An Interview With Chad Silverstein
You don’t need to raise a huge amount of money upfront. There are plenty of ways to fund your startup so don’t rush into a long and complicated VC-style fundraising process. The time for a huge investment round will come and if you played your fundraising cards right at the outset, you will have enough power to decide whether you need it or not.
We are starting a new interview series about the world of entrepreneurship beyond the classroom — a realm where theory meets grit, and education meets real-world challenges. We want to hear about critical business wisdom that often goes unspoken in academic settings. I had the honor of interviewing Connie Stack, CEO at Next DLP.
Connie Stack is Next’s Chief Executive Officer. Connie is a cybersecurity industry veteran having most recently served as Managing Director/GM of the Data Protection Business Unit for HelpSystems, which included the Digital Guardian, Titus, Boldon James and Vera brands. Prior to acquisition by HelpSystems, Stack served as chief strategy officer and chief marketing officer of Digital Guardian.
Thanks for being part of this series. Let’s jump in and focus on your early years. Can you share who was your biggest influence when you were young and provide specific examples of what you learned from them that helped shape who you’ve become and how you live your life today?
Terry Fox was a big influence on me during my youth. He was a Canadian athlete, humanitarian, and cancer research activist. On 12 April 1980, with one leg having been amputated due to cancer, he embarked on an east-to-west cross-Canada run to raise money and awareness for cancer research. I was in Cape Spear, Newfoundland when Terry dipped his artificial leg into the Atlantic Ocean to start his cross-country “Marathon of Hope” and I was watching on television on 1 September 1980 when he was forced to end his run outside Thunder Bay, Ontario. Like millions of other Canadians I was devastated to learn the cancer that took his leg had now invaded his lungs.
Terry taught me grit and resilience. Despite the abrupt end of his Marathon of Hope, he never gave up on his mission to raise funds for cancer research. Through his foundation, Terry has raised more than $850 million and funded 1,300 innovative cancer research projects, bringing hope and health to millions suffering from cancer. I supported those efforts in some small ways and was awarded the Terry Fox Humanitarian Award, a four-year academic scholarship, as a result. I was incredibly proud to be associated with Terry and still use that grit and resilience today.
Staying on the topic of influence, who has been your biggest catalyst more recently and what can you share that you’ve learned from them that led you to making changes in your life?
Mo Rosen, the former CEO of Digital Guardian. I have aspired to be a startup CEO for much of my career, but like many other women, I had fears about my ability to do the job. Mo helped me squash those fears and pave a path to becoming a CEO. He mentored, coached and guided me through our years working together at Digital Guardian and gave me the confidence to seek out and ultimately land a CEO role. The biggest thing Mo taught me was the importance of building a great leadership team and as a CEO I have taken special care to ensure my management team is cohesive and performs strongly as a unit.
In this interview series, we aim to reveal what seasoned entrepreneurs wish they had known when they were starting out and capture what the textbooks and college professors left out. Mistakes are invaluable. Can you name one specific mistake that you made early on, and learned the most from, but wish you’d been forewarned about?
When it comes to people management I used to subscribe to the “treat others as you would like to be treated yourself” principle. I wanted to be treated maturely and professionally. I didn’t want my managers to pull any punches and preferred real-time, direct and candid feedback and I would correct immediately and not dwell on anything. As I started to manage others I was doing the same with them and I quickly learned a softer hand was required for some. Not all my team members responded well to unvarnished feedback without guidance on how to adjust their approach. This shifted my thinking away from treating others like I wanted to be treated to treating them the way they wanted to be treated. It seems like a subtle difference but it was a massive one for me.
I now fully appreciate that different needs motivate different people. Some of us are motivated by power, others strive to achieve. Some want money while others want autonomy. Some would relish public shout-outs while others would rather crawl into a hole than be singled out! I take this key-learning with me in all my interactions with direct reports and team members.
Is there a leadership myth you believed early on that you’ve since debunked through your real-world experience?
Leaders need to know everything. I believe that myth held me back from becoming a CEO earlier in my career. I used to think I had to be an expert in all areas of business from HR to software engineering to finance in order to add meaningful value and lead these functions.
That logic may have held during the Industrial Revolution when an assembly line worker became a manager by knowing how to perform every job on the factory floor. With today’s rapidly shifting business culture, that’s just not possible, or even advantageous. Today’s leaders need to be willing and able to tap into the skills and expertise of the talented people around them and that’s something I now do every day.
What’s the key operational insight you’ve gained since running your business that was never mentioned in any classroom?
There is a famous Peter Drucker quote that says “culture eats strategy for breakfast”. I learned a lot about strategy in the classroom, but I never learned anything about how to build a great company culture. Culture is the invisible stuff that binds organizations together and includes things like purpose and values. Sometimes that’s hard to codify and even harder to measure and therefore, manage.
After working in business and technology for over 30 years, I can say with confidence: culture will eat strategy, every time. Strategic imperatives mean nothing in a vacuum. If the strategy conflicts with what your team already believes, how they behave or make decisions it will falter and ultimately fail. Conversely, a dynamic team with a robust culture can turn a so-so strategy into a winning plan. Execution matters and a strong culture drives execution with excellence.
Did college prepare you for scaling a business? What specifically was missing?
Somewhat. I completed a Bachelor of Commerce degree in Canada and much of the course work was focused on the core functions of a business so it gave you a solid grounding in the basics, but beyond the basics, there wasn’t much discussion about scaling issues (at least when I was in uni in the 1990s). In my years working in start-ups I’ve come to learn about the top issues of scaling and any discussion around these topics would have been very helpful:
- Scaling before perfecting product-market fit.
