The Account Executive at Oak St. Health is a critical, mission-driven sales and community outreach role. Unlike traditional corporate sales positions, this role is deeply rooted in grassroots marketing, community engagement, and patient advocacy. You will act as the face of Oak St. Health in local neighborhoods, building trusted relationships with Medicare-eligible seniors, community leaders, faith-based organizations, and senior housing administrators. Your primary objective is to educate older adults on the benefits of the value-based care model and guide them through the process of becoming patients at your local clinic.

This position directly impacts the health and well-being of underserved senior populations. By driving patient acquisition, you help seniors transition from fragmented, fee-for-service healthcare to a coordinated, preventive care model that keeps them healthy and out of the hospital. You will work closely with local clinic teams, including Practice Managers and medical staff, to ensure a seamless onboarding experience for new patients.

Success in this role requires a unique blend of sales grit, high empathy, and outstanding communication skills. You are not just selling a service; you are building a community network and offering a life-changing healthcare experience to vulnerable individuals. If you are energized by field-based outreach, relationship building, and making a tangible social impact, this role offers a highly rewarding career path.

The interview process at Oak St. Health is designed to evaluate both your sales capabilities and your alignment with the company's patient-first mission. The questions outlined below are compiled from real interview experiences and represent the core patterns you will encounter during your evaluation.

Behavioral & Mission Alignment

These questions assess your empathy, your passion for working with the senior population, and your ability to thrive in a mission-driven environment.

• Why do you want to work with seniors and Medicare-eligible populations?
• Tell me about a time you had to build trust with someone from a completely different demographic or background.

Preparing for an Account Executive interview at Oak St. Health requires a dual focus on your sales metrics and your personal empathy. You must demonstrate that you are a high-performing sales professional who operates with the heart of a social worker.

Mission Alignment & Empathy – You must show a genuine care for the senior community. Interviewers look for candidates who listen actively and treat older adults with dignity. Be prepared to share personal stories or professional experiences that highlight your patience and compassion.

Outreach & Pipeline Management – You need to show that you are self-motivated and capable of managing a field-based sales pipeline. Be ready to discuss how you track leads, follow up systematically, and move prospective patients from initial contact to a scheduled clinic tour.

Communication & Influence – You must be able to simplify complex healthcare terminology into clear, reassuring language. Practice explaining how Medicare and Oak St. Health work in a simple, compelling way that builds immediate trust.

Resilience & Adaptability – Grassroots marketing involves navigating constant change, weather challenges, and rejection. You must demonstrate a positive, resilient attitude and a proven ability to pivot when plans change.

The hiring process for the Account Executive position at Oak St. Health is structured to be swift, practical, and highly interactive. The company values transparency and speed, often moving candidates through the entire pipeline in a matter of weeks or even days.

You will typically begin with a brief phone screen or an on-the-spot virtual interview with a recruiter. This initial conversation focuses on your basic qualifications, your interest in the healthcare space, and your salary expectations. This is followed by a series of virtual or in-person interviews with regional sales leadership and clinic Practice Managers.

A unique and critical component of the Oak St. Health process is the scenario-based process test. This written and verbal assessment presents you with real-world outreach challenges, requiring you to write descriptive, scenario-based answers detailing how you would handle objections, build community partnerships, and manage your daily schedule.

The interview process timeline shown above outlines the typical sequence of stages from your initial application to the final decision. Candidates should use this timeline to pace their preparation, ensuring they focus heavily on scenario-based practice before reaching the assessment stage. While the process is designed to be highly structured and fast, the exact progression can occasionally vary depending on local clinic hiring needs.

To excel in your interviews, you must understand the specific competencies Oak St. Health evaluates at each stage of the process.

Community Outreach & Grassroots Marketing

This area evaluates your ability to generate leads from scratch without relying on warm corporate data. You will be assessed on your creativity, community knowledge, and local networking skills.

Be ready to go over:

• Local partnership development – How to identify, approach, and secure partnerships with local businesses, churches, and food pantries.
• Event planning and execution – How to organize, promote, and host engaging community events that attract senior attendance.
• B2C lead generation – Your strategies for approaching seniors in public spaces respectfully and initiating conversations about their health.
• Advanced concepts (less common) – Leveraging local demographic data to map out untapped neighborhoods and optimizing event return on investment (ROI).

Example questions or scenarios:

• "Walk me through how you would establish a brand presence in a brand-new neighborhood where Oak St. Health is completely unknown."
• "How do you transition a casual conversation at a community health fair into a scheduled clinic tour?"

Scenario-Based Objection Handling

During the process test and subsequent interviews, you will face realistic scenarios designed to test your communication skills under pressure. Seniors are often fiercely loyal to their existing doctors or highly suspicious of sales representatives.

Be ready to go over:

• De-escalation and trust-building – Techniques for calming anxious or defensive prospects.
• Value proposition delivery – Clearly explaining the benefits of value-based primary care over traditional fee-for-service models.
• Navigating family gatekeepers – How to talk to the adult children of seniors who manage their parents' healthcare decisions.

Example questions or scenarios:

• "A senior tells you they love their current doctor but complain that they have to wait three weeks for an appointment. How do you position Oak St. Health as the solution?"
• "How do you handle an adult child who accuses you of trying to scam their elderly parent?"

Behavioral & Cultural Fit

Oak St. Health has a strong, values-driven culture. They look for collaborative team players who are willing to support their clinic colleagues and put the patient's needs above all else.

Be ready to go over:

• Collaboration with clinic teams – Working with Welcome Coordinators and medical staff to ensure a warm handoff.
• Adaptability – Thriving in a fast-paced environment with evolving goals and changing community dynamics.
• Ethical sales practices – Maintaining absolute integrity and compliance with healthcare regulations (such as HIPAA and Medicare marketing guidelines).

Example questions or scenarios:

• "Describe a time you had to work closely with a colleague from a different department to achieve a shared goal."
• "How do you ensure you stay compliant with healthcare regulations while aggressively pursuing your outreach goals?"

As an Account Executive at Oak St. Health, your days will be highly active, self-directed, and split between field outreach and clinic-based activities. You are responsible for driving the growth of your assigned clinic by executing a comprehensive local outreach strategy.

You will spend a significant portion of your time in the community, building relationships with local influencers and hosting educational events. You will set up informational tables at senior housing complexes, present at community centers, and partner with local faith-based organizations to educate seniors on their healthcare options. Your goal is to generate high-quality leads and invite seniors to tour the local Oak St. Health center.

Once a lead is generated, you will manage the relationship through the entire onboarding pipeline. This includes conducting follow-up phone calls, scheduling clinic tours, and introducing prospective patients to the doctors and care teams. You will collaborate daily with the clinic's Practice Manager and Welcome Coordinators to ensure that every prospective patient receives a warm, welcoming, and seamless introduction to the practice.

Additionally, you will maintain accurate records of your outreach activities and lead pipeline in the company CRM. This data-driven approach helps you and your regional leadership track the effectiveness of different outreach channels and optimize your local marketing strategy.