VP, Strategic Sales

Sorry, this job was removed at 06:12 p.m. (CST) on Friday, Feb 27, 2026
Hiring Remotely in US
Remote
200K-250K Annually
Healthtech
The Role

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.  This role will prospect within the Central region: Minnesota, Iowa, Missouri, Arkansas, Louisiana, Mississippi, Alabama, Tennessee, Illinois, Indiana, Michigan, Wisconsin.

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 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. 

Transcarent Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Transcarent and has not been reviewed or approved by Transcarent.

  • Healthcare Strength The company publicly lists comprehensive medical, dental, and vision coverage, and health insurance quality is described as strong with competitive breadth. Mental health and wellness offerings accompany the core plans.
  • Leave & Time Off Breadth Flexible or unlimited PTO for many exempt roles, front‑loaded sick time, paid parental leave, caregiver support, and volunteer time off are emphasized. A defined set of paid holidays complements these policies.
  • Equity Value & Accessibility Equity participation for all employees is explicitly stated and is a meaningful element of total compensation in several functions. Ownership is positioned as a standard component of offers.

Transcarent Insights

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The Company
HQ: San Francisco, CA
225 Employees
Year Founded: 2020

What We Do

Transcarent is a health and care experience company that makes it easy to get the high-quality, affordable health and care that everyone and their families deserve – where and when they want it, on their terms. Transcarent puts health consumers back in charge by directly connecting them with an integrated ecosystem of high-value providers and health solutions, providing transparent information, and offering trusted guidance – in as little as 60 seconds, 24/7/365, from the palm of their hand, often at no cost to Members and at a lower cost to their employer. Transcarent takes accountability for results – offering at-risk pricing models and transparent impact reporting to align incentives towards measurably better experience, better health, and lower costs.

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