Chief of Staff

About Engine

Engine is the all-in-one travel and spend management platform trusted by 38K+ businesses and groups representing 1.8M+ travelers. We're the retailer and the rails of business travel, one of the fastest-growing companies in travel tech, built on a decade of proprietary technology, supply, and pricing no one else can replicate. Other travel and AI companies run on our infrastructure to book real trips, hold rates, and move payments, without building any of it themselves. We built it, AI-forward at every layer, from how travelers book to how the rails run. That work has earned recognition as one of Fast Company's Best Workplaces for Innovators (2025), TravelTech's Reservation Platform of the Year (2026), and one of Built In's Best Places to Work (2020–2026). We're looking for bold, ambitious people to help redefine how businesses manage and experience travel. Working here, you can expect exponential growth, an ambitious pace, full ownership, and high-caliber colleagues who push you to do the best work of your career. Every hire raises the bar.

Come outpace the ordinary and build the future of travel with us.

We're looking for an exceptional Chief of Staff to serve as a critical strategic partner to our Founder/CEO. This isn't just an operational role; it's a unique chance to amplify the CEO's impact, act as a force multiplier, and ensure the Executive Leadership Team (ELT) operates seamlessly as a unified front. You'll serve as the first line of defense and a trusted confidant, freeing the Founder to laser-focus on our most critical growth initiatives and core product strategy, operating at the very heart of our leadership team.

What You'll Do

CEO Leverage & Force Multiplication

Amplify Impact: Act as a true force multiplier, taking on operational burdens, navigating ambiguity, and executing special projects that allow the CEO to dedicate more time and energy to core product vision, market strategy, and external relations.

First Line of Defense: Streamline the CEO's operational cadence, manage priorities, and optimize their time, acting as a critical filter and enabler for information flow.

Trusted Confidant: Serve as a confidential thought partner and sounding board for the CEO on a range of strategic, organizational, and personnel challenges.

Represent the CEO: Confidently represent the CEO in various internal forums when appropriate, embodying his vision and priorities.

Executive Team Operations & Organizational Alignment

Ensure ELT Alignment: Drive the operating cadence of the ELT, ensuring the team is operating as one. You will own the design and execution of monthly ELT meetings, weekly agendas, and subsequent read-outs to the broader organization.

Cross-Functional Communications: Serve as a central hub for seamless, cross-functional communication between the CEO and a diverse executive team. Anticipate organizational bottlenecks and proactively facilitate discussions to drive efficient decision-making.

Facilitate Key Strategic Forums: Prepare the CEO for critical internal and external discussions, including Board meetings, investor updates, and executive reviews, ensuring materials are sharp and discussions are productive.

Special Projects: Lead high-impact special projects that don't neatly fit into existing departments, managing them from ideation through execution.

AI Enablement: Drive the adoption of modern AI productivity tools across the leadership office to automate administrative overhead and optimize workflows.

Who You Are

Experienced Strategist: You have 10+ years of progressive experience in high-growth environments, preferably within a technology startup (Series B/C or later stage), strategy consulting, or a similar fast-paced, analytical role.

Master Communicator & Connector: Your written and verbal communication skills are exceptional. You can articulate complex ideas clearly and compellingly across cross functional teams and to senior leadership.

Low Ego, High Impact: You are naturally collaborative, humble, and prioritize collective success. Yet, you possess the presence and diplomacy to command a room, drive tough conversations, and build alignment among senior leaders.

Analytical & Solutions-Oriented: You're a natural problem-solver with a data-driven approach, capable of dissecting complex issues and designing practical, effective solutions.

AI-Forward Operator: You are proficient with and enthusiastic about leveraging modern artificial intelligence tools (e.g., generative AI, LLMs) to streamline executive reporting, synthesize large datasets, and scale operational efficiency.

Proactive & Resilient: You thrive in ambiguity, anticipate needs, and adapt quickly to change. You're incredibly organized, can manage multiple priorities under pressure, and have a strong bias for action.

Relationship Builder: You excel at building strong, trusting relationships across all levels of an organization, fostering collaboration and earning respect.