Regional Sales Director (Mid-Market)

Job Description

We are seeking a driven, ambitious, and intellectually curious Mid-Market Regional Sales Director to sell Lively’s benefits solutions (HSA, FSA, HRA, Lifestyle Spending Accounts, COBRA and more)! This role will target employee benefits brokers who manage clients with 100-2,000 employees. You will also be responsible for driving growth by partnering 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 contacting warm inbound leads. You’ll drive self-sourced leads for your pipeline, while also partnering closely with internal stakeholders to achieve team goals.

You will execute on a territory plan to deliver maximum revenue potential. This role is a mix of transactional and solutions-oriented sales motions, so the ideal candidate must be able to adapt based on the prospect.

Responsibilities:

• Drive new HSA and other benefits product sales within your territory
• Day-to-day management of all sales activity in your assigned territory
• Conduct proper discovery, create an upfront contract, handle objections, and close employer business
• Meet or exceed personal sales quotas and activity metrics including dials, emails, connects, in-person & virtuals meetings, and demos
• Conduct inbound and outbound phone and email sales discussions with prospective employee benefits brokers
• Cultivate new employee benefit broker relationships
• Map out various decision-makers and influencers needed to close deals, effectively engaging all to win new business for Lively
• Effectively manage your broker-generated sales pipeline
• Partner with marketing and product departments to execute sales strategy as the company introduces enhancements to existing solutions and/or releases new products
• Provide market feedback to help further refine our ideal customer profile across industries within the employee benefits broker channel

Skills & Experience

• 5+ years of experience in an outbound sales role in HR-tech, or employee benefits industries; having previously sold through the employee benefits broker channel is required
• Proven track record of meeting or exceeding quota and outperforming activity metrics
• Must be proficient in Salesforce CRM, as well as other sales automation softwares to support a modern sales approach (Gong, ZoomInfo)
• Working knowledge of health insurance (Consumer Driven Health) or employee benefits is required
• Experience building out a territory and creating new business opportunities
• Desire and commitment to do what it takes to be successful in sales
• Impeccable presentation skills with the ability to influence and engage various audiences
• Highly interpersonal, solutions-oriented, and analytical in nature
• Positive outlook and a strong ability to take responsibility for their successes and failures
• Ability to communicate with customers in a clear, memorable, and inspirational way
• Demonstrated ability to work effectively in a fast-paced, rapidly changing environment
• A good sense of humor and a down-to-earth personality. We work hard, have fun, and treat people with respect

This position has a base salary of $110k - $130k, with on target annual earnings of $255k - $275k. Commission is uncapped, and additional earning are possible when exceeding goals.