Outside Sales Representative - Pittsburgh, PA

The Role You’ll Play 

ClassPass is seeking a driven Field Sales Executive to expand our merchant base by acquiring and onboarding high-potential local businesses in the fitness and wellness space. This is a highly field-based role (70–80% travel) and best suited for individuals energized by being in front of customers, building relationships, and representing our brand as a trusted local expert. With a growing team and evolving strategy, this role offers the opportunity to help shape the future of our field sales approach.  

What You’ll Do 

• Build and grow our merchant network by prospecting, pitching, and closing new businesses in your assigned territory. 

• Lead with a field-first approach: visit prospective merchants daily, attend local events, and nurture relationships with community and industry insiders. 

• Own the full sales cycle, from outreach and drop-ins to negotiation and close, using a mix of in-person, phone, email and virtual touchpoints. 

• Consistently achieve or exceed monthly acquisition quotas and pipeline conversion targets. 

• Act as a local market expert, identifying untapped opportunities that align with customer demand. 

• Maintain a disciplined pipeline, tracking key activity and performance metrics in Salesforce. 

Travel Expectations 

• Travel will make up 70–80% of your time, including both local day trips and extended multi-night regional travel. 

• Depending on business needs, there may be occasional travel outside of your assigned region. 

• Travel may be by car or flight — flexibility is essential to meet customer needs and maximize coverage. 

 The Experience You’ll Bring 

• 3–5 years of outbound field sales experience, complemented by strong inside sales skills. 

• Full-cycle sales methodology expertise with emphasis on conversion optimization. 

• Strong B2B negotiation, organizational, and time management skills. 

• Self-motivated, proactive, and receptive to feedback. 

• Proven track record of exceeding quotas and OKRs in a fast-paced environment. 

• Familiarity with local industries (fitness, wellness, spas, or related sectors) and existing networks a plus. 

• Proficiency in Salesforce, SalesLoft, and Microsoft Office Suite. 

Pay Transparency

It is Playlist’s intent to pay all Team Members competitive wages and salaries that are motivational, fair, and equitable. The goal of Playlist’s compensation program is to be transparent, attract potential employees, meet the needs of all current employees, and encourage Team Members to stay with our organization.

Actual compensation packages are based on several factors that are unique to each candidate, including but not limited to skill set, depth of experience, certifications, and specific work location.

The base salary range for this position in the United States is $52,125 to $76,450. The total compensation package for this position may also include performance bonuses, benefits, and/or other applicable incentive compensation plans.