The Players Who Win Put Their Employees First: An Interview with Please Assist Me’s Co-Founder and CEO, Stephanie Cummings
Please Assist Me offers a personal home assistant at your fingertips. Residents can come home to everything done, freeing them up for what really matters. Partner properties can provide personalized service for modern living. Learn more at https://www.pleaseassistme.com/.
Please Assist Me was a finalist at the Black New Venture Competition. Learn more about the BNVC here.
Stephanie Cummings is Please Assist Me’s co-founder and CEO.
HBS Entrepreneurship Club: Did you always know you wanted to be an entrepreneur?
Stephanie Cummings: No. *laughing* I didn’t know what I wanted to do. I was working a 9–5 corporate job but knew that wasn’t a true fit for me. I know that I wanted to “rule the world,” but I didn’t really know what that path would look like.
HE: In that case, how did starting your business come about?
SC: Please Assist Me came from a personal need — I was the one that needed help around the house. And it really hit me when I started seeing female colleagues leaving the workforce. I don’t have kids yet, and I didn’t at that time, but I was wondering, how do women do this? And I realized, a lot of women don’t. They experience burnout, or maybe they don’t go for the promotion. They really start sacrificing their careers for family, because obviously family is more important. I really started thinking about why women have to play this sacrificial role. Obviously there are larger things at play, like gender roles and parenting — there are all these dynamics that we didn’t have fifty years ago.
I really wanted at first to create a solution for working, busy, female professionals to stay in the workforce. But as we got started we realized this wasn’t just exclusive to females — home management is actually stressing everyone out. Now we’re probably 50/50 in terms of serving male and female clients. We see ourselves as a source of helping people find work/life balance. Sometimes people say oh work life balance is a myth, but it’s a myth because there aren’t solutions that you have found that really make it work for you. We find that a lot of our clients have a real lifestyle change…it makes things so much easier, and when you put those things in place, work/life balance becomes more of a reality.
HE: What made you decide to take the leap and actually create Please Assist Me, when you did?
SC: I was at a start-up that got acquired. I was working with the parent company at the time, and I started realizing — to be totally transparent — where the corporate job would take me, and what the limits of that would be. Like I was starting to climb the ladder, and I saw that it would be lucky if I made VP, or a C-suite position, and that would come with a lot of work. And the company I was at, I saw that they had no minorities in the C-suite, no minorities in a VP position.
If I had stayed I would obviously be working really hard and to me, I wondered: do I want to spend the next forty years of my life climbing the corporate ladder? Or do I want to set off and try to start something? At the time I was only twenty-seven, so I thought if I wanted to do it, I had to do it now, before I got too serious at work and couldn’t go back, before I had kids or all these other commitments. So I kinda took the plunge. I thought, I don’t want to live with regret. I don’t want to later think I wish I could have tried it. So instead here we are — I thought let’s just do it, see where we land, and it’s definitely been a great ride so far.
HE: What’s the most fun part of running your company?
SC: My husband is my co-founder, so I think the most fun part is that we run it together. I definitely think it’s strengthened our marriage, and it’s our superpower because we wake up talking about Please Assist Me and we go to sleep talking about Please Assist Me. Some people think that’s not healthy but honestly you are married to your cofounder — people use that analogy a lot. I think it actually helps because I’m not worrying about whether he took this the wrong way, or what his true opinions are. We’re both 100% all-in to this, and I think that it’s been so transformative for our relationship, and so transformative for the business because we’re 100% on the same page. It just makes things go faster and easier.
Sometimes it scares away investors, but with cofounders breaking up as much as they are, wouldn’t you want to support cofounders who’ve made a commitment to each other beyond just what the business offers? We also see ourselves as life partners and we want to grow together in each part of our lives. And when you have that kind of working relationship it just makes it — I don’t know, for us we see it as a superpower.
HE: On the other hand, what’s the hardest part?
SC: The hardest part has been…hmm. Throughout my life, I’ve always succeeded at school, graduated with honors, been valedictorian…so I’ve always been at the top, so I came with this mindset that if I work hard enough and always put my best foot forward, and I’m always the best in every situation, then that will be recognized by investors. But I’ve found that there are just obstacles that come with being African-American and female, in tech…that show up, in every situation going in.
Someone once asked me, is it harder being African-American, or harder being female? And it depends where you are. But I always will find that either a male, or a Caucasian, will always end up in the end with the investor conversation, for things that people can’t explain. And it’s 100% that people are attracted to people who look and think like them. A lot of female investors may not be used to minorities, so when you approach them, there’s still a disconnect; or a lot of minority investors are still male, so there’s sometimes a disconnect. So our biggest backer is Arlan Hamilton, who happens to be an African-American female. It clicked with her because I think there’s just synergies there. But there’s not that many Arlans, right, in the world?
