Sales Manager, Account Executives (Chicago)
Hotel Engine
$180,000 - $240,000 / year
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Description
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 40,000 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 Engine recognition as TravelTech's Reservation Platform of the Year (2026), a spot on Inc.'s Power Partners list (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.
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 9/1/26 or until the role is filled. We encourage you to apply early, as we may begin reviewing applications before the deadline
OTE 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. In addition, all roles receive equity. 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
Benefits
- stock options
About this role
Hotel Engine is seeking a Sales Manager to build and lead a team of Account Executives in Chicago. You'll own team development from day one—coaching junior sales talent, setting performance metrics, and creating accountability systems that drive results. This is a hands-on role where you'll spend significant time diagnosing performance gaps, removing operational blockers, and working directly with your reps to help them hit targets. You'll also partner with sales leadership and cross-functional teams to refine strategy and ensure your team has the tools and support needed to succeed.
The ideal candidate has 4–5 years of experience managing sales teams, with a track record of developing early-career Account Executives and BDRs. You'll need strong communication skills, a data-driven approach to performance management, and the resilience to adapt quickly in a fast-moving environment. This role requires someone who thrives in high-energy, ambitious settings and is genuinely invested in growing people alongside the business.
The position is full-time and based in Chicago. Compensation ranges from $165,000 to $205,000 OTE (base plus variable), with equity included for all employees. Applications are being reviewed on a rolling basis through September 1, 2026.
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Pay for this role
$180,000 to $240,000 per year
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