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VP, Strategic Sales

Transcarent

US - Remote (Remote) Remote permanent

Posted: December 3, 2025

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Job Description

About this role

Great sales are the result of strong purpose, conviction and pride – pride in your ability and pride in your product. Bring along your passion and do your best work while selling solutions that truly improve the lives of others.

The Vice President of Strategic Sales is an individual contributor primarily responsible for generating revenue and developing new business through a consultative selling process. VPs of Strategic Sales execute strategic plans for selling direct to large self–funded employers in this quota-carrying role.

What you’ll do

• Develop and implement comprehensive sales strategies to achieve national sales targets and deliver significant bookings to the company.

• Manage complex sales cycles and processes, ensuring successful deal closures.

• Cultivate and maintain relationships with senior executives (C-suite) and health plan leaders overseeing the largest organizations (generally with more than 25K employees).

• Establish and sustain strong partnerships with brokers, consultants, and third-party administrators (TPAs).

• Deliver compelling presentations both in-person and virtually to employers, brokers, consultants, and at industry events to promote Transcarent solutions.

• Conduct follow-ups on prospect meetings and expertly negotiate with prospects and their associated brokers, consultants, and TPAs.

• Ensure smooth client transitions to Implementation and Account Services post-sale.

What we’re looking for

• An entrepreneurial spirit. You’re comfortable building the plane while it’s in the air. You’re engaged in finding solutions and not passing problems or hiccups off to others. You’re creative with available resources.

• Open-minded. You don’t get flustered with the change that comes with being a part of a fast-growing organization. You enjoy learning and are curious about the latest trends in business and healthcare.

• A Team Player. While you can’t lose sight of your own goals, you are ready to roll-up your sleeves and add to a conversation, support a teammate, contribute to thought leadership, or contribute to a project or initiative with enthusiasm.

• A person with Integrity. You have fantastic planning and execution skills, tons of energy and great follow through when your company and our partners need you. You don't get overwhelmed and enjoy working with people trying to solve complex healthcare issues. You do the right thing, always.

• A Bachelor’s degree

• A minimum of 10+ years of experience successfully selling benefits, wellness, healthcare technology, or insurance solutions on a national level.

• A proven track record of developing a large organic pipeline with fortune 500 companies.

• Prior experience working in a fast-paced, high growth environment and comfortable with the nuances of such

• Industry knowledge along with well-established relationships with employers, consultants, brokers, and TPA’s within territory

• Excellent presentation skills with experience presenting to executives and direct-level benefits professional and consultants Exceptional written, verbal, and interpersonal communications skills along with a captivating presentation style

• Demonstrated ability to successfully negotiate complex contract negotiations

• Demonstrated ability to accurately forecast monthly, quarterly, and annual revenue

• Strong aptitude with business software tools (Word, Excel, PowerPoint, Outlook etc) and CRM (Salesforce)

• An ability to travel up to 50% of the time with overnight travel included

As a remote position, the salary range for this role is:
$200,000—$250,000 USD

Who we are

Transcarent and Accolade have come together to create the One Place for Health and Care, the leading personalized health and care experience that delivers unmatched choice, quality, and outcomes. Transcarent’s AI-powered WayFinding, comprehensive Care Experiences – Cancer Care, Surgery Care, Weight – and Pharmacy Benefits offerings combined with Accolade’s health advocacy, expert medical opinion, and primary care, allows us to meet people wherever they are on their health and care journey. Together, more than 20 million people have access to the combined company’s offerings. Employers, health plans, and leading point solutions rely on us to provide trusted information, increase access, and deliver care.

We are looking for teammates to join us in building our company, culture, and Member experience who:

• Put people first, and make decisions with the Member’s best interests in mind

• Are active learners, constantly looking to improve and grow

• Are driven by our mission to measurably improve health and care each day

• Bring the energy needed to transform health and care, and move and adapt rapidly

• Are laser focused on delivering results for Members, and proactively problem solving to get there

Total Rewards

Individual compensation packages are based on a few different factors unique to each candidate, including primary work location and an evaluation of a candidate’s skills, experience, market demands, and internal equity.

Salary is just one component of Transcarent's total package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock options.

Our benefits and perks programs include, but are not limited to:

• Competitive medical, dental, and vision coverage

• Competitive 401(k) Plan with a generous company match

• Flexible Time Off/Paid Time Off, 12 paid holidays

• Protection Plans including Life Insurance, Disability Insurance, and Supplemental Insurance

• Mental Health and Wellness benefits

Transcarent is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. If you are a person with a disability and require assistance during the application process, please don’t hesitate to reach out!

Research shows that candidates from underrepresented backgrounds often don’t apply unless they meet 100% of the job criteria. While we have worked to consolidate the minimum qualifications for each role, we aren’t looking for someone who checks each box on a page; we’re looking for active learners and people who care about disrupting the current health and care with their unique experiences.

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