Home
About Us
Testimonials
Jobs
Hire
Referrals
Collaborate
The Network
Learn
Community
Privacy
Contact

Cloudwise Solutions

Home
About Us
Testimonials
Jobs
Hire
Referrals
Collaborate
The Network
Learn
Community
Privacy
Contact
Darren Kane
August 6, 2026
MARKETING & SALES

Health & Benefits Sales Professional – Mid-Market | Multiple U.S. Locations

Darren Kane
August 6, 2026
MARKETING & SALES

Health & Benefits Sales Professional – Mid-Market

📍 Location: Multiple US Office Locations
🏢 Work Arrangement: Hybrid – Three Days Onsite, Two Days Remote
💼 Employment Type: Full-Time
📈 Experience Level: Mid-Senior
🎓 Education: Bachelor’s Degree Required
🚫 Visa Sponsorship: Not Available
🚚 Relocation Assistance: Not Available
👥 Openings: Three

Priority Hiring Locations

The highest-priority location for this search is:

  • Washington, DC

Additional priority locations include:

  • Atlanta, Georgia

  • Charlotte, North Carolina

  • Salt Lake City, Utah

Other approved locations may include:

  • Chicago, Illinois

  • Houston or Dallas, Texas

  • Pittsburgh, Pennsylvania

  • Norwalk, Connecticut

  • Sunrise/Fort Lauderdale, Florida

  • Las Vegas, Nevada

  • Irvine or San Diego, California

  • Southfield, Michigan

Candidates must live within commuting distance of an approved office and be able to work onsite at least three days per week.

Overview

A leading global health and benefits consulting organization is seeking an accomplished Health & Benefits Sales Professional to drive new business growth within the mid-market employer segment.

This is a true business-development and hunter position. The successful candidate will identify, pursue and close new client relationships with organizations typically employing between 1,000 and 5,000 people.

The role requires strong knowledge of employee benefits and health and benefits consulting, an established professional network, and the ability to gain access to C-suite and senior HR decision-makers. Candidates should be comfortable managing the complete sales lifecycle, from prospecting and initial engagement through proposals, presentations, negotiation and closing.

Key Responsibilities

New Business Development

  • Develop and execute sales strategies focused on acquiring new mid-market health and benefits clients.

  • Prospect into organizations with approximately 1,000–5,000 employees.

  • Generate new opportunities through cold outreach, market relationships, networking, referrals and industry events.

  • Conduct frequent prospecting calls, client meetings, sales presentations and executive-level discussions.

  • Build relationships with C-suite executives, HR leaders, benefits professionals and other senior decision-makers.

  • Maintain a healthy pipeline of qualified opportunities and consistently achieve or exceed sales targets.

Consultative Selling

  • Develop a thorough understanding of each prospective client’s employee-benefit, healthcare and workforce challenges.

  • Position relevant consulting services and solutions based on the client’s strategic and financial priorities.

  • Translate complex health and benefits offerings into clear commercial value for senior stakeholders.

  • Use market intelligence and internal service expertise to create compelling reasons for prospects to engage.

  • Identify opportunities to introduce additional services and support broader cross-selling initiatives.

Sales Execution

  • Lead complex sales opportunities from initial identification through final negotiation and closing.

  • Develop persuasive sales proposals, presentations and responses to requests for proposals.

  • Coordinate internal subject-matter experts and service teams throughout the sales process.

  • Lead pricing, scope, service and expectation discussions with prospective clients.

  • Secure commercially beneficial outcomes while maintaining a positive client experience.

  • Accurately track pipeline activity, sales performance and expected revenue.

Market Development

  • Research target industries, markets and employers to identify new business opportunities.

  • Analyse market trends and competitor activity to refine sales strategies.

  • Build and maintain a strong network across the employee-benefits and business community.

  • Participate in relevant professional organizations, conferences and regional industry events.

  • Represent the organization within the market and develop long-term relationships with prospective clients and referral partners.

Required Qualifications

  • Bachelor’s degree from an accredited institution.

  • At least five years of relevant sales, business-development or employee-benefits experience.

  • Demonstrated experience selling health and benefits, employee-benefit consulting or closely related services.

  • Experience selling to mid-market employers with approximately 1,000–5,000 employees per client group.

  • Strong track record of achieving or exceeding new-business sales goals.

  • Evidence of genuine hunting ability, including personally originating and closing new client relationships.

  • Experience managing complex, consultative sales cycles.

  • Strong understanding of employee benefits and health and benefits consulting products and services.

  • Ability to gain access to and influence C-suite executives and senior HR or benefits leaders.

  • Strong proposal development, presentation, negotiation and closing skills.

  • Ability to work from an approved office at least three days per week.

  • Current authorization to work in the United States without employer sponsorship.

Preferred Qualifications

  • Active Life and Health Insurance License.

  • Experience with a major or regional employee-benefits consulting or brokerage organization.

  • Established network of C-suite, HR and employee-benefits decision-makers.

  • Proven success selling into the 1,000–5,000 employee market.

  • Experience managing a substantial book of business or consistently delivering strong annual production.

  • A stable career history, including sustained tenure and measurable progression with a recognized broker or consulting organization.

  • Experience selling medical, ancillary or broader employee-benefit solutions in a consultative, broker-style environment.

Candidates coming from insurance carriers, PEOs or benefit-technology vendors may also be considered when they can demonstrate strong direct prospecting, new-logo acquisition and mid-market consultative selling experience.

What Will Make You Successful

The strongest candidates will be able to clearly demonstrate:

  • Annual new-business sales and production results.

