Field Sales Representative - Kissimmee, FL

At Booksy, we believe in the power of feeling fantastic every day. We’re building a global team dedicated to helping people thrive—empowering entrepreneurs to build successful businesses and supporting their customers in arranging essential 'me time' moments.

Working at Booksy means embracing a rapidly growing and evolving environment. If you thrive in a dynamic, self-driven setting with opportunities for career growth as we scale globally, you’ll love what we offer.

As a Field Sales Representative in the Kissimmee region, you won’t just be a salesperson—you’ll be the face of Booksy, an ambassador for our mission, and a key driver of growth in South Florida. Your role will focus on expanding our presence, building lasting relationships, and educating clients on our innovative solutions.

Key Responsibilities:

Expand Booksy’s presence: Grow our footprint in South Florida by empowering small businesses with our solutions.

Build relationships that matter: Leverage face-to-face interactions to create lasting connections and share impactful business solutions.

Drive growth and success: Manage a pipeline of potential clients through cold calls, walk-ins, and social media outreach to expand your book of business.

Educate and enable: Attend industry events, conduct demos, and educate clients on our app’s features to ensure their long-term success.

Requirements:

Essentially, to succeed in this role, you’ll need:

• 2–4 years of prior exposure to field sales (preferred).
• Must be located in the Kissimmee area with access to a vehicle for client visits.
• A results-driven attitude with a track record of exceeding sales targets.
• Fluency in Spanish (required).

It will also help if you have:

• Experience in the Beauty industry (preferred, but not required).
• Experience selling for technology/SaaS companies or working with small business clients.
• Familiarity with Salesforce for managing your sales process and pipeline.

Benefits:

The Booksy benefits package includes:

• Remote work with flexible schedules (market-dependent, but always remote-first).
• $50/month home phone/internet reimbursement.
• Comprehensive health, dental, and vision coverage with UHC.
• Company-paid STD/LTD and basic life insurance (up to $250,000).
• FSA/HSA contributions ($1,000/$2,000 for employee/employee+).
• Voluntary accident/hospital/critical illness plans.
• 401k with 50% match up to 8% (3-year vesting).
• PTO: Unlimited (exempt) or 160 hours/year (non-exempt, non-rolling).
• 12 observed holidays.
• 12 weeks of paid parental leave.
• EAP (Employee Assistance Program).
• Voluntary pet insurance.
• Financial wellness tools via SoFi and Ladder.
• Discounts through Perkspot.
• $50/month credit for Booksy app services.

A bit about Booksy:

We’re a global team focused on helping people feel great every day—empowering entrepreneurs and supporting customers in their 'me time' moments. Our mission is to thrive and feel fantastic.

Working at Booksy means embracing change, initiative, and growth in a fast-paced environment. If you’re a self-starter who thrives in ambiguity, you’ll fit right in.

Our Diversity and Inclusion Commitment:

We foster an inclusive environment for all backgrounds. If you have accessibility needs or require adjustments during the interview process, contact belonging@booksy.com.

How AI Helps Us Find Great People:

Our AI tool assists recruitment by reviewing applications for skills alignment, ensuring fairness and consistency. However, AI never makes hiring decisions—real people handle every final call. We regularly review the tool’s use to maintain ethical compliance.