Account Executive

Whimstay; United States; Remote; USD 74,000 - 83,000; Full time

Job summary

Whimstay is seeking a driven Account Executive to manage sales processes and build relationships with vacation rental property managers. This remote role offers a competitive salary and the chance to be part of a mission-driven team focused on spontaneous travel. Candidates should have sales experience and thrive in a fast-paced environment, with opportunities for growth and development.

Benefits

Flexible PTO

Base + commission, equity, and benefits

Collaborative, high-performance culture

Qualifications

• 1+ years of experience in a closing sales role—ideally in tech, SaaS, or vacation rentals.
• Hungry, self-motivated, and energized by a fast-paced, startup environment.
• Ability to listen, ask great questions, and be coachable.

Responsibilities

• Own and manage a full-cycle sales process from prospecting to close.
• Educate prospective partners on the value of listing with Whimstay.
• Build relationships with operators of all sizes.

Skills

Sales

Relationship Building

Communication

Self-Motivation

Education

1+ years in a closing sales role

Job description

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Account Executive – Whimstay (Remote – US Based)

Full-Time | Sales | Vacation Rental Tech | Remote First

Whimstay is the go-to vacation rental marketplace for last-minute travelers—and we’re growing fast. Our platform helps property managers fill unsold nights, maximize revenue, and reach travelers who are booking just days (sometimes hours!) before check-in. We're on a mission to become the #1 platform for spontaneous travel, and we’re looking for a driven, curious, and high-energy Account Executive to help us get there.

What You'll Do

• Own and manage a full-cycle sales process from prospecting to close with vacation rental property managers across the US
• Educate prospective partners on the value of listing with Whimstay (hint: it’s all about driving incremental revenue with no extra work!)
• Build relationships with operators of all sizes—from boutique managers with 10 properties to national players with 500+
• Collaborate cross-functionally with onboarding, marketing, and account management to ensure a smooth handoff and great partner experience
• Consistently exceed monthly sales targets and pipeline goals
• You have 1+ years of experience in a closing sales role—ideally in tech, SaaS, or vacation rentals
• You’re hungry, self-motivated, and energized by a fast-paced, startup environment
• You know how to listen, ask great questions, and are coachable
• You love working toward goals, thrive on feedback, and bring positive energy to the team every day

Why Whimstay

• Be part of a scrappy, mission-driven team shaping the future of last-minute travel
• Fully remote with flexible PTO
• Base + commission, equity, and benefits
• Collaborative, high-performance culture with room to grow

At Whimstay, our mission is to help travelers discover amazing properties at great prices, turning spontaneous decisions into memorable experiences. We are an emerging player in the rental market, providing the best value on last-minute stays. Our rates are always lower than those found on other major vacation rental sites within the 30-day booking window. We offer an extraordinary collection of vacation homes, condos, cabins, villas, and resorts, all at competitive prices.

Seniority level

• Seniority level

  Entry level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Sales and Business Development

• Industries

  Technology, Information and Internet

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