Chief of Staff

About Engine At Engine, we’re transforming business travel into something personalized, rewarding, and simple. For too long, managing travel and spend has been overwhelming and fragmented — we’re here to change that. We believe the future of travel should be seamless and powered by technology that delights customers at every step. That’s why we’re building a platform that brings together corporate travel, a powerful charge card, and modern spend management in one place. To make this vision real, we’re looking for exceptional, mission-driven people to help redefine how businesses manage and experience travel. More than 30,000 companies already rely on Engine to support over 1 million travelers and billions in annual bookings each year. Cash flow positive with rapid growth, we pair exclusive Engine-only rates, industry-leading rewards, and intelligent automation to help businesses save money while delivering world-class personalization and convenience. Backed by Telescope Partners, Blackstone, and Permira, Engine has been recognized as one of the fastest-growing travel and fintech platforms in North America, with honors including the Deloitte Fast 500 and Built In’s Best Places to Work. 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. Compensation Our compensation packages are based on several factors, including your experience, expertise, and location. In addition to a competitive base salary, total compensation may include equity and/or variable pay (OTE). Your recruiter will share your complete compensation package as you move through the process. Base Pay Range $190,000 — $230,000 USD The Engine Edge: Perks & Compensation We believe in rewarding great work with great benefits: Compensation: Competitive base pay tied to role and experience, with opportunities for bonuses, commissions, and equity. Benefits: Check out our full list at engine.com/culture . Environments for Success: Different roles have different needs in terms of the environments that drive success which is why we have a hybrid-hub model. Whether you are in one of our amazing offices or fully remote, we’ll make sure you have what you need to succeed. Perks and benefits may vary based on employment type, location, and more. Ready to Build the Future of Work Travel? Join us on our mission to transform how work travel works—for businesses, for travelers, and for the industry. Apply now and let’s make travel simpler, smarter, and more enjoyable—together.