Director, Sales

Hotel Engine • Chicago, IL

272d • Remote

About The Position

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. 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.

Requirements

• 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.

Responsibilities

• Develop and mentor sales managers, ensuring they have the skills, tools, and support to succeed.
• Establish and enforce clear performance metrics and accountability frameworks.
• Regularly review team and individual performance, providing constructive feedback and support.
• Analyze key sales metrics to identify trends, challenges, and opportunities.
• Implement data-driven strategies to address problems and optimize the sales process.
• Oversee pipeline management to ensure accurate forecasting and consistent deal flow.
• Collaborate with sales managers to refine pipeline health and improve close rates.
• Develop and execute strategic plans to drive revenue growth and market share.
• Align sales strategies with company goals, ensuring a clear path to success.
• 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.
• 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.

Benefits

• Competitive base pay tied to role and experience, with opportunities for bonuses, commissions, and equity.
• Hybrid-hub model for work environments, allowing for both office and remote work.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Industry: Accommodation