Senior Manager, People Operations

The posting, as Olly Olly wrote it

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ABOUT THE ROLE

We're hiring a Senior Manager, People Operations to own HR end to end: payroll, benefits, employment tax, compliance, employee relations and our HRIS. You'll be our senior-most HR leader, reporting to the Chief of Staff and partnering closely with our hands-on CEO. Much of our workforce is global contractors, so you'll support both U.S. employees and an international contractor population.

This is a hands-on role. Much of our People foundation was built quickly, and we've inherited processes that work but need attention. Your job is to keep day-to-day operations accurate and reliable while steadily improving how we work, so the function matures with the business.

Best fit: an experienced HR or People Ops manager who has done the hands-on work and is ready to own the whole function. There's room to grow toward “Director” level as the function and scope grows.

WHAT YOU'LL OWN

PAYROLL, BENEFITS AND TAX

• Run multi-state payroll, audits and reconciliations, and resolve issues quickly
• Own benefits administration, annual renewal, open enrollment and broker relationships, with clear employee communication
• Keep employment tax filings and registrations accurate and on time, including Q4 filings and W-2s
• Manage compliance for our global contractor population

HRIS AND SYSTEMS

• Lead our in-flight migration to BambooHR: data cleanup, testing, parallel payroll runs, cutover and adoption
• Own PeopleOps systems, vendors and budget
• Keep employee data clean and audit-ready

EMPLOYEE RELATIONS AND COMPLIANCE

• Handle HR cases: investigations, corrective action, performance issues, accommodations and terminations
• Coach managers through sensitive situations, and bring in outside counsel when needed
• Own the handbook, policies and compliance calendar (I-9, EEO-1, ACA, leave laws, postings)

EMPLOYEE LIFECYCLE

• Own onboarding through offboarding, including new-hire orientation
• Turn manual, inconsistent processes into documented, repeatable ones
• Partner with leaders on performance management, role clarity and org design

LEADERSHIP AND PARTNERSHIP

• Lead and develop 2 PeopleOps Generalists (global contractors): Payroll & Benefits, and HR Operations
• Work daily with IT Support, Facilities and Recruiting on onboarding, offboarding, access and hiring
• Act as HR Business Partner to department leaders, especially Sales and Customer Success
• Partner directly with the CEO and leadership team, bringing data, risks and clear recommendations

WHAT SUCCESS LOOKS LIKE

FIRST 90 DAYS

• Year-end payroll and tax work (Q4 filings, W-2s) is completed accurately and on time
• Benefits renewal and open enrollment run smoothly, and employees understand any changes before they enroll
• Every open HR case is triaged and documented, w

[…]
keep moving.

• Constant multitasking, and this is one of the biggest parts of the job. You'll move quickly between live conversations, Slack notifications and a full inbox of questions, often at the same time, and go from fixing a payroll issue to guiding a leader through a hard termination within hours.

YOU'LL THRIVE HERE IF YOU

• Would rather fix a broken process yourself than wait for a tool or a team
• Make sound calls with incomplete information and adjust as you learn
• Enjoy working directly with a hands-on CEO: you bring clear recommendations, push back respectfully and follow through
• See messy systems as a chance to build
• Learn the history before you change it, respecting what works while improving what doesn't

THIS ROLE MAY NOT BE THE RIGHT FIT IF YOU:

• Do your best work in an established HR function with mature systems and a larger team
• Want a primarily strategic or advisory role with less hands-on work
• Prefer to execute a strategy someone else has set, rather than shape and advocate for one
• Are looking for a predictable 9-to-5 schedule, or eventually a fully remote setup
• Prefer to focus on one thing at a time, rather than juggling constant requests and frequent change
• Need direction from a single leader. You'll report to the Chief of Staff but work closely with our hands-on CEO, so priorities will sometimes come from both

These are all reasonable things to want. In the spirit of transparency, one of our core values, we share them so you can decide whether this role fits what you're looking for.

Must be authorized to work in the United States. We are unable to provide visa sponsorship at this time.

Olly Olly is an equal opportunity employer. We welcome applicants of all backgrounds and do not discriminate on the basis of any protected characteristic.

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