Winner of the HERImpact Pitch competition, Stephanie Cummings tells why she created this masterful app, designed to make everyday tasks a breeze so we can make time for the things that matter. 

Stephanie Cummings, co-founder and CEO of Please Assist Me realized that her work-life balance wasn't so balanced while working at a Fortune 500 company—and she wasn't the only person who felt this way. Cummings observed working mothers in her office, forced to choose between their careers and their personal lives, many of them leaving their jobs after having children. 

About 83 percent of workers in the United States experience work-related stress, which could be a result of a poor work-life balance. Another report shows that the same percentage of workers that are stressed about work also consider work-life balance to be the essential factor in evaluating a potential job. Work-life balance is necessary, but it's not often obtained.

Cummings describes a piece of her balancing act with home and work as "killing it in the office, but pieces of home were suffering." Dishes in the sink, an empty fridge, loads of laundry, and a growing to-do list—does any of that sound familiar? But she was able to create a solution through Please Assist Me (PAM), a household management app for apartment residents.

This is how PAM works—residents can go on the app to hire a personal home assistant to complete tasks from grocery shopping, laundry, house-cleaning, Goodwill drop-offs, seasonal services like gift-wrapping, and more. This service is useful for those who need a personal assistant without paying the price for a full-time assistant. 

Please Assist Me

Photo Courtesy: Jocelyn Burke

The mission and brand are simple—helping people make time for the things that matter. Cummings leads the business with a passion and enjoys hearing how her company has helped saved people time and allowing other areas of their lives to flourish. Some users have even said that the app has made them a better mom or saved their marriage. Trust is also a critical component of the PAM brand; that's why each personal home assistant wears a body camera while completing tasks in the home for transparency. Employees are also insured for $1 million per visit and must complete a background check. 

Since the company's launch in 2017, the company has won big in pitch competitions. Cummings took home 25,000 as the first-place winner at the HERImpact Pitch competition this past September during D.C. Startup Week, and in the same week, won another 20,000 grand prize at the Vinetta Project 2019 Venture Challenge. The secret sauce to Cumming's pitches is practice. She credits her pageant experience as Miss Chattanooga 2015 and communication resources like Toastmasters for improving her public speaking skills. Her advice for owning presentations is to be present, have an elevator pitch ready, and practice in front of the mirror often.


Photo Courtesy: Jocelyn Burke

The company has seen much growth since its inception and now partners exclusively with selective apartment complexes in Nashville, Tennessee, and Washington, D.C. Before offering services to apartment complexes, Cummings admits to spending a lot of time in her car traveling to meet the needs of her clients. Her new business model has pulled her into Washington, D.C., as many of her clients are headquartered there.

As of January of 2019, PAM made the nation's capital its headquarters and currently serves Bozzuto properties in Dupont and Shaw neighborhoods. Cummings and her co-founder, who is also her husband and accountability partner, feel very welcomed in D.C. She shares that their marriage is their superpower when it comes to doing business together. They appreciate D.C.'s advocacy for the startup culture as well as its diversity.

"It's not uncommon to see a minority business owner or CEO in D.C.," says Cummings. She describes that as rewarding and believes it to be an opportunity to open doors for other minority business owners. However, she did not always experience this. 

Entrepreneurship can be rewarding, but it also comes with its fair share of challenges. Cummings shares that in the beginning, it was hard to be taken seriously, and she was often underestimated, but one piece of advice she shares is to always "keep moving forward." Understanding the complexities of entrepreneurship, she encourages entrepreneurs to expand their network by attending events, setting up coffee dates to ask the right questions of potential mentors, and taking advantage of resources. She recommends seeking out accelerator programs like Backstage Capital to assist with business planning. 

Since Cummings and her team are committed to making the lives of others less stressful, it's only fair that she would use her own service, but ironically enough, her location doesn't yet qualify for Please Assist Me. However, she's still finding a work-life balance of her own, starting with a weekend getaway to Miami. But more than quick trips and extended downtime, Cummings shares that it's important to understand that our work is a marathon—and not a sprint.  

Milenkovic, M. (2019, September 9). Job Satisfaction Statistics: Keep Your Workers Happy and Your Business Healthy. Retrieved from
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