Senior Director, Workforce Transformation

About Engine

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 38,000 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 OPPORTUNITY

Engine has spent the last two years building an AI-native operating model, and the results are showing up across the business — customer service resolving autonomously at scale, engineering shipping dramatically more per person, revenue per employee climbing quarter after quarter. The technical foundation is real. The productivity gains are real.

Now the People team is taking the next step: leading how the workforce itself evolves as a result.

This role owns Workforce Transformation; surfacing the productivity story across the enterprise so we can measure impact consistently, redesign roles ahead of the shift, and build the skills our workforce needs next. The traditional playbooks for workforce planning, hiring, and development assume a workforce that grows linearly with the business. Engine's doesn't — and won't. As AI absorbs more work in every function, the questions get harder: What roles do we need? What skills matter now?

Where should we invest, and where should we automate? This role answers those questions ahead of the curve, not behind it.

You'll report to the CPO and partner with the leaders of AI Platform and Applied AI to bring this to life.

WHAT YOU'LL OWN

Productivity & Efficiency Insights

Own how Engine measures AI's impact on the workforce — the productivity gains, efficiency shifts, and capacity reallocation happening across every function.

Surface the enterprise productivity story every quarter — where work is being streamlined, where AI is driving compounding gains, where roles are shifting. This is the narrative the board, the ELT, and the workforce see.

Build the data infrastructure that makes Workforce Transformation a predictive function — anticipating where productivity gains show up next, not just reporting where they landed last quarter.

Job Architecture & Workforce Planning

Redesign roles and career pathways as AI absorbs tasks — moving from historical benchmarks to a forward-looking job architecture that reflects how work is actually changing.

Own workforce planning as a strategic function — where Engine hires, where we automate, where we upskill, and how we sequence the shifts.

Partner with functional leaders on the workforce implications of every AI-driven redesign — so we're planning for the workforce we're becoming, not the one we were.

Skills of the Future

Define the skills Engine's workforce needs next — technical, judgment-based, and AI-fluent — and build the enablement, training, and manager development to build them.

Lead the shift from role-based to skills-based rewards, career development, and workforce planning as AI reshapes what work looks like.

Make AI fluency a real capability across the workforce — not a slogan, not a one-time training, but a durable competency the company builds toward.

Governance & Responsible Use

Set enterprise policy for how AI is deployed in people and business decisions — privacy, fairness, explainability, human oversight — in partnership with Legal, Compliance, and IT.

Build the risk oversight and controls that let Engine move fast with AI without incurring the failure modes that other companies are learning about publicly.

WHAT YOU BRING

• AI-native operator
• — Uses AI in your own work, understands LLMs, agents, and evaluations well enough to hold builders accountable, and thinks about how to bring AI-native rigor to the workforce function itself.
• Transformation & operating-model leadership
• — Has stood up measurement systems, job architecture, and workforce planning that changed how an organization actually operates — not just how it reports.
• Forward-looking workforce judgment
• — Anticipates how AI is reshaping roles, skills, and career pathways, and builds ahead of the curve rather than in reaction to it.
• Skills-based workforce design
• — Has architected role redesign, career architecture, leveling, and workforce planning for a workforce evolving under AI.
• Change leadership
• — Proven ability to drive adoption and influence without authority across functions — especially with senior functional leaders who own their own redesigns.
• Consultative posture
• — A partner and challenger to functional leaders, not the decision-maker on their work. Authority lives in the insights, not the fiat.
• Responsible-AI judgment
• — Knows AI's limits and builds privacy, fairness, and human oversight into people decisions from the start.
• Applications for this role will be accepted through November10th, 2026 or until the role is filled. We encourage you to apply early, as we may begin reviewing applications before the deadline.