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    Regional Sales Director (Mid-Market) - East (NYC Metro)

    Lively

    Remote
    Remote
    Financial
    Hybrid
    See your match score
    Posted Today
    Work Type

    Remote

    Vertical

    Financial

    Source

    jobscollider

    About this role

    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:

    Drive new business sales within your territory Day-to-day management of all sales activity in your assigned territory Meet or exceed

    Selling Motion

    Sales Cycle

    Mid-Market

    1–6 month cycles, moderate deal complexity

    Prospecting

    Hybrid

    Mix of inbound leads and outbound prospecting

    Buyer Persona

    C-Suite

    Selling to executive decision-makers

    Territory

    Geographic

    Region-based territory assignment

    Requirements at a Glance

    Bachelor's Degree·Required
    Prospecting·Required skill
    Negotiation·Required skill
    Consultative Selling·Required skill

    Typical Day — Sales Rep

    High-volume calls50–80/day
    Quick demos6–10/week
    Activity metricsDaily

    Estimates based on role type and selling motion — actual may vary by company.

    Role Signals

    Green Flags

    ✓
    Inbound Leads

    Warm leads provided

    ✓
    Remote Friendly

    Location flexibility

    Financial Services — Interview Intel

    Typical Sales Cycle

    3–6 months (Retail) · 6–18 months (Institutional)

    Common Buyer Objections

    • "Regulatory concerns — need compliance approval"
    • "We already have a vendor for this"
    • "Need to see 3-year track record"
    • "Committee-based decision — multiple approvers"

    Key Industry Metrics

    AUM (Assets Under Management)Risk-Adjusted ReturnsCompliance Pass RateClient Retention RateRevenue Per Advisor

    Hot Topics to Reference

    • • AI in fraud detection and compliance
    • • Open banking APIs
    • • ESG investing mandate shifts
    • • Embedded finance partnerships

    Use these insights to speak the buyer's language in interviews.

    Tags

    sales
    —

    How do you coach underperforming reps?

    Template question
    —

    Describe your forecasting methodology.

    Template question
    —

    How do you structure onboarding for new hires?

    Template question
    Research Lively's product, recent news, and key competitors
    Review relevant certifications and licensing requirements
    Prepare to discuss your home office setup and self-management discipline
    Review the job description and map your experience to each requirement
    Role Insights

    Sales leadership roles require balancing individual contributor revenue with team performance management.

    Financial services sales requires strong compliance awareness and regulatory knowledge.

    Remote positions in sales offer flexibility but require strong self-discipline and proactive communication with distributed teams.

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