Specialty Booking Coordinator

About the Outdoorsy Group and Wheelbase Pro

Founded in 2015, the Outdoorsy Group pioneered access to the outdoors by creating the world's leading outdoor travel ecosystem. Millions of guests trust the Outdoorsy.com RV rental marketplace to help them create lifelong family memories, while host partners are empowered to grow their businesses.

Wheelbase , the Group’s industry-leading fleet management platform , underpins the professional RV rental ecosystem, serving as the essential, cloud-based software that enables professional operators to streamline operations, maximize revenue, and manage fleets across multiple channels. This transformative tool handles everything from online bookings and payment processing to real-time inventory synchronization with Outdoorsy.com.

The Role

Outdoorsy is seeking a Specialty Booking Coordinator to join our team in Austin, TX. This person will own and scale our high-value, complex booking channels: one-way rentals, long-term bookings, and group reservations. Currently, these specialized bookings require significant manual coordination, creating operational bottlenecks while representing substantial untapped revenue across our Wheelbase platform.

By facilitating just 8-12 specialty bookings per month (conservative estimate), this position will generate $150K-300K+ in annual revenue while delivering significant lifetime value to our professional rental operators.

The Opportunity

We're at an inflection point. Guests are asking for one-way rentals, long-term bookings, and group/event reservations —but we lack the infrastructure and dedicated resources to capture this demand efficiently. You'll build the playbook, own the relationships, and prove out these revenue channels.

Group event bookings are particularly important, as we look to expand our relationship with different industries to support events.

Requirements

Who You Are

You're a logistics thinker who loves solving puzzles. You thrive on making impossible bookings happen, get energized by building relationships with operators, and understand how to balance customer delight with operational efficiency. You're comfortable in ambiguity and excited to build something from scratch. You are personally invested in the experience of our customers.

• Revenue-Driven: You understand that every booking you facilitate directly impacts both our business and our pros' success.
• Relationship Builder: You can quickly build trust with rental operators and become their go-to person for complex bookings.
• Operationally Savvy: You think in systems and processes, documenting what works so it can scale.
• Problem Solver: When there are 5 obstacles to a booking, you figure out creative solutions to all 5.
• Startup Mentality: Comfortable with rapid iteration, shifting priorities, and lean operations.
• Community builder: Excels in building strong relationships with new and existing partners.

Key Responsibilities

Direct Booking Facilitation

• Aggressive Deal Facilitation: Own the full sales cycle for high-value bookings, converting inbound leads into closed contracts through proactive negotiation and relentless follow-up.
• Strategic Supply Hunting: Actively source and "sell" unique booking opportunities to our network of rental operators and P2P owners to unlock inventory for specialized demand.
• Logistics Engineering & Upselling: Solve complex logistics (positioning, transfers, multi-location) by pitching creative, high-margin solutions to both owners and renters.
• High-Touch Client Acquisition: Serve as a dedicated concierge for VIP clients, leveraging a "whatever it takes" attitude to ensure premium bookings cross the finish line.
• Rapid Response Execution: Maintain a competitive edge by engaging leads and resolving inquiries within a strict 2-hour window—prioritizing speed to lead.

Relationship & Network Building

• Develop trusted relationships with 20-30 core pros across key markets who can reliably fulfill specialty bookings and cancellations.
• Understand each operator's fleet, geographic coverage, and appetite for different booking types.
• Create informal "networks" of pros who can support each other with vehicle positioning and transfers.
• Host quarterly check-ins with top specialty booking partners.

Process Development & Scaling

• Document successful booking patterns and create playbooks for each specialty booking type.
• Identify product/tech requirements to reduce manual work and scale operations.
• Build pricing frameworks for one-way fees, long-term discounts, and group bookings.
• Develop understanding of competitor landscape and identify opportunities to partner and/or improve.
• Track metrics on inquiry-to-booking conversion, average booking value, and operator satisfaction.
• Collaborate with Product and Engineering teams to prioritize features that enable self-service for specialty bookings.

Revenue Optimization

• Maximize conversion rates on specialty booking inquiries (target: 60%+).
• Identify and pursue high-value corporate/long-term booking opportunities.
• Create upsell opportunities within specialty bookings (insurance, add-ons, etc.).
• Build relationships with corporate travel coordinators, event planners, and relocation services.

Qualifications

Required:

• 2+ years in operations, logistics, sales operations, or account coordination.
• Track record of revenue generation or quota achievement.
• Exceptional communication skills—both written and verbal.
• Highly organized with the ability to manage multiple complex transactions simultaneously.
• Comfortable with data and metrics to drive decisions.
• Startup or high-growth company experience.
• Able to work in-person from the Austin office 5 days/week.

Preferred:

• Experience in the rental, hospitality, travel, or logistics industries.
• Familiarity with fleet management, vehicle rentals, or marketplace dynamics.
• Previous role involving B2B relationship management.
• Knowledge of RV or automotive rental operations.

Nice-to-Haves:

• Experience with SaaS platforms or dual-sided marketplaces.
• Background in sales or business development.
• Understanding of insurance/protection products in rentals.

Success Metrics (KPIs):

Primary:

• Specialty bookings closed per month (one-way, long-term, group).
• Total booking value facilitated monthly/quarterly.
• Conversion rate on specialty booking inquiries.

Secondary:

• Number of active "network pros" participating in specialty bookings.
• Average days to close specialty bookings.
• Customer satisfaction scores from both renters and pros.
• Percentage of repeat specialty bookings from same pros.

ROI Target: Generate minimum $150K annual commission revenue (3x+ loaded compensation) within 6 months.

Benefits

Why You'll Love Working Here

• Competitive Salary: The base salary for this position is $50,000, with an On-Target Earnings (OTE) of $65,000 - $80,000 due to earned commission.
• Growth Opportunity: Join a company in its early stages and help build its foundation for success.
• Equity: Opportunity to earn equity compensation.
• Comprehensive Benefits: We offer a full health and welfare benefits package, a 401(k) match, and flexible Paid Time Off.
• Fun Office Atmosphere: Lively office, stocked with endless snacks, regular Happy Hours, catered lunches, and team building events.
• Work-Life Balance: Enjoy RV rental discounts and a company culture that values a healthy balance between work and adventure.