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People Operations Manager

Remote position, 🇺🇸 United States

$90k - $150k (est.)


Thimble, a leading insurtech platform for small businesses, is seeking a dynamic and experienced People Operations Manager to join their team. In this role, you will play a critical role in nurturing the company culture and driving HR initiatives. Responsibilities include developing HR strategies, managing employee relations, overseeing recruitment, and planning team-building activities. The ideal candidate will have a strategic mindset, excellent interpersonal skills, and a passion for employee engagement and development. Thimble offers a fully remote work environment, comprehensive benefits, and a fun and inclusive company culture. If you're ready to make a positive impact in a fast-growing insurtech company, this role is for you!

Job Description

About Us Thimble is a leading insurtech platform for small business customers and agents. Thimble allows customers to quickly get insurance coverage by the job, month or year using its award-winning app, website, or over the phone.

Founded by serial entrepreneurs Jay Bregman and Eugene Hertz, Thimble works with a variety of carriers to bring the best insurance solutions to small businesses, brokers and agents. Since it was founded, Thimble has delivered more than 170,000 policies to small businesses across the United States.

Thimble was acquired by Arch Insurance, a unit of Arch Capital Group Ltd. (Nasdaq: ACGL), a publicly listed Bermuda exempted company with approximately $15.6 billion in capital at Dec. 31, 2022. Arch, which is part of the S&P 500 Index, provides insurance, reinsurance and mortgage insurance on a worldwide basis through its wholly owned subsidiaries.

Thimble's innovative culture and technical expertise are an incredible addition to Arch Capital’s portfolio of offerings. The acquisition expands Arch’s suite of digital solutions for small business customers and brokers. Thimble will remain a separate subsidiary, working closely with the Arch Group team. 

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Our Values Our unique culture is built around our six core values:

Think Wild, Act Tame Be relentlessly creative. Question everything. Get to know the rules so well, you can use them in new ways. Be the industry’s compliant radicals.

Green Means GO Act. Move forward. Learn. You can only make a decision based on the best information you have – so make it.

Own Every Detail Be ruthlessly precise. Disciplined. Sweat the small stuff.

Simplify, Simplify, Simplify Get to the point. Make it crystal clear. Cut everything else. It’s our job to make insurance easy – however hard that is for us.

Every Moment Counts Show up early and ready. Deliver on time or before. Make the most of your time, so others can make the most of theirs.

Stay Human Treat every person, and their ideas, with respect. Cherish diversity.

About the Role Thimble is seeking a dynamic and experienced People Operations Manager to join our team.  This role will report to the Chief of Staff and will play a critical role in nurturing our company culture and driving human resources-related initiatives.  This role involves managing HR processes, planning remote teambuilding activities, and ensuring that employees have the best experience. The ideal candidate will have a strategic mindset, excellent interpersonal skills, and a passion for employee engagement and development.


  • Develop and implement HR strategies and initiatives aligned with the overall business strategy.
  • Bridge management and employee relations by addressing demands, grievances, or other issues.
  • Manage the recruitment and selection process.
  • Develop and monitor overall HR strategies, systems, tactics, and procedures across the organization.
  • Nurture a positive working environment.
  • Oversee and manage a performance reviews.
  • Maintain benefits program.
  • Plan team-building activities.


  • 2+ years proven working experience as an HR Manager.
  • People-oriented and results-driven.
  • Demonstrable experience with Human Resources metrics.
  • Knowledge of Justworks and other HR databases.
  • Excellent active listening, and presentation skills.
  • Competence to build and effectively manage interpersonal relationships at all levels of the company.

What You’ll Do in 30 Days

  • Get familiar with our systems (Microsoft, Slack, Zoom, Justworks, Asana, etc.)
  • “Meet” Arch HR Team
  • Take over onboarding (and offboarding) including coordinating with our parent company and IT vendor
  • Draft and collect signed offer letters
  • New Hire forms
  • Handbook
  • Create and maintain a first-class new hire onboarding experience

What You’ll Do in 60 Days

  • Design and send out Thimble swag.
  • Take over the People and Culture section of All Hands.
  • Work with contract recruiter to coordinate interview schedule and collect roundtable feedback.
  • Collect Wellness, Office, and Childcare reimbursements and coordinate with Finance for payment.

What You’ll Do in 90 Days

  • Collaborate and launch performance reviews.
  • Organize in person event.

Thimbler Benefits & Perks -Fully remote company -Thimble Fridays! (out of office at 12:00pm local time) -Comprehensive health, vision, and dental coverage -PTO: 20 days vacation, 8 floating days, 10 company-wide holidays, 1 VTO (Volunteer Time Off), and unlimited sick time -Parental Leave: 100% paid 12 weeks + 2 weeks gradual return -Company computer hardware of your choice -Work from home setup reimbursement -Monthly co-working space and/or child care reimbursement -Monthly ClassPass credit -Quarterly wellness reimbursement -Other health & wellness perks including: One Medical, Teladoc, Talkspace, Kindbody, and Health Advocate -Virtual events, happy hours, trivia, and fun!

Salary and compensation

                                                                                                        No salary data published by company so we estimated salary based on similar jobs related to Finance and Finance jobs that are similar:

                                                                                                                                                             $90,000 — $150,000/year



                                                💰 401(k)

🌎 Distributed team

⏰ Async

🤓 Vision insurance

🦷 Dental insurance

🚑 Medical insurance

🏖 Unlimited vacation

🏖 Paid time off

📆 4 day workweek

💰 401k matching

🏔 Company retreats

🏬 Coworking budget

📚 Learning budget

💪 Free gym membership

🧘 Mental wellness budget

🖥 Home office budget

🥧 Pay in crypto

🥸 Pseudonymous

💰 Profit sharing

💰 Equity compensation

⬜️ No whiteboard interview

👀 No monitoring system

🚫 No politics at work

🎅 We hire old (and young)


United States

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About Thimble

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