Implementation Manager - Pro Division

About the Outdoorsy Group

Founded in 2015, Outdoorsy Group pioneered access to the outdoors by building the world’s leading outdoor travel ecosystem. Millions of guests trust Outdoorsy to create lifelong family memories, while hosts rely on its products and innovations to grow their businesses and unlock life-changing sources of income. Outdoorsy Group’s portfolio includes Outdoorsy.com, the largest outdoor travel and hospitality marketplace; the Destination Network, a growing collection of campgrounds and glamping retreats set in some of the country’s most iconic landscapes; and Roamly, its proprietary insurtech platform powering Outdoorsy.comand enabling insurance infrastructure for global marketplaces. Together, Outdoorsy Group’s businesses are united by a long-term mission: to restore our relationship with the outdoors—and with one another.

About Wheelbase

Outdoorsy is the world's largest RV rental marketplace, connecting vehicle owners with travelers across North America and beyond. Wheelbase is the all-in-one operating system built for the next generation of independent mobility businesses. More than just a calendar, Wheelbase provides the infrastructure to scale—integrating professional-grade fleet controls with Roamly’s embedded episodic insurance. We remove the barriers of risk and compliance so operators can stop worrying about liability and focus on growth. From boutique startups to enterprise franchises, Wheelbase empowers you to automate operations, maximize yield, and regain total control of your customer data. It’s your fleet, your brand, and your rules. Learn more at www.wheelbasepro.com.

About the Role

Outdoorsy is looking for an Implementation Manager to join our Pro Division team in Austin. In this role, you'll be the first point of contact for new Wheelbase customers—both RV rental operators and automotive/carshare businesses—guiding them from signed contract to fully activated account.

You'll own the onboarding journey: scheduling and conducting training sessions, ensuring website integrations are complete, and setting customers up for long-term success before handing them off to our Customer Success team. This is a high-impact role where you'll directly influence customer activation rates and time-to-value.

This role will report directly to the Manager of Implementation and Account Management.

Requirements

Key Responsibilities

Onboarding & Training

• Lead the end-to-end onboarding process for new Wheelbase RV and Wheelbase Auto accounts.
• Conduct 1-2 hour virtual training sessions, walking customers through platform setup, vehicle listings, pricing configuration, and booking management.
• Ensure customers complete critical activation milestones: website integration, first vehicle listed, and payment processing enabled.
• Create and follow up on action items post-training to keep customers moving toward full activation.
• Support enterprise accounts with in-person visits when needed (occasional travel).

Activation & Handoff

• Own the customer relationship from closed-won through the first 30 days post-activation.
• Monitor activation metrics and proactively reach out to customers who are stalling.
• Ensure a smooth handoff to the Customer Success team with complete documentation of the customer's setup, goals, and any outstanding issues.
• Flag at-risk accounts early and escalate when needed.

Process & Documentation

• Document onboarding workflows and identify opportunities for improvement.
• Contribute to training materials, help articles, and onboarding checklists.
• Provide feedback to the Product team on common customer pain points during setup.
• Help maintain and improve our LMS (learning management system) content.

Key Performance Indicators (KPIs)

• Onboardings Completed: Number of accounts successfully onboarded per month.
• Time to Activation: Days from closed-won to fully activated (website integrated, first booking enabled).
• Activation Rate: Percentage of assigned accounts that reach full activation within 30 days.
• Customer Satisfaction: CSAT scores from onboarding surveys.

Who You Are

We're looking for someone who loves helping people get up and running with new technology and thrives on the satisfaction of turning a new signup into an active, successful customer.

• Customer-Obsessed: You genuinely enjoy helping people succeed and can stay patient and positive even when customers are frustrated or confused.
• Clear Communicator: You can explain technical concepts in simple terms, demonstrate processes clearly, and adapt your communication style to different audiences—from tech-savvy fleet operators to first-time software users.
• Organized & Detail-Oriented: You can manage multiple customer onboarding processes simultaneously without compromising quality. You document everything and follow up relentlessly.
• Tech-Comfortable: You're not intimidated by SaaS platforms, website integrations, or walking someone through technical setup. You don't need to be a developer, but you should be able to troubleshoot basic issues.
• Self-Starter: You take initiative, ask questions when stuck, and don't wait to be told what to do next.

Qualifications

Required:

• 2-3 years of experience in customer onboarding, implementation, training, or customer success.
• Experience with SaaS platforms (as a user, trainer, or implementer).
• Strong written and verbal communication skills.
• Comfortable with video calls and screen sharing for remote training.
• Based in Austin or willing to relocate; able to work in the office Monday-Friday.

Nice to Have:

• Experience in RV rental, automotive, fleet management, or travel/hospitality industries.
• Familiarity with website integrations, iframes, or basic HTML.
• Experience with CRM tools (Salesforce, HubSpot) or customer success platforms.
• Background in a startup or high-growth environment.

Benefits

Why You’ll Love Working Here

• Competitive Compensation: Base salary of $60,000 - $65,000 DOE.
• Growth Opportunity: Join a company in its early stages and help build its foundation for success.
• Equity: Opportunity to earn equity compensation.
• Comprehensive Benefits: 100% company-paid medical premiums for employees, 401(k) [Match], and Flexible PTO.
• Vibrant Culture: Lively Austin HQ with catered lunches, Happy Hours, and team-building events.
• Work-Life Balance: Enjoy RV rental discounts and a company culture that values a healthy balance between work and adventure.