This is our monthly feature where we recap the biggest tech hires in Chicago over the past month. Want daily updates on personnel moves, fundings and other Chicago tech news? Sign up for our daily newsletter The Beat

SMS Assist

SMS Assist, a cloud-based multisite property management company and one of Chicago’s “unicorn” tech companies valued at $1 billion or more, announced it has hired Taylor Rhodes as its new CEO. Rhodes was previously the chief executive at Rackspace, a cloud computing company. Rhodes is also a former US Marine Corps infantry officer.

Trunk Club

Trunk Club, the Chicago-based personalized style service, announced it has hired Candice Savino as its new vice president of engineering. Savino comes to Trunk Club after spending 5 years at Groupon, where she was most recently senior director of engineering. She’s also worked at Encyclopedia Britannica and IBM.


Sittercity, a platform that connects parents with babysitters and other childcare providers, announced Elizabeth Harz has been hired as its newest CEO. Harz was previously CMO at marketing insights company Adara, and has held leadership positions at Chegg, Electronic Arts, Yahoo and CNET. Sittercity also announced it hired Sandra Dainora to be senior vice president of product. She was previously senior director of product at Grubhub.

UI Labs

UI Labs announced that it has hired Brenna Berman as the executive director of City Digital, UI LABS’ urban innovation program. Berman was previously the chief information officer for the City of Chicago, where she helped launch the Array of Things project, among other initiatives.


VillageMD, a Chicago-based health tech startup, announced it has hired Brent Asplin as its chief operating officer. Asplin was most recently chief clinical officer for Mercy Health, a hospital system across Ohio and Kentucky.


Savo, a provider of enterprise-grade sales enablement solutions, announced it has hired Jeremy Schultz as executive vice president, strategy. Schultz previously held leadership positions at Office Max and Dex Media. Savo also announced that it has hired Chad Greeley as senior vice president, North American sales. Greeley previously led sales teams at Monster, Information Builders, Automic Software and IBM.

Peanut Butter

Peanut Butter, a Chicago-based startup that allows companies to provide student loan repayment as an employee benefit, has hired Marci McCalmon as VP of Customer Success. Marci previously served as VP of operations at Chicago startup Rippleshot. announced it has named Jennifer Newman as its editor-in-chief. Newman has been with for nine years in various editorial roles, and previously worked at the Chicago Sun-Times, Boston Herald and The Times of Northwest Indiana.


Ensono, a Downers Grove-based hybrid IT services provider, announced it has hired Jason Deck as vice president of Hyperscale Cloud products and marketing. Before joining Ensono, Deck was senior vice president of strategy at Logicworks, and also spent time at Cisco Systems, Brocade Communications and Equinix.