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VP, Strategic Sales

Transcarent

Remote · USJobPosted 4 days agoStill listed today

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At a glance

Compensation
No compensation found
Location
Remote · US
Work Authorization
Not specified

Olive lists jobs from US employers, including remote roles you can work from the United States.

Requirements

Credentials this posting asks for.

Bachelor's degree, required

Job overview

The Vice President of Strategic Sales is an individual contributor responsible for generating revenue and developing new business by selling directly to large self-funded employers. The role executes strategic sales plans, manages complex sales cycles, builds relationships with senior executives and health plan leaders, and develops partnerships with brokers, consultants, and third-party administrators. It also presents solutions, negotiates with prospects, and supports smooth post-sale client transitions.

Skills & qualifications

RequiredNice to have

Skills

Sales Planning, nice to haveConsultative Selling, nice to haveRelationship Management, nice to havePublic Speaking, nice to haveNegotiation, nice to haveNew Business Development, nice to haveHealth Technology, nice to haveMarket Analysis, nice to haveSales Strategy, nice to haveComplex Sales, nice to havePresentation Skills, nice to haveRevenue Forecasting, nice to haveMicrosoft Office, nice to haveSalesforce, nice to haveEntrepreneurial Mindset, nice to haveAdaptability, nice to haveTeamwork, nice to havePlanning and Execution, nice to haveWritten Communication, nice to haveVerbal Communication, nice to haveInterpersonal Communication, nice to have

Qualifications

Bachelor's Degree, nice to have10+ Years Sales Experience, nice to haveFortune 500 Pipeline Development, nice to haveHigh-Growth Environment Experience, nice to haveHealthcare Industry Knowledge, nice to haveEmployer and Broker Relationships, nice to haveTravel Up to 50%, nice to have

Benefits

Medical Insurance
Dental Insurance
Vision Insurance
401(k) Match
Paid Time Off

Full job description

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

Who we are

Transcarent is the One Place for Health and Careᵀᴹ, bringing medical, pharmacy, and point solutions together with the WayFindingᵀᴹ experience, the first and only generative AI-powered health and care platform for health consumers.

Our WayFinding experience, paired with transparent and consumer-driven pharmacy care, 2nd.MD expert medical opinions, and virtual primary care, works seamlessly with comprehensive Care Experiences – Cancer Care, Surgery Care, and Weight Health – to support people with all of their health needs, simple or serious. More than 1,700 employers and health plans rely on us to provide information, guidance, and care, empowering health consumers with more choice, an experience they love, access to higher-quality care, and lower costs for 21 million Members. For more information, visit transcarent.com, and follow us on LinkedIn.

At Transcarent, our values guide everything we do:

  • People First: We prioritize our Members, clients, and each other in every decision

  • Care: Every decision starts with improving health and care for our Members

  • Resilience: We push boundaries and take the uncharted path to change an industry

  • Results: We take ownership, solve with speed, and deliver for our people and each other

  • Humble and Human: We lead with humility, bring fun to tough moments, and go further together

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, 13 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.

How this job compares

Set against the 2,291 open Sales Executive jobs on Olive Jobs, counted November 10, 2026.

Pay
  • This postingNot listed
  • Pennsylvania median$143–218K/yr51 salary ranges
  • US median$33–39/hr36 hourly ranges
Openings
Olive Jobs lists 62 open Sales Executive jobs in Pennsylvania and 2,291 across the US. 10% of them nationwide are listed as remote or flexible.
Hiring the most in Pennsylvania
Experience
This posting asks for at least 10 years of experience; Sales Executive postings that state a minimum ask for 5 years at the median (1,712 postings).
Education
This posting asks for a bachelor's degree; 297 of the 2,291 open Sales Executive jobs (13%) ask for a bachelor's degree or higher.

Counted across the open, public US postings on Olive Jobs on November 10, 2026. Pay medians are the middle values of the low ends and of the high ends of postings that list both ends of a range in the same cadence (a yearly salary or an hourly rate); a range's midpoint is halfway between its ends. Pay and experience figures resting on fewer than 20 postings are left out.

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