Mid-Market Enterprise Account Executive

At Rectangle Health, we believe that our team members are our most important asset. We grow our team by hiring best-in-class talent. We encourage all employees to contribute their individual talents and ideas to strengthen our team, our brand, and our services. We promote a culture that serves to empower and motivate employees beyond the standard corporate rhetoric one might see on motivational posters. Employees understand their individual roles in serving our customers, and this clarity of purpose encourages high job performance.

Position Overview:

If you are ready to combine your healthcare knowledge with your ability to build relationships and close complex business, Rectangle Health offers an exciting opportunity. As an Enterprise Sales Account Executive, you will help large healthcare groups and organizations transform the way they manage patient payments by introducing technology that streamlines operations, consolidates payment processes, and improves the overall patient experience.

You will play a key role in growing Rectangle Health's Enterprise business by hunting for new-logo opportunities, building pipeline through targeted prospecting and outreach, leading consultative sales conversations, and building lasting relationships with executive stakeholders. Supported by experienced internal partners, you will guide prospects through the full sales cycle and help position Rectangle Health as their trusted healthcare payments partner. If you want to be part of something exciting, please read on!

Primary job duties:

• Become a trusted enterprise advisor in healthcare payments by developing a deep understanding of the operational, revenue cycle, and patient payment challenges facing large healthcare organizations.
• Hunt for new business opportunities within enterprise healthcare groups and organizations through targeted prospecting, cold outreach, networking, referrals, and industry engagement, consistently generating a qualified pipeline of net new opportunities.
• Own complex sales cycles from initial discovery and solution alignment through demonstrations, executive presentations, negotiation, and contract execution.
• Build executive relationships with key decision-makers and sponsors by connecting Rectangle Health’s solutions to their business needs, financial goals, and patient experience priorities.
• Lead cross-functional deal strategy by coordinating pre-sales, value management, bid management, marketing, product, implementation, and sales support resources.
• Deliver consultative product presentations that clearly communicate the value of Rectangle Health’s payment technology and differentiate it from legacy payment processing solutions.
• Manage your territory and book of business using data, CRM tools, and disciplined time management to prioritize opportunities and maximize selling activity.
• Maintain accurate pipeline and forecast data by keeping customer records, opportunity stages, next steps, and projected close dates current and reliable.
• Achieve assigned sales goals by consistently generating pipeline, progressing qualified opportunities, overcoming objections, and closing net new enterprise business.

Minimum qualifications:

• 5+ years of quota-carrying sales experience selling SaaS, fintech, healthcare technology, revenue cycle, payment, or financial solutions to enterprise or mid-market organizations.
• Proven success managing complex sales cycles involving multiple stakeholders, executive decision-makers, procurement processes, and cross-functional internal teams.
• Demonstrated success hunting new-logo business and self-generating pipeline through cold outreach, strategic prospecting, networking, referrals, and relationship development.
• Strong consultative and value-based selling skills with the ability to connect business challenges to measurable solution outcomes.
• Healthcare market knowledge including familiarity with revenue cycle, patient payments, and the needs of dental, orthopedic, fertility, ophthalmology, or other high patient out-of-pocket specialties.
• Strong presentation and communication skills with the ability to simplify complex technology and financial concepts for executive audiences.
• CRM proficiency required with a consistent record of maintaining accurate pipeline, activity, and forecast data.
• Proven ability to work independently while collaborating effectively across sales, marketing, product, operations, and implementation teams.

Preferred qualifications:

• Bachelor’s degree or equivalent combination of education and relevant experience.
• Salesforce experience or proficiency with a comparable CRM platform.
• Experience with enterprise healthcare organizations including DSOs, multi-site physician groups, management service organizations, or specialty healthcare networks.
• Experience selling cloud-based or SaaS solutions and explaining the business value of modern technology architecture.
• Background in payments, fintech, healthcare technology, or revenue cycle management within a regulated or consultative sales environment.

Compensation & Benefits: 

• $200,000 - $400,000 annual total compensation (commensurate with experience)
• Competitive Medical Health Plans, Low, Mid, High.
  • Employer Paid Low Medical Plan for Employee & Dependents (HSA Eligible)
  • Employer Paid Dental & Vision for Employee 
  • Employer Paid Life Insurance for Employee 
  • Employer Paid Long-term Disability for Employee 
  • Employer Paid Hospital Confinement for Employee ~ (If enrolled in Medical) 
  • + Voluntary Supplemental Insurance Coverage Options
• 15 days PTO & 7 Sick Days Annually  
• 10 Fixed Paid Holidays Off Annually
• 401(k) Matching up to 3% 

About Us: 

Rectangle Health, a leading financial technology company, empowers medical, dental and specialty practices with seamless and secure technology to drive revenue by increasing patient payments and streamlining practice management and payment processing. Since 1992, the company’s innovative solutions have reduced administrative burden and rebalanced the ledger for its thousands of healthcare providers in the U.S., reliably processing billions of dollars in payments annually.