Remote
Financial
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.
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 ac
Selling Motion
Sales Cycle
Enterprise
6–18 month cycles, complex multi-stakeholder deals
Buyer Persona
C-Suite
Selling to executive decision-makers
Territory
Geographic
Region-based territory assignment
Requirements at a Glance
Typical Day — Sales Rep
Estimates based on role type and selling motion — actual may vary by company.
Role Signals
Green Flags
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
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
How do you coach underperforming reps?
Template questionDescribe your forecasting methodology.
Template questionHow do you structure onboarding for new hires?
Template questionSales leadership roles require balancing individual contributor revenue with team performance management.
Trust-building is paramount — prospects need confidence in your expertise.
Remote positions in sales offer flexibility but require strong self-discipline and proactive communication with distributed teams.
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