Lively, Inc. develops technology-enabled employee benefits solutions across healthcare, finance, and healthcare insurance. Its platform supports Health Savings Accounts, Flexible Spending Accounts, Health Reimbursement Arrangements, and other employer-sponsored accounts, with additional offerings including COBRA, Direct Bill, Lifestyle Spending Accounts, and Medical Travel Accounts. Lively focuses on making benefits administration easier for employers while helping individuals manage healthcare-related spending and savings.
Regional Sales Director, Mid-Market – Lively (Remote, United States)
Lead mid-market sales of Lively’s HSA, FSA, HRA, and related employee benefits solutions to employers across the United States. Build broker partnerships, manage a territory, and create new-business pipeline.
Description
- Sell Lively’s employee benefits portfolio, including HSA, FSA, HRA, Lifestyle Spending Accounts, Commuter, and COBRA solutions.
- Identify, source, and close employer opportunities covering 250–3,000 benefits-eligible employees.
- Follow up on warm inbound leads while building a self-generated pipeline.
- Lead discovery, online and mobile demonstrations, objection handling, contract negotiations, and deal closes.
- Build and execute a territory plan focused on maximizing revenue potential.
- Generate new-business sales within the assigned territory.
- Oversee daily sales activity across the territory.
- Achieve or exceed individual sales quotas and activity targets.
- Conduct outbound phone and email conversations with benefits brokers and employers.
- Build and grow relationships within the employee benefits broker channel.
- Identify decision-makers and influencers and engage them to secure new business.
- Manage leads and opportunities while strengthening broker relationships.
- Collaborate with marketing and product teams on sales strategy, solution improvements, and product launches.
- Share market insights to help refine the ideal customer profile.
Requirements
- At least three years of account executive experience in SaaS, HR technology, or employee benefits.
- Prior experience selling through employee benefits brokers.
- Experience managing the full sales cycle, from opportunity generation through closed business.
- Demonstrated success meeting or exceeding quotas and surpassing activity targets.
- Strong outbound sales experience across calls, email, in-person meetings, and events.
- Proficiency with Salesforce and sales automation tools such as Gong and LinkedIn Sales Navigator.
- Working knowledge of health insurance, including Consumer Driven Health, or employee benefits.
- Experience developing a territory and creating new-business opportunities.
- Outstanding presentation skills.
- Strong interpersonal, analytical, and solutions-focused capabilities.
- Ability to communicate with customers clearly, memorably, and inspiringly.
- Ability to perform effectively in a fast-paced, rapidly changing environment.
- Must currently be authorized to work full time in the United States.
Benefits
- Competitive compensation.
- Stock options.
- Medical insurance.
- Dental insurance.
- Vision insurance.
- Life insurance.
- Disability insurance.
- HSA with an employer contribution.
- Flexible Spending Account.
- Paid parental leave.
- Medical travel benefits.
- 401(k) plan.
- Flexible vacation policy.
- Lifestyle Spending Accounts.