Director of Sales & Growth

Position Overview

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.

POSITION RESPONSIBILITIES INCLUDE, BUT NOT LIMITED TO:

• 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
• Maintain an understanding of 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

QUALIFICATIONS

• Proven experience Directing a Sales area a conversion-focused environment, travel, hospitality, or subscription preferred
• Strong analytical instincts and comfortable finding the story in the data and bringing a clear point of view
• 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

BENEFITS

• 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

COMPANY CULTURE

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