Senior Consultant, Benefits (Fractional HR)

HR Kickstart•,

3d•$90 - $150•Remote

About The Position

HR Kickstart is a boutique HR consulting firm that partners with dynamic startups, creative businesses, and media companies to build thoughtful, scalable people practices. We specialise in providing fractional and project-based HR leadership, from foundational infrastructure to strategic advising, designed to meet the evolving needs of fast-growing organizations. Our approach is grounded in real-world experience, business pragmatism, and a deep respect for the culture and values of each client we serve. Whether we’re standing up core HR systems or helping leaders navigate team growth, performance, and compliance, HR Kickstart delivers HR solutions that are tailored, agile, and built to scale. 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.

Requirements

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
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)

Nice To Haves

running an established consulting business or previous employment at a consulting firm

Responsibilities

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
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
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