Director, Sales Strategy and Operations - Global Sales

Director, Sales Strategy and Operations - Global Sales

Chicago, Illinois, United States

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.

The Director of Strategy & Operations, Sales is the day-to-day thought partner to the VP of Global Sales and owns how the sales organization plans and executes.

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.

• 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,…