Thoughtful Automation Raises $5 Million Seed Round to Automate Soul-Crushing Work and Improve Employee Happiness for Mid-Market Companies

The first and only cost-effective, scalable, and intelligent business automation solution for the middle market

Thoughtful Automation, the first and only cost-effective automation-as-a-service platform for mid-market companies, announced a $5 million Seed funding round. The round was led by Columbus-based venture capital firm Drive Capital.

Thoughtful Automation provides mid-market companies with a digital workforce management platform that offers customization, implementation, and continued monitoring and optimization of digital workers (or “bots”). As companies across the healthcare, legal, and financial services industries continue to grapple with labor shortages and decreasing employee satisfaction with manual work, Thoughtful Automation’s digital workers provide a much-needed boost to companies struggling to fill back office roles while also freeing up staff for higher value and more fulfilling work.

HR Technology News: Jimmy John’s Leverages DailyPay for Competitive Edge in Hiring and Retaining Employees

“Digital workers are transforming large enterprises, but until now, mid-market companies have been priced out,” said Alex Zekoff, cofounder and CEO of Thoughtful Automation. “Thoughtful Automation helps mid-market companies rapidly introduce digital workers, becoming more productive and freeing up staff for more engaging and higher value work. The platform is easy to use and has a fast onboarding experience with 300% return on investment in the first year alone.”

With Thoughtful Automation’s platform and digital workers, mid-market companies can:

  • Accelerate Growth: Companies can launch digital workers in just a few weeks and at a fraction of the cost compared to legacy automation providers. Instead of four to six months, Thoughtful Automation digital workers get to work in a matter of weeks.
  • Increase Efficiency: Thoughtful Automation’s intelligent automation technology builds customized digital workers for healthcare, legal, behavioral health, and other industries featuring repetitive back office responsibilities, like processing invoices, payroll, data entry, financial transactions, and more. Its digital workforce management platform monitors bot performance over time while optimizing performance and eliminating human error.
  • Reduce Fixed Costs: Because back office work is automated, businesses can expect to reduce overhead costs by up to 66%. Clients also enjoy low or zero implementation fees and businesses pay monthly based on their unique service needs.
  • Improve Quality Control: Because it’s built on Thoughtful Automation’s cloud-based digital workforce management platform, business processes, documents, workflows, digital worker automation rules, and more are all updated instantly, and include a track record of changes.
  • Increase Employee Satisfaction and Productivity: Digital bots handle mundane tasks and work alongside human employees, removing the drudgery of routine and empowering human workers to do more fulfilling and creative work.

HR Technology News: HR Technology Highlights – HR Tech Daily Round-Up For 24-Sep-2021

“Ultimately, our vision is to open our platform to other automation developers. We want to build trust and transparency between humans and their digital co-workers,” added Zekoff.

The seed funding will be used to expand Thoughtful Automation’s platform and further develop offerings and capabilities to support business automation for middle market companies. The company also recently relocated to Chicago’s West Loop neighborhood from San Francisco.

“Software automation is an entirely new category of work, and just like the traditional work done by people, work handled by software needs to be managed and optimized,” said Nick Solaro, Partner at Drive Capital. “Thoughtful Automation understands this new work paradigm and their solution is making software automation accessible, affordable, and easy to deploy for mid market companies.”

HR Technology News: New Workforce Development Book Provides Solutions to Fill 10-Million Open Jobs

To share your insights with us, please write to