Senior Account Executive - Enterprise Segment

About 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.

The Opportunity

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