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Salary: USD 110,000 - 130,000 / annual
Lively is a remote-first benefits technology company headquartered in San Francisco. The company modernizes employee benefits delivery through user-centric design and innovative technology, offering HSA, FSA, HRA, Lifestyle Spending Accounts, Commuter benefits, COBRA, and related solutions.
You will serve as Regional Sales Director for the East region (CST + EST time zones), responsible for driving new business sales within a defined territory targeting mid-market employers with 250–3,000 benefits-eligible lives. Your primary sales channel is through employee benefits brokers and consultants.
Key responsibilities include:
- Execute territory plan to maximize revenue potential
- Conduct full-cycle selling: identify, source, and close good-fit prospects through consultative selling and warm inbound leads
- Perform discovery, deliver online and mobile demos, handle objections, negotiate contracts, and close deals
- Drive self-sourced pipeline development while meeting personal sales quotas and activity metrics
- Manage day-to-day sales activity, including outbound phone and email outreach to brokers and employers
- Map decision-makers and influencers; engage all stakeholders to win new business
- Develop and expand employee benefits broker channel relationships
- Partner with marketing and product teams on sales strategy execution as new solutions and products launch
- Provide market feedback to refine ideal customer profile across industries
This role blends transactional and solutions-oriented sales motions, requiring adaptability based on prospect needs.
Requirements:
- 3+ years as an account executive in SaaS, HR-tech, or benefits industries, with prior experience selling through employee benefits brokers
- Full-cycle selling expertise from opportunity generation through close
- Proven track record of meeting or exceeding quota and outperforming activity metrics
- Relentless hunter conducting significant outbound activities (calls, emails, in-person meetings, events)
- Proficiency in Salesforce CRM and modern sales automation tools (Gong, LinkedIn Sales Navigator)
- Working knowledge of health insurance (Consumer Driven Health) or employee benefits; brokerage/consultant experience is a plus
- Strong presentation skills with ability to influence diverse audiences
- Experience building out territories and creating new business opportunities
- Highly interpersonal, solutions-oriented, and analytical mindset
- Ability to communicate clearly, memorably, and inspirationally
- Demonstrated ability to work effectively in fast-paced, rapidly changing environments
- Must be currently authorized to work in the United States on a full-time basis
