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Jennifer Cyphers of Pynwheel Tells Us How the Tour Application Engages Prospective Residents in a Unique Way

kokou adzo



Jennifer Cyphers Pynwheel

First of all, how are you and your family doing in these COVID-19 times? 

Jennifer Cyphers: Strange times, indeed! I feel very fortunate to have the ability to run my company from home with no inconveniences or interruptions, which has made things a little easier for my family and myself. We miss going to the theater, going to movies, traveling, and spending time with friends and family, but we’re grateful for what we have and for this opportunity to practice patience! 

Tell us about you, your career, how you founded Pynwheel.

Jennifer Cyphers: I have worked in marketing technology for real estate for the length of my career. I was an early hire at a couple of different start-ups, and, after helping them grow, I served the Director of I then spent some time consulting for marketing technology companies and brands entering the space, such as,, and Facebook Marketplace. Around the same time, I founded a company (Multifamily Edge, later called Engrain) to help multifamily companies with digital marketing strategies. I later split from that company and founded Pynwheel to standardize on-site tour technology for the industry. 

How does Pynwheel innovate? 

Jennifer Cyphers: We have a small team that allows us to stay loose and dynamic. We zoom in to focus on our strengths and zoom out to read the industry to uncover problems we can solve. Then we zoom back in to get laser-focused on product and process. For example, we zoomed in on creating a great interactive map for touchscreens installed in multifamily properties. We zoomed out and saw that there was a need for prospects to take self-guided tours of properties. We zoomed back in and leveraged our existing technology to create the best self-guided tour user experience possible.  

How the coronavirus pandemic affects your business, and how are you coping?

Jennifer Cyphers: In March, most of our clients put the breaks on to regroup and decide what to do next. Offices were closed, and contracts sat unsigned. We used the pause to bring our Self Tour mobile application out of its pilot phase and into the market and tweak it to be used to tour properties remotely. Giving people the ability to tour properties remotely or independently is desirable in any conditions, but necessary under current circumstances. We ramped up our product development team and added more features and integrations. We’ve been thrilled with the reaction that we have been getting. We knew it was the best Self Tour experience, but it’s nice to hear that from clients!

Did you have to make difficult choices, and what are the lessons learned?

Jennifer Cyphers: Didn’t we all! I sat down on March 13th with spreadsheets and reviewed all of our options, including worst-case scenarios. We immediately cut a lot of expenses – including all travel, sales, and entertainment expenses – for the remainder of the year. It’s easy to see now that this was the right decision to make, but most companies were reluctant to take such sweeping decisions that would affect the next nine months. Because of those changes, we were able to ramp up spending in product development and, more importantly, we got to tell all of our employees that their livelihoods were safe and valued. They rallied behind Pynwheel and worked very hard. We were able to reward everyone this month with raises and bonuses, which felt great! The lesson learned: when times are tough, don’t hesitate to make difficult decisions; get focused; value your people. 

How do you deal with stress and anxiety? How do you project yourself and Pynwheel in the future?

Jennifer Cyphers: We landed a couple of big clients last month. The first thing I did was to buy new running shoes. We had all been working very hard, and I knew that we would continue to work hard and that I would need the release. Running with my dogs in the mornings helps me wake up (I don’t drink caffeine), to stay focused during the day, and to sleep well at night. There are days, and sometimes weeks, when I wake up earlier to work and burn the midnight oil, squeezing in exercise (for me: running, walking/hiking, playing tennis) when I can help me to keep my head on straight and gives my brain space to project. I am also a fan of morning meditation, which helps to keep anxiety at bay. 

Who are your competitors? And how do you plan to stay in the game?

Jennifer Cyphers: There aren’t any other companies out there who are doing what we’re doing. Some companies do some of what we do, or a different version of it, but we’re nailing the interactive mapping and content game for property tours. The way we stay in the game is by:  

1) I purposely don’t pay attention to what other companies that compete with us are doing. (What I usually find is that they are copying us, which is flattering but frustrating. I find that focusing on that makes you petty and doesn’t help you to grow.) 

2) I focus on the product. Sales, marketing, operations – everything else can only be successful if our product is good. 

3) We take good care of our customers with consistent processes and services. 

Your final thoughts?

Jennifer Cyphers: We’re not done yet! Pynwheel has big plans, and we’ve been invigorated by the challenges brought to us by the pandemic.  

Your website?

Kokou Adzo is the editor and author of He is passionate about business and tech, and brings you the latest Startup news and information. He graduated from university of Siena (Italy) and Rennes (France) in Communications and Political Science with a Master's Degree. He manages the editorial operations at

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