- Choosing the wrong people to work with or hiring for quantity vs. quality.
- Scaling shifts your team’s focus.
- Scaling is expensive.
- Lack of business alignment across business functions.
Any unexpected challenges in team dynamics that your academic experience didn’t prepare you for? How did you handle it?
My academic experience did not offer any relevant support for operating an international business. I run a company with employees and department heads located in the United States and the United Kingdom. While both countries have a lot in common, I soon learned that there are a number of cultural differences in how those from the US vs. the UK work and conduct themselves in a work or business setting and those differences need to be recognised and respected. As an example, I did hire a US-based leader for a department whose employees were exclusively located in the UK and it was not a good cultural fit. From the minor issues of time zone differences to major issues around working style, it took a lot of time and energy to make this work in the short term and in the long term the leader ultimately decided it wasn’t a good fit and we amicably parted ways.
Have you had to unlearn any widely-accepted business ‘wisdom’ in your journey? What was it and how did it affect your strategy?
A great product is all you need. If I heard that once over the past 25 years, I’ve heard it a thousand times, the best product always wins. I now know the best products aren’t always the winners; and I’ve seen some not-so-great products lead the market — often due to very well-executed marketing. The reality on the ground is very few startups come out the gate achieving product-market fit with their V.1 products. The very first version of many winning products is what we now refer to as minimum viable product (MVP). MVPs are invaluable at testing the market’s response and you can iterate from there.
What’s your advice for new entrepreneurs? What are your “5 Things You Won’t Learn in College But Must Know to Succeed in Business”?
1. Passion for your business is critical. Things can get really tough, really fast and if you don’t have a true passion for your business, you will struggle. In tough times remind yourself why you originally started your business to rekindle that passion.
2. Culture matters, even in the early days. Culture is always vital to startup success, even in the beginning. A company’s core values will help entrepreneurs stay focused on what your company stands for and what you’re working towards.
3. You don’t need to raise a huge amount of money upfront. There are plenty of ways to fund your startup so don’t rush into a long and complicated VC-style fundraising process. The time for a huge investment round will come and if you played your fundraising cards right at the outset, you will have enough power to decide whether you need it or not.
4. Disrupting a legacy category isn’t easy. Put simply, it’s hard. There are generally valid reasons why the old guard persists and ignoring those reasons will be at your peril.
5. Grit and persistence will be your top qualities as a new entrepreneur. Related to #1, you will hear “no” and “not now” a lot. Get comfortable with rejection and persist through it to the YES!
How do you ensure your team not just understands but embodies your business principles? Any techniques you wish you’d known earlier?
Short answer — transparent and frequent communications. Whether it’s at your weekly senior management team meetings, on your All Hands calls, or with posts on collaboration engines like Slack and Teams you need to communicate your business principles constantly. I love the old adage, “Tell them what you are going to tell them, tell them, then tell them what you told them.” That is how it works.
If we were sitting together two years from now, looking back at the past 24 months, what specifically has to happen for you personally and professionally, for you to be happy with your results?
Professionally, I want to grow our company Next DLP to $100M in annual recurring revenue. That is such a critical step for tech startups in particular, and hitting that milestone keeps all paths open to the business and to me as CEO.
Personally, I’ve never been good at work-life balance and I throw myself into work with abandon. Two years from now I will have put the work-life balance to the side in favor of “work-life integration”. I will have achieved a work-life integration that brings both work and family life into “more harmony” and I’ll “design my days” so that both work and life are in balance.
Looking back over the last two years, what key accomplishments make you satisfied with your progress?
Achieving in excess of 100% sales booking growth at Next in 2023 vs. 2022. As a cyber-security start-up facing stiff competition and economic headwinds, this accomplishment is very satisfying for me as well as for my team that made it happen.
Building a strong and enduring company culture. This was not without its challenges given half our company is based in the UK and half is in the US, with most working remotely. The required stellar communication skills that drove successful team collaboration. My team helps each other, speak to each other respectfully and efficiently, and we’ve accomplished great things as a result.
Delighting our customers! We have strived to deliver a customer experience that triggers great enthusiasm for our Reveal Platform. We’ve done that by catering to customers’ needs and consistently delivering on our core data and employee security value proposition. Hearing customers say things like, “Next DLP is an invaluable partner,” is priceless and we hear that a lot.
As someone with significant influence, what’s the one change you’d like to inspire that would benefit the most people?
If I could, I would endeavor to improve civil discourse in the USA and around the globe. Civil discourse isn’t just about polite conversation, it’s a vital ingredient to better leadership and the common good of all.
How can our readers keep up with your work?
LinkedIn is the best way to keep up and connect with me.
This was great. Thanks for taking time for us to learn more about you and your business. We wish you continued success!
About the Interviewer: Chad Silverstein, a seasoned entrepreneur with over two decades of experience as the Founder and CEO of multiple companies. He launched Choice Recovery, Inc., a healthcare collection agency, while going to The Ohio State University, His team earned national recognition, twice being ranked as the #1 business to work for in Central Ohio. In 2018, Chad launched [re]start, a career development platform connecting thousands of individuals in collections with meaningful employment opportunities, He sold Choice Recovery on his 25th anniversary and in 2023, sold the majority interest in [re]start so he can focus his transition to Built to Lead as an Executive Leadership Coach. Learn more at www.chadsilverstein.com
Connie Stack Of Next DLP On 5 Things They Forgot To Mention In College was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.