Director, Engineering

Job Description

Tripleseat is the leading web-based event management and sales platform designed for restaurants, hotels, and unique venues. Our mission is to simplify and streamline the event planning process, allowing our clients to focus on delivering exceptional customer experiences. We pride ourselves on fostering a collaborative, innovative work environment that encourages growth and development.

The Director, Engineering at Tripleseat is pivotal in driving revenue growth through strategic platform enhancements and product integrations. This is a unique opportunity to collaborate with Engineering and Product leaders on projects like scaling the core platform, globalizing the Payments service, expanding Add-On offerings, integrating cutting-edge GenAI features, and enhancing the innovative 3D floor plan product.

This role is responsible for leading a remote team of managers, technical leaders, and software engineers, fostering their growth, and ensuring the successful delivery of impactful features for Tripleseat’s global hospitality customers. The Director champions technical excellence, strategic thinking, innovation, and collaboration while aligning team efforts with Tripleseat’s mission and values.

Location: This position is open to remote candidates eligible to work in the United States. 

Travel Expectations: If the ideal candidate is located outside the Concord, MA area, they must complete initial onboarding at our Concord, MA office. Quarterly travel may be needed for team collaboration and training.

Core Responsibilities:

Technical Leadership and Strategic Thinking:

• Direct one or more engineering functional areas, overseeing multiple engineering teams

• Drive data-driven architecture decisions and establish engineering best practices, standards, and metrics

• Partner with business leaders on strategic planning and technical roadmaps

• Interface with executive leadership on technical decisions and risk management

• Drive high-impact cross-functional initiatives

• Integrate M&A products and teams into Tripleseat

Talent Management:

• Recruit, onboard, and retain top talent for a remote engineering team of managers, technical leaders, and software engineers

• Role-model a culture of accountability, engagement, and technical excellence

• Oversee organizational talent assessments and performance reviews

• Drive individual and team growth through effective development planning

• Build an inclusive team culture aligned with company values

Project Management:

• Apply agile expertise to plan, track, and deliver sprints effectively

• Manage large-scale projects across multiple sprints and stakeholders

• Identify and mitigate risks to ensure the successful delivery of critical initiatives

• Maintain clear communication with all stakeholders on project goals and progress

• Prepare periodic Operations Reviews on the state of  teams and projects

• Continuously improve planning and tracking practices to enhance team efficiency

• Other related duties as assigned.

Knowledge, Skills, and Abilities:

• Proven Management Experience: 6+ years leading cloud-based software development teams; 12+ years of overall experience in multiple technical roles

• Data-Driven Technical Leadership: Data-driven engineering leader who transforms metrics into strategic technical decisions while providing clear direction across multiple teams and functional areas. Experienced mentor to managers, technical leads, and engineers.

• Strong Talent Management: Skilled in recruiting, developing, and retaining high-performing technical talent. Drives accountability and engagement through metrics-based performance frameworks that align team objectives with measurable business outcomes.

• Technical Expertise: Proficiency with Ruby on Rails, React, and MySQL/PostgreSQL in scalable distributed systems

• Strategic Thinking: Experienced in making architecture trade-offs and driving organizational changes. Ability to balance technical debt with feature development while maintaining system reliability

• Executive Communication: Skilled at translating complex technical concepts for business stakeholders

• Agile Practitioner: Proven experience leading multiple scrum teams and driving continuous improvements

• Remote Work: Strong time-management skills to lead distributed teams effectively.

• Values Alignment: A customer-focused business-first attitude and the ability to build rapport across teams.

Preferred Experience:

• Worked in PE-backed companies and/or integrated talent and technologies from acquired companies 

• Professional Scrum Master (PSM)  or Certified Scrum Master (CSM) 

• Experience with modern development practices (Generative AI, DevOps, CI/CD, Automation, DevEx)

• Track record of improving technical processes for scalability

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.