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Account Executive - Mid Market; SaaS​/Healthcare IT​/EHR​/RCM

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60601, USA
Listing for: Raintree Systems
Remote/Work from Home position
Listed on 2026-06-05
Job specializations:
  • Sales
    Sales Development Rep/SDR, Sales Representative
Salary/Wage Range or Industry Benchmark: 60000 - 80000 USD Yearly USD 60000.00 80000.00 YEAR
Job Description & How to Apply Below
Position: Account Executive - Mid Market (SaaS/Healthcare IT/EHR/RCM)

Account Executive – Mid Market (SaaS/Healthcare IT/EHR/RCM)

Remote U.S. – The Account Executive – Mid Market is responsible for prospecting, developing, and managing sales into Physical Therapy (Pediatrics) office environments within their defined territory. This is a quota‑carrying position with responsibility to drive annualized revenue across the product lines offered by Raintree, including but not limited to EMR/EHR/PM Software, SaaS offerings, Revenue Cycle Management (RCM), and third‑party partner products.

The role focuses on software and RCM business generation from new customers.

Duties and Responsibilities
  • Independently manage a sales territory to achieve assigned quarterly and annual sales targets while working as part of a team
  • Generate new business from product and services sales to mid‑sized to large Physical Therapy practices
  • Prospect for potential customers using direct methods, such as calls and face‑to‑face meetings, and indirect methods such as networking
  • Identify and qualify new prospects to continually build pipeline
  • Promptly and effectively engage with prospects identified through marketing lead generation efforts
  • Provide useful feedback to marketing group on lead quality
  • Accurately track each prospect through the sales stages within CRM system
  • Manage current quarter business and subsequent quarters' pipeline proactively and consistently
  • Drive the sales cycle from initial customer engagement to closure
  • Provide accurate forecasts around sales pipeline on a monthly basis
  • Implement business and marketing initiatives to drive quota achievement
  • Develop and maintain key account plans that identify opportunities to deliver value, including strategic motivators, main stakeholders, buying processes, and forecasted sales
  • Articulate and evangelize the vision and positioning of the organization and its solutions to differentiate capabilities to clients
  • Develop and maintain a high level of domain and competitive knowledge on industries and products to leverage in the sales cycle
  • Effectively demonstrate products and services
  • Provide feedback to Sales Management related to the market and competitor environment
  • Contract negotiations with prospective clients
  • Travel within assigned territory and/or for industry events up to 50% of the time
Position Proficiencies and Requirements
  • Bachelor's degree or relevant work experience. Doctorate of Physical Therapy (DPT) welcomed.
  • At least five years of documented success in sales within SaaS/Healthcare IT.
  • Experience selling EMR/EHR or other Systems of Record preferred.
  • Knowledge of the healthcare IT industry and/or healthcare practice experience preferred.
  • General computer proficiency, including working knowledge of Google Suite, Microsoft Office Applications (Word, PowerPoint, Excel), Outreach.io and
  • Well‑developed verbal, listening and phone communication skills.
  • Good written communication skills with the ability to write routine correspondence.
  • Ability to add, subtract, multiply, and divide in all units of measure, using whole numbers, common fractions, and decimals.
Competencies to Drive Success
  • Ability to define problems, collect data, establish facts, and identify trends.
  • Ability to exercise good judgment and elevate issues appropriately.
  • Demonstrates relationship building skills both internally and externally.
  • Strong organizational skills and ability to execute manual detailed tasks.
  • Strong customer service focus and commitment.
  • Ability to establish and maintain effective working relationships within the team.
  • Ability to work well with diverse personalities.
  • Tactful, mature and flexible.
Our Perks
  • Remote Work/Work From Home
  • Paid Time Off/11 Paid Holidays/Year‑End Holiday Break
  • Health, Dental, Vision, HSA/FSA
  • 401K with Company Match
  • Disability & Life Insurance
  • Employee Assistance Program
  • Paid Parental Leave
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