Regional Sales Director (Mid-Market) - East (CST + EST)

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, Commuter, COBRA and more)! This role is focused on winning employer clients between 250-3,000 benefits eligible lives and driven through benefits brokers and consultants. You will identify, source, and close good-fit employer prospects using strong consultative selling skills, and contacting warm inbound leads. You will conduct discovery, online and mobile demos, handle objections, negotiate contracts, and close-win business. 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 business sales within your territory
• Day-to-day management of all sales activity in your assigned territory
• Meet or exceed personal sales quotas and activity metrics
• Conduct outbound phone and email sales discussions with prospective employee benefits brokers and employers
• Drive sales strategies by developing and expanding employee benefits broker channel relationships
• Map out various decision-makers and influencers needed to close deals, effectively engaging all to win new business for Lively
• Manage a pipeline of leads and opportunities to identify, engage, and develop relationships with brokers
• 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

• 3+ years of experience as an account executive in SaaS, HR-tech, or benefits industries; having previously sold through employee benefits brokers
• Full-cycle selling from generating opportunities through close-winning business
• Proven track record of meeting or exceeding quota and outperforming activity metrics
• You are a relentless hunter conducting significant outbound activities including calls, emails, in-person meetings, events, etc. 
• Must be proficient in Salesforce CRM, as well as other sales automation softwares to support a modern sales approach (Gong, Linkedin Sales Navigator)
• Working knowledge of health insurance (Consumer Driven Health) or employee benefits is required; previous brokerage and/or consultant experience is a plus
• 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
• Experience building out a territory and creating new business opportunities
• 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.
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The base salary range listed below for this position is inclusive of all U.S. States and Washington D.C. Actual pay will depend on the candidate’s location and experience.

We encourage you to apply if you do not meet all of the qualifications but feel you would be a good fit for the position.

Applicants must be currently authorized to work in the United States on a full-time basis.