Regional Director of Sales, Employer

verawholehealth· Castlight Health, Inc
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🌍 Remote📍 Pennsylvania, USAFull time💰 USD 131K–197K
Full timeRemote - Full TimeCastlight Health, Inc

About this role

Job Description Summary

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We are seeking a results-driven Regional Director of Sales with deep experience in healthcare technology and SaaS sales, particularly in selling into large employers (1,000+ employees). The ideal candidate has a proven track record of success in healthcare navigation and advocacy solutions and is skilled at managing complex sales cycles involving multiple stakeholders.

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How will you make an impact & Requirements

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**This is a remote position; however candidates located in Eastern or Central time zones are preferred.**

Regional Director of Sales


Seeking an experienced sales person with a record of successfully meeting and exceeding quota. A hunter mentality that can build top of funnel while driving opportunities to close.

Key Responsibilities:

  • Drive new business sales across a multi-state region, focused on large employers with over 1,000 employees.

  • Manage a robust pipeline and lead opportunities through a consultative and strategic sales process.

  • Consistently exceed quota through high-impact prospecting, solution selling, and strategic territory planning.

  • Develop and execute a territory strategy that leverages relationships with key stakeholders including benefit leaders, consultants, and strategic alliance partners.

  • Collaborate closely with internal cross-functional teams including Marketing, Product, and Customer Success to align on client needs and product capabilities.

  • Maintain expert-level knowledge of company solutions, including healthcare navigation and advocacy platforms.

  • Build and nurture strategic relationships with benefits consultants, point solution partners, buying consortia, and other key influencers.

  • Provide accurate forecasting and regular pipeline reporting to senior leadership.

  • Represent the company at industry events, trade shows, and webinars as a thought leader and subject matter expert.


Preferred:

  • 8+ years of successful sales experience in healthcare technology or SaaS, with a focus on selling to large employers.

  • Demonstrated success in selling healthcare navigation, advocacy, or related benefits solutions.

  • Strong relationships and experience working with benefit consultants and other ecosystem partners.

  • Track record of consistently meeting or exceeding sales quotas.

  • Highly skilled in territory management, consultative selling, and strategic account planning.

  • Exceptional communication, negotiation, and presentation skills.

  • Comfortable navigating complex sales environments with multiple decision-makers.


Requirements:

  • Bachelor’s degree required; MBA or relevant advanced degree a plus.

  • Experience with enterprise sales cycles of 6-12+ months.

  • Knowledge of healthcare benefits trends and employer-sponsored benefits strategies.

  • Experience working with or selling alongside ecosystem partners such as TPAs, carriers, and digital health vendors.

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Compensation Range:

$131,243.00

to

$196,865.00

 

The anticipated base salary range represents the Company's good-faith estimate of the compensation it reasonably expects to pay for this position at the time of posting. Actual compensation will be determined based on factors including experience, skills, qualifications, geographic location, internal equity, and business needs.

Frequently Asked Questions

What is the salary for the Regional Director of Sales, Employer role at verawholehealth?
The listed salary for this Regional Director of Sales, Employer position at verawholehealth is USD 131K–197K. This is a remote Full time role.
Is the Regional Director of Sales, Employer job at verawholehealth remote?
Yes, this Regional Director of Sales, Employer position at verawholehealth is remote, with team members based in Pennsylvania, USA. You can work from home or anywhere in the supported regions.
Is the Regional Director of Sales, Employer role at verawholehealth full-time or part-time?
This is listed as a Full time position. It is posted as a Regional Director of Sales, Employer role in the Castlight Health, Inc department at verawholehealth.
Which team or department does the Regional Director of Sales, Employer at verawholehealth belong to?
This Regional Director of Sales, Employer position is part of the Castlight Health, Inc department at verawholehealth. See the full job description for more information about the team structure and responsibilities.
How do I apply for the Regional Director of Sales, Employer position at verawholehealth?
Click the "Apply Now" button on this page. You will be redirected to verawholehealth's official application portal hosted on workday where you can submit your application directly.
When was the Regional Director of Sales, Employer job at verawholehealth posted?
This Regional Director of Sales, Employer position at verawholehealth was posted on Jul 28, 2026. Apply as soon as possible — early applications are often reviewed first.
Regional Director of Sales, Employer
verawholehealth · 💰 USD 131K–197K
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You'll be redirected to verawholehealth's official application page on Workday.