Roundtrip Associate Account Executive (Remote) Remote, MD · Remote, PA · Remote, VA · Remote, FL · Remote, CO · Remote, CA · Remote · Full time Company website

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Founded in 2016, Roundtrip is committed to removing transportation barriers and revolutionizing healthcare access. With a passion for patient care, we harness cutting-edge technology to provide unrivaled scheduling and coordination of non-emergency medical transportation. Our clients include some of the most prestigious healthcare providers and forward-thinking Medicare Advantage health plans, all benefiting from our innovative SaaS platform and Navigation Center services. By leveraging our solution, our clients have successfully reduced patient no-shows, expedited the patient discharge process, improved patient and staff satisfaction, and decreased healthcare expenditures on patient rides.

Position Summary:

The Associate Account Executive position is an entry-level position ideal for individuals who are comfortable with outbound engagement, skilled in active listening and critical thinking and motivated to build strong client relationships.

In this role, you will actively learn alongside our Chief Revenue Officer, gaining hands-on experience and a deep understanding of our product, sales process, and customer needs. You will learn to develop pipelines, engage prospective clients, and support the sales process while building the foundation to become an Enterprise Account Executive.

As we expand our enterprise footprint through new logo acquisition, this role will focus on both pipeline creation and developing the skills to close business. This is not a traditional sales development role as you’ll be actively shadowing our CRO in live enterprise deals from day one. With a structured, progressive training path and guidance from experienced team members, you’ll build the skills needed to independently own and close smaller deals within 12–18 months.

Role Structure & Compensation:

This role is part of our Growth team, reports directly to the Chief Revenue Officer, and is fully remote except for required travel. Travel is seasonal and driven by client needs, conferences, and company-wide meetings, with up to 40% travel expected during peak periods.

While the role is open to candidates nationwide, the team primarily operates on Eastern Time (ET), with core collaboration hours from 11 AM to 4 PM ET; schedules outside of those hours are flexible based on role and customer needs.

The salary range for this role is $60,000 - $70,000, based on experience and level of work independence. After a defined period of hands-on learning, this role offers a pathway to commission eligibility through an incentive-based structure, contingent on successful independent selling.

What You’ll Do: 

During your first six months:

• Actively learn alongside our CRO, gaining hands-on experience and a deep understanding of our product, sales process, and customer needs
• Learn Roundtrip's value proposition, customer stories, and patient transportation ecosystem
• Be taught how to independently prepare for enterprise discovery calls
• Support the CRO in deal prep, discovery calls, follow-up, proposal support, and CRM hygiene
• Become skilled in pipeline development & meeting generation

During your first year:

• Lead portions of enterprise sales conversations
• Manage smaller deals independently
• Develop your own pipeline of deals
• Operate confidently in complex healthcare discussions
• Possess Enterprise AE-ready skills  

What We’re Looking For:

• An eagerness to learn and grow in a fast-paced, professional environment
• Comfort operating with ambiguity and in a client-facing role (sales experience not required)
• A Growth-oriented individual, with curiosity about our product, industry, and customers’ businesses (Basic knowledge of healthcare or EMS space is a plus)
• Comfort using Excel, Outlook, Word, Notion, Teams, Slack, or similar tools
• Someone who is exceptionally organized and detail-oriented
• An attentive listener who asks thoughtful follow-up questions & a critical thinker who can synthesize complex conversations
• Familiarity with CRM tools such as Salesforce or HubSpot is a plus but not required

What We Offer:

• Comprehensive Medical, Dental, and Vision Coverage: Roundtrip offers competitive benefits designed to meet a variety of needs. We cover 100% of the employees’ premium for our base medical plan, with buy-up options and family coverage available at an additional cost.
• 401(k) with Matching and Immediate Vesting: Roundtrip matches employee contributions up to 3% and all employer contributions are 100% vested from day one.
• Company Stock Options Plan: Option grants to allow each employee to share our success with the opportunity to own a piece of the company.
• Fully Remote Team – Work from anywhere in the U.S. (role dependent). As a remote-first company, we stay connected daily through Slack and Teams, with in-person gatherings to bring the team together.
• Flexible, Unlimited Time Off: We trust our team to take the time they need, for rest, vacation, or personal matters. Minimum of 10 days off per year required, 11 paid company holidays observed annually and Paid Parental Leave.
• Flexible Fridays: We reserve Friday afternoons (after 12pm ET) for focused work and flexibility by limiting internal meetings, helping you close out the week at your own pace.
• Lifestyle Benefits: Use your company issued credits in our online marketplace to choose from hundreds of well-being and lifestyle services, including Uber Eats, DoorDash, Airbnb, coffee subscriptions, and more.
• Fixed Monthly Remote Work Stipend: To offset any costs you may incur as a remote employee, such as internet, cell phone, or supplies etc. (company laptop provided).

Employment Eligibility & Equal Opportunity Statement:

At Roundtrip we are not only focused on our mission but also hold ourselves to high standards when it comes to our team. Being part of the Roundtrip team isn't just about showing up and doing your job, it's about living our values every day: Lead with Empathy, Own the Outcome, Innovate Responsibility, Embrace Evolution and Partner for Impact.

Diversity & Inclusion is more than initiative at Roundtrip. Our team is committed to creating a diverse environment and is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or other protected class. If, due to a disability, you need accommodation during the interview or application process, please email [email protected].

Due to the nature of our business all applicants must be located in the United States and authorized to work for any employer. Roundtrip is unable to sponsor or take over sponsorship of an employment visa.

What happens next:

Our team will carefully review all applications. Due to the high volume of interest, we’re unable to contact every applicant individually. If your experience aligns with what we’re looking for, a member of our team will reach out to move you into the interview process.

Interview Process: Our process is designed to be transparent, practical, and reflective of the role. All interviews will take place over Teams.

Initial Screen (30 minutes) Meet with People Operations to review your experience and assess alignment with the role requirements.

CRO Interview & Role Fit Exercise (60 minutes) A working session with our CRO to understand your thinking, learning approach, and how you would approach real sales scenarios. (additional context will be provided in advance)

Team Panel Interview (45 minutes) Meet members of our Growth Team.

Final Interview: Mock Discovery Call (45–60 minutes) A live role-play with the CRO to assess your discovery approach, communication, and coachability. (prompt provided in advance)