SkillBridge Training Program - People Operations Specialist

Position Overview 

Hypori’s People Team is looking for a SkillBridge participant who already has a people operations foundation and is ready to put it to work — fast. This is not an entry-level learning experience; it’s an opportunity to step into a real contributor role, help iterate on existing programs and processes, and make a tangible impact on a small, high-performing team. The participant will work directly with the Head of People in a fully remote environment, supporting day-to-day operations, benefits administration, and people programs with genuine ownership from week one. 

 Eligibility Requirements:

• Active SkillBridge eligibility – commanding officer approval and within transition window 

• Ability to work remotely during EST to PST business hours 

• Reliable internet connection and home office setup suitable for remote work 

WhatYou’ll Work On 

• Continue developing your people operations practice in a commercial, remote-first technology company 

• Apply existing compliance knowledge to real workflows — I-9s, policy documentation, audit readiness — and help us improve them 

• Deepen your experience with HRIS and benefits administration across multiple platforms (BambooHR, Fidelity, Cigna, Flores, Bennie) 

• Help us move active people programs and culture initiatives forward — not just participate in them 

• Bring your point of view: identify gaps, surface ideas, and iterate on what’s already in motion 

 Key Responsibilities

• Own new hire onboarding workflows including documentation, system provisioning, and HRIS coordination in BambooHR 

• Manage benefits administration tasks: enrollment tracking, employee inquiries, and vendor coordination with Fidelity, Cigna, Flores, and Bennie 

• Maintain and improve people team documentation, compliance records, and internal knowledge in Confluence 

• Drive assigned people programs and culture initiatives — from planning through execution 

• Support offboarding logistics, exit documentation, and compliance tracking — with an eye toward process improvement 

 12-Week Plan

Phase 1: Orientation (Week 1) 

• Get oriented to Hypori’s systems, tools, and how the People Team operates 

• Review active priorities, get access to everything, and begin identifying where you can contribute 

• Ask questions, observe, and come prepared with a point of view 

Phase 2: Full Contribution (Weeks 2–9) 

• Begin taking on real responsibilities early — onboarding, offboarding, compliance, and documentation 

• Ramp into benefits administration and start fielding employee inquiries with increasing independence 

• Step into active people programs and culture work with growing ownership and accountability 

• Surface ideas and iterate on existing processes — don’t just maintain, improve 

• Bring your perspective and drive work forward proactively 

 Phase 3: Deliver & Hand Off (Weeks 10–12) 

• Lead and complete a defined deliverable — an improved process, a program, or a documentation overhaul 

• Present your work and recommendations to the People Team 

• Document your contributions so they live on, and transition any ongoing work cleanly 

 Mentorship & Support

• Dedicated mentor: Grace Twesigye, Head of People 

• Weekly 1:1 check-ins and ongoing feedback throughout the program 

• Full participation in team meetings, all-hands, and cross-functional collaboration 

• Access to Confluence documentation and internal people team resources from day one 

 Who We’re Looking For 

• Someone with a real people operations or military HR background — you already know the fundamentals (e.g., 42A or equivalent MOS) 

• Experience building or running people programs, culture initiatives, or employee engagement efforts 

• Strong writer and communicator — policies, emails, and documentation you’d be proud to put your name on 

• High attention to detail, especially with compliance records, forms, and HRIS data 

• Comfortable with ambiguity and able to work autonomously in a remote, fast-moving environment 

• A bias toward action — you see what needs to happen and you make it happen 

• Discretion and sound judgment with sensitive employee information 

 Tools & Systems

Tool / Platform 

Purpose 

BambooHR 

HRIS – employee records, onboarding/offboarding, time-off tracking 

Fidelity 

401(k) and retirement benefits administration 

Cigna 

Health insurance benefits management 

Flores 

FSA and COBRA administration 

Bennie 

Benefits enrollment and employee benefits hub 

Lattice 

Performance management, engagement surveys, and people analytics 

Microsoft 365 

Core productivity suite – Word, Excel, and PowerPoint 

DocuSign 

Electronic signatures for offer letters, change letters, and compliance documents 

Globalization Partners 

Employer of Record (EOR) platform for international team members 

Confluence 

Internal documentation, people team policies, and knowledge base 

 Expected Outcomes

• Deepened experience applying people operations skills in a commercial technology environment 

• Independent ownership of benefits administration and employee lifecycle workflows 

• At least one completed people team project or deliverable that outlasts the program 

• A stronger readiness for a people operations, generalist, or coordinator role in the commercial sector 

• A professional network and reference within a high-growth technology company