Senior Benefits Consultant, Enterprise

About Bennie

Bennie ( is an employee benefits services and technology firm that helps companies create a healthier workplace. Bennie provides services and technology that are beyond what growing companies typically receive, yet exactly what they need.

Bennie has built the ultimate benefits platform that connects disparate systems across the benefits supply chain to deliver a complete experience for employees, employers, and partners. Bennie’s technology, benefit plans, and service model are designed to enable employers and their employees to experience best-in-class outcomes that reduce overall health plan costs. Bennie’s team members use the platform and its data to supplement their market knowledge and bring innovative solutions to Bennie’s customers.

Bennie is headquartered in Stamford, CT, and is a remote-first company with employees across the U.S.

Core Values at Bennie

As an organization, we value our team members who are Optimistic , Accountable , Thoughtful , and Healthy . We believe these values, known as our O.A.T.H. , are essential for our collective success. The ideal candidate for this role will embody these values by:

• Maintaining a positive attitude throughout our journey of building our company.
• Being responsible for the quality of their work and for meeting their goals.
• Respecting our differences and looking out for one another.
• Believing in living complete lives that balance our work and personal time.

About the Role:

The Enterprise Senior Benefits Consultant is responsible for driving overall customer strategy, complex benefit plan designs, service execution, and long-term retention for Bennie’s enterprise-segment customers (~500+ lives). This role serves as a trusted advisor to C-suite and HR leadership, managing multi-year benefit strategies, self-funded and fully-insured plan architectures, complex carrier negotiations, and vendor ecosystems.

Reporting to: Director of Enterprise Consulting

Who You Are: The ideal candidate possesses deep benefits consulting expertise, exceptional financial and analytical acumen, and a proven track record of managing large, multi-state employer accounts. You are excited to leverage your industry expertise in a technology-forward environment to redefine exceptional consulting service and experience to Bennie’s largest and most complex customers.

The Enterprise Senior Benefits Consultant should exhibit the core attributes of the Bennie consulting team:

1. Possess a growth mindset to drive the business upward and forward.
2. Take a proactive approach to value creation and delivery for customers, colleagues, and partners.
3. Seize the consultative opportunity in every interaction with customers, colleagues, and partners.
4. Maintain a curiosity about the industry, Bennie’s customers, and Bennie’s business.
5. Bring relentless intensity to the creation of value.
6. Take ownership of one’s impact and influence on customers, colleagues, and partners
7. Work collaboratively with customers, colleagues, and partners.
8. Act with compassion in every interaction, every time.

Responsibilities include:

• Customer Strategy & Ownership: Own a strategic book of enterprise-level customers, driving multi-year benefits strategies, plan designs, and executive-level business reviews.
• Complex Financial & Plan Architecture: Guide customers through self-funding, captive options, contribution strategies, stop-loss placement, and pharmacy benefit management (PBM) optimization.
• Carrier & Partner Negotiations: Lead high-stakes RFP processes, carrier renewals, and contract negotiations to secure optimal pricing and coverage for enterprise customers.
• Data & Analytics Integration: Collaborate with analytics resources to analyze claims data, identify cost-drivers, and deliver actionable insights and ROI modeling to executive stakeholders.
• Cross-Functional Leadership: Direct internal service teams (Client Experience Managers, Analysts, Financial Consulting, and Technology Operations) to ensure seamless plan implementation, compliance management, and daily service execution of benefit programs and Bennie’s overall platform.
• New Business & Onboarding: Partner with Enterprise Sales Account Executives during the sales process to present strategic solutions and lead the smooth transition of newly closed enterprise accounts.
• Product & Platform Feedback: Partner with internal Product, Engineering, and Operations teams to communicate high-level enterprise customer needs and help guide platform feature development.

Requirements:

• 5+ years of employee benefits consulting experience, specifically managing enterprise/large-group accounts (500+ lives).
• Active Life & Health Producer’s License.
• Deep knowledge of complex plan structures (self-funded, level-funded, fully-insured), PBMs, stop-loss, and multi-state compliance (ERISA, ACA, FMLA, COBRA).
• Proven executive presence with strong presentation and communication skills geared toward C-suite decision-makers.
• Strong proficiency in data analysis, financial modeling, and MS Excel, Word, and PowerPoint.

Nice-to-Have:

• Professional designations (e.g., CEBS, GBA, RHU).
• Experience with enterprise HR/Benefits technology platforms and HCM integrations.
• Team leadership and/or project leadership experience.

Compensation & Benefits:

We offer a competitive salary for this fully remote position, commensurate with experience and qualifications. The estimated annual salary range for this role is USD115,000 to USD145,000*.

*Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

Please note that the compensation details listed above reflect the base salary only, and do not include incentive pay, equity, or benefits. Bennie offers a total rewards package that includes stock options and employee benefits for full-time employees.

Our total rewards package includes the following:

• Flexible Time Off: We have a flexible vacation policy and offer paid company holidays
• Remote-first environment: Bennie is 100% remote (must be based in the US)
• Health Benefits that include:
  • Medical/Dental/Vision
  • HSA & FSA, HRA, Life, Disability, & Employee Assistance Program
• Wellness Benefits that include:
  • Headspace
  • Wellhub
  • Rocket Lawyer
  • One Medical Membership
  • Kindbody
  • Financial education with Betterment
• Stock Options: All full-time employees are granted stock options
• Remote Work Stipend: A $1,000 WFH Stipend
• Paid Parental & Bonding Leave
• Employee Referral Bonus Program

Bennie is an Equal Opportunity Employer

Bennie is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.