.

At Tripleseat, we place a high value on our employees' well-being and happiness, recognizing that they are the driving force behind our success. We are committed to fostering a positive and supportive work environment. We take pride in our work and the collaborative spirit of our team We are proud to be an equal-opportunity employer, not discriminating based on race, color, ethnicity, ancestry, religion, sex, national origin, sexual orientation, age, citizenship status, marital status, disability, gender identity, gender expression, veteran status, or genetic information. We are dedicated to fostering a culture of inclusion, diversity, and equity. Tripleseat empowers all team members to realize their full potential. Everyone Valued – Everyone Included.