Client Executive | Employee Benefits

Deeply Rooted to Serve

Oakbridge Insurance Agency is a new kind of insurance and risk management agency with the mission to transform and elevate the way business is done in our industry.

For over 100 years, the founding firms of Oakbridge worked alongside each other in small towns and cities throughout the Southeast, cultivating similar company cultures and best practices, and earning each other's respect in the industry. They envisioned a way to impact the future of insurance and formed Oakbridge Insurance Agency on January 1, 2021. Since forging this different path, we are proud to have added additional partners to Oakbridge who reflect our vision, demonstrate our core values, and share our commitment to doing what is right for our friends and neighbors.

Our most important asset is our people. We offer a friendly and flexible work environment and offer first-class benefits to meet the needs of you and your family. Benefits include a 401k plan with immediate participation, company match, and immediate 100% vesting. Company-paid benefits include life insurance and short- and long-term disability. We have a strong health insurance plan and many supplemental, voluntary offerings.

Oakbridge Insurance is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based on race, color, sex, religion, sexual orientation, national origin, disability, genetic information, pregnancy, or any other protected characteristic as outlined by federal, state, or local laws.

This policy applies to all employment practices within our organization, including hiring, recruiting, promotion, termination, layoff, recall, leave of absence, compensation, benefits, training, and apprenticeship. Oakbridge Insurance makes hiring decisions based solely on qualifications, merit, and business needs at the time.

For more information visit our website:

Deeply Rooted Insurance Agency | Oakbridge Insurance - Oakbridge Insurance

The Employee Benefits Client Executive is responsible for developing new employee benefits business and expanding revenue within existing client relationships. This role serves as a strategic advisor to employers on health and welfare benefit programs, helping clients manage cost, improve plan performance, support employees, and navigate an increasingly complex benefits environment. The Client Executive leads prospect strategy and client relationships while partnering closely with Account Management, Analytics, Marketing, Compliance, Communications, and other internal specialists to deliver coordinated solutions and strong retention.

Work Performed

• Meet activity, new business, retention, and revenue goals jointly established with management and regularly report progress toward those goals.
• Proactively identify and qualify employee benefits prospects; conduct discovery meetings to understand business objectives, workforce demographics, current plan structure, pain points, funding arrangements, renewal history, and decision-making process.
• Develop and present tailored employee benefits strategies and proposals, clearly communicating Oakbridge's capabilities, recommended solutions, implementation approach, and expected value to prospects and clients.
• Target opportunities that align with agency account quality, size, revenue, and strategic standards to support profitable organic growth.
• Lead the overall client relationship and establish clear expectations regarding scope of services, stewardship cadence, deliverables, responsibilities, and decision timelines.
• Conduct regular client strategy, stewardship, and renewal-planning meetings and coordinate service needs with the assigned Account Manager and broader Employee Benefits team.
• Provide ongoing consultative guidance on plan design, funding strategy, cost containment, contribution strategy, network options, pharmacy benefits, stop-loss, employee engagement, and other solutions appropriate to the client's objectives.
• Identify and pursue cross-sell opportunities, including voluntary benefits, life and disability, executive benefits, retirement, property & casualty, and other Oakbridge capabilities when appropriate.
• Collaborate with Oakbridge producers and specialists across Employee Benefits, Property & Casualty, Personal Lines, Retirement, and other practice areas; share leads and facilitate joint client and prospect meetings where appropriate.
• Maintain an active, disciplined pipeline; participate in sales meetings, pipeline reviews, prospect strategy sessions, and growth planning discussions.
• Partner with Employee Benefits marketing and analytics resources to develop renewal and market strategies, prepare carrier/TPA/RFP submissions, evaluate proposals, negotiate terms, and present financial comparisons and recommendations.
• Build productive relationships with medical, pharmacy, stop-loss, ancillary, TPA, benefits administration, and other vendor partners while representing Oakbridge professionally and advocating for clients.
• Stay current on employee benefits trends, funding strategies, carrier and vendor capabilities, healthcare cost drivers, and relevant regulatory developments; complete professional development goals established by management.
• Maintain a professional demeanor and actively support Oakbridge's reputation in the business community through client service, networking, referral relationships, and industry involvement.

• Active Life & Health / Accident & Sickness insurance license as required by applicable state law.
• Proven record of successful employee benefits sales, relationship management, and client retention, with a strong commitment to consultative service.
• Strong working knowledge of employer-sponsored health and welfare benefits, including medical, dental, vision, life, disability, voluntary benefits, and common funding arrangements such as fully insured, level-funded, and self-funded plans.
• Ability to manage multiple prospects, renewals, client priorities, and deadlines in a fast-paced, production-oriented environment.
• Excellent written, verbal, and presentation skills, including the ability to explain complex benefit, financial, and healthcare concepts clearly to executives, HR leaders, finance teams, and employees.
• Demonstrated ability to prospect, build executive-level relationships, lead a consultative sales process, generate new business, and retain and expand existing accounts.
• Ability to interpret renewal data, claims and utilization reporting, benchmarking, contribution strategies, carrier/vendor proposals, and plan-performance information in partnership with internal subject-matter experts.
• Ability to travel to existing and prospective clients and conduct in-person meetings, presentations, enrollment-related meetings, and relationship-building activities as needed.

Preferred Education & Experience

• Bachelor's degree in business, finance, risk management, human resources, healthcare, or a related field preferred.
• 5+ years of employee benefits brokerage, consulting, carrier, TPA, or related benefits sales/client management experience preferred.
• Professional benefits designations (e.g., CEBS, RHU, REBC, GBA) and/or demonstrated expertise in self-funding, alternative funding, cost containment, or healthcare analytics are highly desirable.