Head of Operations -(Outdoor Recreation / Self-Service Kiosk Rentals) - 64248550813

Role: Head of Operations (Outdoor Recreation / Self-Service Kiosk Rentals)
Priority Location: LATAM

Working hours: Full-time, not a normal 40 hour a week job (Requires US ET overlap. Our partners and vendors work US business hours)

Type of contract: Independent Contractor 

Type of job: Remote

Start date: ASAP

 

About the Company: The company operates a nationwide network of unstaffed, self-serve rental kiosks for kayaks and paddleboards across 102 locations in 23 states. Customers handle the entire rental process—booking, Bluetooth-unclocking equipment, and returning it—via their smartphones. Behind the scenes, the automated business model is supported by a lean internal operations team and a remote network of local contract technicians who handle field maintenance and support.

About the Role:  Your mission is to own day-to-day operations, optimize field logistics, and build durable, automated systems that allow the business to run seamlessly and independently. Need a "hungry operator" who thrives on building systems from the ground up, not just directing traffic. Lead with humility, earning authority by mastering the details rather than managing from a distance.

• Systems Architect: Identify manual friction, document institutional knowledge, and replace ad-hoc workflows with scalable processes and software.
• Humility & Grit: Embrace the "backstop" reality of a lean team. Willing to jump into customer support queues or handle weekend field escalations because you know that mastering the friction points first-hand is the only way to build better systems.
• Operational Mastery: Bring deep operational experience—ideally in hardware, field logistics, or tech-enabled physical networks—and surpass the founder in operational expertise.

 

The Team You Are Inheriting:

You will lead a high-performing, self-directed team of three who have successfully managed daily operations without a direct leader. They take initiative, solve problems independently, and hold deep operational insight.

In this environment, title alone confers no authority—it is earned through humility, deep operational understanding, and adding immediate value to their work. We need a partner who learns how the operation actually works, not someone arriving to direct traffic.

Key Responsibilities:

 

• Team Leadership & Field Network: Direct daily operations for our 3-person core team and nationwide 1099 technician network—setting priorities, running team cadences, and hiring as we scale. (Note: Core team members retain functional reporting to the founder for marketing, website, and automation specs).
• Operating System Architecture: Build our operational infrastructure from scratch—codifying SOPs, decision trees, escalation paths, inventory tracking, and location health metrics.
• Operational Continuity & Handoffs: Eliminate single-point-of-failure risks by creating clear handoff protocols, centralized thread visibility, and active coverage monitoring so no task stalls silently.
• Performance & Data Ownership: Establish, track, and report on core KPIs (uptime, issue resolution speed, installation readiness). Maintain real-time reporting so operational health is fully transparent.
• Escalation Management: Serve as the final authority and backstop for all complex field, customer, or logistics issues the team cannot resolve.
• Partner & Vendor Operations: Own day-to-day relationships with park managers and vendors, managing the site installation program end-to-end.
• Active Backstopping: Jump into the trenches—including working the CS queue and handling weekend spikes—using hands-on exposure to continuously identify friction points and build better automations.

 

What We Are Looking For:

• Proven Systems Builder: 5+ years in distributed/multi-site operations. Most importantly, you have built an operational system from scratch.
• Willingness to Do the Work: You draft the escalation policy and willingly take 7 PM Saturday calls during peak season. You lead by doing, not delegating.
• Professional Communication: Clear, authoritative written and spoken English to represent us to park managers, state agencies, and vendors.
• Centralized Work Management: Mastery of single-system operations (we use ClickUp for end-to-end accountability, reporting, and tracking—not static spreadsheets).
• Calm in Chaos: Exceptional problem-solving when handling real-time operational mess (contractor no-shows, urgent multi-issue threads).
• AI-First Mindset: You naturally look to automate processes before hiring headcount.
• Relentless Follow-Through: Obsessive about closing loops so critical tasks never stall.

This Is Not For You If: You expect a pre-made playbook, rigid 40-hour weeks, or someone else to make the tough calls. Peak season requires evening and weekend availability.

Nice to Have: No-code/automation skills, field service or route-based logistics experience, US 1099 network management, outdoor rec/parks background, or Spanish fluency.

 

What Success Looks Like:

Rather than arbitrary dates, success is measured by hitting four core operational milestones:

• Deep Operational Mastery: You know the business inside out—from hardware failures to park manager complaints—and deliver a clear, written diagnostic and roadmap for the future.
• Escalation Ownership: You step in as the primary backstop. Operational issues and escalations route to you instead of the founder.
• Active, Living Systems: Documented playbooks, rules, and workflows are actively used by the team daily, making self-sufficiency the default.
• Scalable Operations: The network expands over Year 1 without adding proportional headcount, freeing you to focus on high-level operational growth rather than daily firefighting.

 

Submit with your resume:

 

Tell me about an operation you built or inherited: what was broken, what you changed, and how you knew it worked. Numbers welcome. Skip the cover letter.