Benefits Specialist

guidepointsecurity

Remote

Posted Jul 30, 2026

Other
Remote
Human Resources

Job description

GuidePoint Security provides trusted cybersecurity expertise, solutions and services that help organizations make better decisions and minimize risk. By taking a three-tiered, holistic approach for evaluating security posture and ecosystems, GuidePoint enables some of the nation’s top organizations, such as Fortune 500 companies and U.S. government agencies, to identify threats, optimize resources and integrate best-fit solutions that mitigate risk.

Benefits Specialists at GuidePoint Security are autonomous, detail-oriented, and organized individuals that support the HR and Benefits teams and contribute to overall corporate growth. Our Benefits Specialists are responsible for the accurate administration of all benefit plans. The continuing growth of GuidePoint Security allows for our employees to consistently advance their knowledge and experience in our fast-paced atmosphere.

Primary Responsibilities:

Reconcile benefit deductions to monthly vendor bills.
Upload vendor bills into company accounting software.
Perform monthly benefit audits to ensure accuracy of W-2 information.
Assist with HSA, COBRA, and STD pay processes.
Assist with employee benefit inquiries.
Assist with updating Benefits webpages with current documents and details.
Assist with Wellness Program communications and activities.
Consistently look for ways to improve the efficiency of systems and processes.
Other duties as assigned.

Desired Skills & Experience:

BA/BS in Finance/Accounting required, or equivalent in work experience.
3-5 years’ experience in benefits, payroll, or accounting.
Ability to identify and resolve problems in a timely manner.
Strong MS Excel skills, including vlookups, pivot tables, and csv file uploads.
Experience with UKG, NetSuite, and third party benefit brokers preferred.
Demonstrates a willingness to learn and use AI-enabled tools.
Attention to detail is a must.
Excellent communication skills, including phone etiquette and a demonstrated ability to communicate professionally in both verbal and written forms.
Possess the ability to self-manage and adapt to changes, delays, or unexpected shifts in priorities while maintaining focus and productivity in a fast-paced environment.
Ability to work flexible work schedule required.

We use Greenhouse Software as our applicant tracking system and Zoom Scheduler for HR screen request scheduling. At times, your email may block our communication with you. Please be sure to check your SPAM folder so that you don't miss updates on your application.

Why GuidePoint?

GuidePoint Security is a rapidly growing, profitable, privately-held value added reseller that focuses exclusively on Information Security. Since its inception in 2011, GuidePoint has grown to over 1,300 employees, established strategic partnerships with leading security vendors, and serves as a trusted advisor to more than 6,200 customers.

Firmly-defined core values drive all aspects of the business, which have been paramount to the company’s success and establishment of an enjoyable workplace atmosphere. At GuidePoint, your colleagues are knowledgeable, skilled, and experienced and will seek to collaborate and provide mentorship and guidance at every opportunity.

This is a unique and rare opportunity to grow your career along with one of the fastest growing companies in the nation.

Some added perks….

Remote workforce primarily (U.S. based only, some travel may be required for certain positions, working on-site may be required for Federal positions)
Group Medical Insurance options: Zero Deductible PPO Plan (GuidePoint pays 90% of the premium for employees and 70% for family plans (spouse/children/family) or High Deductible Health Plan with HSA (GuidePoint pays 100% of the employees premiums and 75% for family plans (spouse/children/family). If you choose the High Deductible / HSA plan, GPS will contribute in 4 equal quarterly installments: ($850 per EE annually / $1750 per family annually (includes spouse/children/family options)
Group Dental Insurance: GuidePoint pays 100% of the premium for employees and 75% of family plans
12 corporate holidays and a Flexible Time Off (FTO) program
Healthy mobile phone and home internet allowance
Eligibility for retirement plan after 2 months at open enrollment
Pet Benefit Option