Director of Sales

Director of Sales

Our client is a fast-growing, venture-backed company transforming how tour and activity operators manage bookings, payments, and guest experiences. They believe work should be meaningful, fast-paced, and a little bit adventurous. With a fully remote team powering the experiences industry, they’re helping operators grow their businesses with tools that actually work.

This is a small, scrappy team that values progress over perfection, action over ego, and results over buzzwords. No fluff. No layers of hierarchy. Just real work with real impact.

Our client is seeking a Director of Sales to drive the success of their go-to-market efforts. You’ll report directly to the Founder & CEO and own the strategy, team building, and execution needed to scale a high-performing sales organization. This is a foundational leadership role at a pivotal stage of growth.

You'll lead the sales team day-to-day, help shape GTM strategy, and serve as a player-coach who can drive results hands-on. You'll also help define how the team leverages AI-driven insights, automation, and personalization to improve prospecting, forecasting, and customer engagement.

What You’ll Do

• Lead the sales organization day-to-day, ensuring strong performance, accurate forecasting, healthy pipeline, and scalable processes

• Build and manage a high-performing Account Executive team - setting expectations, coaching, and holding reps accountable to quota

• Serve as a player-coach - refining messaging, jumping into complex deals, and helping the team close business

• Design and implement repeatable sales processes, playbooks, and reporting systems

• Drive pipeline generation and territory strategy - establish outbound programs and ensure full-funnel coverage

• Partner with Marketing, Product, and Customer Success to align messaging, lead flow, and overall customer experience

• Deliver accurate, data-driven pipeline insights and forecasts to company leadership and the board

• Develop fluency in the tours and activities space and translate customer insights into actionable product and strategy feedback

What You Bring

• 5+ years of progressive B2B SaaS sales experience with a proven record of top performance

• Experience closing complex, high-value mid-market or enterprise deals

• Proven ability to forecast accurately and manage disciplined pipelines

• Hands-on leadership style with strong execution and people development skills

• History of hiring, coaching, and scaling sales teams to exceed goals

• Strong communication and executive presence with ability to influence cross-functionally

• Familiarity with AI-powered sales tools (conversational intelligence, forecasting models, automation, personalization)

• Comfort building processes from scratch and operating in a high-growth, fast-changing environment

• Industry experience in tours and activities, travel tech, or hospitality preferred

• Background in fintech or payments (transaction or booking-based revenue models) a plus

• HubSpot CRM experience preferred

What Makes You a Great Fit

• Grab a shovel - You’re hands-on and proactive. When something needs doing, you jump in.

• We win together - You value collaboration and shared success over individual credit.

• Push further - You thrive on growth, seek out challenges, and continuously raise the bar.

• Think like an operator - You build practical solutions that improve the customer experience.

• Driven by results - You are motivated by hitting and exceeding goals.

• A coach at heart - You build teams, develop people, and give clear, actionable feedback.

• Strategically minded - You think beyond the quarter and build systems that scale.

• Hands-on and pragmatic - You model the behavior you expect and stay close to the field.

• Data-informed - You use insights to drive performance, strategy, and continuous improvement.

• Customer-obsessed - You listen, learn, and always connect solutions to real operator needs.

• Adaptable and entrepreneurial - You thrive in ambiguity and love building things from the ground up.

Why Join This Client

• Fully remote - Work where and how you’re most productive

• Top-tier health benefits - 100% medical premium coverage plus dental and vision plans

• 401(k) match - Full 3% employer match

• Equity - All employees are owners

• Generous PTO - Take the time you need to recharge

• Great people - Join a low-ego team that values impact and collaboration

• Values-driven culture - Built on initiative, ownership, and delivering value to customers