The Tennessee Department of Commerce and Insurance (TDCI) has refused to respond to an interview request regarding its 2017 licensing of Rippling Insurance Services despite growing scrutiny over the company’s inconsistent disclosure of founder Parker Conrad’s disciplinary history.
In 2017, Rippling (formerly known as Waveling Insurance Services) disclosed to Tennessee regulators that Conrad, who previously resigned as CEO of Zenefits amid a high-profile compliance scandal, had been subject to regulatory penalties and settlements tied to his role at the company.
However, Rippling withheld similar details in its application with the Illinois Department of Insurance.
The filing included detailed admissions about Conrad’s past, including a $66,000 settlement with the California Department of Insurance, in which he surrendered his insurance license, and a $35,000 fine from Texas stemming from unlicensed insurance sales during his tenure at Zenefits.
A letter submitted at the time by a Waveling executive disclosed Conrad’s regulatory background but noted that he held no official role at the company.
This contrasts sharply with Rippling’s filings in Illinois just one month earlier, and again in 2019, where the company answered “no” to questions about whether any company leaders had been subject to license revocation, surrender or administrative penalties.
In an effort to clarify Tennessee’s stance on Rippling’s license, Volunteer State News submitted a formal interview request to the TDCI earlier this month, seeking comment on how the department evaluated Rippling’s 2017 disclosures, whether the discrepancy with Illinois filings was noted at the time, and whether any reassessment has occurred in light of recent litigation and renewed media attention.
The agency declined to respond.
As regulators remain silent, questions persist about the strength of the multi-state insurance licensing process and whether companies like Rippling are taking advantage of its weaknesses by selectively disclosing material facts.
Critics argue that such inconsistencies not only undermine public trust but expose potential weaknesses in how state insurance regulators vet applicants and communicate across jurisdictions.
Rippling’s licensing controversy has resurfaced as the company faces a lawsuit from competitor Deel, Inc., which accuses Rippling and Conrad of repeating past misconduct, including the misclassification of client payroll funds as company revenue.
The lawsuit alleges that the same lack of compliance that plagued Zenefits is now resurfacing under Conrad’s leadership at Rippling.
Despite these issues, Rippling’s insurance licenses in both Tennessee and Illinois remain active. Rippling has not publicly addressed the discrepancies in its regulatory filings, nor has it responded to questions from Volunteer State News.
The Illinois Department of Insurance has also declined to comment on the matter.
