Director, Sales

Join Our Journey at Engine

At Engine, we’re revolutionizing work travel. Our modern travel platform isn’t just about booking trips; it’s about transforming how businesses and their teams experience travel. From seamless booking options with top airlines, hotels, and car rental providers to single-invoice billing and flexible trip modifications, we make travel not only easier to manage but also enjoyable. Backed by powerhouse investors like Telescope Partners, Blackstone, Elefund, and Permira, we’re growing fast—and we want you to be part of it.

About the Role:

We are seeking an experienced and driven Director of Sales to lead and inspire our team, ensuring sustained growth and operational excellence. The Director of Sales will take full ownership of our sales operations new business organization in Chicago, building and scaling a high-performance culture while driving accountability and results in our brand new office space. This role requires a hands-on leader who can set clear expectations, effectively coach Managers, drive accountability to achieve results, leverage data to identify and address challenges and develop strategic plans to achieve aggressive growth targets. If you thrive on living and driving the business every day, this role is for you.

Key Responsibilities: 

Team Leadership and Coaching: 

• Develop and mentor sales managers, ensuring they have the skills, tools, and support to succeed. 
• Foster an environment of continuous improvement, accountability, and professional growth across the team. 

Accountability and Performance Management: ‘

• Establish and enforce clear performance metrics and accountability frameworks.
• Regularly review team and individual performance, providing constructive feedback and support.

Data-Driven Problem Solving:

• Analyze key sales metrics to identify trends, challenges, and opportunities.
• Implement data-driven strategies to address problems and optimize the sales process.

Pipeline Management and Forecasting: 

• Oversee pipeline management to ensure accurate forecasting and consistent deal flow
• Collaborate with sales managers to refine pipeline health and improve close rates.

Strategic Planning and Execution: 

• Develop and execute strategic plans to drive revenue growth and market share. 
• Align sales strategies with company goals, ensuring a clear path to success. 

Building Culture: 

• Champion a positive, results-oriented sales culture focused on collaboration, excellence, and accountability. 
• Create an environment where team members are motivated, empowered, and inspired to perform at their best. 

Driving the Business Daily: 

• Be hands-on in the business, actively engaging with managers and team members to ensure operational excellence. 
• Lead from the front by embodying a “driver” mentality, setting the tone for the team through active involvement and leadership.

Required Skills and Qualifications: 

•  7+ years’ experience in a senior sales leadership role, with a focus on scaling and leading an outbound full-cycle new business team in a high-growth environment 
• Strong track record of coaching and developing high-performing sales managers.
•  Demonstrated ability to drive accountability and foster a culture of excellence.
•  Demonstrated experience building and maintaining a culture anchored around collaboration, learning, accountability, and winning together. 
• Expertise in leveraging data to identify problems and implement solutions. 
• Proficiency in pipeline management and accurate forecasting. 
• Strategic thinker with the ability to execute plans and deliver results. 
• Exceptional interpersonal and communication skills. 
• Hands-on leader who thrives on being deeply involved in day-to-day operations. 
• A strong team player, and a self-starter who thrives in a fast-paced, high-growth start-up environment. 
• A self-driven, high-energy leader with excellent cross-functional collaboration skills.

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.

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.