Remote-First Strategic Enterprise Sales Director

Lively; San Francisco (CA); Remote; USD 140,000 - 160,000; Full time

Benefits offered by this job

Stock options

Medical, dental, vision

HSA with employer contribution

FSA

401k

Flexible vacation

Job summary

Lively is a remote-first company seeking an Enterprise Regional Sales Director to sell our benefits solutions (HSA, FSA, HRA, and more) to employer clients with 3,000+ lives. This role targets brokers, consultants, and direct-to-employers across the United States.

You will manage a full-cycle sales process, build a robust pipeline, and collaborate with marketing and product on strategy. The ideal candidate has 5+ years in SaaS/HR-tech sales, excellent presentation skills, and a proven quota

Qualifications

• 5+ years as an account executive in SaaS/HR-tech or benefits.
• Full-cycle sales experience from lead to close.
• Proven quota attainment and outbound sales experience.
• Strong presentation and relationship-building skills.

Responsibilities

• Drive new business sales within territory and meet quotas.
• Manage day-to-day sales activity and pipeline.
• Engage brokers, consultants, and named accounts.
• Collaborate with marketing and product on strategy.
• Present demos and negotiate contracts.

Skills

Account Executive

Full-cycle selling

Quota attainment

Outbound selling

Stakeholder mapping

Salesforce

Gong

Benefits knowledge

Brokerage experience

Presentation skills

Territory development

Analytical skills

Customer communication

Adaptability

Cultural fit

Tools

Salesforce CRM

Gong

BenefitsFlow

Job description

Lively is a remote-first company seeking an Enterprise Regional Sales Director to sell our benefits solutions (HSA, FSA, HRA, and more) to employer clients with 3,000+ lives. This role targets brokers, consultants, and direct-to-employers across the United States.

You will manage a full-cycle sales process, build a robust pipeline, and collaborate with marketing and product on strategy. The ideal candidate has 5+ years in SaaS/HR-tech sales, excellent presentation skills, and a proven quota