VP, Strategic Sales
Accolade
Remote (US) · Posted November 6, 2026
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Sales jobs in the rankings
Rankings about sales jobs
- Best cities for sales jobs #1 New York (2,774 openings)
- Best cities for sales pay after cost of living #1 Santa Clara ($175k)
- Most requested AI skills in sales jobs #1 AI tools in daily work (4.1%)
- AI tools named most often in sales jobs #1 Gong (0.93%)
- Employers with the most sales jobs #1 Charter Communications (389 roles)
How AI is used in this kind of work
AI use among sales managers is little observed so far. Measured exposure for sales managers: 4% (little observed).
Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.
Skills this job asks for
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About the job
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
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