Sales Consultant, CDHP and Compliance

Flexible Benefit Service LLC (Flex); Chicago (IL); On-site; USD 90,000 - 140,000; Full time

Job summary

Flexible Benefit Service LLC (Flex) in Chicago is seeking an experienced Sales Consultant to drive new business growth through broker, carrier, and consultant partnerships. You will position Flex as a strategic partner for employers seeking cost-effective, compliant benefits solutions.

As a true hunter, you will prospect, build relationships, and close high-volume opportunities in a fast-paced market, with autonomy to grow your own broker network and deliver compelling presentations, demos, and

Qualifications

• 3–5+ years of sales experience in employee benefits or related B2B space.
• Experience selling to brokers, carriers, and consultants.
• Proven ability to prospect, build pipeline, and close net-new business.
• Strong communication and presentation skills.

Responsibilities

• Drive new business growth through broker, carrier, and consultant partnerships.
• Build and manage a strong pipeline of qualified opportunities.
• Consistently achieve and exceed revenue and activity targets.
• Manage CRM data, forecast deals, and close effectively.
• Lead RFP responses and proposal development.

Skills

Prospecting

Pipeline development

Relationship building

Negotiation

CRM proficiency

Presentation skills

Communication skills

Tools

CRM (Salesforce)

Job description

Join Flexible Benefit Service LLC (Flex), a trusted benefits administrator with over 38 years of industry leadership, delivering consumer-directed health plans and compliance solutions nationwide.

We’ve built a strong foundation through service, technology, and broker partnerships—and now we’re accelerating growth. This is your opportunity to join a rapidly growing market leader and play a direct role in taking Flex to the next level.

At Flex, we combine powerful technology with a high-touch service model to deliver real value to employers and brokers navigating an evolving benefits landscape.

If you’re a driven seller looking for a fast-paced environment, strong earning potential, and a company on the rise, this role offers the platform and momentum to deliver.

Role Overview

The Sales Consultant is responsible for driving new business growth through broker, carrier, and consultant partnerships, positioning Flex as a strategic partner for employers seeking cost-effective, compliant benefits solutions.

This role is built for a true hunter—someone who thrives on prospecting, building relationships, and closing business in a fast-moving, high volume/high-opportunity market.

What You’ll Do

Drive New Business

• Prospect and develop relationships with brokers, carriers, consultants, and employer groups
• Build and manage a strong pipeline of qualified opportunities
• Consistently achieve and exceed revenue and activity targets

Sell Strategically

• Position Flex’s solutions across:
• HSA, FSA, HRA, COBRA, LSA, Commuter, and compliance services
• Conduct consultative discovery around:
• Cost containment
• Compliance exposure
• Deliver compelling presentations, demos, and proposals
• Work with broker and distribution partners to close new business

Expand Broker Channel

• Develop and activate broker relationships to drive deal flow
• Conduct broker education and co-selling opportunities
• Identify new referral sources and growth channels

Operate With Discipline (CRM & Pipeline Management)

• Maintain accurate, real-time CRM data (pipeline, activities, next steps)
• Track all broker interactions, opportunities, and follow-ups
• Manage pipeline health, forecast accurately, and drive deals to close
• Ensure all opportunities are fully documented and progressed consistently
• Use CRM insights to prioritize activity and improve conversion
• Lead RFP responses and proposal development
• Partner with implementation and service teams to ensure smooth onboarding
• Participate in meetings, events, and enrollment presentations

What Makes This Role Exciting

• Aggressive growth environment with strong market demand
• Uncapped earning potential tied directly to performance
• Autonomy to build your own territory and broker network
• Sell a full, competitive product suite—not a one-dimensional offering
• Backed by a company known for technology, service, and long-standing industry expertise

What You Bring

• Preferred 3–5+ years of sales experience in:
• Employee benefits, TPA, insurance, or related B2B space
• Significant sales or related experience in other industries may be considered, with a proven track record of required skills and discipline
• Proven ability to:
• Prospect and build pipeline
• Develop broker relationships
• Close net-new business

Working knowledge of

• HSA, FSA, HRA, COBRA, and/or self-funded plans
• Strong communication, presentation, and consultative selling skills
• Experience using CRM systems for pipeline and activity management
• Life & Health license (or ability to obtain within 2 months of employment)

How Success Is Measured

• New business revenue and quota attainment
• Pipeline growth and conversion rates
• Broker engagement and production
• Consistency and quality of CRM documentation and activity tracking

Who Thrives Here

• Self-starters who are motivated by a fast-paced, high-volume sales environment
• Competitive sellers who want control over their income
• Sales professionals who combine technical expertise with relationship-building
• Individuals who want to grow with a scaling, opportunity-rich organization

The Bottom Line

If you’re looking for a role where you can build a book, grow your income, and make a visible impact within a high-growth company, Flex offers the platform, product, and support to do it.