PRODA’s Powerful Women Of Proptech – Stephanie Rall

PRODA powerful women of proptech - Stephanie, Gayle, dana

– A Blog Series By Proda

We’re back with another post in our blog series: PRODA’s Powerful Women of PropTech (#PWPT). This week, we spoke to three of the senior women at Homesnap – Stephanie Rall (SVP of Industry Relations), Gayle Weiswasser (SVP of Business Development & Communications and Dana Aldis (SVP of People and Customer Experience).

This week, we’re back with another post in our blog series: PRODA’s Powerful Women of PropTech, and we are very excited to feature 3 women from the senior team at Homesnap – Stephanie, Gayle and Dana. If you have missed any previous blog posts from the series, you can catch up on them, here.

Homesnap is an industry-endorsed platform that leverages real-time data from over 200 MLSs to empower millions of consumers with a superior home search experience, while providing over 85% of U.S. agents with access to powerful mobile tools that automate their work. We sat down with Stephanie, Gayle and Dana to speak about the different roles each of them play behind the scenes of Homesnap, and got their take on what it’s like being a woman in the PropTech sector, on the other side of the pond.

Read the full interview below

MV: Can you tell us a little bit about each of your professional journeys, and how you have all ended up working at Homesnap?

Stephanie: To give you some background, I’ve been in the industry for over 27 years. I started out in the foreclosure side then as a licensed real estate agent, and then became a broker. Serving many years in volunteer leadership, I was a local Board President as well as board member sitting on the board of the National Association of Realtors and the state board. During this time, I made a lot of connections in the industry. My friend, John Heithaus, introduced me to a new opportunity with StreetEasy. It was intimidating at first as I knew nothing about tech and didn’t even know how to use a Mac! I ended up getting the job at StreetEasy which was acquired by Zillow during my time there.

A few months after the acquisition the same friend who recommended me to StreetEasy called about Homesnap and how they were launching a pro platform for real estate agents. I met with Steve and Guy, the co-founders of Homesnap, and absolutely fell in love with how sincere they were. At this point, I wanted Homesnap to be successful regardless of whether I worked for them or whether I used it as a broker so during my interview I introduced them to Brian Donnellen the then COO of MRIS. It’s been almost 7 years since we launched MRIS successfully as our first MLS and we now have hundreds of MLS’s and I am still here (and I know how to use a Mac now!)

Gayle: I came to the industry in a completely different way, I used to be a lawyer, and pivoted my career into the communications world, after I had children. I had worked in crisis PR, corporate PR and social media for a large media company here in DC, and I networked my way into an interview with the same people Steph just spoke about. I was also impressed with Guy and Steve, and the app, and was very interested in tech in general. So, my way into Homesnap was through persuasive communications and that’s what I do now; run our industry business development and corporate PR. It seems like a strange circuitous route, but looking back, it does make sense.

Dana: The quick version of my professional journey is that I’ve always had a huge passion for venture and growth stage tech start-ups and have been repeatedly drawn to them. I started my career in sales management and then worked for LivingSocial where I was in more of an operational leadership role.

I then moved into a full blown HR and cultural leadership role which was a really cool and enriching experience. Prior to Homesnap, I was the head of HR for a hospitality company and my former boss at LivingSocial became the former COO of Homesnap. He reached out to me in 2017 with a really exciting opportunity to lead the HR and customer experience functions at Homesnap. Similar to Steph and Gayle’s experiences, when I met with the founders I fell in love with the whole team and couldn’t stay away!

MV: What does a ‘typical’ workday look like for all of you, behind the scenes of Homesnap?

Stephanie: I oversee the training team and half of my team, before COVID, worked remotely anyway so it feels very typical for us. I myself come into the office 1 or 2 days a week as I travel a lot. The only thing that is quite unusual now is not being able to see each other and attend events. A typical remote day for me includes getting up and scanning industry news. I then check social media and see what’s happening with my connections — whether anyone has gotten married recently or had any grandchildren. I’m very socially connected as most agents are innately!

I also go through emails, check on my team, and then get on Slack. I actually have a funny way of handling meetings. I think they should only be called when absolutely necessary – to have a meeting just for the sake of it is beyond my comprehension. So, my team meets 3 times a week only if we really have to. I don’t think we need to waste anyone’s time, especially with all the virtual meetings we need to attend due to the current situation.

