Market Manager - Florida

Company Overview

We build software for property management companies in the vacation rental industry. Our first product, Project MainSail, is an Owner Management Suite and the first third-party platform of its kind. It connects directly with a Property Management Company's existing Property Management Software (PMS), giving homeowners a modern experience with better reporting, a unified inbox, greater visibility into their investment, and a seamless onboarding process.

Property management companies use Project MainSail to strengthen homeowner relationships, reduce churn, and deliver a more professional ownership experience without adding operational complexity.

We're an early-stage SaaS company with ambitious growth plans and a clear vision for the future. Our team moves quickly, values great ideas over bureaucracy, and believes everyone should have the opportunity to make a meaningful impact. As one of our first Market Managers, you'll play a direct role in shaping our growth strategy while building something that truly matters within the vacation rental industry.

Position Summary

We're looking for an entrepreneurial Market Manager to launch and grow Project MainSail's presence throughout Florida. This isn't a traditional sales territory. It's an opportunity to build a market.

You'll become the face of Project MainSail across one of the largest vacation rental regions in the country, developing relationships with property management companies, attending industry events, generating new business, and helping establish our reputation as the premier homeowner communication platform in the industry.

Success in this role requires someone who enjoys being in front of customers, thrives with autonomy, and is motivated by building lasting relationships rather than simply closing transactions. You'll have the opportunity to influence our sales strategy, provide product feedback directly to leadership, and help define the playbook for future Market Managers as we continue to scale.

If you're energized by face-to-face selling, enjoy creating opportunities where others see challenges, and want to join a company where your work directly influences growth, we'd love to meet you.

Key Responsibilities

• Own and execute the growth strategy for the Florida market.

• Prospect, develop, and maintain relationships with property management companies throughout Florida.

• Conduct discovery meetings, product demonstrations, and sales presentations for prospective clients.

• Represent Project MainSail at local, regional, and national vacation rental industry events, conferences, and networking opportunities.

• Build and maintain a healthy pipeline while accurately managing opportunities within HubSpot CRM.

• Negotiate and close new subscription agreements while delivering an exceptional customer experience throughout the sales process.

• Partner closely with Customer Success to ensure smooth onboarding and long-term customer satisfaction.

• Identify expansion and referral opportunities within existing customer relationships.

• Share customer insights and market feedback with Product and Leadership to help shape future development.

• Help establish best practices, sales processes, and market strategies that future Market Managers will build upon.

Required Qualifications

• Demonstrated success selling B2B products or services with a proven history of closing new business.

• Strong relationship-building and networking skills with the ability to earn trust quickly.

• Experience managing a disciplined sales pipeline and CRM system. HubSpot experience is preferred.

• Comfortable working independently with minimal oversight while managing your own schedule and priorities.

• Excellent presentation, communication, and negotiation skills.

• Ability and willingness to travel extensively throughout Florida.

• Must reside in Florida.

Preferred Qualifications

• Experience selling SaaS solutions.

• Experience within the vacation rental, hospitality, real estate, or property management industries.

• Existing relationships within the short-term rental industry are a plus.

• Experience attending industry conferences and networking events to generate business opportunities.

Compensation & Benefits

Base Salary: $60,000 - $80,000 annually

Performance-Based Commission

Our uncapped commission plan rewards both new customer acquisition and long-term customer success.

• Monthly commission paid on accumulated Monthly Recurring Revenue (MRR).

• Additional earnings for onboarding fees closed each month.

• No commission clawbacks.

• Top performers have the opportunity to earn up to 200% of their On-Target Earnings (OTE).

Benefits

• Comprehensive medical, dental, and vision insurance

• Life insurance

• Paid time off, including vacation and sick leave

• Flexible work schedule with significant autonomy

• Remote, field-based work environment

• Mileage reimbursed and a healthy travel & entertainment budget

• Workplace perks such as recreation activities, food and coffee, and flexible work schedules

• Opportunity to help shape the future of a rapidly growing SaaS business

Schedule

This is a full-time, field-based position with flexibility to manage your own schedule.

• While most customer meetings take place Monday through Friday, occasional evening and weekend availability is expected to support industry events, conferences, customer meetings, and networking opportunities.