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Automation startup relocates from SF to Chicago and raises $5M


Alex Headshot v3 (1)
Thoughtful Automation CEO Alex Zekoff
Thoughtful Automation

A software firm that helps companies automate business processes like payroll and data entry has relocated to Chicago from San Francisco and raised $5 million in new funding.

Thoughtful Automation announced the fundraise Thursday, which was led by Columbus-based Drive Capital. The startup, founded in 2020, relocated from San Francisco this month and has set up shop in Chicago's West Loop neighborhood. 

Led by CEO Alex Zekoff, Thoughtful Automation creates software that helps companies automate mundane and repetitive tasks like invoice processing, financial transactions and payroll processing. Specifically targeting middle-market firms that traditionally haven't been able to afford automation technology, the startup aims to provide a cost-effective solution to automating specific tasks and workflows.

The company says its tech is helping businesses that are struggling to fill back office roles automate work, while also freeing up staff to focus on higher value tasks. Its customers include companies in health care, legal and financial services industries.

Thoughtful Automation currently has 20 employees and expects to grow to around 40 by early 2022.



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