Square paid $8 million for a super star tech lawyer, then she stepped down after 16 months on the job

SquareFormer Square General Counsel Hillary Smith, left, and CEO Jack Dorsey
  • Hillary Smith has stepped down from her general counsel role at Square.
  • Smith, who led Zenefits through a period of legal turmoil, joined Square in November 2016.
  • Smith made $US8 million for her first two months of work.
  • She is replaced by a five-year veteran of Square and a key member of the team the helped launch bitcoin trading on the Cash App.

Just 16 months after joining the $US22.5 billion payments company Square as General Counsel, Hillary Smith stepped down from the role.

Smith, who joined Square in 2016 with a rich $US8 million compensation package, officially resigned on March 18. She’ll stay on as an employee at the company through September to manage the transition.

It’s unclear why Smith is stepping down. She did not respond to a request for comment and Square would not provide details about the change in its top legal post, which will be occupied by Sivan Whiteley.

But whatever the reason, the lawyer swap puts an executive familiar with bitcoin into a key role at Square just as the company pushes deeper into the cryptocurrency market, and as other companies like Facebook launch their own blockchain efforts.

Square CEO Jack Dorsey’s has acknowledged that the company’s decision to support bitcoin in its product was contentious within the company. Whiteley’s promotion could signal the company’s commitment to digital currencies.

Square first announced Smith’s resignation in a public filing on March 2 but little has been reported about the change.

Smith, a veteran of Yahoo! and SAP’s SuccessFactors, joined Square in November 2016 from the top legal role at Zenefits. She had been brought in at Zenefits in July 2015 in the midst of chaos at the company. Though once valued at $US4.5 billion, the company faced ostracization from the payroll application ADP, missed its revenue goals and was accused of having insufficient regulatory compliance. Zenefits founder and former CEO Parker Conrad resigned in February 2016.

Smith’s replacement is a Square veteran and expert in tech law

SquareSivan Whiteley is Square’s new general counsel.

Whiteley has held senior roles on Square’s legal team since 2013, and was a key member in Square’s bitcoin project, which launched in January.

A graduate of Harvard Law, Whiteley was actually already co-general counsel on an interim basis from August 2016 until Smith was hired, after the company’s first-ever lawyer Dana Wagner vacated the role.

Wagner eventually landed at Impossible Foods, the company behind the veggie burger that bleeds. But his departure from Square was a turning point for the company. He was the first executive to leave Square after its initial public offering.

Like Smith, Whiteley has spent time in-house across the tech industry – first at eBay, and then at an electric car battery compay called Better Place.

While at Square, she helped the company launch several key projects including merchant cash advances and bitcoin trading on the Cash app.

Square made $US34.1 million in revenue from its bitcoin product in the first quarter – compared to its $US14.4 million in hardware revenue and $US523 million in transaction revenue. But launching the bitcoin product cost the company $US33.9 million, according to its first quarter earnings.



Read more about the lawyers helping companies navigate the wild world of cryptocurrency.

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