Regional Enterprise Sales Director – West

Lively, Inc.

. Sell Lively’s benefits solutions, including HSA, FSA, HRA, Lifestyle Spending Accounts, Commuter, and COBRA .

Posted 10/7/2026full-timeRemote • United StatesLead💰 $140,000 - $160,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in full-cycle sales processes, including lead generation, contract negotiation, and closing deals within the benefits solutions sector. Proven ability to build and maintain relationships with brokers and employers while effectively communicating value propositions to diverse audiences.

Highest-signal resume keywords

5+ Years Account Executive ExperienceFull-Cycle Selling ExperienceProficiency in Salesforce CRMSignificant Outbound Sales Activity ExperienceWorking Knowledge of Health Insurance

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales Pipeline ManagementContract NegotiationLead GenerationQuota AchievementTerritory Planning

Soft Skills

Strong Presentation SkillsInterpersonal CommunicationAnalytical ApproachSolutions-Oriented MindsetAbility to Influence Audiences

Tools & Technologies

Salesforce CRMGongBenefitsFlow

Industry Keywords

Employee BenefitsHealth Savings Account (HSA)Flexible Spending Account (FSA)Health Reimbursement Arrangement (HRA)Consumer Driven Health

About the role

Key responsibilities & impact

Sell Lively’s benefits solutions, including HSA, FSA, HRA, Lifestyle Spending Accounts, Commuter, and COBRA
Win employer clients with more than 3,000 benefits-eligible lives through benefits brokers, consultants, and direct-to-employer named-account strategies
Identify, source, and close good-fit employer prospects
Conduct discovery, online and mobile demos, objection handling, contract negotiation, and deal closing
Drive self-sourced leads and manage the sales pipeline
Execute a territory plan to maximize revenue potential
Coordinate with employer prospects’ benefits consultants to create win-win solutions
Drive new business sales and manage all sales activity in the assigned territory
Meet or exceed personal sales quotas and activity metrics
Conduct outbound phone and email sales discussions with benefits brokers and employers
Educate prospects on how Lively can reduce healthcare costs and increase employee engagement
Develop and expand employee benefits broker and consultant channel relationships
Map decision-makers and influencers to close new business
Follow up promptly on generated leads
Conduct outbound activities for named accounts, including calls and campaign sequences
Partner with marketing and product teams on sales strategy, solution enhancements, and new product releases
Provide market feedback to refine Lively’s ideal customer profile

Requirements

What you’ll need

Candidate must be located in the PST or MST time zone
5+ years of experience as an account executive in SaaS, HR-tech, or benefits industries
Previous experience selling through employee benefits brokers
Full-cycle selling experience from generating opportunities through close-winning business
Proven track record of meeting or exceeding quota and outperforming activity metrics
Significant outbound sales activity experience, including calls, emails, in-person meetings, and events
Ability to map influencers and decision-makers and handle complex sales processes
Proficiency in Salesforce CRM and other sales automation software, including Gong and BenefitsFlow
Working knowledge of health insurance (Consumer Driven Health) or employee benefits
Previous brokerage and/or consultant experience is a plus
Strong presentation skills and ability to influence and engage varied audiences
Experience building a territory and creating new business opportunities
Analytical, solutions-oriented, and interpersonal approach
Ability to communicate with customers clearly, memorably, and inspirationally
Ability to work effectively in a fast-paced, rapidly changing environment

Benefits

Comp & perks

Competitive salaries
Stock options
Medical coverage
Dental coverage
Vision coverage
Life coverage
Disability coverage
HSA with employer contribution
FSA
Paid parental leave
Medical travel benefits
401(k) plan
Flexible vacation policy
Lifestyle spending accounts