Associate Account Executive; Remote

Associate Account Executive

We're looking for an Associate Account Executive eager to start a career in Healthcare SaaS sales and grow quickly in a high-impact environment.

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.

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.

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.

• 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

• 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

• 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 Hub Spot is a plus but not required

• Comprehensive Medical,…