Account Executive – Sales & Customer Success (B2B)

We're looking for a motivated, outgoing, and tech-savvy Account Executive to help grow our SaaS business. This is a sales-focused role for someone who enjoys making calls, building relationships, finding new opportunities, and turning prospects into customers.

You'll take an active role in expanding into new markets, developing relationships with property management companies, and growing our customer base. During our busy summer season, you'll also help maintain strong relationships with existing customers and ensure they're having a great experience.

We're looking for someone who is independent, proactive, and comfortable taking ownership of their work, with the opportunity to make a direct impact on our company's growth.

This is a full-time, in-office position in Columbia, Maryland. Remote work is not available.

Compensation & Benefits

• Base Salary: $65,000–$75,000 annually
• Bonus: Eligible for up to a 10% annual performance bonus
• Health insurance
• Dental insurance
• Paid time off
• Paid holidays
• Full-time, year-round employment
• Professional growth and advancement opportunities
• Direct involvement in growing a SaaS startup

What You'll Do

Sales & Business Development (Primary Focus)

• Make a high volume of outbound sales calls and send prospecting emails to generate new business.
• Research and identify new property management companies, HOAs, and residential communities.
• Find decision-makers, initiate conversations, and build relationships with prospective customers.
• Develop new geographic markets and identify opportunities for expansion.
• Schedule and conduct product demonstrations via Zoom and in person.
• Prepare proposals, follow up with prospects, and help close new business.
• Build and maintain an organized sales pipeline using our CRM.
• Develop relationships with management companies to generate opportunities across multiple properties.
• Attend industry conferences, trade shows, and networking events to develop new business.

Customer Relationships & Seasonal

Support

• Build and maintain strong relationships with existing customers.
• Proactively reach out to customers during the summer season to ensure satisfaction.
• Assist with customer onboarding and help customers get the most out of our platform.
• Respond to customer questions and coordinate solutions when issues arise.
• Conduct occasional on-site visits to communities and perform service quality checks.
• Identify opportunities for renewals, referrals, and additional business.

What We're Looking For

• Excellent verbal and written communication skills.
• Confident and comfortable making cold calls and conducting outbound sales outreach daily.
• Self-motivated, persistent, and able to work independently.
• Strong interpersonal and relationship-building skills.
• Organized, detail-oriented, and consistent with follow-ups.
• Comfortable using CRM systems, email, Zoom, and other business software.
• Tech-savvy and able to learn new software quickly.
• Comfortable speaking with business owners, property managers, and decision-makers.
• Willingness to travel, including occasional overnight trips for conferences, trade shows, and customer meetings.
• Previous B2B sales, business development, or account management experience preferred.
• Experience with SaaS, technology, property management, or related industries is a plus.

About Us

PoolEntry is a growing SaaS startup providing digital pool passes, resident management, and access control solutions for residential communities, homeowners associations (HOAs), and property management companies.

We're a small, entrepreneurial company focused on simplifying how residential communities manage their pools and amenities.

This is an opportunity to join a growing business, work directly with company leadership, and play an important role in expanding our customer base.

Why Join Us?

• Work directly with founders and decision-makers.
• Take ownership of your sales activities and help develop new markets.
• Be part of a small team where your contributions make a direct impact.
• Gain experience in B2B software sales and customer relationship management.
• Opportunity to grow professionally as the company expands.

Important

Video Introduction Required

Because this is a communication-focused sales position, we'd like to get to know you beyond your resume.

Please submit a short 1–2 minute introduction video covering:

• Tell us briefly about yourself and your professional background.
• Why are you interested in a sales position that involves daily cold calling and developing new business?
• Imagine you're calling a property management company for the first time. How would you introduce yourself and start the conversation?

You can record your video using your phone or computer. No editing or professional production is necessary.

Upload your video to YouTube as Unlisted and include the link in the Cover Letter section of your application.

The video is required to move forward in our hiring process. Applications without a video will not be considered for an interview.

Pay: $65,000.00 - $75,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Flexible schedule
• Health insurance
• Paid time off
• Vision insurance

Application Question(s):

• Did you include a link to your unlisted video in your application or cover letter? Please note that applications without the video will not be considered.
• Are you willing to make outbound cold calls to prospective businesses every workday?
• How many years of outbound sales or cold-calling experience do you have?
• Have you previously generated new business through cold calling or prospecting?
• Can you work full-time, in person, in Hanover, MD?

Work Location

In person