Director of Sales & Growth

Trek Travel provides global cycling, hiking, and walking vacations of a lifetime with the goal of helping more people actively explore and experience the world. We are hiring a Director of Sales & Growth in Madison, Wisconsin. You will lead a high-performing sales team, own revenue growth, and build the strategies, processes, and partnerships that turn interest into bookings and first-time guests into lifelong travelers. This position requires a high-level thinker who is also detail-oriented, able to analyze the business, translate insights into action, and drive consistent execution in a dynamic environment. This is your opportunity to join the Trek Travel team and leave your mark on our company, on the active travel industry and on the world at large. **POSITION RESPONSIBILITIES INCLUDE, BUT NOT LIMITED TO:** **LEADERSHIP** - Lead, coach, and develop a high-performing team of Trip Consultants and Guest Services Coordinators - Set clear expectations, accountability structures, and performance standards - Contribute to company strategy and planning as a core member of the leadership team - Build strong cross-departmental relationships and foster a culture of collaboration and continuous improvement across the organization - Monitor the competitive landscape, market trends, and share insights proactively with leadership - Partner with Operations and Product on trip performance, guest feedback, and capacity management - Deliver quarterly business plan updates to the leadership team - Foster a positive and inclusive culture that reflects the Trek Travel values **OWN REVENUE STRATEGY & PERFORMANCE** - Own revenue targets, sales forecasts, and pipeline performance - Develop and execute strategies to drive demand and increase conversion - Optimize lead management, follow-up cadence, and pipeline visibility - Drive initiatives to increase repeat bookings and lifetime guest value - Align with Finance on revenue planning and forecasting - Act as the voice of the guest and bring real-time insights into cross-functional conversations and decision-making **DRIVE THE DIGITAL SALES FUNNEL** - Partner with Marketing across the full funnel, from demand generation and campaign strategy through lead quality, messaging, and conversion - Align digital and human-assisted sales channels so the guest experience is seamless regardless of how they come in - Use funnel data and attribution to identify where marketing and sales can work better together **BUILD A WORLD-CLASS SALES PROCESS** - Own the lead-to-booking journey and all conversion metrics - Build a sales culture rooted in expertise, personalization, and genuine guest advocacy - Build re-engagement, referral, and repeat booking touchpoints into the sales process - Own and grow the online direct booking channel and design the processes, team behaviors, and follow-up systems that support it - Ensure consistency in how the Trek Travel brand is represented across all sales interactions - Drive adoption and optimization of CRM and sales tools including HubSpot and NetSuite - Build scalable playbooks, processes, and reporting frameworks the team can execute consistently - Champion automation, AI-assisted tools, and digital solutions to improve team efficiency and guest experience - Leverage data and analytics to continuously improve pipeline health and conversion performance **YOU HAVE:** **REQUIRED** - Proven experience Directing a Sales area a conversion-focused environment, travel, hospitality, or subscription preferred - Demonstrated ability to own and grow a digital or online channel metric - Strong analytical instincts and comfortable finding the story in the data and bringing a clear point of view - Collaborative by nature and someone who partners with marketing and technology rather than waiting on them - Clear, proactive communicator in both a remote and in person environment - A learn-it-all mindset and comfortable developing fluency in BI tools, CRM platforms, and emerging technology - W…