Sammy Courtright: “Be comfortable selling something that is not perfect”

Be comfortable selling something that is not perfect. Initially, this concept stressed me out. How could I ever put something in front of a prospect that wasn’t up to my standard?! Then I had to ask myself: what is worse? A new customer interacting with a not-so-perfect feature or no customer at all? Be transparent […]

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Be comfortable selling something that is not perfect. Initially, this concept stressed me out. How could I ever put something in front of a prospect that wasn’t up to my standard?! Then I had to ask myself: what is worse? A new customer interacting with a not-so-perfect feature or no customer at all? Be transparent that your product is always evolving but don’t miss out on an opportunity to close new business.

As a part of our series about women who are shaking things up in their industry, I had the pleasure of interviewing Sammy Courtright.

Hailing from Australia, Sammy Courtright is the co-founder and Chief Brand Officer of Ten Spot, an all-in-one platform that helps companies connect, engage, and manage remote and on-site employees.

After finding it frustrating to stay healthy in a typical 9-to-5 environment, Sammy and her co-founder, Jonathan Cohn, teamed up in 2014 to create Fitspot, whose mission was to deliver wellness where employees needed it the most — at work. Renamed Ten Spot in 2020, the company not only rebranded to expand beyond wellness, but now offers a centralized solution for companies to increase their productivity, boost retention, and build a strong culture.

When COVID hit, Sammy learned that customers were facing a similar issue: how do we ensure employees feel like they work for the same company when they are not in the same place? Through research, she discovered that leadership was struggling to manage distributed teams. This led to Ten Spot’s expansion to the workforce engagement platform it is today.

With a BA in Fine Arts from the University of Miami, Sammy is a certified Pilates instructor who brings a blend of grit and imagination to the zillions of tasks that confront every startup. While she wears many hats, Sammy’s passion for building culture has created an atmosphere at Ten Spot dedicated to positive thinking and collaboration.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I’ve always been very creatively inclined, and in school, I studied theatre. However, at the same time, there’s always been part of my brain hyper-focused on solving problems.

Anytime I go into a restaurant or a store, I find myself thinking about all the ways it could be more efficient and scalable, and have even emailed the owners with my ideas (I know, I am that person). That is how I met Jon, my co-founder. Mutual friends introduced us and once I heard about what he was working on, I started telling him all the ideas I had to make it scale.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

COVID-19 has upended the workplace as we know it. As we’ve navigated this new world for Ten Spot and worked to solve our own issues with how to make our now distributed workforce as engaged, supported and productive as possible, we’ve been innovating in such a way that has enabled us to solve these same issues — and more — for our customers. Distributed teams aren’t going anywhere. We don’t want our customers to have to piece together a fragmented solution to connect, engage, and manage their distributed teams. That is why we built the all-in-one workforce engagement platform that takes the heavy lifting off your plate whether your team is on-site or remote.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Last fall, I was sitting in a cafe in New York, having a cup of coffee, and some guy I’d never met before approached me and said, “Sammy?” I was thinking, “I’ve never met this person before…right?” and replied, “Yeah?” And he said, “Ten Spot, right? My friend’s cousin sent me your pitch deck.”

Moral of the story: your pitch deck isn’t your business card. We always prefer it when people ask to share company collateral before sharing it with others!

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

LJ Kwak Yang, who is a Leadership Development expert is a godsend. We met at Techstars. We work together to develop my leadership skills. At times, I am sure she feels like my therapist, but the best part is that she allows me to vent, then she gives me tangible next steps and exercises. She helps me navigate the ups and downs that come with running your own business.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

Being disruptive is a coin with two sides. On one side, things are very positive, and the result of being disruptive is solving problems, making things easier, better, and more exciting.

Innovating for this kind of disruption is important — challenging the old assumptions to uncover new possibilities is a big part of disruption today — it’s not one big thing all at once, but incremental changes that lead to positive disruption.

Take Uber, for example. Paying for rides wasn’t new, nor was getting paid to give someone a ride. But Uber put the power into the hands of drivers and riders alike, giving drivers a new way to make money and riders a faster, more efficient, and cost-effective option for transportation.

If you take a closer look at the negative side of disruption, social media is a great example.

