What are the responsibilities and job description for the Product Sales Expert position at Confidential?
The Opportunity:
We are looking for a driven, consultative sales professional to serve as the foremost authority on our healthcare and benefits platform someone who can command a room, win broker relationships, and close deals while building lasting client partnerships. This is a revenue-generating, client-facing role at the intersection of healthcare technology, payroll, and compliance.
About Us:
We are a healthcare and benefits technology company helping employers across staffing, hospitality, healthcare, and large workforce industries deliver accessible, cost-effective healthcare solutions fully integrated with payroll and benefits systems. We expand healthcare access, reduce employer benefit costs, and simplify the path to compliance.
Our culture is fast-paced, collaborative, and mission-driven. We move with urgency, take ownership, and work side-by-side with clients to deliver measurable outcomes. If you thrive in high-growth environments where your performance directly shapes company success, this is where you belong.
What You Will Do:
As Product Sales Expert, you are the primary revenue driver for broker-sourced leads and internal prospects. You will own the full sales presentation experience from compelling product demonstrations to closing conversations while serving as the definitive subject matter expert on our platform, plan design, payroll integration, and compliance.
Implementation support is a secondary but important function of this role. You will ensure clients launch successfully and adopt solutions in ways that maximize value, retention, and expansion revenue.
Key Responsibilities:
Sales & Revenue Generation (Primary Focus)
▪ Lead all product demonstrations, sales presentations, and proposal conversations for broker-referred leads and internal prospects with a relentless focus on conversion
▪ Serve as the definitive product and compliance authority in every sales engagement, instilling confidence in brokers, HR leaders, payroll teams, and executive decision-makers
▪ Own the solution-positioning narrative: translate platform capabilities into compelling ROI stories that resonate with employer audiences
▪ Identify and pursue upsell, cross-sell, and expansion opportunities within existing client relationships to grow account revenue
▪ Conduct discovery sessions with prospects to uncover workforce structure, payroll needs, compliance gaps, and budget drivers, then connect those findings directly to solutions
▪ Partner with sales leadership to develop and refine messaging, competitive positioning, and go-to-market strategies for target industries
▪ Maintain disciplined pipeline visibility and account health tracking within CRM systems
Product & Compliance Expertise:
▪ Function as the go-to internal and external authority on the platform: plan design, payroll integration, Section 125 structures, IRS tax codes, and benefits compliance
▪ Stay ahead of healthcare, payroll, compliance, and insurance industry developments that affect clients, positioning, and growth opportunities
▪ Translate complex technical and regulatory requirements into clear, confident language that moves deals forward and builds buyer trust
Client Implementation & Success (Secondary Focus)
▪ Support client onboarding and implementation following a closed sale, ensuring smooth, timely launches with strong adoption rates
▪ Train clients on platform functionality, enrollment processes, reporting tools, and ongoing administration
▪ Monitor implementation progress, proactively surface risks and gaps, and convert challenges into opportunities for expanded service usage
▪ Gather client feedback and partner with product and technology teams to sharpen the platform and inform new revenue opportunities
▪ Maintain accurate records of client interactions, milestones, and support activities across CRM and operational systems
Core Requirements | Skills & Attributes:
▪ 5-7 years in healthcare insurance or employee benefits
▪ Deep knowledge of Section 125, IRS tax codes, and payroll deductions
▪ Proven track record presenting and selling complex solutions
▪ Strong CRM discipline and pipeline management habits
▪ Experience in payroll implementation or HRIS integration
▪ Experience working with payroll providers or insurance technology platforms
▪ Background in insurance operations or benefits administration
▪ Ability to manage multiple client relationships simultaneously
▪ Comfort engaging C-suite, HR, and broker audiences
▪ Consultative mindset: you lead with questions, not pitches
▪ Active Alabama Life & Health License (or ability to obtain)
▪ Thrives in fast-paced, high-growth, quota-bearing environments
Preferred Experience:
▪ Industry background in staffing, healthcare, hospitality, PEO, or large workforce environments
▪ Familiarity with payroll integration platforms and implementation methodologies
▪ Demonstrated success identifying upsell, cross-sell, or expansion opportunities
▪ Exposure to healthcare compliance or benefits-related regulations
▪ Experience supporting or leading business development conversations
▪ Bachelor’s degree in business, Accounting, Finance, Human Resources, or a related field preferred
What Success Looks Like In the First 90 Days:
▪ Master the platform and product story
▪ Complete required licensing if not already active
▪ Deliver first independent sales presentations
▪ Build rapport with broker partners and internal stakeholders
▪ Consistent conversion of broker leads and prospects
▪ High client satisfaction and retention scores
▪ Identified and closed expansion revenue opportunities
▪ Recognized internally as the product authority
Why Join Us:
This is not a support role with sales exposure. This is a sales role with deep product authority. You will be the face of the organization in front of brokers and prospects — the person who wins deals, shapes client relationships, and directly contributes to company growth.
You will work at the intersection of healthcare, technology, payroll, and compliance in a collaborative, mission-driven environment that rewards ownership, urgency, and results. If you want to make a measurable impact and grow with a company that is reshaping healthcare access for employers and employees alike, this is your opportunity.