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 39,000 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 recognition as one of Fast Company's Best Workplaces for Innovators (2025), TravelTech's Reservation Platform of the Year (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, 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.
What You'll DoStrategy and Planning- 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.
- 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.
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
Skills Required
- 8+ years of experience in sales or expansion strategy and operations or revenue operations
- Substantial experience in a high-growth B2B SaaS, fintech, or marketplace business
- Experience serving as the primary strategic and operational partner to a VP or C-level revenue leader
- Track record of implementing AI and automation at scale in an expansion motion
- Deep knowledge of NDR, GRR, book of business design, renewal forecasting, and compensation plan design
- Strong analytical skills and ability to build models independently
- Ability to influence senior leaders without direct authority
What the Team is Saying
Engine Compensation & Benefits Highlights
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Leave & Time Off Breadth — Unlimited PTO is frequently highlighted alongside paid volunteer time and family leave, and is seen as a major perk for flexibility and balance. Feedback suggests time-off policies are a standout element of the package.
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Equity Value & Accessibility — Stock options are made broadly accessible to full-time employees and are positioned as a meaningful part of total compensation. This ownership component is repeatedly cited as a core strength of the package.
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Healthcare Strength — Medical, dental, and vision coverage is consistently described as comprehensive, with mental-health/EAP resources and HSA/FSA options also noted. Feedback suggests the overall health-and-wellness offering is robust on paper.
Engine Insights
What We Do
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 40,000 customers and 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. Engine has been recognized as one of Fast Company's Best Workplaces for Innovators (2025), named TravelTech's Reservation Platform of the Year (2026), and one of Built In's Best Places to Work (2020–2026).
Why Work With Us
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.
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Engine Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
We're remote-centric, not remote-only. With four offices across the US and our investment in regular team onsites, we make sure our people stay connected in person – fueling collaboration, creativity, and shared momentum.