Dana: On the people experience (HR) side there’s definitely not a typical day. Generally speaking, the people experience team works to create and maintain the best possible workplace for our Homesnappers. That includes everything from assessing cutting edge benefits to engaging with our employee-led Culture Crew, a group of employees working to sustain our innovative, enriching culture. We have been voted one of Inc. Magazine’s Best Workplaces and a Washington Post Top Workplace for 3 years running, and this year we were also named one of Forbes’ Best Startup Employers. So, a lot of work goes into maintaining our culture.

Gayle: My role is split between managing our corporate PR and communications, our events team, and also handling business development among our industry partners. So, on any given day I may be reviewing a press release, content for the website, or collateral for our events. I might be strategizing on how we can bring value to our partners or working with our events team to plan our presence at an upcoming event. I also write and draft language and edit pieces that will be released publicly. Unfortunately, there are sometimes a lot of meetings which have only increased during the current crisis, but I am working on reducing these. That’s my typical work day with a lot of different aspects, but I really enjoy doing each on a daily basis!

“I haven’t seen a lot of change in terms of the makeup of men and women in leadership roles in PropTech. I see a lot of the same faces at conferences and events. It’s important to have women in these senior roles because I think women bring a different perspective to product design and functionality, for example. “

MV: Having been female leaders in the PropTech sector for a number of years, do you believe a shift is taking place towards a narrower gap between males and females, in the PropTech space, within the US?

Gayle: I’ve been at Homesnap for 6 and a half years, and I have to say I haven’t seen a lot of change in terms of the makeup of men and women in leadership roles in PropTech. I see a lot of the same faces at conferences and events. I think that there are women out there, but there are mostly men. It’s important to have women in these senior roles because I think women bring a different perspective to product design and functionality, for example. They have different styles of leadership, different ways of doing business and communicating, and I think it’s really important to get women into these roles. I don’t see a big change happening but personally, I would welcome the chance to work with more women. All 3 of us here are very used to working with men, but I think that we would definitely welcome the chance to broaden that.

Stephanie: I don’t see much change in the leadership of women in PropTech either, however, there are some very strong women in leadership roles. It doesn’t bother me so much that there aren’t as many women as there are men. I think regardless of the gender, the right person for each role should be placed in that position. I found between 2-5% of leadership roles are by women in PropTech and I know of one woman personally, so I don’t think much has changed within the industry itself, in that regard. This could have something to do with women not thinking they can do a tech type of role. I was very intimidated by the tech side of things initially, so maybe women don’t realise the skills that they can carry over into this side of the industry.

Dana: I tend to look at this through my own perspective as well as through a people experience (HR) lens. It’s no secret that diversity of all types, including gender diversity, really needs to improve at senior levels for most industries and PropTech is not an exception. While it’s not a problem that can be solved overnight, the first thing companies need to do if they see a gap is to set quantitative recruitment and promotion goals to ensure that they’re making meaningful progress over time.

I can’t tell you the amount of times I’ve heard companies say “gender diversity and diversity in general is very important to us and I feel like our representation is strong on all levels”, but when they take the time to look at the data they find the gap to be much larger than they initially realized. The point there is, if companies don’t know where they currently stand, they are not able to make a data-driven, actionable commitment to diversity.

“All 3 of us have daughters and I think we can agree that when they take steps forward in their own careers, we want them to be able to look up the ranks and see members from all underrepresented groups, including women. We want them to see female leaders and be able to envision themselves in those roles.”

MV: Do you feel any pressure as female leaders in the PropTech industry, particularly where there is such a small number of females in similar senior positions?

Stephanie: So, there’s always pressure especially in this industry regardless of gender. When I first got involved in the tech side of the industry, my children were in middle and high school and still needed to be driven to sports events. The truth of the matter is, there are pressures that are external; you have to keep up with everything and you have to do it all. You don’t want to miss anything in your child’s life and you also want to be everything for your company as well. There is some pressure as a female – and that’s not to say fathers are not involved in this – but generally speaking when your child gets sick at school it is usually the mom who gets the phone call to go get them, and that does put pressure on you.

Moving forward from that, where my son has graduated from college and my daughter is in her third year of college, it’s a different season in my life. I don’t have that pressure anymore, so it’s a different feeling. There’s no complacency, but there’s a different kind of pressure and different level of responsibility when you become a leader. You want to lead your team well, be a good mentor, set a good example, be truthful, and provide feedback for your team’s growth and development. So, as the different stages of your life flow, the pressures become different, but they never go away.

