Build the Future with Us — EquipmentShare is Hiring a Senior Benefits Specialist - Leave

At EquipmentShare, we’re not just filling a role — we’re assembling the best team on the planet to build something that’s never been built before. We’re on a mission to transform an industry that’s been stuck in the past by empowering contractors and communities through innovative technology, real-time support, and a team that truly cares.

We’re hiring a Senior Benefits Specialist - Leave for our Corporate HQ in Columbia, MO and we’re looking for someone who’s ready to grow with us, bring energy and drive to their work, and help us build the future of construction. 

The Senior Benefits Specialist - Leave is a key member of the benefits team. This person will oversee and administer the leave requests, including short term and long term disability, military, Family Medical Leave (FMLA), state-run, company provided leave, and unpaid time off. This team member is the organizational subject matter expert on external and internal leave programs and benefits and is the primary point of contact for employees.

Primary Responsibilities

• Act as the primary point of contact for leave requests, communicating directly with and supporting employees and leaders through the leave process.  
• Coordinate and administer all company, state and federal leave programs.
• Counsel and guide employees regarding leave of absence options. 
• Receive and review leave request and supporting documentation from medical providers
• Determine leave eligibility through consistent, equitable and compliant procedures 
• Track and send all required internal and external entity notices, forms and letters.
• Coordinate return to work with employees and leaders, including determination of and administration of reasonable accommodations where applicable. 
• Track continuous and intermittent leaves, both paid and unpaid, in accordance with internal policies; record leave and time tracking in our HR system (Workday).
• Coordinate with Payroll to ensure paychecks are accurately processed for employees on leave. 
• Coordinate with Benefits Manager on the benefits impacts of leave; educate employees on these benefits impacts
• Create and update leave of absence materials and guides for employees across the company. 
• Maintain accurate, confidential and timely electronic leave of absence files.
• Partner with the HR team to determine reasonable accommodations (ADA) requests.

Continuous Improvement and Compliance 

• Partner with the Benefits Manager to update company intranet materials related to leave and time off requests.
• Ensure compliance with related state and federal policies and regulations. 
• Monitor changes to federal and state leave laws and coordinate with the Payroll and Benefits Manager to implement necessary changes. 
• As part of the annual planning process, benchmark leave of absence programs within our industry to assess competitiveness. 
• Develop and continuously improve internal leave of absence policies and programs. 
• Support special projects and benefits-related initiatives as needed.

Why EquipmentShare?

Because we do things differently — and we think you’ll feel it from day one. We’re a people-first company powered by cutting-edge technology. That means our proprietary T3 platform doesn’t just run our business — it also makes your job easier, safer, and more connected. Whether you’re behind the wheel, under the hood, leading a branch, or closing deals — tech supports you, and you drive us forward.

We’re a team of problem-solvers, go-getters, and builders. And we’re looking for teammates who take pride in doing meaningful work and want to be part of building something special.

Perks & Benefits

• Competitive compensation
• Full medical, dental, and vision coverage for full-time employees
• Generous PTO + paid holidays
• 401(k) + company match
• Gym membership stipend + wellness programs (earn PTO and prizes!)
• Company events, food truck nights, and monthly team dinners
• 16 hours of paid volunteer time per year — give back to the community you call home
• Career advancement, leadership training, and professional development opportunities

About You

You want to be part of a team that’s not just changing an industry for the sake of change — we’re transforming it to make it safer, more secure, and more productive. You bring grit, heart, and humility to your work, and you’re excited about the opportunity to grow within a f