When people first started using social media, it was a great, fun way to stay in touch with friends and family. Today, social media platforms are flooded with misinformation, divisiveness, and are, as we’ve recently learned from the Netflix documentary, ‘The Social Dilemma,’ loaded with psychological manipulation. Information can be bought by and written by anyone. This is an example of the ‘not so positive’ side of disruption.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

Be comfortable selling something that is not perfect. Initially, this concept stressed me out. How could I ever put something in front of a prospect that wasn’t up to my standard?! Then I had to ask myself: what is worse? A new customer interacting with a not-so-perfect feature or no customer at all? Be transparent that your product is always evolving but don’t miss out on an opportunity to close new business.

Solve the most important problems your users and customers have, not the ones they wish they had or which you know how to solve. Have conversations with your customers with minimal agenda. You need to know about them and their lives, not just whether they ‘like’ your product. The most interesting opportunities at Ten Spot have come when an offhand comment sparks a new idea.

Hire slow and fire quickly. This is an oldie but a goodie. We run a thorough interview process at Ten Spot because every hire greatly impacts our team at this stage. If it is not working out with someone, it’s usually something you can assess within their first four-six weeks, and move on.

We are sure you aren’t done. How are you going to shake things up next?

Right now, we’re obsessed with the idea of peer-to-peer learning. So many companies are tasked with not only hiring, but onboarding and training employees they have never met in person, and that they may not meet in person for a long time. This creates a lot of awkward challenges for both the employer and the new employee. How do you make sure the new employee is getting trained effectively, what are the areas they need to develop skills in, and perhaps most importantly, do they feel like they are part of their team and the company?

So, what we’re exploring is a peer-to-peer learning tool designed to help employees acclimate to their new company, learn company systems, and get to know their team members. Additionally, the program will provide outlets for employees to both teach and gain new skills — so both the mentee and mentor are improving and growing, and feel acknowledged and recognized by their company, team and co-workers.

In your opinion, what are the biggest challenges faced by ‘women disruptors’ that aren’t typically faced by their male counterparts?

More VCs need to take a chance on ambitious and capable women. In 2009, only 10 percent of companies were female co-founded companies. That number has since doubled, which means things are on the right track, but there is still work to be done to support female founders financially.

I’m grateful for the VC that led our series A round. Neither of us, me or my male co-founder, had prior startup experience, but we are relentless and passionate about what we do and they saw the potential.

Other big challenges for women is making sure that women feel both emotionally and physically safe at work. This is just one survey in one field, but in a survey of 474 astronomers, 40 percent of women of color reported feeling “unsafe in the workplace as a result of their gender or sex,” and 28 percent said they had felt unsafe at work because of their race. If someone doesn’t feel safe at work, how in the world are they going to be able to thrive and succeed?

Do you have a book/podcast/talk that’s had a deep impact on your thinking? Can you share a story with us?

A great book that explores entrepreneurship and being a founder is “The Hard Thing About Hard Things’” (Ben Horowitz) — if you want a taste of what a founder goes through when starting a business, pick up this book.

Another great book is “Never Split the Difference” (Chris Voss) because there are skills you can learn outside of any formal education, and negotiation is one of those.

It’s one of the best books I’ve read over the last few years because negotiation comes in all shapes and sizes and occurs in all types of everyday situations–whether we realize it or not. I’ve learned so many invaluable techniques. I am mad I didn’t read this earlier in my career (*cue time machine*.)

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I value education, and I don’t believe that learning should stop when you leave school. I recently read a report that said to remain relevant in the workforce and your job, you need to be learning and developing new skills at least every four years. This creates one of those challenges that I’d like to help solve, starting with Ten Spot’s customers.

Going back to school is expensive, and it usually doesn’t keep someone in the job market while attending, meaning learning and skill development needs to either occur on the job or with your employer’s support.

We are in the process of rolling out peer-to-peer mentoring on Ten Spot’s platform but envision it going beyond mentoring and expanding into important skills training. This can start with live sessions that are ultimately recorded and archived for use by new employees or anyone needing a refresher course.

I feel if we can help companies do this across the board, we’re helping make education more accessible. Employees can then learn and develop new skills without sacrificing their jobs and without their employers losing them.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Life is inherently risky. There is only one big risk you should avoid at all costs, and that is the risk of doing nothing.” — Denis Waitley.

It is not easy running an early-stage company. I am, ironically, quite risk-averse. This quote reminds me to always take the plunge, make the tough decision, and speak up because any path taken involves risk.

How can our readers follow you online?





This was very inspiring. Thank you so much for joining us!

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