Regional Sales Director (Mid-Market) - East (NYC Metro)
Required skills
- Mid-Market
- Regional Sales Director
- benefits solutions
- HSA
- FSA
- HRA
- Lifestyle Spending Accounts
- Commuter
- COBRA
- employer clients
Nice to have
- previous brokerage
- consultant experience
- good sense of humor
- down-to-earth personality
Role summary
Lively is seeking a driven and ambitious Mid-Market Regional Sales Director to sell employee benefits solutions (HSA, FSA, HRA, etc.) to employer clients with 250-3,000 eligible lives, primarily through benefits brokers and consultants. The role involves full-cycle selling, including identifying, sourcing, and closing prospects using consultative selling skills, managing inbound leads, conducting demos, negotiating contracts, and driving self-sourced leads. Responsibilities include managing territory sales activity, meeting quotas, developing broker relationships, mapping decision-makers, and partnering with internal teams. The ideal candidate has 3+ years of experience in SaaS, HR-tech, or benefits sales, proficiency in Salesforce and sales automation tools, and working knowledge of consumer-driven health or employee benefits.
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, Commuter, COBRA and more)! This role is focused on winning employer clients between 250-3,000 benefits eligible lives and driven through benefits brokers and consultants. 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. This is a location specific role. Candidate MUST be part of NYC metro ecosystem for consideration.
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:
Skills & Experience
The base salary range listed below 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.
We encourage you to apply if you do not meet all of the qualifications but feel you would be a good fit for the position.
Applicants must be currently authorized to work in the United States on a full-time basis.
The base salary listed is a range for this position. Actual pay will depend on the candidate’s location and experience.$110,000—$130,000 USDWe 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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