Customer Stories: Meet Tyler Smith, Founder & CEO of SkySlope

May 18, 2016


Tyler Smith, founder and CEO of SkySlope, is bringing the real estate game into the 21st century. SkySlope is a B2B SaaS platform that is focused on helping real estate agents manage their transactions online.

Based in sunny Sacramento, California, SkySlope differentiates itself with resources like 24/7 support and CEO’s Corner featured on their website. CEO’s Corner is a chance for Tyler to give back to the industry by sharing tips, tricks as well as other high value and interesting real estate content such as how he doubled his business with pizza.

Hungry to know more? Meet Tyler and SkySlope.


What was life like before SkySlope and what motivated you to quit your day job and start your own business?

When I was 19 going on 20, I worked at a steakhouse restaurant as a server —I was in college at the time and it was how I paid my bills. My best friend and I really wanted to move out of our parents house. So, what we did was save up what we could to put a down payment on a house… and our realtor was not a great one. So I thought ‘if this realtor can make all this money doing a bad job, imagine what I could make doing an amazing job. Sign me up — I’m in!’

At that point, I left the restaurant and got into real estate. So now I was my own boss which was different because there was no accountability or processes in place like when you’re an employee.

As a realtor, I was constantly looking for a solution, I tried them out and they all fell flat. The solution I came up with wasn’t originally supposed to be a business, it was just meant to help me out as a realtor.

Tyler’s 3 pearls of wisdom for entrepreneurs:

  1. Hire the right people
  2. Be accountable: Find a mentor or an accountability partner or coach who you need to check in with every couple weeks
  3. Value time: Your time is better spent working on your strengths, so you need to delegate your weaknesses

Describe the biggest challenge you’ve experienced as a small business owner and how you dealt with it.

Our number one challenge is finding good talent and coaching and developing them into great leaders. We’ve doubled in size and will likely do it again in the next 12 months.

We are always looking to hire the bar raiser. As you keep finding the bar raisers, it makes everyone else want to be better. You can’t go wrong if you truly hire the best. The best people who we hire are from referrals, so we are focusing on ways to encourage and empower employees to spread the word using social media. One thing we are looking into now is SnapChat geofilters; all of your employees can SnapChat that you’re hiring to their friends. We’re also trying to tell stories through videos on our culture page — we want to be able to show what it might be like to be a SkySlope family member.

Skyslope / snapchat

As far as coaching and developing our leaders, we are really trying to empower them with programs that will help them become the best leaders. We want to create an environment that allows our employees to feel comfortable doing uncomfortable things. We don’t want people putting a toe outside the box, we want them swan diving.

Share a story where you went above and beyond to solve a problem.

At SkySlope, we want our customer service to be next level. We guarantee to pick up a call on the second ring, to give a response on a chat within 10 seconds and to reply to an email in 5 min. If we don’t meet that, we will send a $5 Starbucks gift card.

We have a joke on our website that you can even call us to order pizza for you. This one time, a guy called in with his credit card number and actually asked us to order pizza for him. Lo and behold, we ordered it and the pizza showed up — we delivered on our promise. So that was kind of funny.

It’s a typical work day. Where would we find you?

We all work primarily from the headquarters in Sacramento; there are about 60 of us. We like to have everyone in the office because our culture is so ingrained here. Sometimes we go offsite to a cool coffee shop to have a quick jam session, but then we will come back and get right back at it.

Inspiration or perspiration?

Inspiration. As leaders, we have to inspire and help everyone understand where the company is going and how to make a difference. My goal is to play defence and give everyone at our company the ball. I want to move blockers out of the way and make it easy for them to run the ball down the field. I’m always trying to empower our SkySlopers, not just to move a yard, but to score those “Hail Marys”.

Who is your role model?

There’s a lot of people: For one, your CEO Mike [McDerment]. I’ve read his book, I love the software and I like that you’re also friendly and playful as a company.  The CEO of Zendesk, Mikkel Svane  – a company we use to power our support – they are really great with marketing and very clean and intuitive as a software. I also like Salesforce because you can see how it’s grown. Marc Benioff is a phenomenal CEO and I’ve read his book too.

These are all bigger companies and, as a smaller company, we always want to grow and have goals. I like being the small fish in a really big pond so that I can grow. Safety for me sucks. It clouds my judgement and makes me feel suffocated, so being around more successful people helps me set bigger goals.

Do you have a motivational mantra or inspirational quote that helps you get you out of bed in the morning?

‘Without promotion, something terrible happens. Nothing’ – PT Barnum

Work-Life balance is *tough* for a small business owner. How do you stay balanced?

Work-life balance? What’s that? [laughs] I do go on vacations but I set them, whether it’s 2 or 10 days. Then, I’ll work as hard as I can and crush every day so that when I’m out I can be ‘off’. Although, I’m never really off, but when I’m on vacation I actually sleep in which is so odd. On a normal day I’ll be up at 3am but on vacation I’ll sleep until 6.

What’s next for SkySlope?

We are going to continue to grow. We have been growing every year and plan to continue that growth for a long time.

FreshFact:

SkySlope is a dog friendly office and they even offer their employees pet insurance! Similar to his role models, Tyler has also written a book: Going Paperless: Taking Real Estate into the 21st Century.

A photo posted by SkySlope (@skyslope) on


Learn more about Tyler and SkySlope:  

Website | Facebook | Twitter | Instagram


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about the author

Content Editor, FreshBooks Amanda is a content editor at FreshBooks, writing and producing blog content to help small business owners achieve their goals and enjoy (yes, actually enjoy!) running their business. Amanda’s background in education and customer support makes her a natural communicator who loves empowering others to succeed. When she’s not writing and editing content, Amanda takes her dog, Jonny, on adventures searching for the best coleslaw in Toronto.