Senior Consultant, Benefits

Role Description

We are hiring a Senior Consultant, Benefits to lead high-impact client engagements across benefits strategy, plan design, open enrollment, and ongoing benefits administration. This is not a back-office processing role.

You will typically enter client environments through a defined project (e.g., open enrollment execution, benefits redesign, vendor consolidation), quickly assess gaps, execute with precision, and then elevate the conversation to more strategic work. Our clients tend to stick with us for repeat engagements.

Our best consultants don't just complete the project — they become indispensable.

What Success Looks Like

• You stabilize and optimize benefits operations quickly and effectively, building immediate client trust.
• You are forward-thinking and identify upstream and downstream risks — compliance exposure, rising costs, plan gaps, and scalability issues — before they become problems.
• You are able to synthesize complex benefits data and nuance to the business leaders you support, translating operational issues into strategic recommendations that you are able to support leadership teams to action.
• You expand our services and our value to clients organically by uncovering additional needs and opportunities.
• Clients request to extend your engagement or broaden your role beyond the initial project.

Key Responsibilities

• Client Delivery & Execution
  • Support clients in standing up their benefits - either for the first time or for new entities (domestic and international).
  • Lead open enrollment processes end-to-end, including plan evaluation, employee communications, and enrollment support.
  • Oversee day-to-day benefits administration across medical, dental, vision, life, disability, and ancillary lines.
  • Manage broker and carrier relationships, renewals, and vendor negotiations.
  • Diagnose and resolve benefits issues, coverage gaps, and compliance risks (ACA, ERISA, COBRA, state mandates).
  • Own benefits transitions, implementations, and platform migrations.
• Strategic Advisory
  • Assess and redesign benefits programs to support company growth (50–500+ employees).
  • Advise on plan design strategy — contribution modeling, funding approaches, and competitive benchmarking.
  • Identify cost optimization opportunities across benefits structures without compromising employee experience.
  • Partner with leadership to align benefits and total rewards with talent strategy and business goals.
  • Advise on benefits considerations for multi-state and, where applicable, global expansion.
• Client Expansion & Influence
  • Build strong relationships with founders, executives, and functional leaders.
  • Collaborate with the HR Kickstart team on opportunities to bring in additional specialists (e.g., payroll, comp, recruiting, HRBP support).
  • Identify additional needs beyond initial scope and contribute to expanding engagements by leaning into broader HR consultant support where appropriate.

Qualifications

• 7+ years of experience in employee benefits at scaling organizations, including plan design, administration, and open enrollment leadership.
• Prior success at setting up benefits programs for new entities both in the US and globally.
• Strong knowledge of benefits compliance — ACA, ERISA, COBRA, HIPAA, Section 125, and state-specific mandates.
• Demonstrated ability to lead complex benefits redesigns, vendor transitions, or open enrollment overhauls.
• Experience managing broker and carrier relationships, including RFPs and renewals.
• Comfortable advising on benefits strategy, not just administration, including modeling, benchmarking, and cost containment.
• Experience across a range of benefits platforms, HRIS systems and PEO environments common at most scaling companies (Rippling, Gusto, Justworks, Paylocity, Deel, and Remote.com preferred).
• Comfortable operating asynchronously in ambiguous, fast-changing client environments.
• We are specifically looking for consultants running an established consulting business or previous employment at a consulting firm. Due to the nature of the work, we are not a match for individuals who are trying out consulting for the first time or are currently committed to a W2 role.

Engagement Details

• Contract (1099)
• Remote from the US
• Typically 5–25 hours/week (varies by client and project)
• Must operate through your own business entity and carry liability insurance (if you don’t already have liability insurance, you must be willing to obtain it).
• Payrate: $90 - $150/hr (varies by client and project)