Director, Sales Strategy and Operations - Global Expansion

Engine • Chicago, IL

13h • $170,000 - $230,000 • Hybrid

About The Position

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.
About the Role
The Director of Strategy & Operations, Expansion is the day-to-day thought partner to the VP of Global Expansion and owns how the expansion organization plans and executes.
Global Expansion runs a complex, multi-motion book, with specialized teams covering the full customer journey from implementation through retention, growth, and specialty motions.
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 expansion 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 operations 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.

Requirements

• 8+ years in sales/expansion strategy & operations, revenue operations, 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 expansion motion, and evidence of shipping it at scale.
• Deep knowledge of post-sale mechanics: NDR, GRR math, book of business design, renewal 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.

Responsibilities

• Own segmentation, account scoring, book of business design, and rules of engagement across the expansion motions.
• Partner with GTM Finance on the capacity model, quotas, and headcount plan.
• Define the metrics and instrumentation for the business, including NDR, GRR, product attach, and Engine X GMV.
• Build and run the expansion operating cadence: annual planning, weekly pipeline and risk reviews, monthly business reviews, and renewal forecasting.
• Standardize the motion: handoffs, opportunity types, stages, exit criteria, and rules of engagement.
• Partner with Revenue Enablement to translate strategy into training, playbooks, and tools the field will use.
• Partner with GTM Finance on comp design and visibility.
• Set the AI strategy for the expansion motion and lead the rollout across risk scoring, customer health, data auditing, comp visibility, and rep-facing insights.
• 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.

Benefits

• Competitive base pay tied to role and experience, with opportunities for bonuses, commissions, and equity.
• Check out our full list at engine.com/culture.
• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed