Pineapple Academy is a fast-growing SaaS training platform built for the frontline workforce in healthcare and senior living. We deliver bite-sized video training (under 5 minutes) that helps organizations onboard faster, operate better, and reduce turnover.

Backed by HealthStream, Right Side Capital Management, and KCRise Fund, we’re scaling quickly and building something that actually matters.

Description of Duties

This is the first Account Executive on our team, which will be a high-impact role for a proven seller who wants ownership and autonomy. As an early member of the sales team, your insights will help shape our sales playbook and define our go-to-market strategy.

• Full-Cycle Ownership: Manage the end-to-end sales process from initial prospecting and demos to closing.
• Pipeline Generation: Build a robust pipeline by leveraging your network and hunting new opportunities through strategic outreach.
• Revenue Performance: Consistently hit revenue and pipeline quotas to drive company OKRs.
• Strategic Collaboration: Partner with the VP of Sales and Marketing to refine messaging and optimize the sales funnel.
• Growth Feedback: Provide direct market feedback to help us build and scale our sales playbook.

Reporting Relationship

This role reports to the Vice President of Sales.

Responsibilities

• Close net-new ARR in healthcare & senior living organizations
• Own deals end-to-end: discovery → demo → close
• Prospect into new and existing accounts
• Sell both quick wins and multi-site enterprise deals
• Forecast pipeline and collaborate directly with leadership

Minimum Qualifications

• Bachelor’s degree preferred; business, marketing, or communications emphasis preferred
• 5-8 years of experience in sales, preferably in B2B SaaS
• Demonstrable success selling into healthcare or senior living (HR, Ops, Compliance), preferably having closed $15k-$100k+ ARR deals
• Self-driven, competitive, and motivated by upside
• Excellent Communication skills, verbal and written, along with strong public speaking skills
• Write reports, business correspondence, and process’
• Ability to work effectively in a team environment
• This position requires driving a personal vehicle or a rented vehicle on behalf of the company; therefore, all Company team members must successfully complete a motor vehicle history check, possess and maintain a current, valid driver's license in their state of residence

Physical Requirements

• Regularly required to move throughout the day within an office environment, as well as to and within other places of business, including standing for prolonged periods of time during work-related conferences and meetings
• Planned travel of up to 50% a month is possible for this position. Global travel may be required as we develop new markets with regional teams
• Routinely lift and/or move 50+ pounds

Why This Role Is Different

• Being the first Account Executive, you help develop the playbook
• High autonomy, real influence on future hires and comp
• Direct impact on company growth

Compensation & Benefits

• Competitive base compensation + uncapped commission
• Unlimited paid time off policy and 11 paid company holidays
• Fully remote position

Pineapple Academy, Inc. complies with all Equal Employment Opportunity (EEO) laws and regulations. Pineapple Academy does not discriminate on the basis of age, race, religion, color, sex, national origin, marital status, genetic information, sexual orientation, gender Identity and expression, disability, veteran status, pregnancy status or other status protected by law.

Notice to External Search Firms

Pineapple Academy does not accept unsolicited resumes and will not be obligated to pay a placement fee for unsolicited resumes.