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Regional Sales Manager - Employee Benefits

Crawford Thomas Recruiting
San Francisco, CA Full Time
POSTED ON 3/1/2025
AVAILABLE BEFORE 4/18/2025
Regional Sales Manager (Mid-Market) - West (PST MST)

Job Description

We are seeking a driven, ambitious, and intellectually curious Mid-Market Regional Sales Director to sell innovative benefits solutions, including HSA, FSA, HRA, Lifestyle Spending Accounts, COBRA, and more. This role targets employee benefits brokers managing clients with 100–2,000 employees and focuses on driving growth through partnerships with health insurance brokers, benefits consultants, general agencies, and registered investment advisors.

You will identify, source, and close good-fit prospects using strong consultative selling skills and a mix of inbound leads and self-sourced pipeline development. You’ll execute a territory plan to deliver maximum revenue potential, balancing transactional and solutions-oriented sales approaches.

Responsibilities

Drive new sales for benefits products within your territory. Manage all sales activity in your assigned region daily. Conduct discovery calls, create upfront contracts, handle objections, and close employer business. Meet or exceed sales quotas and activity metrics, including calls, emails, meetings, and demos. Cultivate relationships with employee benefit brokers and map out decision-makers to close deals effectively. Manage and expand broker-generated sales pipelines. Partner with marketing and product teams to refine strategies and support new product launches. Provide market feedback to improve the ideal customer profile and enhance sales strategies.

Skills & Experience

5 years in an outbound sales role within HR-tech or employee benefits, with experience selling through the employee benefits broker channel. Proven success in meeting and exceeding quotas and activity metrics. Proficiency in Salesforce CRM and other sales automation tools (e.g., Gong, ZoomInfo). Strong understanding of health insurance or employee benefits (e.g., Consumer-Driven Health). Experience building territories and creating new business opportunities. Exceptional presentation, interpersonal, and analytical skills. Ability to communicate effectively and inspire audiences. Success in a fast-paced, dynamic environment with a positive outlook and a strong sense of responsibility. A sense of humor and collaborative mindset; we value respect, hard work, and fun.

Compensation

Base salary: $110k–$130k USD On-target annual earnings: $255k–$275k USD (commission uncapped; additional earnings possible) Actual pay depends on location and experience.

Benefits & Perks

Competitive salary and stock options. Medical, dental, vision, life, and disability coverage. HSA with employer contribution, FSA, and lifestyle spending accounts. Paid parental leave and medical travel benefits. 401(k) plan with flexible vacation policy.

Salary : $110,000 - $275,000

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