Regional Benefits Sales Director: Grow Partnerships

Lively; New York (NY); On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

Health insurance

Dental

Vision

Employer HSA contributions

FSA

401(k) plan

Life insurance

Commuter benefits

Equity

Unlimited vacation policy

Paid parental leave

Job summary

Lively in New York seeks a Mid-Market Regional Sales Director to drive growth selling benefits solutions to employers with 250-3,000 lives. You will win through brokers and consultants, conduct discovery and demos, negotiate contracts, and close deals.

You will own day-to-day sales activity, manage a territory plan, and collaborate with marketing and product to expand offerings and refine target accounts. A proven SaaS sales background in HR-tech or benefits is required.

Qualifications

• 3+ years of account executive experience in SaaS, HR-tech, or benefits industries.
• Experience building out a territory and creating new business opportunities.
• Proven track record of meeting or exceeding quota and outperforming activity metrics.
• Full-cycle selling from opportunity generation through close-winning business.
• Proficiency with Salesforce CRM and sales enablement tools (Gong, LinkedIn Navigator).

Responsibilities

• Identify, source, and close employer prospects (250–3,000 lives) via brokers and consultants.
• Conduct discovery, online demos, and handle objections to close deals.
• Drive self-sourced leads while partnering with internal teams to hit targets.
• Manage a territory plan and day-to-day sales activity.
• Meet or exceed personal sales quotas and activity metrics.
• Collaborate with marketing and product to refine strategy and expand offerings.

Skills

Territory management

Outbound prospecting

Negotiation

Consultative selling

Closing deals

B2B SaaS sales

Communication

Broker channel

Tools

Salesforce CRM

Gong

LinkedIn Sales Navigator

Job description

Lively in New York seeks a Mid-Market Regional Sales Director to drive growth selling benefits solutions to employers with 250-3,000 lives. You will win through brokers and consultants, conduct discovery and demos, negotiate contracts, and close deals.

You will own day-to-day sales activity, manage a territory plan, and collaborate with marketing and product to expand offerings and refine target accounts. A proven SaaS sales background in HR-tech or benefits is required.