Application Guide

How to Apply for People Operations Manager (Benefits & Payroll)

at FreeWill

🏢 About FreeWill

FreeWill is a mission-driven fintech company that helps people create wills and estate plans for free while facilitating charitable giving—over $1 billion has been pledged to nonprofits through their platform. Working here means joining a remote-first team that values social impact, transparency, and employee ownership (everyone gets equity).

About This Role

As the People Operations Manager, you'll own the operational and compliance backbone of FreeWill's employee experience—from payroll and benefits administration to onboarding, offboarding, and contractor/EOR management. You'll be the go-to expert for pay and benefits questions, partner closely with Finance, and ensure the company stays compliant as it scales. This is a high-ownership role where accuracy and attention to detail directly impact employee trust and company risk.

💡 A Day in the Life

You might start your day answering employee Slack questions about benefits or payroll, then dive into processing a payroll run for the upcoming cycle. Later, you'll meet with your benefits broker to review plan renewals, update compliance documentation, and collaborate with Finance on a contractor agreement. You'll end the day onboarding a new hire, ensuring their benefits enrollment and payroll setup are seamless.

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🎯 Who FreeWill Is Looking For

  • 5+ years of hands-on experience in People Operations, with deep expertise in benefits administration (including open enrollment) and multi-state payroll processing.
  • Direct experience managing relationships with PEOs/EORs (e.g., Justworks, Sequoia, Deel) and benefits brokers, including international benefits coordination.
  • Strong knowledge of employment law, compliance requirements (FLSA, FMLA, ACA, ERISA), and regulatory reporting (e.g., 5500s, 1095-Cs).
  • Extremely detail-oriented and process-driven, with a track record of catching payroll errors before they happen and maintaining airtight compliance documentation.
  • Comfortable working autonomously in a remote environment and collaborating cross-functionally with Finance, Recruiting, and HR.

📝 Tips for Applying to FreeWill

1

Highlight specific experience with Justworks or similar PEO platforms—mention it by name in your resume and cover letter to show you can hit the ground running.

2

Quantify your payroll and benefits impact: e.g., 'Processed semi-monthly payroll for 200+ employees across 30 states with 100% accuracy for 2 years.'

3

Show you understand FreeWill's mission: mention their charitable giving platform and how operational excellence supports a mission-driven workforce.

4

Address the remote nature of the role: give examples of how you've managed benefits and payroll remotely, including tools you've used (e.g., Slack, Zoom, HRIS).

5

Emphasize compliance wins: describe a time you identified and fixed a compliance gap (e.g., missed 5500 filing, misclassified contractor) and the impact.

✉️ What to Emphasize in Your Cover Letter

In your cover letter, emphasize: (1) your hands-on experience with end-to-end benefits administration and payroll, especially with PEOs like Justworks; (2) your track record of maintaining compliance and accuracy in a remote environment; (3) your ability to partner cross-functionally with Finance and other teams; and (4) your enthusiasm for FreeWill's mission and how you can help scale their people operations as they grow.

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🔍 Research Before Applying

To stand out, make sure you've researched:

  • → Research FreeWill's mission and products—understand how their estate planning and charitable giving platform works, and be ready to discuss why that mission resonates with you.
  • → Learn about Justworks and other PEO/EOR platforms they use; familiarize yourself with their benefits administration and payroll capabilities.
  • → Look into FreeWill's recent news, funding, and growth stage to understand the scale of their people operations challenges.
  • → Check out FreeWill's careers page and LinkedIn to get a sense of their remote culture, values, and employee testimonials.
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💬 Prepare for These Interview Topics

Based on this role, you may be asked about:

1 Walk us through your process for managing annual open enrollment from planning to post-enrollment—what tools and timelines do you use?
2 How have you handled a payroll discrepancy or compliance issue in the past? What was the outcome?
3 Describe your experience with Employer of Record (EOR) providers and managing international benefits. How do you ensure compliance across borders?
4 How do you stay current on changing employment laws and regulations, and how do you translate that into actionable policies?
5 Give an example of a time you improved a People Operations process to make it more efficient or compliant. What was the impact?
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⚠️ Common Mistakes to Avoid

  • Being vague about your payroll and benefits experience—hiring managers want specifics: which systems, how many employees, which states/countries.
  • Ignoring the compliance aspect: this role is heavily compliance-focused, so not mentioning regulations like ACA, ERISA, or FLSA will hurt your candidacy.
  • Failing to show you can work autonomously—since it's remote, they need to know you can manage your time and prioritize without constant supervision.

📅 Application Timeline

This position is open until filled. However, we recommend applying as soon as possible as roles at mission-driven organizations tend to fill quickly.

Typical hiring timeline:

1

Application Review

1-2 weeks

2

Initial Screening

Phone call or written assessment

3

Interviews

1-2 rounds, usually virtual

✓

Offer

Congratulations!

Ready to Apply?

Good luck with your application to FreeWill!

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