134 | Massachusetts Wage & Hour Peculiarities, 2025 ed. © 2025 Seyfarth Shaw LLP business of providing dispatch services).774 The Court observed that the medallion owners’ and radio associations’ businesses were “not directly dependent on” the drivers’ services.775 Accordingly, the companies at issue satisfied the second prong. However, in another case, the Appeals Court held that newspaper delivery drivers performed services within the usual course of business where the company described itself as being in the business of “publishing and distributing” newspapers and was “directly dependent on the success of the drivers’ endeavors.”776 Decisions interpreting the meaning of “usual course of business” under the second prong of the Independent Contractor Statute reflect the complex and fact-intensive nature of the issue. For example, the Appeals Court held that a software engineer could be found by a jury to perform services within the usual course of business of a financial services company that managed and invested client funds because the company “publicly advertised the vital role played” by technology workers such as the plaintiff to the success of its business.777 Another court held under the facts of one case that the services of delivery drivers were within the “usual course of business” of a delivery company.778 In reaching that conclusion, the court gave deference to the Attorney General’s interpretation of “usual course of business” in the 148B Advisory and also focused on the manner in which the company held itself out to the public.779 By contrast, in another case decided in the District of Massachusetts, the court held that an insurance agent who sold insurance products performed services outside the “usual course of business” of an insurance company with a primary business function of structuring and drafting insurance products.780 The court drew a distinction between the creation or “manufacture” of insurance products and the sale of those products, concluding that although sales are a critical function to any manufacturing business, that does not make sales the usual course of a manufacturer’s business under the Independent Contractor Statute.781 Even within particular industries there have been mixed decisions regarding the “usual course of business” prong.782 774 Sebago, 471 Mass. at 333-36. 775 Id. at 334, 335. 776 Carey v. Gatehouse Media Mass. I, Inc., 92 Mass. App. Ct. 801, 805, 810 (2018) (quoting Sebago, 471 Mass. at 334). 777 Weiss, 97 Mass. App. Ct. at 9-10. 778 Martins v. 3PD, Inc., Civ. No. 11-11313-DPW, 2013 WL 1320454, *13-17 (D. Mass. Mar. 28, 2013). 779 Id. at *14 (holding that the company hired delivery drivers “for a vital and necessary aspect of the business” and “h[eld] itself out as a delivery company” through its advertising and marketing materials, such as its website). 780 Ruggierro v. Am. United Life Ins. Co., 137 F. Supp. 3d 104, 118 (D. Mass. 2015) (stating “I agree with the defendants that providing information about and fashioning a product one manufactures is not the same as being in the business of directly selling it.”). 781 Id. at 119; see also Valle v. Powertech Indus. Co., Ltd., 381 F. Supp. 3d 151, 167 (D. Mass. 2019) (distinguishing Ruggiero and holding that the plaintiff salesman performed services in the usual course of the defendant manufacturing company’s business, because the defendant “was involved in directly selling its products through its internal sales division”, which included employees who performed sales services similar to the services provided by the plaintiff). 782 Compare Depianti v. Jan-Pro Franchising Int’l, Inc., 39 F. Supp. 3d 112, 127-29 (D. Mass. 2014) (finding that a company satisfied the second prong where its “usual business was establishing a trademark and cleaning system that was then licensed to regional franchisees” who, in turn, sold and provided the actual cleaning services.”) with Awuah v. Coverall N. Am., Inc., 707 F.
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