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Benefits Specialist

Tampa, FL

ConnectWise is an industry and Global leading software company with over 3,000 colleagues in North America, EMEA and APAC. As a community-driven software company dedicated to the success of technology solution providers, our suite helps over 45,000 of our partners manage their businesses better, sell more efficiently, automate service delivery, and remotely control technology so they can consistently deliver amazing customer experiences.

Our company is powered by our connections, our colleagues, and our community. And, we accept all kinds.

Game-changers, innovators, culture-lovers—and humankind.

We invite discovery and debate. We recognize key moments as milestones.

We see you and value you for your unique contributions. Our inclusive, positive culture lays the foundation to ensure every colleague is valued for their perspectives and skills, giving you the choice of how YOU make a difference.

Curious? Read this opportunity to learn how YOU can make a difference at ConnectWise!

 

 

General Summary:

The Benefits Specialist is responsible for administering and managing our colleagues’ benefits and retirement 
programs. This role works in partnership with cross-functional teams to provide our colleagues with guidance and 
support in all areas of benefits.

Essential Duties and Responsibilities:

• Provides support to the Human Resources team, with a high attention to detail
• Researches, analyzes, and documents findings
• May influence others within the Human Resources team through the explanation of facts, policies, and 
practices
• Oversees and administers the benefits program including medical, dental, and vision insurance, 401(k) 
plan, flexible spending accounts, long and short-term disability, supplemental life insurance, accident and 
critical illness insurance, and the employee assistance program
• Provides support in areas of 401(k), payroll, workers’ compensation, FMLA, ADA, and OSHA recordkeeping
• Complies with provisions of COBRA, HIPAA, SOX, ERISA, and ACA and oversees mandated reporting to 
appropriate agencies
• Maintains knowledge of legal requirements and government regulations affecting human resources 
functions
• Ensures policies, procedures, and reporting are in compliance
• Maintains employee confidence and protects operations in keeping all data confidential
• Administers open enrollment for health and life insurance enrollments and changes and processes
retirement applications
• Provides guidance, consultation, and assistance to managers, supervisors, and colleagues on coverage, 
suspension of benefits, dual coverage, loss of coverage, plan changes, enrollment requirements, etc.
• Assists in formal training sessions, orientations, and retirement seminars for colleagues concerning 
benefits programs and changes that occur
• Manages broker relationships
• Supports in identifying and implementing benefit trends to engage and motivate colleagues
• Conducts benefit plan non-discrimination testing
• Conducts annual benefits survey to ensure colleague engagement
• Evaluates the efficiency and value of current benefit programs and makes recommendations for 
improvement
• Reports on benefit utilization quarterly
• Oversees wellness program and wellness committee
• Leads, implements, and administers annual open enrollment through strong communication and ongoing 
support to colleagues

Knowledge, Skills, and/or Abilities Required:

To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

• Ability to work independently on projects and processes with general supervision
• Practical knowledge of applicable work area
• Ability to situationally adapt and understand new technology/processes as per business requirement
• Proficient in Microsoft Office products
• Proficient in Human Resource Information Systems and payroll systems
• Strong analytical and communication skills
• Ability to build and deliver reports 
• Ability to maintain confidentiality
• Strong knowledge of applicable state and federal regulations (ERISA, FMLA, Section 125, ACA, etc.)
• Ability to remain organized and prioritize work in a fast-paced environment
• Ability to consistently meet important deadlines
• Knowledge of benefit plan summary data with ability to translate plan summary information to define 
eligibility and enrollment rules

Educational/Vocational/Previous Experience Recommendations:

• Bachelor’s degree in related field or equivalent business experience
• 2+ years of relevant experience
• Preferred: Experience working with compensation
• Preferred: Experience with international benefits administration
• Preferred: Certified Employee Benefits Specialist (CEBS) certification

Working Conditions:

• 3x/week in Tampa HQ or Pittsburgh Office, depending on location
• 0-10% travel may be required

 

ConnectWise is an Equal Opportunity Employer, dedicated to building a diverse and inclusive workforce and providing a workplace free from discrimination and harassment. ConnectWise provides equal employment opportunities to all employees and applicants without regard to race, ethnicity, color, religion, age, sex (including pregnancy), sexual orientation, gender, gender identity or expression, ancestry, national origin, citizenship status, physical or mental disability, genetic information, military/veteran status, marital status, familial or parental status, or any other characteristic or status protected by applicable federal, state and local laws.

The statements above are intended to describe the general nature and level of work being performed by individuals assigned to this job. Other duties may be assigned as needed. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions of the job and/or to receive other benefits and privileges of employment. If you need a reasonable accommodation for any part of the application and hiring process, please contact us at talentacquisition@connectwise.com or 1-800-671-6898.

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