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About the Role
Guesty is seeking a Senior Sales Professional to drive field sales and lead generation within the Mountain West/Midwest region. This role involves building relationships, closing deals, and representing the Guesty brand in a high-growth territory.
Responsibilities
- Create and execute a comprehensive territory plan to build and maintain a pipeline of opportunities, ensuring attainment of individual revenue targets.
- Lead generation while becoming a central figure in the local business community within the short-term rental (STR) and property management sphere.
- Develop a contact and call strategy to achieve and exceed targets, including daily outreach using discovery, value pitching, and compelling closing statements.
- Conduct high-impact, live product demonstrations both in-person and via video calls.
- Manage all prospect communication and sales pipeline diligently in Salesforce.
- Develop and maintain long-term relationships with key prospects and stakeholders in your target list.
- Negotiate contracts and manage the legal/financial hurdles to getting a deal across the finish line.
- Research your target market and provide ongoing feedback to relevant global teams regarding local U.S. trends.
- Represent the company at regional and national trade shows and industry events.
Requirements
- Must be based in the Mountain West or Midwest region with a deep understanding of the local geography and market dynamics.
- Proven experience in Travel / Hospitality tech sales is a MUST.
- Deep knowledge of the U.S. short-term rental industry and property management landscape is strongly preferred.
- 5+ years of experience in Technological Sales with a specific focus on SaaS (Software as a Service) — this is a MUST.
- Mastery of sales techniques, including cold calling, complex objection handling, and full-cycle pipeline management.
- Skilled in prospecting and eager to hunt for new opportunities; you are a self-starter who doesn't wait for leads to come to you.
- A proven track record of follow-up and persistence when facing challenging or long-cycle sales situations.
- Excellent organizational and interpersonal skills, with the ability to "read the room" in diverse outbound settings.
- High level of comfort with Salesforce or similar CRM systems.
- You are a closer at heart with a competitive nature and a strong work ethic.
Skills
- Field sales methodologies
- Outbound efforts
- Lead generation
- Relationship building
- Closing deals
- Territory strategy
- Community integration
- Outreach
- Product demonstrations
- CRM management
- Salesforce
- Contract negotiation
- Market intelligence
- Technological Sales
- SaaS
- Cold calling
- Objection handling
- Pipeline management
- Prospecting
- Organizational skills
- Interpersonal skills
- Work ethic
Location
- Mountain West region
- Midwest region
Work Type
- Remote
- Field Sales
Experience Level
- Senior
- 5+ years of experience in Technological Sales
Salary/Compensations
- 160-180K OTE annually
Benefits
- Health, dental, vision, life, and disability insurance
- 401(k) Retirement Savings Plan & Employer Match
- Paid time off
- Comprehensive virtual onboarding experience
- Professional development opportunities
About the Company
- Guesty is the all-in-one platform helping hospitality businesses around the world automate, optimize, and scale their operations.
- We’re a fast-growing global startup that’s transforming how the industry works — from guest experience to business growth.
- With a powerful suite of features and integrations with 150+ industry partners — including Airbnb, Vrbo, Booking.com, Expedia, Google Travel, and many more — Guesty empowers property managers to deliver top-tier guest experiences while running more efficient, data-driven operations.
- We’re proud to have over 900+ team members across 16 countries worldwide, all working together to build the future of hospitality technology.
- If you’re looking to grow your career in a dynamic, global, and impact-driven environment, we’d love to hear from you.
Equal Opportunity
- Guesty is proud to be an Equal Opportunity Employer. We provide equal employment opportunities to all employees and applicants regardless of race, color, religion, sex, age, national origin, disability, veteran status, pregnancy, sexual orientation, or any other characteristic protected by law.