Portfolio Company Jobs


Small Business Account Executive



Sales & Business Development
Boston, MA, USA · Remote
Posted on Thursday, June 29, 2023


Anyone needing longer-term care can have a high quality of life in their own setting through access to an excellent & valued health care team.


Provide the best platform for the discovery, on boarding, equipping, management, retention, and assurance of health care professionals and family caregivers to effectively help those who need them.

Job Summary:

The Small Business Account Executive role is an exciting opportunity to drive CareAcademy’s vision and mission through senior care businesses. These senior care businesses are just getting started and are looking for solutions like CareAcademy to help their staff provide excellent care. Your efforts will help senior care businesses attract and retain caregivers by providing them with best-in-class training and an online platform. Best of all, CareAcademy’s online professional development for caregivers is transferable for college credit. Through high-quality education and advancement opportunities for caregivers, CareAcademy-trained caregivers are ultimately helping senior care businesses provide the best possible client outcomes.

The Small Business Account Executive is a hunting role primarily responsible for growing CareAcademy’s market position by prospecting, locating, developing, defining, negotiating, and closing business relationships through proactive outreach channels including phone calls, e-mail communication, video-calls and web-meeting interaction.

This is a growth position and will focus exclusively on new business generation through daily prospecting, lead qualification, discovery, demonstration, and closing. This specific role will focus on generating business within one of our customer segments: Small Business. This team member will work to acquire net new logos and MRR from senior care businesses which have 25 or fewer employees in an assigned geographic territory.

The employee is expected to adhere to ethics policies and practices as established by CareAcademy.

Essential Functions:

  • Consistently close new business to meet or exceed monthly recurring revenue targets and net new logo targets in a high-volume, transactional environment.
  • Responsible for heavy outbound prospecting on a daily basis to generate new opportunities.
  • Qualifies opportunities and performs discovery within an assigned customer segment and qualifies opportunities for other teams within the sales organization that work with other customer segments.
  • Performs discovery activities such as understanding the needs, goals, and business problems of the senior care businesses you work with.
  • Demonstrates value to the prospect by aligning the prospect’s business goals and needs to CareAcademy’s product packaging, and overcoming objections.
  • Performs product demonstrations and is responsible for product knowledge to answer prospect questions during the sales process.
  • Negotiates contracts to close on the forecasted timeline with 90% accuracy.
  • Closes new business deals by aligning CareAcademy’s value proposition to the customer’s needs and goals.
  • Enhances organization reputation by exploring opportunities to add value and provide this feedback to other teams as appropriate.
  • Enters all activity and sales data into Salesforce, CRM.
  • Manages pipeline in Salesforce to consistently update opportunities with the appropriate prospect information.
  • Provides a weekly pipeline update to Manager of Sales.
  • Provides weekly sales metrics on at least the following areas: new prospecting activity, call to connect ratio, connect to opportunity ratio, and opportunity to close ratios.
  • Consistently implements weekly call coaching received from Manager of Sales and peer coaching.
  • Actively engaged in all sales training and coaching opportunities and activities.
  • Other duties as assigned.


  1. 1 - 3 years of experience in technology, software as a service, or healthcare sales environment, preferably as a sales development representative or other roles with a combination of heavy outbound prospecting experience and exceptional results including the closing of small business deals
  2. High school diploma or GED required; Bachelor’s Degree preferred
  3. Excellent verbal and written communication skills
  4. Ability to balance the needs of meetings and prospecting new business
  5. Proven ability to quickly establish rapport
  6. Proficient in Microsoft Office, G-Suite
  7. Comfortable with an array of software products and sales software (Salesforce, Slack, Asana, Tettra)
  8. Thrives in a fast-moving, entrepreneurial environment

Compensation and Benefits:

  1. Competitive salary + commissions, opportunities for advancement with consideration after one year
  2. Equity: TBD
  3. Work from home stipend
  4. A remote-first work environment.
  5. Unlimited PTO
  6. Generous Medical coverage with minimal employee contribution (60% of medical premium paid by Company)
  7. 401K enrollment after six months of employment and up to 4% company matching.
  8. AMAZING team members!