Regional Enterprise Sales Director
US$140,000 – US$160,000 / yr base salary
Posted 7 Oct 2026
Advertised as “Regional Enterprise Sales Director - West (PST + MST)”
BranchFactor Summary
The original posting with the fluff stripped out
- Expected experience
- 5+ yrs
- Management level
- Individual contributor
- Employment
- Remote
| Base salary | US$140,000 – US$160,000 / yr |
|---|
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.
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. 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 and direct-to-employer through a named accounts strategy. 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:
- Coordinate with an employer prospect’s benefits consultants to create win-win solutions
- 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
- Educate and guide prospects through the buyer’s journey to help them learn how Lively can drive healthcare cost reduction to their company and drive up employee engagement
- Drive sales strategies by developing and expanding employee benefits broker and consultant channel relationships
- Map out various decision-makers and influencers needed to close deals, effectively engaging all to win new business for Lively
- Follow–up with all generated leads in a timely manner
- Conduct outbound activities including phone calls, campaign sequences, and similar for all named accounts
- 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
- 5+ 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.
- Understands how to map out influencers and decision-makers and handle complex selling through the sales process
- Must be proficient in Salesforce CRM, as well as other sales automation softwares to support a modern sales approach (Gong, BenefitsFlow)
- 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.
The base salary listed is a range for this position. Actual pay will depend on the candidate’s location and experience.$140,000—$160,000 USD
We encourage you to apply even if you do not meet all of the qualifications, but feel you would be a good fit for the position.
Benefits & Perks
We offer competitive salaries, stock options, medical, dental, vision, life and disability coverage. An HSA with employer contribution, FSA, paid parental leave, medical travel benefits, a 401k plan, flexible vacation policy, lifestyle spending accounts, and more!
At Lively, we believe having diverse teams in which everyone can be their authentic self is key to our success. We encourage people from underrepresented backgrounds to apply. Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. Come join us in our mission to help people optimize their healthcare spending, maximize their savings, and better their livelihood!
Lively Inc. participates in the E-Verify program. Learn more about E-Verify here:
https://e-verify.uscis.gov/web/media/resourcesContents/E-Verify_Participation_Poster_ES.pdf
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