Women Leaders Of Real Estate: “Realize that you need to be a therapist first”, With Hilary Saunders of Side

Jason Hartman
Mar 4 · 12 min read

Realize that you need to be a therapist first; it’s crucial to have empathy and understanding for your clients, so that you can relate to what they need and their long-term vision. Disconnecting from a client will negatively impact your relationship, and can even cost you the sale and the client itself. Buying a home is potentially the most important financial and emotional transaction in your client’s life. If they mention a desired feature because it reminds them of their childhood home, pay attention, because it can impact their decision-making in a vital way.


As a part of my series about strong women leaders of the Real Estate industry, I had the pleasure of interviewing Hilary Saunders, Co-Founder and Chief Broker Officer at Side.

As Side’s Co-Founder and Chief Broker Officer, Hilary Saunders knows firsthand the growing pains associated with opening your own brokerage. Following a successful career in real estate litigation, Hilary leveraged her customer-service focused nature by working as a Broker Associate with Coldwell Banker. In 2012, her entrepreneurial spirit led her to open a boutique brokerage in San Francisco, as well as a law firm focused on estate planning and real estate transactions. At Side, Hilary’s mission is to ensure all Side agent partners have access to top-tier customer service, business management, legal, and brokerage teams to facilitate their success.


My real estate experience dates back to when I was in law school, where I decided to study real estate and tax law. Straight out of law school, I practiced real estate litigation for a number of years, but realized I wanted to be a part of the creation — not the dissection — of the transaction. I was fascinated by how every single property and client had a unique story to tell, and I was hungry to learn more from each transaction. I went on to work as a broker associate at Coldwell Banker, but left after a short tenure, as I was dissatisfied with the level of support I was receiving.

This was when I decided to start my own brokerage (HH Realty), as well as a law office (Hedemark Law) focused on estate planning. Between these two entities, I was able to help people work through two of life’s most important financial decisions, which was extremely satisfying.

While working with other agents, I realized there was a major gap in existing brokerage offerings, as top-performing agents struggled to keep pace with the operational aspects of running a business (such as accounting, financial planning and marketing) while delivering the best value to customers. This is one of the many reasons I joined my two co-founders in creating and developing Side.

The first story that comes to mind is something I experienced while working in litigation in San Francisco. I had a client who owned a property in Pacific Heights, and he had a tenant — a renowned architect — who suffered a mental breakdown that led to him living in squalor, to the point of infecting himself with gangrene.

My client was trying to evict him since he was a serious health hazard to the other tenants in the building, and was damaging private property. Unfortunately for our client, the Assistant District Attorney (ADA) and local rent control laws provided more protections for him as a tenant than they did for the owner.

The case lasted over a year, provoking extremely high emotions, countless rounds of legal briefs, motions, discovery, you name it. Not only did it leave me disheartened, it also put a nail in the coffin for me: I wanted to be a part of a solution that brings people together over complex transactions, not tears them apart.

For now, Side is very much focused on growing our new markets of Texas and Florida. We took our time in California to test our processes and ensure we had a wonderful product market fit. In every market, we determine what works in order to empower our partner agents to deliver the best experiences to their clients. We’ve proven that what we’re offering works in every market. We went into Texas and have gone gangbusters, and we are on the same trajectory in Florida as well.

Side is unique in our agent-first approach. We continually strive to help high-performing agents set up their own boutique real estate brands and businesses, by providing technology and brokerage services.

A story that always warms my heart comes from one of our very first partner agents, Michelle Kim, of Mosaik Real Estate. While she was a top producing agent at Zephyr Real Estate, Michelle struggled to balance work and family. As a mom of three, her family was her top priority but due to limitations, she was never able to take her family on vacation.

Side helped her build a small team of three, and in one year, she was able to represent 45 million worth in transactions, up from 15 million, meeting her 5-year goal in just her first year. Michelle also managed to take a whole month off to go on a vacation with her family, which she was very grateful for, as this would not have been possible in her prior role.

I am definitely most grateful towards my mother. Growing up, I was a competitive swimmer for 14 years, and my mother would drive me to daily double swim practices 30 miles away until I could drive myself.

She has always been such a supportive force in my life and I am constantly inspired by her 100% can-do attitude and her determination. There is no problem or “no” for her; “no” is just a starting point. Even if the going got tough, my mother always found a way to make it work. She taught me about work ethic, endless energy and striving for balance. From her, I learned how to manage — not juggle — set goals and work your butt off to get to them. I still apply this to my life today.

The real estate industry is unlike many other business realms in that it offers flexibility. Realtors can more readily integrate their personal and business lives, which can be beneficial to parents or people attempting to start a family. However, once you start working your way higher up in the ranks — as with many other businesses — it can get more challenging to separate family and professional time.

The California Association of Realtors (CAR) has done a great job in promoting women in leadership roles to push past traditional gender norms. Real estate is in some ways an old-fashioned industry, similar to the legal practice, in that you don’t see many women opening up their own law or real estate firms. It’s up to us women to break past these boundaries.

That’s one aspect we’re really empowering at Side — giving our female partners the platform and the means to be leaders. In fact, more than 43 percent of our partner agents at Side — and 51 percent of our associate agents — are women. There are plenty of capable women out there and it’s part of our job to give them the support and tools to push past the gender leadership imbalance.

Individuals can and should have the utmost confidence in themselves. Don’t be afraid to ask for what you want and what you need. To grow and excel in any male-dominated field, it’s essential to contribute, raise your voice and be confident. Know your worth, do your research, and step forward to take on and lead opportunities.

