Corporate Traveler - Director of Sales - Chicago, IL

Corporate Traveler - Director of Sales – Chicago, IL

We’re seeking an accomplished Director of Sales to lead our established Central Region sales organization and build on our existing momentum. Reporting to the VP of Sales, you’ll oversee two experienced Team Leaders and their teams of Account Executives and SDRs, driving consistent revenue performance and operational excellence across the territory.

This role offers the opportunity to make an immediate impact by optimizing current processes, developing talent, and identifying untapped growth opportunities within your market. You will have the autonomy to shape strategy for your region while collaborating closely with cross‑functional partners to deliver results. If you’re a hands‑on sales leader who excels at coaching teams, hitting targets, and maximizing productivity with the resources at hand, we’d love to hear from you.

• Develop and execute a comprehensive sales strategy to drive revenue growth and market penetration in the central region of the US.
• Own and exceed quarterly and annual revenue targets, ensuring consistent performance against company objectives.
• Partner with executive leadership to align sales initiatives with broader business goals and market opportunities.
• Analyze market trends, competitive landscape, and customer insights to inform strategic decision‑making.

• Directly manage, mentor, and develop two Team Leaders/Sales Managers, ensuring they have the tools and guidance to succeed.
• Build a high‑performance culture focused on accountability, collaboration, and continuous improvement.
• Conduct regular 1‑on‑1s, performance reviews, and coaching sessions with direct reports.
• Establish clear KPIs and performance metrics for Team Leaders, AEs, and SDRs.
• Identify and develop future leaders within the organization through succession planning and career pathing.

• Implement and refine sales processes, methodologies, and best practices across the team.
• Ensure CRM hygiene and accurate pipeline forecasting to provide visibility into revenue projections.
• Collaborate with Sales Operations and Revenue Operations to optimize workflows and remove friction.
• Monitor key sales metrics and create actionable insights to drive performance improvements.

• Partner with Marketing to ensure alignment on lead generation, messaging, and campaign effectiveness.
• Work closely with Customer Success to ensure smooth handoffs and drive customer retention and expansion.
• Collaborate with Product and Solutions teams to communicate market feedback and customer needs.
• Coordinate with Finance on forecasting, budgeting, and resource allocation.

• Drive talent acquisition efforts to build and scale a world‑class sales team.
• Establish hiring standards and interview processes that attract top‑tier sales talent.
• Onboard new team members effectively to accelerate time‑to‑productivity.

• Participate in strategic customer meetings and help close high‑value opportunities.
• Represent the company at industry events, conferences, and networking opportunities in the NYC market.
• Build relationships with key stakeholders and decision‑makers in target accounts.

• 2+ years’ experience building and leading front‑line sales teams; ability to grow and scale upward with the company; mid‑management experience a plus.
• 4+ years direct selling experience to SMB/Mid‑Market businesses and finance personas, is required.
• Strong record of achieving sales targets.
• Excellent leadership and influencing skills; ability to build strong business partnerships both outside and within the organization.
• Highly professional persona and polished demeanor. Strong verbal/written communication and presentation skills; effective at delivering executive‑level presentations.
• Experience using modern sales tools like Salesforce and Gong to make and execute upon data‑driven sales strategies.
• Success adapting in fast‑growing and changing environments.
• Bachelor’s or MBA preferred.

• Have fun:
  At the heart of everything we do at…