So realizing that being the best and working the hardest is not always going to be enough. Being okay with that, and understanding that I’m going to have to create my own path, and accepting that if no one gives this to me it’s fine. That’s been the hardest. There’s still so much bias — and it’s not just bias, when it comes to start-ups, there’s just so much uncertainty that people more often than not lean back on something that’s close to them or that they can easily understand, versus purely on logic. So again it’s not just about going in, being the best, and being the most prepared. There are particular challenges to being an African-American female founder in tech, and that’s been hard to wrap my head around.
HE: Please Assist Me has to balance working with partners (the properties) and also hiring and training the employees who provide the service to residents. How do you navigate all your different stakeholders?
SC: It is a people-intensive business. And there’s a trend right now in business, like Uber and Lyft, to label employees as 1099’s because they’re gig economy workers. But I think we have a unique proposition in that we focus on the trust component, we focus on being in people’s homes, and I just don’t think that’s an avenue where 1099 is appropriate. So we do have W-2 part-time employees.
I think that even just labeling them W-2 employees instead of 1099, there’s this sense of trust and understanding in our employees, that means they’re really part of the PAM-fam. 100% of our employees are female or minorities. So we almost see ourselves as job trainers, where we’re providing W-2 part-time work for people who maybe aren’t comfortable doing Uber driving, or maybe don’t feel comfortable doing Postmates or whatever it might be. Maybe you’re looking for dedicated work in between the hours where your kid goes to school, or maybe you’re looking after an elderly parent. These types of jobs are slipping away, so we pride ourselves on being a job provider. We know our PAMS can be a resource. They’re always looking for creative ways for us to be better, go faster, be more efficient, serve clients better. They really are our front-line, so we really lean on them, as we grow, to make the best decisions for our company. They’re really part of our team
We always look first for cultural fit. We can teach you how to clean. We do look for people with cleaning experience or personal assistant experience, but searching for cultural fit and finding the right person matters. Maybe it’s the overqualified candidate that people haven’t given a chance, or the emerging student who is looking for work. Whoever it might be, it depends on cultural fit, and then teaching them to build the skills necessary. We’re very big on promoting from within. PAMS can become Lead PAMS, become Territory Managers…there’s a lot of space to grow, even if it’s part-time.
We want to provide resources for people to grow. We never want to treat our hourly workers like second-rate employees. I believe the players who win, especially in the home services space, are those who put their employees first. And I think we see that especially in our clients who sign up for our weekly bundle — they stay with us until they move. We have amazing cohort engagement statistics. We have a whole different mechanism to allow us to move forward, and that’s our focus on people.
HE: How do you go about determining that culture fit for your PAMS?
SC: It’s a multi-step process. It starts with submitting the applications online. We start looking at things like how you reply with emails, whether you’re timely. Then the next step is we ask people to schedule a block of time on Calendly for a virtual interview. And you’d be surprised at how many people actually drop off at that stage because they didn’t take the initiative to block off their time at that point. And then we do a virtual interview on the phone, with our Chief of Staff, where she digs into your experience, and who you are. Then we do an in-person interview, usually with me or one of the other founders. We drill into your strengths and criticisms, what attracted you to Please Assist Me, what do you already know about it — that kind of stuff.
Lastly we have a trial, in the apartment, where we see if it’s a good fit for you and for us, and we have a scorecard. Beyond that, there’s an intense trial period of 90 days where we constantly check in on progress and training, at the 30-day mark, 60-day mark, and so on. By the time we go through this whole process, we should be 100% sure if they’re a good PAM or not. Some people say that’s a lot to do for part-time employees. But I think if you hire smart, then you won’t have churn down the road. Because you did the steps on the front-end to make sure that you’re choosing the right people. I think if you spend a lot of time making sure that they’re a good fit, then they’ll stay with you. And we have PAMS that have been with us for 6 months, 12 months, for two years — since we started. So that’s something that’s very important to us.
HE: If you think back to when you were starting this company, or any difficult time, what’s advice that you wish you knew back then?
SC: Number one: this truly is a marathon. Number two would be, focus on building a great company, not getting investment. At the end of the day, if you build a great company, the investors will come to you. I think a lot of people raise a lot of money and then two years later they’re out of business. Sometimes they scale too quickly. Building a great company, building a framework that can be repeatable, can also be scalable — spend the time on the front-end to make it good, then the capital will come to just put fire into something that’s already working. That can work better than putting capital in early, when you don’t have everything ironed out.
This article was written by Isabel Yap from the Harvard Business School Entrepreneurship Club. Special thanks to Tyler Simpson of the Harvard Business School African-American Student Union for her help in preparing the article.
