Regional Sales Director – Mid-Market

Lively, Inc.

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

Posted 10/7/2026full-timeRemote • United StatesLead💰 $110,000 - $130,000 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 within the SaaS and employee benefits sectors, with a strong focus on building broker relationships and executing territory plans to drive new business. Proficient in utilizing Salesforce CRM and sales automation tools to manage leads and exceed sales quotas.

Highest-signal resume keywords

Full-Cycle SellingSalesforce CRM ProficiencyOutbound Sales ActivityEmployee Benefits KnowledgePresentation Skills

ATS Keywords

Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Full-Cycle SellingSalesforce CRMSales Automation SoftwareContract NegotiationObjection HandlingMarket Feedback AnalysisPipeline GenerationTerritory PlanningQuota AchievementHealth Insurance Knowledge

Soft Skills

Interpersonal AbilitiesSolutions-Oriented MindsetAnalytical AbilitiesEffective CommunicationAdaptability

Tools & Technologies

GongLinkedIn Sales Navigator

Industry Keywords

SaaSHR-TechEmployee BenefitsConsumer Driven HealthBroker Relationships

About the role

Key responsibilities & impact

Sell Lively’s benefits solutions, including HSA, FSA, HRA, Lifestyle Spending Accounts, Commuter, and COBRA
Identify, source, and close employer prospects with 250–3,000 benefits-eligible lives
Contact warm inbound leads and generate self-sourced pipeline
Conduct discovery, online and mobile demos, objection handling, contract negotiation, and deal closing
Execute a territory plan to maximize revenue potential
Drive new business sales within the assigned territory
Manage all day-to-day sales activity in the territory
Meet or exceed personal sales quotas and activity metrics
Conduct outbound phone and email sales discussions with benefits brokers and employers
Develop and expand employee benefits broker channel relationships
Map decision-makers and influencers and engage them to win new business
Manage leads and opportunities and develop broker relationships
Partner with marketing and product departments on sales strategy, solution enhancements, and new product releases
Provide market feedback to refine the ideal customer profile

Requirements

What you’ll need

3+ years of experience as an account executive in SaaS, HR-tech, or benefits industries
Previous experience selling through employee benefits brokers
Full-cycle selling from generating opportunities through close-winning business
Proven track record of meeting or exceeding quota and outperforming activity metrics
Significant outbound sales activity, including calls, emails, in-person meetings, and events
Proficiency in Salesforce CRM and sales automation software including Gong and LinkedIn Sales Navigator
Working knowledge of health insurance (Consumer Driven Health) or employee benefits
Experience building out a territory and creating new business opportunities
Impeccable presentation skills
Strong interpersonal, solutions-oriented, and analytical abilities
Ability to communicate with customers in a clear, memorable, and inspirational way
Ability to work effectively in a fast-paced, rapidly changing environment
Applicants must be currently authorized to work in the United States on a full-time basis

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
401k plan
Flexible vacation policy
Lifestyle spending accounts