DC Entrepreneur Combines High-Tech Savvy with Low-Tech Services for Big Success

Black and white profile headshot of Stephanie Cummings Stephanie Cummings


CEO and Co-founder of Please Assist Me

Washington, D.C.

I was working at a Fortune 500 company wondering: how do women do this? And then I realized, a lot of women don't. They may be killing it in the office, but home is suffering. Coming home to dishes in the sink, loads of laundry, an empty refrigerator is no fun.

"Whether we like it or not, women bear the burden of home chores. Work-life balance is a myth."

Cummings is not only a software developer with an MBA, she is a natural problem-solver. In 2017, she and her husband, Rashad Cummings, who has a background in property management, co-founded a company that uses both of their talents and puts the elusive work-life balance within reach.

Please Assist Me is unique in the extremely competitive in-home services industry. It's an easy-to-use app that gives customers a single point of contact for every home-management task—from cleaning the house and buying groceries to returning that Amazon item you wished you hadn't ordered. Customers use the app to order from a menu of services, and a PAM, a Please Assist Me employee, is assigned the work. All PAMs are W2 employees.

To give their business a kick start and leverage Rashad's property management expertise, the owners targeted apartment buildings. This allows the company to achieve economies of scale, keep costs down and pay employees higher than minimum wage, between $15 and $18 an hour.

"We consider ourselves the personal assistant for the 99 percent," Cummings said. "We provide an affordable service of complete home management without the cost of a full-time home assistant.

Stephanie Cummings speaks on stage with seated female watching

"Second, we have a hyper-focus on trust. Your home is your most sacred, and we work hard to gain and maintain that trust. Every customer is assigned a dedicate home assistant who is insured for over $1M per visit, background checked, and wears a body camera when they enter your home. We believe that by making trust a big part of our brand, people truly feel comfortable getting the help they need."

Indeed. After piloting the business in Nashville for about a year, the couple moved to Washington, D.C. in 2019. In those two years, Please Assist Me has grown from 300 to 2,000 units.

In Washington D.C., Cummings entered Please Assist Me in HI-HERImpact Pitch Competition for women social entrepreneurs and received a $25,000 grant from Ford Fund as the first-place winner among 170 applicants. HI-HERImpact is a joint initiative between Ford Motor Company Fund and 1863 Ventures, that helps women social entrepreneurs start and grow their businesses by providing business coaching and leadership development resources culminating in a presentation competition with financial awards.

Cummings won because her company aims to help those needing flexible, part-time employment that pays higher than minimum wage and makes them W2 employees eligible for benefits. Please Assist Me also focuses on providing affordable home services to low and middle-income earners.

Cummings used the Ford Fund grant as operating capital to hire more PAMs, expand marketing efforts and continually improve the technology.

Cummings has also helped other women entrepreneurs and shared her knowledge as lessons learned serving as a panelist at the HI-HERImpact Entrepreneurship Summit in Miami in 2019. Women entrepreneurs who are currently operating or have plans to start up a socially responsible business are encouraged to participate in the free events and pitch competitions as part of the HI-HERImpact program. Information on cities where HI-HERImpact will conduct its next competition can be found at https://herimpact.net.


HI-HERImpact is a joint initiative between the Ford Motor Company Fund and 1863 Ventures to help female social entrepreneurs scale their enterprises in order to increase their impact and long-term sustainability. HERImpact offers educational opportunities, technical assistance, mentoring, coaching, and financial resources, and its Entrepreneurship Summits and Pitch Competitions are designed to build community and provide investment in early and growth stage companies in the region. For more information, visit https://herimpact.net.