Employee Benefits Sales Associate

Henderson Brothers; Pittsburgh (Allegheny County); On-site; USD 60,000 - 95,000; Full time

Benefits offered by this job

Hybrid work arrangement

Downtown Pittsburgh office

Job summary

Henderson Brothers in Pittsburgh is seeking an Employee Benefits Sales Associate to originate new-logo opportunities for our Employee Benefits practice. You will collaborate with experienced Sales Consultants, Producers and Benefits Experts to learn how complex benefits decisions are made while developing prospecting, business acumen and relationship skills.

This developmental role advances to Sales Consultant/Producer within 2–3 years, equipping you to manage relationships, lead sales processes

Qualifications

• Bachelor’s Degree preferred; 2+ years in health insurance required.
• Experience in B2B sales within complex decision environments.
• Excellent verbal and written communication skills.
• Ability to multitask and manage time effectively.

Responsibilities

• Originating new-logo opportunities for our Employee Benefits practice.
• Schedule meetings and partner with internal marketing and sales resources.
• Drive attendance to seminars, events, and thought-leadership initiatives.
• Track all activity in Salesforce to create visibility, accountability, and momentum.
• Develop working knowledge of employee benefits strategy and carrier solutions.

Skills

Health insurance experience

Excellent verbal and written communic

B2B sales experience in complex env

Sales prospecting

CRM exposure (Salesforce)

Education

Bachelor’s Degree

Tools

Salesforce

Job description

• Reports To: Employee Benefits Sales Leader
• Contract: Yes
• FLSA status: Exempt
• Pay Grade: $60k base salary plus activity driven incentives and 5% revenue share on booked new business.
• Compensation at Plan: $80-95k

Position Description

At Henderson Brothers, we develop great sellers the right way - through mentorship, training and an unwavering commitment to your success.

As a Sales Associate, you will be responsible for originating new‑logo opportunities for our Employee Benefits practice. You will work alongside experienced Sales Consultants, Producers and Benefits Experts, learning how complex benefits decisions are made while developing the prospecting, business acumen, relationship management and communication skills required to succeed at the highest level of consultative selling.

This is not purely a prospecting role. This is a career‑building opportunity for someone who is intellectually curious, highly accountable, competitive, driven to constantly improve and motivated by long‑term growth rather than short‑term comfort.

This is a deliberately developmental role. Successful Sales Associates typically progress into a Sales Consultant / Producer role within 2–3 years, fully equipped to manage relationships, lead sales processes, and advise executive‑level buyers.

The Employee Benefits Sales Associate role is the foundation of our organic talent pipeline and the proving ground for the next generation of Sales Consultants and Producers at Henderson Brothers.

What You’ll Do

Build the Front End of the Sales Engine

• Proactively source and schedule new‑business meetings through a disciplined, multi‑touch prospecting approach
• Identify target organizations, buying windows, decision‑makers, and influencers (CFOs, HR leaders, executive teams)
• Maintain segmented prospect lists by industry, size, renewal timing, and competitive landscape

Execute with Precision

• Partner with internal marketing and sales resources to execute targeted outreach and campaign follow‑up
• Drive attendance to seminars, events, and thought‑leadership initiatives
• Track all activity accurately in Salesforce to create visibility, accountability, and momentum

Learn the Business—Deeply

• Develop a working knowledge of employee benefits strategy, market dynamics, and carrier solutions
• Understand Henderson Brothers’ value proposition, differentiators, and consultative sales approach
• Attend industry events, workshops, and training sessions to continuously elevate your expertise

Build a Long‑Term Network

• Drive for Results: Can be counted on to meet or exceed goals, successfully. Consistently a top performer who can self-motivate but can also motivate others.
• Effective Communication: Can clearly articulate oneself in a professional manner with the ability to read the audience and adapt. Possesses the intuition on what information to communicate, feedback to provide, and the right manner of delivery. Practices active listening with patience and can restate opinions accurately, as needed.
• Perseverance: Pursues everything with energy, drive, and the need to finish. Seldom gives up, even in the face of resistance or setbacks.
• Networked: Thrives when interacting with others to exchange information and develop professional or social contacts.
• Integrity: Conducts business with the utmost moral decency. A trusted advisor who displays the highest standard of ethics.
• Heroic Service: White glove approach to client service and satisfaction. Can anticipate needs, and consistently exceeds expectations.
• Teamwork: Works well with others towards a shared goal. Actively participates, shares responsibilities and rewards, and contributes to the effectiveness of the group.
• Kindness: Shows concern and consideration for others. Is generous with time, talent, and overall possess a willingness to help.

Qualifications

• Bachelor’s Degree- preferred
• 2+ years of health insurance or related industry experience required
• Pennsylvania Life, Accident & Health License preferred
• B2B sales experience in a complex decision-making environment-preferred
• Exposure to Salesforce.comor another CRM system-preferred
• Excellent verbal and written communications skills.
• Ability to multitask, prioritize, and manage time effectively.
• Hybrid work: 3 days a week in the field or working from our downtown Pittsburgh office
• Local travel maybe be required.

While performing the responsibilities of the job, these work environment characteristics are representative of the environment the job holder will encounter. Reasonable accommodations may be made to enable people with disabilities to perform the essential functions of the job.

EEO Statement

Henderson Brothers supports workplace diversity and does not discriminate on the basis of race, color, religion, gender identity or expression, national origin, age, military service eligibility, veteran status, sexual orientation, marital status, physical or mental disability, or any other protected class.