Sales Manager, Account Executives (Chicago)

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 20,000 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. Your Mission Engine is seeking a dynamic and driven Sales Manager, Account Executive to lead a team of motivated sales professionals. This individual will play a crucial role in shaping the success of our sales team, especially those early in their careers. The ideal candidate is passionate about developing young talent, fostering a culture of accountability, and driving measurable results through hands-on coaching, data analysis, and performance management 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. What You'll Bring to Engine: 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. Applications for this role will be accepted through 6/24/26 or until the role is filled. We encourage you to apply early, as we may begin reviewing applications before the deadline 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.