Regional Enterprise Sales Director - West (PST + MST)

About Lively

Lively set out to raise the bar on benefit solutions, because we believe no one should have to sacrifice personal wellness for financial wellness. While traditional benefits focus more on transactions and less on the humans using them, Lively harnesses user-centric design and innovative technology to deliver an effortless experience for employers and account holders alike. Our modern HSA is consistently top-rated, and we have since expanded our offerings to provide a full suite of other benefits and services for companies, consumers, and financial institutions.

Lively is a remote-first company, headquartered in San Francisco with employees across the US. Come join us and help make getting the value out of your benefits as simple as it should be.

Note: The candidate must be located in the PST or MST time zone.

Job Description

We are seeking a driven, ambitious, and intellectually curious Enterprise 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 above 3,000 benefits eligible lives driven through benefits brokers and consultants, as well as direct-to-employer through a named accounts strategy.

You will identify, source, and close good-fit employer prospects using strong consultative selling skills, and contact warm inbound leads. You will conduct discovery, online and mobile demos, handle objections, negotiate contracts, and close-win business. You will drive self-sourced leads for your pipeline while partnering closely with internal stakeholders to achieve team goals.

Responsibilities

• Coordinate with an employer prospect’s benefits consultants to create win-win solutions.
• Drive new business sales within your assigned 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.
• Educate and guide prospects through the buyer’s journey to show how Lively drives healthcare cost reduction and boosts employee engagement.
• Drive sales strategies by developing and expanding employee benefits broker and consultant channel relationships.
• Map out decision-makers and influencers needed to close deals, effectively engaging all parties to win business.
• Follow up with all generated leads in a timely manner.
• Conduct outbound activities including phone calls, campaign sequences, and similar efforts for all named accounts.
• Partner with marketing and product departments to execute sales strategy during new product releases or enhancements.
• Provide market feedback to help refine the ideal customer profile across industries within the employee benefits broker channel.

Skills & Experience

• 5+ years of experience as an account executive in SaaS, HR-tech, or benefits industries, with prior experience selling through employee benefits brokers.
• Full-cycle selling expertise from lead generation through deal execution.
• Proven track record of meeting or exceeding quota and outperforming activity metrics.
• Strong background in outbound prospecting (calls, emails, in-person meetings, events).
• Ability to map out influencers and decision-makers and navigate complex selling processes.
• Proficiency in Salesforce CRM and sales automation tools (e.g., Gong, BenefitsFlow).
• Working knowledge of health insurance (Consumer Driven Health) or employee benefits required; brokerage or consultant experience is a plus.
• Impeccable presentation skills with the ability to influence diverse audiences.
• Experience building out a territory and creating new business opportunities.
• Interpersonal, solutions-oriented, analytical, and highly adaptable in fast-paced environments.

Compensation & Benefits

Base Salary: $140,000 — $160,000 USD (Actual pay depends on location and experience)

Benefits & Perks:

• Stock options
• Medical, dental, vision, life, and disability coverage
• HSA with employer contribution & FSA
• Paid parental leave & medical travel benefits
• 401(k) plan
• Flexible vacation policy
• Lifestyle spending accounts & commuter benefits