Remote opportunity at
LivelyRegional Sales Director (Mid-Market) - East (NYC Metro)
Lively is seeking a Regional Sales Director (Mid-Market) - East (NYC Metro) to join its remote team and expand market share for its user-centric benefits solutions.…
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About This Role
Lively is seeking a Regional Sales Director (Mid-Market) - East (NYC Metro) to join its remote team and expand market share for its user-centric benefits solutions. Lively operates as a remote-first organization headquartered in San Francisco, building modern health savings accounts and associated financial wellness offerings for employers, consumers, and financial institutions. This position specifically requires the candidate to reside within the NYC metro ecosystem. In this role, you will…
Job Description
Lively is seeking a Regional Sales Director (Mid-Market) - East (NYC Metro) to join its remote team and expand market share for its user-centric benefits solutions. Lively operates as a remote-first organization headquartered in San Francisco, building modern health savings accounts and associated financial wellness offerings for employers, consumers, and financial institutions. This position specifically requires the candidate to reside within the NYC metro ecosystem.
In this role, you will focus on winning new business accounts ranging from 250 to 3,000 benefits-eligible lives, working primarily through employee benefits brokers and consultants. The position blends transactional and solutions-oriented sales tasks. You will manage territory activity, build out pipelines, handle contract negotiations, and guide prospects through online and mobile product demonstrations.
This opportunity suits a driven, curious sales professional who thrives in a fast-paced environment and possesses background experience in SaaS, HR technology, or the benefits sector. You will partner with internal marketing and product groups to execute territory strategies, provide vital market feedback, and meet personal sales quotas.
Responsibilities
- Drive new business sales within the assigned territory
- Manage daily sales activities and maintain a robust pipeline of leads and opportunities
- Meet or exceed personal sales quotas and performance metrics
- Conduct outbound phone and email discussions with prospective employee benefits brokers and employers
- Build and expand employee benefits broker channel relationships
- Map decision-makers and influencers to successfully close deals
- Partner with marketing and product departments to execute sales strategies for existing and new solutions
- Provide market feedback to help refine the ideal customer profile across industries
Requirements
- Reside within the NYC metro ecosystem
- Have at least 3 years of experience as an account executive in SaaS, HR-tech, or benefits industries
- Possess previous experience selling through employee benefits brokers
- Demonstrate a track record of meeting or exceeding quota and activity metrics
- Be proficient in Salesforce CRM and modern sales automation tools such as Gong and LinkedIn Sales Navigator
- Have a working knowledge of health insurance or employee benefits
- Be currently authorized to work in the United States on a full-time basis
Qualifications
- Previous brokerage or consultant experience
Core Skills
Benefits
- Competitive base salary ranging from $110,000 to $130,000 USD
- Stock options
- Medical, dental, vision, life, and disability coverage
- Health Savings Account with employer contribution
- Flexible Spending Account
- Paid parental leave
- Medical travel benefits
- 401k plan
- Flexible vacation policy
- Lifestyle spending accounts
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
Is this position remote?
Yes, Lively is a remote-first company. However, this specific role requires the candidate to be part of the NYC metro ecosystem.
What is the salary range for this role?
The base salary range is $110,000 to $130,000 USD, with actual pay depending on the candidate's location and experience.
What level of experience is required?
Candidates must have at least 3 years of experience as an account executive in SaaS, HR-tech, or benefits industries, including previous experience selling through employee benefits brokers.
Sample Interview Questions
AI-generated questions tailored to this specific role — a preview of the full practice set.