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 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 

• 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 

• 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

• 8-10 years of proven experience directing a Sales area, sales team, a conversion-focused environment, travel, hospitality, and/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 
• Willingness to travel as needed to support training, events, and team development 
• Passion for premium guest experiences and the Trek Travel brand 

• Experience in travel, hospitality, or consumer-direct sales 
• Experience managing managers or layered sales teams 
• Passion for cycling, active travel, and/or outdoor adventure 

• A fast paced, casual, fun, and flexible company culture where initiative and pro-activity are highly valued 
• Competitive health care   
• Dental and vision insurance   
• Flexible Spending Accounts (FSA)   
• 6 weeks paid parental leave  
• Short Term /Long Term Disability and Life Insurance   
• Competitive Paid Time Off package   
• Paid Holidays   
• 401(k) with company match   
• Employee trip discounts and industry discounts

At Trek Travel, we think outside the box, continuously improve, encourage feedback, and ‘give it all we got, all the time, no exceptions. This is a full-time position based in Madison, Wisconsin, and reports to the President & CEO.

If you have what it takes to join our team and the desire to help shape Trek Travel’s future, we wish you the best of luck and look forward to your application!