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Gideon Stein: “Empower your team”

It’s important to share credit. This one goes without saying, but it was hard to internalize when I was starting out. You can’t build a company without great people, and when they do great work, CEOs need to acknowledge and commend it. From my daily interactions with the team to interviews such as this, I […]

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It’s important to share credit. This one goes without saying, but it was hard to internalize when I was starting out. You can’t build a company without great people, and when they do great work, CEOs need to acknowledge and commend it. From my daily interactions with the team to interviews such as this, I make a point to thank my colleagues, co-workers and friends who are in this just as much as I am.


As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Gideon Stein, CEO of Write Label.

Gideon Stein is the CEO of Write Label, the leading provider of on-demand short form writing for media companies, agencies and brands. Prior to Write Label, Gideon spent more than a decade founding and running both for-profit as well as non-profit organizations in the education space. In particular, Gideon was the Founder and CEO of LightSail Education, the adaptive reading platform that helps students, classrooms and school districts significantly exceed their literacy goals. Prior to LightSail, Gideon co-founded and served as President of Future Is Now Schools, an organization focused on school turnarounds and union reform work. A leader in the national education landscape, Gideon serves on boards of several nonprofit organizations including New Classrooms, Narrative 4, Chalkbeat, and Slader, an education technology company. Gideon is also the President of The Moriah Fund, a private foundation focused on supporting human and civil rights in the US and around the world. Earlier in his career, Gideon was Founder, Chairman, and CEO of the enterprise messaging company Omnipod, Inc. (now a division of Symantec). Gideon has a B.A. from Wesleyan University.


Thank you so much for joining us! Can you tell us the story about what brought you to this specific career path?

I have always been an entrepreneur. I started working in finance straight out of college and quickly realized that I wanted to start and build things. I founded my first company at age 22, which sold quickly to E! Entertainment, and from there, I began as an Angel Investor and serial entrepreneur both starting and investing in companies — first Omnipod and then LightSail. Write Label is actually the first company that I have worked for where I have not been the founder, which has been an interesting challenge and great opportunity to work for and with a bunch of people whom I respect immensely.

Can you share one of the major challenges you encountered when first leading the company? What lesson did you learn from that?

I was brought into my current position by the Chairman of Write Label who wanted the company to head in a different direction. Quite soon after joining, I had to make some tough senior staffing decisions, all while running and growing the business. This was certainly a major challenge, and I learned a lot from listening to the team, understanding their frustrations as well as their solutions on how to improve the business.

What are some of the factors that you believe led to your eventual success?

When it comes to Write Label’s success, I truly believe this has come from enabling the team and listening to everyone’s point of view on our product and business goals. By simply listening, and letting the team be part of the decision making process, we were able to sign our first major enterprise client within 90 days of my joining the company. That led to Write Label increasing revenue seven-fold from the year before I joined.

Generally, I think my personal success is really rooted in these values around listening, having patience and allowing the team to have real input and a level of autonomy.

What are your “5 Things I Wish Someone Told Me Before I Became CEO”? Please share a story or example for each.

1. There is no substitute or short cut for experience. Starting out as an entrepreneur in my early 20’s, I thought I was really smart and knew more than others that had decades more experience. While you can have great ideas, knowing how to implement and execute them, and get others to buy into your vision, takes more gravitas than I had in the beginning.

2. Listening and patience is crucial. As I’ve stated above, listening and having patience, even when business demands are moving at lightspeed, is critical to enabling a work environment where everyone knows what they’re doing and feels good about doing it.

3. Empower your team. Fostering trust and buy-in from the team is essential, and the best way to do that is to empower people to make decisions and move the business forward. There are too many things to do and too many great ideas from the group not to have everyone pulling together. As an example, when we were developing our pitch for an enterprise rollout across one of our largest clients, I wanted to focus on the ROI our solution delivered during their eight week pilot. Whereas, two members on our sales team wanted to broaden the focus of the presentation to include more qualitative benefits. Given that they were so adamant about the expanded approach, I relented. I’m more than happy to admit that those added slides were what helped seal the deal on a seven figure contract.