Dana: In terms of extra pressure, the honest answer is yes for me. I think it’s very important to have females in leadership roles in all industries, including PropTech. The unfortunate truth is that leaders in underrepresented groups, including females, are going to take on a trailblazer role at some point in their career which will hopefully yield more equitable representation over time.

All 3 of us have daughters and I think we can agree that when they take steps forward in their own careers, we want them to be able to look up the ranks and see members from all underrepresented groups, including women. We want them to see female leaders and be able to envision themselves in those roles. So, I definitely view what we are doing as trailblazing, and taking steps in the right direction so that future will present itself one day.  

Gayle: The pressure I do feel in my role has nothing to do with my gender. At the same time, I agree with what Dana has said in that I feel it is very important to set a good example. I’m always very proud to represent Homesnap and want people to get used to seeing women in senior roles. I’m not sure if Steph and Dana feel the same, but you can sometimes go into a meeting and sense the body language of the men in the room either dismissing or ignoring me. Once I open my mouth and start talking to share my experience, I notice their body language change and they begin to pay more attention. It’s an annoying progression of events that takes place, but I guess I’d rather be there to pave that way than to not be there at all.

“I think PropTech is helping to keep the industry alive right now – so many of the things that are making transactions happen, helping people communicate, see homes remotely and so on, is all happening because of PropTech.”

MV: What excites you the most when you think of the new future of PropTech that we are heading towards?

Dana: On the customer experience team we’re seeing firsthand how COVID has created challenges for so many people. Our industry is not exempt by any stretch. COVID has shone a spotlight on how important digital presence and great online tools are right now. I see a much more efficient world in our future with all kinds of transactions becoming more digital.

Stephanie: I’m excited about taking the remote work opportunities to a much larger scale, and I’m glad that it’s now being taken more seriously. I have been a remote worker for 6 years and I felt that there was an assumption that we weren’t doing much work at home. Just because you’re at the office and being seen every day doesn’t mean your work is more efficient than the person at home. Maybe that meant that you were passed over for promotions because you’re not visible all of the time and people don’t know what you do. Remote work is being looked at in a different way now and that’s a great thing for the industry. I think that the value of remote work is being put at the forefront. It means we can now have a much more diverse employment pool to draw from. Dana will know better than me, but I think this is really cool and a unique opportunity that is being looked at more seriously now.

MV: Finally, what advice would you give to any young women or women in general who may be considering a career in PropTech, but feel there may be a barrier due to preconceived notions regarding gender?  

Gayle: I would say it’s very important to sharpen your analytical skills. Coming from a legal and communications background, I had not prioritized that but if I could go back that’s something I would address. For someone who has the benefit of having lots of years ahead of them in their career, I would say take whatever you’re good at, and combine that with analytics – that makes a very powerful combination that people don’t always expect from women and it will make you extremely marketable and powerful.

Dana: That’s some great advice from Gayle! If I could speak to a younger version of myself or a woman who is interested in getting into this industry, I would say that if you’re feeling nervous or getting imposter syndrome, that’s probably a good signal that you’re moving in the right direction. I would encourage women to challenge and trust themselves and remember that no one knows all the answers. Some people may appear to be more confident than you, but remind yourself that there’s no reason you shouldn’t be the one to take on a challenging opportunity. Whether you succeed or fail, doing what you’re afraid of is the most important gift that you can give the next generation. Other women will see you in those leadership roles and that may give them the courage to follow in your footsteps.

Stephanie: My advice is to have a good network and find a mentor. I had wonderful mentors in the beginning of my PropTech career and still do. I have a strong network of female leaders who build each other up. I have been very fortunate in having a little luck as well to connect with amazing people through other wonderful people. Know your value and speak up if you believe that you aren’t being valued in your role. Lastly, sometimes you might have to take a job to get the experience that you need to find a fulfilling career and there’s no shame in that.


Written by Manisha Veja, Featuring Stephanie Rall, Gayle Weiswasser and Dana Aldis.

A special thank you to Stephanie, Gayle and Dana for taking part in our blog series. If you are interested in featuring in the series please email

 We will be back next week with the final edition of our blog series. In the meantime, for the latest news and updates follow us on Twitter and Linked In.

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