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Territory Sales Manager (Midwest)

Help Rent.Fun scale outdoor recreation by making kayaks, bikes, and other equipment instantly rentable right from a phone in parks and public spaces across the Midwest.

Rent.Fun is looking for a proven, relationship-driven sales professional who knows how to win and grow business with municipalities, parks & recreation departments, and public agencies. If you've successfully navigated government procurement, built territory strategy, and closed complex B2G deals, you'll play a key role in expanding our self-service rental solutions into new communities.

The Opportunity

As the Territory Sales Manager, you'll own a defined region and lead full-cycle sales from prospecting and discovery through proposal, procurement, contract close, and expansion. You'll work closely with city leaders, parks directors, and community organizations to deploy self-service rental stations that increase access to outdoor recreation while reducing operational burden for public partners.

This is a growth-focused role for someone who thrives in a fast-moving environment, enjoys building relationships with public-sector stakeholders, and is excited to help communities deliver better park experiences.

What You'll Do

• Own and grow a territory by developing a clear account plan, pipeline strategy, and target list across municipalities and public agencies.
• Drive full-cycle government sales: outreach, discovery, demos, proposals, negotiations, contracting, and implementation handoff.
• Build strong relationships with decision-makers and influencers (parks & rec leaders, city administrators, procurement teams, and community partners).
• Navigate procurement confidently, including RFPs/RFQs, vendor registration, budgeting cycles, and compliance requirements.
• Position value clearly by connecting Rent.Fun's solutions to community goals like public access, tourism, revenue generation, and operational efficiency.
• Collaborate cross-functionally with marketing, operations, and leadership to ensure smooth launches and long-term partner success.
• Expand existing accounts through renewals, additional locations, and new equipment categories.

What Success Looks Like

• A healthy, consistent pipeline of qualified municipal and parks opportunities
• Closed agreements with new cities/parks and successful deployments
• Strong partner relationships that lead to renewals and multi-location growth
• Clear territory execution: accurate forecasting, disciplined CRM hygiene, and repeatable sales motion

Who You Are

• An experienced sales professional with a track record of selling to government or public-sector organizations

• Comfortable selling to municipalities, parks & recreation departments, public agencies, and community organizations
• Skilled at complex, consultative sales and managing multiple stakeholders
• Familiar with government purchasing processes (RFPs, budget cycles, vendor onboarding, compliance)
• Organized, persistent, proactive, and able to create momentum and drive deals forward
• Motivated by mission-driven work and improving access to outdoor recreation
• Tech-savvy and data-driven, with experience using CRM tools (Hubspot) and sales analytics.
• Hybrid, effective working remotely, willing to work in office.

Who We Are

Rent.Fun is part of Contactless Holdings, dedicated to transforming rental and sharing experiences through technology, simplicity, and community impact.

Our brands include:

• Movatic - Rental and sharing software
• Tandem Mobility - The USA's largest provider of bikeshare programs for small to mid-size cities
• Rent.Fun - The largest self-service kayak rental provider operating in 200+ locations

We partner with municipalities, government agencies, and community organizations to deliver seamless outdoor recreation experiences. We're growing rapidly self-funded because we operate with innovation, integrity, and a strong commitment to the communities we serve.

Why Join Rent.Fun?

Competitive Pay + Uncapped Upside

• Base Salary: $45,000 - $60,000 (DOE)
• Commission: 4%, uncapped
• On-Target Earnings (OTE): $80,000 - $100,000+ at plan

A Sales Motion That's Already Proven

You won't be guessing what works. We have 3 years of performance data that clearly defines the meeting-to-close math and the activity levels that lead to success so you can build pipeline with confidence and forecast accurately.

Strong Ramp to Help You Win Early

We support your first months with a monthly commission guarantee (draw) during your first 4 months. The guarantee amount is negotiable based on your previous sales track record.

Real Growth + Meaningful Work

Rent.Fun is growing fast and so are the opportunities. You'll have a clear path for career progression in a mission-driven company that's expanding access to outdoor recreation across cities and communities.

A Team Culture Built for High Performers

Work alongside a passionate team that values:

• Autonomy (you own your territory and outcomes)
• Innovation (we build and improve quickly)
• Impact (your work directly benefits communities)