Engine

Director, Sales Strategy and Operations - Global Sales

$170K–$230KFull-time · Chicago, IL
✓ Verified live on the employer's own system · added 10 days ago
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Senior · 8+ yrs exp

Requirements

Experience: 8+ years

Skills & tools

OperationsSalesTeam LeadershipHiringFinancial AnalysisMachine LearningCoachingB2B Sales
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Full job description

we're looking for exceptional, mission-driven people to help redefine how businesses manage and experience travel.

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.

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Compensation: Competitive base pay tied to role and experience, with opportunities for bonuses, commissions, and equity.

- 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.

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.

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