Regional Sales Director – Mid-Market

This is a fully remote position, open to applicants in United States.

📋 Description

• Promote Lively’s benefits offerings, which include HSA, FSA, HRA, Lifestyle Spending Accounts, Commuter benefits, and COBRA.

• Identify, prospect, and secure employer clients with 250–3,000 benefits-eligible employees.

• Engage with warm inbound leads and cultivate a self-generated sales pipeline.

• Perform discovery calls, deliver online and mobile demonstrations, manage objections, negotiate contracts, and close deals.

• Implement a territory strategy to optimize revenue opportunities.

• Propel new business sales within the designated territory.

• Oversee daily sales operations in the territory.

• Achieve or surpass individual sales targets and activity benchmarks.

• Initiate outbound phone and email sales conversations with benefits brokers and employers.

• Build and strengthen relationships within the employee benefits broker channel.

• Identify decision-makers and influencers to engage for securing new business.

• Manage leads and opportunities while fostering broker relationships.

• Collaborate with marketing and product teams on sales strategies, solution improvements, and new product launches.

• Provide market insights to refine the ideal customer profile.

⛳️ Requirements

• Minimum of 3 years of experience as an account executive in the SaaS, HR-tech, or benefits sectors.

• Prior experience in sales through employee benefits brokers.

• Expertise in full-cycle sales from opportunity generation to closing business.

• Demonstrated success in meeting or exceeding sales quotas and outperforming activity metrics.

• High volume of outbound sales activities, including calls, emails, in-person meetings, and events.

• Proficient in Salesforce CRM and sales automation tools such as Gong and LinkedIn Sales Navigator.

• Solid understanding of health insurance (Consumer Driven Health) or employee benefits.

• Experience in developing a territory and creating new business opportunities.

• Exceptional presentation skills.

• Strong interpersonal, solutions-focused, and analytical skills.

• Ability to convey information to customers in a clear, impactful, and inspiring manner.

• Capacity to thrive in a fast-paced, dynamic environment.

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

🏝️ Benefits

• Competitive salaries

• Stock options

• Medical coverage

• Dental coverage

• Vision coverage

• Life coverage

• Disability coverage

• HSA with employer contribution

• FSA

• Paid parental leave

• Medical travel benefits

• 401k plan

• Flexible vacation policy

• Lifestyle spending accounts