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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.

The Role

Tripleseat is in the middle of a major transformation: rewiring how R&D operates to take full advantage of what AI makes possible. This is not a tooling project. It is a fundamental shift in how engineering, product, and design work together, move from idea to production, and deliver customer value.

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 will own the R&D transformation roadmap, drive the Agentic SDLC across engineering, product, and design, run the executive program cadence, and serve as Chief of Staff across the Technology and Product organizations. You are not building product features. You are building the conditions under which R&D can build great products, faster, with higher quality, and with less friction.

This is a Director-level role that requires equal comfort operating at the leadership level and getting hands-on to define and demonstrate what good looks like. This role requires a low-ego builder and facilitator: someone who listens deeply to Engineering, Product, Design, CS, and GTM, synthesizes the best ideas from the people closest to the work, and turns that shared understanding into practical operating change. This role reports to the SVP of Technology with a dotted line to the CPO, operating at the intersection of Engineering, Product, and Design. 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

1. Drive the R&D Agentic SDLC Operating Model

Tripleseat's competitive advantage depends on engineering, product, and design operating as a single AI-native system. You will be accountable for turning the collective expertise of R&D leaders and teams into a clear, practical operating mode, listening deeply, synthesizing the best ideas, and making the “map” real across all three disciplines.

• 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

2. Own R&D Metrics and Visibility

What gets measured gets managed. This role owns the metrics layer that tells R&D leadership whether the transformation is working.

• 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.

3. Run the R&D Executive Operating Cadence

Two senior leaders (SVP Technology and CPO) need to operate as one aligned R&D leadership team. This role makes that happen.

• 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

4. Drive R&D Strategic Initiatives

Some of the highest-leverage work in R&D does not fit neatly into a product pod or an engineering team. This role provides the leadership capacity to drive those initiatives from inception to outcome. Examples include standing up the AI products development motion, coordinating cross-functional technical initiatives, and owning R&D-wide programs that require dedicated ownership to move.

• 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

5. Drive Adoption and Capability Building Across R&D

New tools and processes do not transform an organization on their own. This role owns the change management required to make the new operating model stick.

• 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

What You Bring

• 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

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.