Engine is the AI-native platform for intelligent travel. For a decade, Engine has built the proprietary technology and supply behind modern business travel, serving over 40,000 customers and nearly 2 million travelers, along with leading travel and AI companies that build on Engine's infrastructure. One system powers business travel, group travel, human agents, and AI agents.
That work has earned Engine recognition as TravelTech's Reservation Platform of the Year (2026), a spot on Inc.'s Power Partners list (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.
The Director of Strategy & Operations, Travel & Spend is the day-to-day thought partner to the VP of Global Sales and owns how the sales organization plans and executes.
Travel is Engine's core product and our biggest growth opportunity. Global Sales is around 150 people today and is expected to reach 250 or more by the end of FY27. Your mandate is to uplevel how it runs. You will influence strategic direction and help drive execution, while finding and unblocking the productivity bottlenecks that slow the team down. AI is central. You will decide where AI belongs in the sales motion and hold the team accountable to real productivity gains.
This is a hands-on role. You will get into the data yourself and build the analysis leadership acts on. You will hire and lead a team of two to four analysts and strategy partners over the next 12 to 18 months.
Strategy & Operations sits inside Revenue Operations alongside GTM Systems, Revenue Enablement, and GTM Finance. You will also partner closely with Growth, Central Data, and Corporate Finance.
What You'll DoStrategy and Planning- Own segmentation strategy: ICP, account scoring, and territory design.
- Partner with GTM Finance on capacity modeling, goal setting, and multi-year headcount planning.
- Define the metrics, instrumentation, and executive-ready analysis leadership uses to steer the business.
- Build and run the sales operating cadence: annual planning, forecasting, pipeline reviews, and QBRs.
- Design and enforce the end-to-end sales process, and the standards for how the team sells, forecasts, and reports.
- Partner with Revenue Enablement to translate strategy into training, playbooks, and tools the field will use.
- Set the AI strategy for the sales motion and lead the rollout across prospecting, forecasting, deal execution, and coaching.
- Partner with GTM Systems on the build and adoption of the tools, AI, and insights the field runs on.
- Develop and test hypotheses on segmentation, coverage, and productivity, and translate the results into decisions.
- 8+ years in sales strategy & operations, revenue operations, or top-tier consulting, with substantial time in a high-growth B2B SaaS, fintech, or marketplace business.
- A track record as the primary strategic and operational partner to a VP or C-level revenue leader.
- A clear point of view on where AI and automation belong in a modern sales motion, and evidence of shipping it at scale.
- Deep knowledge of sales mechanics: pipeline math, capacity models, territory design, forecasting, and comp plan design.
- Strong analytical skills and a bias to build models yourself before handing them off.
- Proven ability to influence senior leaders without direct authority, in rooms with strong opinions and competing priorities.
Compensation
Our compensation packages are based on several factors, including your experience, expertise, and location. In addition to a competitive base salary, all roles receive equity. Depending on the role, total compensation may also include an annual bonus. Your recruiter will share your complete compensation package as you move through the process.
The Engine Edge: Perks & Compensation
We believe in rewarding great work with great benefits:
- Compensation: Competitive base pay tied to role and experience, with equity for all employees. Some roles are also eligible for bonuses or commissions.
- 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
Engine Chicago, Illinois, USA Office
Our office is in Chicago's West Loop, directly above Ogilvie Station and a short walk from Union Station, an easy commute from anywhere in the metro, and right between the Loop and Fulton Market's restaurants, cafes, and rooftops.
Similar Jobs at Engine
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
