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Regional Enterprise Sales Director - West; PST + MST

Remote / Online - Candidates ideally in
San Francisco, San Francisco County, California, 94199, USA
Listing for: LIVELY
Remote/Work from Home position
Listed on 2026-10-10
Job specializations:
  • Sales
    Sales Representative, Business Development, B2B Sales, Sales Development Rep/SDR
Salary/Wage Range or Industry Benchmark: 140000 - 160000 USD Yearly USD 140000.00 160000.00 YEAR
Job Description & How to Apply Below

United States - Remote

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…
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