4. Being the CEO involves a series of highs and lows. I’m always struck by how great the victories feel and how devastating the challenges can be. Having experience running a number of startups over the last 25 years has given me a lot of perspective on the highs and lows. I still experience them — thankfully, as they’re a fundamental part of being an entrepreneur, but they’re now more muted than when I was starting out.

5. It’s important to share credit. This one goes without saying, but it was hard to internalize when I was starting out. You can’t build a company without great people, and when they do great work, CEOs need to acknowledge and commend it. From my daily interactions with the team to interviews such as this, I make a point to thank my colleagues, co-workers and friends who are in this just as much as I am.

What advice would you give to your colleagues to help them to thrive and not “burn out”?

I’ve been so focused on worrying about burn-out with my team that I’ve paid less attention with respect to myself. In regards to the current environment, working from home has been great in a number of ways, but it eliminates the clear division between work and home. That’s been a challenge for a number of folks on our team, and, even though we’re super busy, I’m encouraging people to take breaks and schedule a vacation this summer to promote work-life balance during a period where it is increasingly difficult.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My business partner of 20+ years, Ryan Alexander. While Ryan and I aren’t working together full time right now, he’s currently the CFO of Write Label and we have a number of business and philanthropic ventures that we continue to run together. Ryan is a much better operator than I am, and I constantly find myself thinking about how he would handle various situations and challenges (I also call him and ask for his advice).

What are some of the goals you still have and are working to accomplish, both personally and professionally?

Personally, I’m still working on trying to control emotion during these hard times, and keep an even keel when frustration strikes. By nature, I am not a patient person, but as a CEO and leader, having patience is critical and something I am always striving to improve on and develop.

Professionally, because I have a hard time separating work and life, I look at these quite similarly. Outside of being CEO of Write Label, I am also president of a private foundation, so having two leadership roles takes a lot of time, energy and focus. For me, it’s not just work-life balance, but work-work-life balance. I aim to be disciplined with how I spend my time, which is always a constant challenge, and it’s always my goal to do better. I am also on a number of profit and non-profit boards, so as you can imagine I have a lot of responsibility to juggle, but it keeps things interesting!

When it comes to Write Label, we have experienced huge growth (300%) in our platform over the last few months, as folks explore their work from home and freelance options and brands look to pivot their content quickly in this uncertain and rapidly changing climate. My goal for the company is to focus on expanding into new verticals and extending the platform beyond writing into visual advertising (display and video).

We are also making a commitment to becoming a more diverse company. As of now, 23% of our writing community is minority, and we have a goal of getting this to at least 30% within the next 60–90 days. Also, while our clients can always choose to receive project submissions from people of color, we are making it our ongoing goal to promote these services to clients ensuring projects have diverse talent submitting creative ideas and that this is the norm being promoted within the industry.

What do you hope to leave as your lasting legacy?

I hope people say I was effective, impactful and a great partner. And of course, that I made a lasting difference in the businesses and charities I have worked for over the years.

You are a person of great influence. If you could start a movement that would enhance people’s lives in some way, what would it be? You never know what your idea can trigger!

Separately from my role with Write Label, I run a private foundation that just helped launch a new fund focused on supporting Black leaders at a national level, as well as at a community/local level. So far, we’ve raised nearly 1 million dollars for this initiative we’re calling the Amplifying Black Voices Fund.

The fund is led by Robinhood CEO Wes Moore, former Secretary of Education John B. King, Jr., New Leaders’ CEO Jean Desravines, Lawyers Committee for Civil Rights’ President Kristen Clarke, and Education Reform Now’s CEO Shavar Jeffries and has support from The Moriah Fund, Galaxy Gives, Chan Zuckerberg Initiative, CityBridge Foundation, and the Bridge Alliance Education Fund. Amplifying Black Voices helps to make immediate and urgent investments directly in Black leaders and the Black community. We are just getting started on it, and have exciting plans for the future. We all need to do a better job with hiring and retaining people of color in our own ranks, and as I mentioned, this is also a huge focus for Write Label and our community.

How can our readers follow you on social media?

@writelabel

@gideonstein

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