Remote Director Of Human Resources Jobs in Ridgefield, CT

About The Difference Card

Difference Card is transforming the way employers provide healthcare benefits by delivering innovative solutions that lower costs while improving the member experience. As a fast-growing, private equity-backed company, we're building a high-performing, remote-first team that's passionate about making a meaningful impact for our clients and each other. As we continue to scale, we're looking for our first HR Operations Lead to build and lead the people operations from the ground up.

Role Overview

We're looking for our first HR Operations Lead to build the operational foundation of our growing People team. You'll own the day-to-day execution of HR operations, ensuring our processes are efficient, compliant, and employee-focused—from maintaining HR data and supporting payroll to administering benefits and leave programs, driving employee engagement, and continuously improving how HR supports the business.

This is a unique opportunity to shape how HR operates as we continue to grow, building scalable processes and partnering closely with leadership to create a best-in-class People function. Reporting to the Vice President of Human Resources, success in this role means becoming a trusted operational partner who delivers exceptional service while enabling the business to scale.

What You'll Do

HR Operations

• Own day-to-day HR operations across the employee lifecycle, including onboarding, job changes, and offboarding.
• Serve as the primary administrator for ADP Workforce Now, ensuring data accuracy and system integrity.
• Build and continuously improve HR processes, workflows, and standard operating procedures.
• Partner with Finance to prepare and audit payroll changes.

Benefits, Leave & Compliance

• Administer employee benefits, including new hire enrollments, life events, and annual Open Enrollment.
• Coordinate employee leave administration, including FMLA, ADA accommodations, state leave programs, workers' compensation, and disability leaves.
• Help ensure compliance with federal, state, and local employment laws across our multi-state workforce.
• Maintain HR records, I-9s, E-Verify, personnel files, and employment documentation.

Employee Experience & Partnership

• Manage the HR inbox and provide timely support to employees.
• Coordinate employee engagement initiatives, onboarding logistics, and Learning & Development administration.
• Prepare HR reports and dashboards to support business decisions.
• Partner with the VP of HR on strategic initiatives, acquisitions, and special projects.
• Partner with the HR Business Partner to support employee relations matters, performance documentation, and manager requests as needed.

What We're Looking For

• 5-8 years of progressive Human Resources experience, including significant HR operations responsibility.
• Experience administering an HRIS (ADP Workforce Now preferred).
• Strong knowledge of payroll, benefits administration, employee leave, and multi-state HR compliance.
• Exceptional organization, attention to detail, and project management skills.
• Strong customer service, communication, and problem-solving abilities.
• Ability to manage confidential information with professionalism and discretion.
• Bachelor's degree in Human Resources, Business, or a related field preferred.
• SHRM-CP or PHR certification is a plus.

Why This Role

This is a unique opportunity to step into a role where you won’t just support HR- you’ll help build what it becomes. As we continue to grow as a PE-backed company, you’ll have a direct hand in shaping the systems, processes, and employee experience that scale with us. You’ll work closely with leadership, have real visibility into the business, and be trusted to make decisions, not just execute tasks. If you’re someone who enjoys rolling up your sleeves while also thinking about how things should work, this role gives you both.

We also believe in taking care of our people:

• Competitive salary range of $95-105k, depending on experience
• Excellent medical, dental, and vision benefits
• 401(k) match program and professional development funds to invest in your future
• 11 company-paid holidays + generous PTO so you can actually take time off
• A genuinely supportive, down-to-earth, and fun culture - we work hard, but we like each other too

Location: 100% Remote, with occasional travel

Job Type: Full-Time/Exempt

EB Employee Solutions, LLC is an Equal Opportunity Employer that does not discriminate on the basis of actual or perceived race, creed, color, religion, alienage or national origin, ancestry, citizenship status, age, disability or handicap, sex, marital status, veteran status, sexual orientation, genetic information, arrest record, or any other characteristic protected by applicable federal, state or local laws. We are dedicated to this policy with respect to recruitment, hiring, placement, promotion, transfer, training, compensation, benefits, employee activities and general treatment during employment

Company Mission
The Difference Card helps organizations build the most cost-effective health plan. Since 2001, The Difference Card has provided its clients with an average net savings of over 18%. The product utilizes proprietary medical reimbursement systems, risk transfer solutions and wellness strategies. In doing so, The Difference Card has delivered millions of dollars in savings to its clients while at the same time providing the highest level of employee benefits. With offices across the United States, The Difference Card provides a national presence combined with local expertise and service. Through strategic broker partnerships, The Difference Card delivers custom plan design solutions that exceeds the needs of both employers and employees across the country. For more information, visit www.differencecard.com