Sales Manager, Account Executives (Chicago)

About the Position

Sales Manager, Account Executives (Chicago)

Chicago, Illinois, United States

Engine is the all-in-one travel and spend management platform trusted by 38K+ businesses and groups representing 1.2M+ travelers. We're the retailer and the rails of business travel, the fastest-growing company in travel tech, built on a decade of proprietary technology, supply, and pricing no one else can replicate. Other travel and AI companies run on our infrastructure to book real trips, hold rates, and move payments, without building any of it themselves. We built it, AI-forward at every layer, from how travelers book to how the rails run.

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.

Responsibilities

Here’s what you’ll do:

• Team Leadership and Development: Lead, mentor, and develop a team of Account Executives to exceed sales goals through impactful coaching, motivation, and skill development. Foster a collaborative, high-performance culture by implementing team-building activities, recognition programs, and accountability-driven incentives.
• Performance Management and Coaching: Set clear performance goals and metrics while leveraging data and one-on-one meetings to track progress and provide actionable feedback. Address performance issues promptly and constructively, using a data-driven approach to drive continuous improvement.
• Sales Strategy and Execution: Utilize sales data and KPIs to diagnose team performance and adjust strategies as needed. Manage day-to-day operations and ensure team productivity is optimized by focusing on key metrics (e.g., activity levels, conversion rates, quota attainment). Regularly track and report on team performance, providing insights to senior leadership.
• Problem Solving and Operational Efficiency: Be deeply involved in the day-to-day operations of the team, actively troubleshooting issues, and helping remove roadblocks to ensure reps can focus on selling. Maintain a proactive approach in identifying and resolving challenges that impact team productivity, both internally and with clients.
• Cross Functional Collaboration: Work closely with the sales leadership team to align on strategy, share best practices, and implement improvements to processes. Partner with cross-functional teams (e.g., marketing, product, and operations) to ensure alignment on lead quality, sales tools, and customer satisfaction.

Requirements

We're looking for someone who's ready to make an impact and grow alongside us:

• Strong Communication Skills: Excellent communication skills, with the ability to motivate and provide constructive feedback.
• Leadership Skills: A hands-on sales leader with 4-5 years of experience managing and developing Account Executives and Business Development Representatives, actively involved in day-to-day operations. Proven ability to coach junior sales talent to exceed targets while holding team members accountable and addressing underperformance to drive success.
• Data Driven Mindset: A data-centric mindset with the ability to analyze and use sales data to drive performance.
• Adaptability: High energy, resilient, and adaptable to changing business needs.

Compensation

In addition to a competitive base salary, our listed compensation range includes the estimated variable target. Your OTE (on-target earnings) are based on several factors including your experience, expertise, and location. Your compensation package may also include equity. Your recruiter will share your complete compensation package as you move through the process.

Total OTE Range (Base Salary + Variable)

$165,000 - $205,000 USD

The Engine Edge: Perks & Compensation

We believe in rewarding great work with great benefits:

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

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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