Regional General Manager Jobs

We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time.

Oak Street Health is a rapidly growing, innovative company of community-based healthcare centers delivering higher quality health and wellness care that improves outcomes, manages medical costs and provides an unmatched experience for adults on Medicare in medically underserved communities. By providing holistic, comprehensive and integrated care right in our patients’ communities, we can help keep them healthy and reinvest cost savings in further care for those same communities and others. Since 2013, Oak Street Health has brought its singular approach to tens of thousands of people across the nation. With an ambitious growth trajectory, Oak Street Health is attracting and cultivating team members who embody Oak Street values and are passionate about our mission to rebuild healthcare as it should be.

For more information, visit www.oakstreethealth.com.

Core Responsibilities:

• Achieve monthly Managed Care Growth targets by identifying and developing assigned region with qualified and engaged agents, while supporting the success of their activity.

  • Train engaged and developing agents on the OSH value proposition; Agents should be proficient at differentiating value-based care versus traditional primary care models.

  • Engage in educational interventions with agents to support collaborative agent relationships that can engage with grassroots and center related activities with OSH staff.

  • Identify appropriate agents who are aligned with our mission, knowledgeable and culturally competent with our patient demographics and neighborhoods to engage in local grassroots and marketing lead generation opportunities in cooperation with the carrier partners and OSH.

  • Quickly identify the Medicare Advantage sales leaders for each carrier in the counties OSH centers serve, including those agents most actively selling during the Special Enrollment Period/Lock-In season.

• Collaborate with regional internal growth partners in accomplishing growth targets by networking and coordinating events with Insurance Agents (IAs), General Agencies, Field Marketing Organization and local carrier leadership.

• Communicate, network, and negotiate with local insurance plan leaders on collaborative activities that mutually benefit the growth of both OSH, the carrier and the agent. Also, a key tactic is building local sales management relationships to where they agree to develop and support lead generation in our 5 mile radii of the centers.

• Establish and nurture relationships with key health insurance brokers, health plans and community influencers who have relationships with individuals on Medicare.

• Be a leader of our regional outreach teams in other capacities as needed, for example, training, CRM optimization, and special projects.

• Train Patient Relations Managers (PRMs) and Outreach Team members on how to compliantly engage, plan and collaborate with culturally competent, knowledgeable IA’s to foster mutual growth in the catchment areas of OSH centers.

• Other duties as assigned

What are we looking for?

• 5+ years of sales and account management experience required

• Previous broker management experience preferred, but not required

• Bachelor degree required

• Ability to travel >50% at various times of the year; ability to also engage in regular evening events and activities

• Knowledge of and related experience with Medicare & Medicaid preferred

• Major account management experience preferred

• A problem-solving orientation and a flexible and positive attitude

• Unique ability to neutralize, adapt and overcome external relationship issues for positive outcomes

• Outstanding networking and relationship management skills

• Strong communication and public speaking skills

• Proven history of developing partners and/or relationships leading to business growth

• Experienced in operating independently, managing regional travel and multiple priorities

• Incredible level of organization and reliability in a matrix environment

• Microsoft Office (Excel) and CRM (Salesforce) familiarity

• Experience working on a multidisciplinary team preferred

• Local managed care knowledge and relationships preferred, but not required

• Bilingual Spanish preferred, but not required

• MBA preferred, but not required

• US work authorization

• Someone who embodies being “Oaky”.

What does being “Oaky” look like?

• Radiating positive energy

• Assuming good intentions

• Creating an unmatched patient experience

• Driving clinical excellence

• Taking ownership and delivering results

• Being scrappy

Why Oak Street?

Oak Street Health offers our coworkers the opportunity to be at the forefront of a revolution in healthcare, as well as:

• Collaborative and energetic culture

• Fast-paced and innovative environment

• Competitive benefits including paid vacation and sick time, generous 401K match with immediate vesting, and health benefits

Oak Street Health is an equal opportunity employer. We embrace diversity and encourage all interested readers to apply to oakstreethealth.com/careers.

Anticipated Weekly Hours

40

Time Type

Full time

Pay Range

The typical pay range for this role is:

$60,300.00 - $132,600.00

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

Additional details about available benefits are provided during the application process and on Benefits Moments.

We anticipate the application window for this opening will close on: 08/30/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.