  • Consistent achievement against quota.

  • The size and value of their current or previous book of business.

  • The typical employee population of the clients they have sold to.

  • Specific examples of clients with between 1,000 and 5,000 employees.

  • How they personally sourced, pursued and closed new accounts.

  • Access to senior HR, finance and C-suite decision-makers.

  • The ability to win business through proactive hunting—not solely through broker-channel relationships or inherited accounts.

This position is ideal for a commercially driven health and benefits professional who enjoys building new relationships, opening doors and leading sophisticated sales opportunities from first contact through close.

 

Tagged: Health and Benefits Sales Professional, Mid Market Benefits Sales, Employee Benefits Sales, Benefits Consulting Sales, Health Benefits Sales, Business Development Executive, Sales Executive, Enterprise Sales Executive, Mid Market Sales Executive, Benefits Business Developer, Health and Benefits Consultant, Employee Benefits Consultant, Benefits Broker, Insurance Broker, Benefits Sales Consultant, Benefits Sales Executive, New Business Development, New Client Acquisition, New Logo Sales, Hunter Sales, Sales Hunter, Strategic Sales, Consultative Selling, Solution Selling, Professional Services Sales, Health and Welfare Consulting, Employee Benefits Consulting, Benefits Advisory, Group Benefits, Group Health Insurance, Medical Benefits, Ancillary Benefits, Voluntary Benefits, Health and Benefits Strategy, Workforce Consulting, Total Rewards Consulting, Human Capital Consulting, HR Consulting, Benefits Brokerage, Insurance Brokerage, Mid Market Employers, Mid Market Accounts, 1000 to 5000 Employees, Large Employer Sales, Employer Benefits, Corporate Benefits, New Business Sales, Revenue Growth, Pipeline Development, Prospecting, Cold Calling, Cold Outreach, Executive Prospecting, Account Development, Market Development, Territory Development, Strategic Account Planning, Target Account Planning, Sales Strategy, Sales Execution, Sales Funnel Management, Opportunity Management, CRM, Sales Forecasting, Revenue Forecasting, Quota Attainment, Sales Production, Book of Business, Annual Production, Business Growth, Client Acquisition, Client Development, Cross Selling, Referral Development, Relationship Building, Executive Relationship Management, C Suite Sales, C Level Engagement, CHRO Relationships, CFO Relationships, CEO Relationships, HR Executive Relationships, Benefits Decision Makers, Senior Stakeholder Management, Consultative Sales Cycle, Complex Sales Cycles, Multi Stakeholder Sales, Enterprise Negotiation, Contract Negotiation, Pricing Negotiation, Scope Negotiation, Proposal Development, RFP Responses, Request for Proposal, Sales Presentations, Executive Presentations, Client Presentations, Closing Skills, Negotiation Skills, Value Based Selling, Business Value Selling, Needs Analysis, Discovery Meetings, Client Discovery, Workforce Challenges, Healthcare Cost Management, Employee Benefits Strategy, Market Intelligence, Competitive Analysis, Industry Research, Target Market Research, Professional Networking, Industry Events, Conferences, Professional Associations, Referral Partners, Broker Relationships, Employer Relationships, Candidate Network, Regional Market Network, Washington DC Jobs, Washington DC Sales Jobs, Atlanta Sales Jobs, Charlotte Sales Jobs, Salt Lake City Sales Jobs, Chicago Sales Jobs, Houston Sales Jobs, Dallas Sales Jobs, Pittsburgh Sales Jobs, Norwalk Connecticut Jobs, Fort Lauderdale Sales Jobs, Sunrise Florida Jobs, Las Vegas Sales Jobs, Irvine California Jobs, San Diego Sales Jobs, Southfield Michigan Jobs, Hybrid Sales Jobs, Hybrid Consulting Jobs, Three Days Onsite, Multiple U.S. Locations, Mid Senior Sales Jobs, Employee Benefits Careers, Health Benefits Careers, Insurance Sales Careers, Consulting Sales Careers, Business Development Careers, Brokerage Careers, Active Life and Health License, Life and Health Insurance License, Bachelor’s Degree Required, No Sponsorship, U.S. Work Authorization Required, Mid Market Benefits Consultant, Benefit Technology Sales, PEO Sales, Carrier Sales, Insurance Carrier Sales, Benefits Vendor Sales, Broker Style Sales, Direct Prospecting, New Account Origination, New Account Closing, Client Retention, Strategic Partnerships, Sales Performance, Commercial Growth, High Production Sales, Stable Career History, Relationship Management, Executive Influence, Communication Skills, Presentation Skills, Negotiation, Closing, Market Presence, Professional Network, Client Facing Sales, Regional Sales, National Sales, Sales Opportunity, Multiple Openings, Three Openings

Newer PostManager, Human Resources – Advanced Manufacturing | Rochester, MN
Older PostLarge Market Business Developer – Health & Benefits Consulting | Washington, DC

Your new job awaits.

Start the process →
Back to Top
Cloudwise Solutions, The Basement, 122 Burnt Ash Road., London, SE12 8PU0203-002-8673info@cloudwisesolutions.co.uk

Cloudwise Solutions
UK: info@cloudwisesolutions.co.uk
US: Info@cloudwise-solutions.com
UK: +44 (0)203 002 6873
US: +1 702 - 966 - 9938

Cloudwise Solutions is a full-service technology consultancy that provides end-to-end consulting services across our 3 core services, Hire, Learn and Collaborate.

Follow our Journey...