Director of Engineering

About the job At TripWorks, we believe work should be meaningful, fast-paced, and a little bit adventurous. We're a team powering the experiences industry—helping tour, attraction, and activity operators grow their businesses with tools that actually work. We’re not big on fluff or hierarchy. We value progress over perfection, action over ego, and results over buzzwords. Our team is small, scrappy, and serious about helping our customers win. If you’re the kind of person who sees a problem and grabs a shovel, who thrives on feedback, and who’s always looking for ways to level up—you’ll fit right in. We’re hiring a Director of Engineering to lead our engineering function. This is a strategic role for someone who can scale teams, ship fast, and drive the development of customer-facing products and platform services. What You’ll Do Lead and grow a high-performing team of engineers and managers, including oversight of full-time employees and third-party contractors. Take full ownership of sprint planning, prioritization, execution, and delivery across multiple product and platform initiatives. Partner closely with Product, Design, and Ops to translate business goals into technical execution—and deliver measurable results. Guide architecture decisions and technical standards, ensuring scalability, performance, and maintainability across our stack. Oversee system infrastructure, security, and reliability—making sure TripWorks remains stable and trustworthy as we scale. Assess and scale the engineering organization—identify skill gaps, propose org structure improvements, and make strategic hiring recommendations to support growth. Mentor engineers and future leaders, and grow into a VP or CTO role as the company expands. What You Bring 8–10+ years of experience in engineering roles, including 5+ years managing high-performing teams. Proven success owning end-to-end delivery of software projects—from strategy through execution. Experience managing both internal teams and external partners (contractors or vendors). Strong grasp of AWS cloud infrastructure, SQL/Redis data architecture, and security best practices in a modern SaaS environment. Mastery of Symfony and Vue frameworks. Familiarity with modern SaaS components like APIs, integrations, data pipelines, and multi-tenancy. Experience working with payment processing platforms, like Stripe, or financial infrastructure is a strong plus. What Makes You a Great Fit Excellence over Ego – You’re someone who seeks feedback and gives it generously Initiative: You’re action-oriented and don’t wait around for someone to tell you what to do Growth Orientated – You get excited by big goals and don’t get discouraged by hard problems Results Focused – You care deeply about outcomes, not just ideas Agile – Comfortable in a fast-moving, remote-first startup environment where priorities shift, execution is prized, and outcomes matter. Full-Stack Technical Awareness – You bring breadth, not just depth. From infrastructure and APIs to product UX and integration architecture, you have a working knowledge of the full ecosystem and can confidently lead across domains. Proven Team Builder – You’ve managed full-time engineers and partnered with external teams or contractors. You know how to scale headcount, shape culture, and identify critical talent and skill gaps as the org evolves. Execution Ownership – You run sprints like a pro, ensuring priorities are clear, blockers are removed, and work gets delivered with speed and quality. You bring structure without bureaucracy. Security & Stability Mindset – You take infrastructure and security seriously—ensuring systems are robust, maintainable, and aligned with best practices from auth to uptime. C-Suite Trajectory – You’re an A-player with executive ambition—ready to grow into a VP or CTO role. You’re not just here to maintain what’s working; you’re here to architect what’s next. High-Trust Communication – You know how to speak to execs, PMs, and ICs alike. You bring clarity, calm, and confidence to every room—and you know how to build cross-functional alignment at speed. Why Join TripWorks? Fully remote team: We trust you to work where and how you’re most productive. Top-Tier Health Benefits: We cover 100% of your medical premium and offer dental and vision plans. 401K Match: Full 3% employer match Equity: All employees are owners in the business. Generous PTO: We encourage time away from work to recharge. Great People: Join a team of smart, kind, low-ego teammates who value impact. Values-Driven Culture: We grow fast, act fast, give feedback, and stay customer-obsessed. Ready to Apply? If you're excited about what we're building and think you'd thrive at TripWorks, we’d love to hear from you.