Ann Gillespie, Director of the Illinois Department of Insurance. | LinkedIn / Ann Gillespie
Ann Gillespie, Director of the Illinois Department of Insurance. | LinkedIn / Ann Gillespie
The Illinois Department of Insurance (IDOI) has declined to respond to interview requests from Prairie State Wire regarding Rippling Insurance Services’ insurance sales license and its founder Parker Conrad’s undisclosed disciplinary history in Illinois regulatory filings.
Recent investigations by Prairie State Wire reveal discrepancies in Rippling’s disclosures to Illinois regulators in 2017 and 2019 when the company was doing business under the name Waveling Insurance Services.
Before founding Waveling Insurance Services, Conrad resigned from Zenefits in 2016 after revelations that employees used software to circumvent licensing requirements, leading to regulatory actions and a settlement in California requiring him to surrender his license and pay $66,000.
Despite this, Rippling’s Illinois applications answered “no” to questions about any administrative penalties involving company leadership.
While the company acknowledged in Tennessee that Conrad had previously surrendered his insurance license and paid fines related to violations during his leadership at Zenefits, these facts were omitted in nearly identical Illinois filings.
Additionally, a December 2017 California application listed Conrad as a “controlling person” owning 60% of the company, contradicting statements made in other states that downplayed his role.
In light of these inconsistencies, Prairie State Wire sought answers from the IDOI on whether the department was aware of Conrad’s disciplinary history at the time of licensing, whether it has reviewed the company’s disclosures, and how it handles potential misrepresentations in multi-state filings.
The IDOI, however, has thus far refused to provide any comment or response to inquiries from Prairie State Wire on the matter.
This refusal to engage raises concerns about regulatory transparency and enforcement, especially as Rippling faces a lawsuit from its competitor Deel, alleging ongoing deceptive practices including misappropriation of client payroll tax funds.
Rippling’s Illinois license has remained active since 2017 despite these unresolved questions.
Ann Gillespie, a former state senator with a background in health insurance and management, currently serves as director of the Illinois Department of Insurance.