Career Life Stories: Erica Alioto, Opendoor

What prompted your transition into startup sales?

When I decided to leave the law firm, I didn’t pursue sales specifically. I approached Yelp because I was really excited about the company and their trajectory. They were a very small company at the time and didn’t need a lawyer, but they did need a salesperson. The opportunity to be part of Yelp’s early team – 12 people when I joined – was enticing enough for me to say “yes”. I joined as an account executive while also advising them on legal matters. Later, when Yelp was ready to hire a general counsel, the COO asked me if I wanted to discuss it. By that point, I was thoroughly enjoying the work I was doing to build the sales organization and decided to continue on that path instead.

You climbed from a junior sales role all the way to the SVP of Local Sales for Yelp in 10 years. What are some things you did as a leader that contributed to your success?

When I started there were only two sales people. Over the course of the next year we hired another 10-12 account executives, spurring the need for sales managers. My counterpart and I both began managing small teams.

I spent a lot of time discovering how to best manage each individual, understanding their expectations, and then pushing them to go beyond those expectations to help them realize more possibility for themselves.

Whenever someone on my team approached me with a challenging situation, I would turn the challenge back on them and ask them how they think it should be solved. This tactic helped me empower and groom the next set of leaders at Yelp. I always say, if you want to create opportunity for yourself, create a lot of great successors. Knowing that Yelp was going to be growing to thousands of people, we had to keep constant focus on developing the next group of leaders which ultimately opened up more opportunities for me as well.

Finally, I made a concerted effort to lead with positivity. That means trying to see the best in people and helping them get the most out of themselves.

What lessons did you learn as your career developed at Yelp?

There were definitely rocky moments as a first-time manager. I made plenty of mistakes and learned a lot in those early days. Ultimately, I grew to understand that I couldn’t expect everyone to operate like me, nor does everybody have the same expectations of themselves as I might for myself. Some of the biggest lessons I learned include:

• As a leader, you can only be direct with people if you’ve created a foundation of trust. I tend to be pretty direct in my feedback which only works if the recipient feels like you’re coming from a good place with their best intentions in mind. I’m now very focused on building strong foundations with my team, while acknowledging that along the way we might need to have tough conversations in order for them to achieve their goals and maximize their potential.
• When a situation is moving in the wrong direction, it can be incredibly tough to turn it around. If you have the conviction to steer the situation in a new direction, be patient and stay the course. We can all be too eager to see change happen overnight, but most big changes require months of patience.
• Leaders rarely obtain consensus. I can recall several times, after delivering a message, 50% of my team would think I was too tough and 50% thought I was too easy. Leaders need to be able to trust their instincts and be comfortable managing through unpopular decisions.
• Finally, jump on great opportunities when they arise even if it might make your life difficult. Try not to overthink all the reasons you shouldn’t do something. For instance, at one point I was asked to move to Phoenix to run our office there which meant completely uprooting my family. We agreed to take a chance on the experience and it ended up being not only one of the highlights of my career but also a wonderful time for our family.

How do you leverage your sales leadership experience in your role as Head of People at Opendoor?

When I took the opportunity to run the Yelp Phoenix office, I ended up working with a number of other departments. A lot of our HR functions were decentralized giving me the opportunity to manage sales recruitment and learning and development, as well as work very closely with the workplace team; these are all things I’m responsible for now – in addition to HR – as the Head of People at Opendoor.

I had always been interested in moving into People Operations. When I reflect back on my time in sales management, I loved the people aspects –training, career development, and, most of all, empowering my team. What I didn’t always love was managing to revenue. My role today at Opendoor is similar in a lot of ways to my role as the SVP of Sales at Yelp but without the revenue piece.

For those that don’t know, what does Opendoor do?

Opendoor empowers people with the ability to move. Many people are unable to move because they don’t have the capital to put a down payment on a new house without first selling their current home. Others may not have the time or energy to fix up their home, move out and stage it for open houses. So, Opendoor will offer to purchase homes, giving people the flexibility to move forward. We provide an alternative to traditional residential real estate models.

I understand mindfulness is important to you. What does mindfulness look like to you, and how has your mindfulness practice impacted you as a professional?

Mindfulness, to me, is about recognizing what is within my control versus what I need to let go. Often times we get caught up in things that are out of our control which creates a lot of wasted time and energy. Chip Conley wrote a book called Emotional Equations in which he describes anxiety as: anxiety = uncertainty x powerlessness (lack of control). Most of the time, we feel anxious over things that may not even happen. It takes practice and discipline to push those anxious thoughts out of your mind which is why I find meditation so beneficial. I typically meditate for 15 minutes first thing in the morning, sometimes using an app like Calm or Headspace, and sometimes in silence.

With two kids, our mornings are very hectic. When I leave the house each day for work, I make a conscious choice to leave the craziness of the morning behind and step into the office with a positive attitude, expecting to have a good day.

What changes have you made as a professional since having kids? How have you seen the startup world evolve for working parents over the last 10 years?

Since having children, I prioritize being home in the evenings as much as possible, especially now that my kids are at an age where they want to talk to me about their days just as much as I want to hear about them; that one or two hours in the evening with them is really crucial time for us as a family.

It seems to me that the stigma around working parents is changing. Companies are becoming more comfortable with work-from-home arrangements, allowing parents to more easily balance family and work. My team knows that if I trust them and they get their work done, then I don’t worry about where they do their work.

We’re starting to see a lot more kids in the workplace as well. Over the last year, we’ve had many occasions at Opendoor when employees needed to bring their children to the office for one reason or another. In Arizona, for instance, there was a teacher’s strike that lasted several days, leaving parents without childcare; our team came together to set up craft tables, pool art supplies, and order pizza for the kids which alleviated parent the unnecessary stress.

Bringing kids to work is not ubiquitously accepted, but the way Opendoor supports parents is, I hope, indicative of how the market is changing. Creating an environment that’s supportive and inclusive for working parents seems to be a trend that’s moving in the right direction.

What is one question you always ask candidates during an interview? Why?

I like to ask questions that give me an indication about whether the candidate is self-aware because self-awareness is important for growth. It’s hard to improve if you aren’t aware of what you need to improve. One of my favorites is:

Tell me about a time you rubbed someone the wrong way. How did you know, and what did you do about it?

This question reveals a candidate’s self-awareness, conflict-resolution skills, and their ability to grow from feedback they’ve received.

What resources (books, podcasts, blogs, conferences, etc.) do you recommend to young professionals who aspire to become leaders?

There are so many great resources, and the following books are some of my favorites, spanning topics related to sales, leadership, behavioral psychology, investing and general business.

• Thinking, Fast and Slow by Daniel Kahneman
• Drive by Dan Pink
• Start With Why by Simon Sinek
• The Effective Executive by Peter Drucker
• The Hard Thing About Hard Things by Ben Horowitz
• Crucial Conversations by Kerry Patterson
• Give and Take by Adam Grant
• Originals by Adam Grant
• The Intelligent Investor by Benjamin Graham

I also recommend subscribing to the HBR newsletter and The Broadsheet newsletter.

What is the best way for people to connect with you?

LinkedIn best way to connect with me.

If you enjoyed Erica’s career journey, please navigate here to read other stories of impressive leaders within our network.