Work at a Portfolio Company

Regional Sales Director (Mid-Market)



Sales & Business Development
San Francisco, CA, USA · Remote
Posted on Friday, February 16, 2024

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.

Job Description

We are seeking a driven, ambitious, and intellectually curious Mid-Market Regional Sales Director to sell Lively’s benefits solutions (HSA, FSA, HRA, Lifestyle Spending Accounts, COBRA and more)! This role will target employee benefits brokers who manage clients with 100-2,000 employees. You will also be responsible for driving growth by partnering with health insurance brokers, benefits consultants, general agencies, and registered investment advisors. You will identify, source, and close good-fit prospects using strong consultative selling skills, and contacting warm inbound leads. 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.


  • Drive new HSA and other benefits product 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 inbound and outbound phone and email sales discussions with prospective employee benefits brokers
  • Drive sales strategies by developing and expanding employee benefits broker channel relationships
  • Map out various decision-makers and influencers needed to close deals, effectively engaging all to win new business for Lively
  • Manage a pipeline of inbound and self-sourced leads to identify, engage, and develop relationships with brokers
  • 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

  • 3+ years of experience in an outbound sales role in HR-tech, or employee benefits industries; having previously sold into employee benefits brokers is required
  • Proven track record of meeting or exceeding quota and outperforming activity metrics
  • Must be proficient in Salesforce CRM, as well as other sales automation softwares to support a modern sales approach (Outreach, Truly, ZoomInfo)
  • 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.

$110k-130k base salary plus variable comp. On-Target total compensation of $255k - $275k, uncapped.

The base salary range listed for this position is inclusive of all U.S. States and Washington D.C. Actual pay will depend on the candidate’s location and experience.
$110,000$130,000 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. However, you must be located in the United States.

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 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: