Smart Benefits: How to Ready Your Org for the Gig Economy

Monday, March 05, 2018
Rob Calise, GoLocalWorcester Business/Health Expert

From professional services to computer programming, a growing number of workers are opting out of traditional career paths to carve out their own schedules and assignments, and can be a big benefit to companies who don’t want to – or can’t – justify employing a full-time worker. But whether you want a freelancer for specialized help for a specific project or as ongoing talent, there are steps you can take to optimize the relationship:

  • Set clear expectations. Be sure to draft a detailed description of the work that includes defined objectives, milestones, deliverables and timelines. And let the freelancers know their point person for any questions or ideas and where they’ll get the information they need for their work.
  • Anticipate technology Needs. From file sharing and remote access to your company’s systems, it’s important to determine what the freelancers will need from a technology standpoint and ensure it’s effective and secure before they start.
  • Ensure compliance. Know the difference between an independent contractor and employee and make sure you classify workers correctly. Remember to secure a W-9 from each freelancer and be sure you send a 1099-MISC form to each that you pay $600 or more throughout the year.
  • Pay. Decide upfront whether you’ll pay freelancers at an hourly rate or on a fixed project cost with payments at pre-set milestones. And determine the frequency of invoicing and the payment terms so everyone’s on the same page in terms of expectations.
  • Maintain the Organizational Culture. With freelancers, it can be challenging to maintain your desired culture so be sure to keep your vision and values in mind when hiring candidates. It’s also important to effectively onboard freelancers and make sure they feel part of the team.
  • Sign an Agreement. Some companies opt to protect their engagements with contractual terms that are spelled out in an agreement signed by both parties. In addition to outlining the scope of work, payment terms, and ownership of the work product, the contracts often include clauses on confidentiality as well.


Utilizing freelancers can help you remain agile, focus on your expertise, and optimize your team’s resources. Just be sure you make the most of the opportunities by establishing the right structure from the start.

Rob Calise is the Managing Director, Employee Benefits of The Hilb Group of New England, where he helps clients control the costs of employee benefits by focusing on consumer-driven strategies and on how to best utilize the tax savings tools the government provides. Rob serves as Chairman of the Board of United Benefit Advisors, and is a board member of the Blue Cross & Blue Shield of RI Broker Advisory Board, United HealthCare of New England Broker Advisory Board and Rhode Island Business Healthcare Advisors Council. He is also a member of the National Association of Health Underwriters (NAHU), American Health Insurance Association (AHIA) and the Employers Council on Flexible Compensation (ECFC), as well as various human resource associations. Rob is a graduate of Bryant University with a BS in Finance 


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