Senior Account Executive - Enterprise Segment

Sales Representative Opportunity at Pearly

Pearly is a cloud-based revenue cycle automation platform powering dental billing for leading Dental Support Organizations (DSOs) and private practices. Pearly centralizes billing, unifies AR reporting and improves decision-making, giving Revenue Cycle Management (RCM) teams the visibility and tools they need to drive higher collections and better financial outcomes at scale.

Pearly is at an inflection point that represents a compelling opportunity for a hungry, high-integrity sales professional: the chance to join a company with proven product-market fit and accelerate what's already working. With 2,800+ dental offices across DSOs, groups, and private practices already on the platform the product works and the market has validated it.

We've built a repeatable sales motion and are now scaling that motion with the right people. You'll own the full sales cycle across a market that is ready to be modernized, working alongside a team that can show you what's working and give you the foundation to go execute against it. There is still plenty of building ahead (new segments, new products, and a GTM org that is growing fast) but you'll be joining a winning motion. In 12 months, you'll have closed deals across multiple practice types, built a strong pipeline, and established yourself as a core contributor to Pearly's next phase of growth. If you're energized by hunting and closing in a market with real momentum and you want to sell something that genuinely improves the way dental practices run their business, this is your opportunity.

What You Bring

• 5+ years of closing enterprise or mid-market deals in B2B vertical SaaS and/or payments ($100K+ ACV)
• Current or recent experience selling SaaS into the Dental DSO space is a plus. OR selling A/R, RCM, patient billing/collections software into healthcare (dental or medical).
• Demonstrated ability to consistently achieve quota through proactive creative problem solving and continued refinement that benefited others on the team.
• Strong outbound instincts: comfortable picking up the phone, building relationships, and finding creative ways into accounts
• Excellent written and verbal communication. You can tailor your message to a practice owner, an office manager, or a DSO executive, and you iterate your approach based on what resonates
• Willingness to travel to for customer and industry events
• Demonstrated comfort and executive presence with C-suite and relatability and empathy with office managers

Responsibilities

• Prospect and develop new business opportunities through outbound outreach, networking, and strategic account planning
• Manage the full sales cycle, including discovery, product demonstrations, Proof-of-Value (Pilot), negotiation, contract execution, and expansion to full DSO office portfolio.
• Develop trusted relationships with prospective customers by understanding their business challenges and aligning Pearly with their business goals.
• Develop and defend ROI business cases tied to collection rate improvement and staff time savings.
• Navigate and close multi-stakeholder deals across ops and finance decision-makers.
• Maintain accurate pipeline and forecasting in CRM.
• Collaborate and partner with CS to ensure complete rollout success.
• Develop strategic referral network and customer relationships

What Success Looks Like

• Fluent in Pearly's product and market positioning within the first 60 days.
• Actively engaging DSO prospects, leveraging existing relationships/domain credibility, within the first 60 days.
• Sourcing or advancing first enterprise deals by day 90.
• Consistently meeting or exceeding pipeline creation and revenue targets within two quarters of ramp.

Benefits

• Competitive salary, equity, and healthcare benefits
• Meeting-light culture
• Work with an A+ smart and passionate team
• Flexible vacation/time-off policy
• Opportunity to make your mark at an accelerating company with great product-market fit