Companies should take a chance on who they’re hiring, and provide leadership opportunities to female employees and leaders within the company. It’s important to implement company-wide initiatives that support women and allow for upward mobility. As for society, this is slowly getting better, but true change won’t arrive until women begin leading the path and taking charge.

Some challenges faced by female executives, that are not typically faced by male counterparts, include the lack of pay transparency, limited leadership roles, lack of mentorship and the general absence of recognition towards women in this space.

The real estate industry in particular needs to work on creating a culture that is mindful and promotes equity in an open environment; it is for these reasons that we at Side work so diligently to provide continuous support, mentorship and opportunities for agents, because this is something the rest of the industry still needs to improve.

This is a tough one because there are so many things I am excited and passionate about! Three things in particular that I’m loving right now are:

  • This is the first time emerging technologies are really being seen and used as a support mechanism for transactions. iBuying, for example, uses an automated valuation model to make cash offers on homes quickly. There are many circumstances where a seller might say, “Yes, I want cash for my house fast,” so this is really interesting.
  • Aside from the traditional Federal Housing Administration (FHA) and Veteran Affairs (VA) programs, other companies are getting into the space of facilitating home ownership for all. Unison is one company, and there are others developing creative solutions such as “renting to own” or “co-owning” or providing down payment assistance. Right now, California is predominantly a renter state; however with these programs, the American Dream can become a reality for more and more people!
  • Over 50 percent of real estate transactions are facilitated by inexperienced agents who don’t provide buyers and sellers with the best experience or results. With the traditional brokerage model focused on commissions versus consumer experience, the perception of the agent’s role and value as a trusted expert and advisor has diminished. This has put the entire industry at risk.

Side’s model, and what we’re seeing as an important shift in the industry, is predicated on the idea that agents should focus on the high-value work of serving clients, while everything else should be handled by technology and specialized support staff. We believe that the future of real estate is local, boutique and agent-owned. Behind every one of our agent partners is a proprietary end-to-end platform built from the ground up that improves productivity, growth, compliance, marketing, and customer experience.

One element that has always concerned me is the low bar of entry in real estate. It’s easy to do harm in this business if you aren’t properly educated or serious about what you’re doing. There is no set mentorship or apprenticeship period. When someone gets a license — depending on state laws — he or she is cleared to practice real estate. I think it would be beneficial, and safer for both consumers and realtors for this to change and become more rigorous.

A second area that concerns me is how consumers view agents. Real estate agents don’t just facilitate a sale — they offer a valuable home buying and selling experience that is deeply personal and truly adds value to the client. There is a perception that agents aren’t worth their commissions as the transactions are “simple.” This is inaccurate. The industry needs to rise up and demonstrate that agents provide exceptional value.

Additionally, there is a fear that millennials are replacing real estate agents with technology. That’s simply not the case. Technology needs to supplement the real estate transaction. As these trends continue, consumers will look to a partner that can address the changing landscape. The adoption of technology has accelerated in the real estate vertical — but it’s not replacing the personal aspect, nor the inherent value and guidance provided by an agent. Values such as honesty, integrity, communication skills and personability will always play a central role in the real estate transaction.

The final area that concerns me is the lack of accuracy in provided information. This comes largely from my background in real estate litigation. There are far too many scenarios where sellers or buyers are negatively impacted because a realtor wasn’t fully knowledgeable on some of the legal matters or fine print that can greatly impact the transaction process. The more knowledge provided in the real estate process, the better, for both parties involved.

The first piece of advice would be to fully understand your audience. This is especially important for female leaders in terms of communicating.

One of my favorite messages on this came from Sheryl Sandberg, who said that effective communication starts with the understanding that there is MY point of view (my truth), and someone else’s point of view (his truth). Rarely is there one absolute truth, so people who believe that they speak THE truth are very silencing of others.

Women often tend to manage down and across, while men keep their eye focused squarely on the next rung of the career ladder. Nothing feels riskier than self-exposure — and for many women this can be a constant hurdle. Feelings can be managed, and risk is nothing more than a matter of perspective. Leadership demands a thick skin, but also a team around you that’s supportive. That can be key in handling any challenge with grace and professionalism.

Realize that you need to be a therapist first; it’s crucial to have empathy and understanding for your clients, so that you can relate to what they need and their long-term vision. Disconnecting from a client will negatively impact your relationship, and can even cost you the sale and the client itself. Buying a home is potentially the most important financial and emotional transaction in your client’s life. If they mention a desired feature because it reminds them of their childhood home, pay attention, because it can impact their decision-making in a vital way.

It’s also important to be mindful of the legal ramifications around transactions; understanding the ‘why’ will give you a leg up from your competition.

Lastly, know your market and who your client is. Show that you care, that you’re paying attention and that you’re proactively working towards their end goal as well — not just yours.

One movement I’d love to inspire would be true gender and pay equality. This is a cause I feel passionately about, and one that I feel especially close to. Creating equal opportunities for women across industries is a space I’d like to support.

Additionally, I’d like to support the community of stay-at-home moms and dads, who care for the next generation, and work just as hard — if not harder — than those who work at a traditional 9–5 job. It’s tough taking on that role, but it’s such an important one to every family dynamic. Society needs to give people in these roles the same amount of support, accolades, attention, and respect as any other traditional or non-traditional role.

You can find Side on LinkedIn, Facebook, Twitter and Instagram. I’m on LinkedIn; feel free to reach out with any questions or any advice for future real estate aspirants.

Authority Magazine

Leadership Lessons from Authorities in Business, Film…

Jason Hartman

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Author | Speaker | Financial Guru | Podcast Rockstar

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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