Outside Sales Representative

About the role

At Playlist, life's richest moments happen when people step away from screens to move, connect, explore, and play. We are building the definitive platform for intentional living, connecting people with inspiring experiences in fitness, wellness, and beyond. This role owns the front line growth initiative for ClassPass by discovering and signing high-potential local businesses in the fitness and wellness space. You will act as a trusted local expert, translating the brand promise into tangible business outcomes for each merchant. The position demands consistent execution of a field-first strategy where relationship building is the primary currency of success. You will be responsible for shaping the future of our field sales approach in a growing and evolving team environment.

Key facts

What you'll do

Identify and prioritize high-value merchant targets within your assigned territory using data-driven insights and local market knowledge.

Lead with a field-first approach by visiting prospective merchants daily, attending local industry events, and cultivating relationships with community stakeholders and influencers.

Own the end-to-end full sales cycle, executing outreach through in-person drop-ins, strategic phone outreach, targeted email communication, and structured virtual touchpoints.

Consistently achieve or exceed monthly acquisition quotas and pipeline conversion targets while maintaining a high standard of sales professionalism.

Act as a definitive local market expert, identifying untapped opportunities that align with customer demand and emerging wellness trends.

Maintain a disciplined, accurate pipeline by tracking all key activities and performance metrics rigorously within Salesforce.

Qualify and develop opportunities through consultative discovery, aligning business needs with ClassPass solutions and value propositions.

Collaborate with internal teams to design and execute tailored proposals, negotiations, and closing strategies that secure mutually beneficial agreements.

Champion the ClassPass brand by delivering exceptional, professional, and knowledgeable experiences that build trust and long-term partnerships.

Provide structured feedback from the field regarding product perception, competitive dynamics, and market opportunities to inform strategic decisions.

Requirements

3-5 years of outbound field sales experience, complemented by strong inside sales skills and a history of consistent quota attainment.

Full-cycle sales methodology expertise with an emphasis on conversion optimization and evidence-based selling techniques.

Strong B2B negotiation, organizational, and time management skills to manage complex sales activities across a dispersed territory.

Self-motivated, proactive mindset that is receptive to feedback, coaching, and iterative improvement in a fast-paced environment.

Proven track record of exceeding quotas and OKRs, demonstrating resilience and adaptability in achieving demanding performance goals.

Familiarity with local industries such as fitness, wellness, spas, or related sectors, and an existing network within these sectors is a significant advantage.

Proficiency in Salesforce, SalesLoft, and Microsoft Office Suite to manage pipelines, communications, and reporting effectively.

Ability to travel extensively, including local day trips and extended multi-night regional travel, often with flexible scheduling that may include travel by car or flight.

Must reside in the Portland, OR region to support regular in-person sales engagements and in-depth prospecting activities.

Practical notes

This Outside Sales Representative role is based in the United States and operates under a field-based engagement model that requires substantial travel. You should expect to dedicate 70-80% of your time to travel, which may include both local day trips and extended multi-night regional travel depending on business needs. Flexibility in travel methods, including driving and flying, is essential to maximize coverage and respond to customer requirements. There may be occasional travel outside of your assigned region to support strategic priorities. The position mandates residence in the Portland, OR area due to the necessity of regular in-person sales engagements and hands-on prospecting activities. No specific working hours are outlined, but the role demands the ability to adapt to evolving business needs and travel schedules. There are no visa requirements specified at this time as the role operates within the United States. This role is positioned to help shape the future of ClassPass field sales through a combination of entrepreneurial ownership, disciplined execution, and deep market engagement.