Regional Sales Director

Handpicked Health combines the best of Advanced Primary Care (APC) and high-quality specialty care, all within a single, streamlined contract. Our innovative model enables employers to offer a healthcare benefit that integrates intelligent care navigation with exceptional care standards. The result? A superior member experience, better access to the best providers, and quality outcomes for employees and their families.

We seek an experienced Regional Director of Sales to expand Handpicked Health’s customer base of large employers and public purchasers. This individual will lead sales efforts across a defined region, develop and close new business, and serve as a strategic partner to prospects and collaborators in the employer-sponsored healthcare ecosystem. Ideal candidates will bring consultative enterprise sales experience, a strong network, and a deep understanding of healthcare benefit offerings.

Handpicked Health takes pride in close collaboration, honesty, empathy, friendliness, and our commitment to diversity. We operate in an agile fashion, keeping processes to a minimum, enabling team members to focus on their work.

We currently work remotely but will require travel to team and client meetings that may occur as frequently as quarterly. Unfortunately, we are not able to provide H1B sponsorship.

Responsibilities

Business Development & Sales Leadership

• Develop and execute a regional go-to-market strategy that aligns with Handpicked Health’s growth targets.
• Identify, qualify, and close new business opportunities with large employers (typically 3,000+ employees).
• Build and manage a strong sales pipeline using consultative, relationship-driven approaches.
• Work with the CEO to collaborate with benefits consultants, channel partners, and ecosystem collaborators to generate demand and advance opportunities.
• Serve as a credible thought partner to HR, benefits, and procurement leaders on Handpicked Health’s value proposition.

Relationship Management & Collaboration

• Develop deep relationships with key external stakeholders including clients, brokers, and healthcare partners.
• Partner cross-functionally with internal teams (Marketing, Customer Success, Clinical, Product, Operations) to ensure successful transitions from sale to launch.
• Represent Handpicked Health at industry conferences, webinars, and events.

Sales Process & Strategy

• Maintain accurate and timely CRM records, forecasts, and reporting.
• Refine sales collateral and messaging based on market feedback.
• Contribute insights to inform pricing strategy, product positioning, and expansion opportunities.

Qualifications

• 6+ years of experience in enterprise sales, business development, or partnerships—preferably in healthcare or employer benefits.
• Proven track record of exceeding quota with consultative sales approaches and complex, multi-stakeholder deals.
• Experience selling to self-insured employers and/or working with benefit consultants and carriers.
• Strong strategic thinking, negotiation, and communication skills.
• Comfortable in a remote startup environment with the ability to self-direct and operate independently.

Required And Highly Preferred Experience/Skills

• Background in healthcare navigation, value-based care, or employer-sponsored benefits.
• Existing relationships with benefit consultants, brokers, TPAs, or employer health coalitions.
• Familiarity with digital health, SaaS solutions, or health tech platforms.
• Experience managing a multi-state territory and understanding regional market dynamics.

Details

Location

Remote with potential travel for team meetings or client engagements


Job Type

Full-time

Visa Sponsorship

Not Available

Compensation

This role offers a base salary range of $150,000 to $180,000, with uncapped commission opportunities based on sales performance.

Benefits

We offer a comprehensive benefits package to support your health, well-being, and future. This includes:

• Medical Insurance - Multiple plan options
• 401(k) with Company Match - Save for retirement with employer contributions
• Paid Time Off (PTO) & Holidays - Generous vacation and holiday schedule

Background Check

Handpicked Health believes hiring qualified individuals to fill positions contributes to its strategic success. Background checks are an essential part of the selection process at Handpicked Health. This information is collected to promote a safe work environment for current and future Handpicked Health employees.

Background checks also help Handpicked Health obtain additional applicant-related information that helps determine the applicant's overall employability, ensuring the protection of the organization's current people, property, and information.

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Please Send a Resume With Cover Letter To

[email protected]