Inspirational Women Leaders Of Tech: Heather Stratford of Drip7 On The Five Things You Need To Know In Order To Create A Very Successful Tech Company

An Interview With Doug Brown

Keep Learning. The technology world is changing every day. Literally, applications and processes that were followed just 5 years ago are gone. As a leader and someone who is going to create a lasting company, continued learning is critical. Listen to podcasts, read or listen to books, talk to a variety of people, meet with mentors, take classes, sign up for volunteer opportunities, take on new projects. Learning is a lifelong skill. Those who understand that the world is continually changing will be okay with uncertainty, thrive when not knowing all the answers, and be able to teach the next generation through a wide range of experiences.

As a part of my series about “Lessons From Inspirational Women Leaders in Tech”, I had the pleasure of interviewing Heather Stratford.

Heather Stratford is the Founder of Drip7 a microlearning platform focused on cybersecurity education. Heather writes, speaks, and is a thought leader on cybersecurity and women in technology. She has started multiple national companies and believes that technology can solve the current problems in our lives.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

I remember getting my first computer, a Texas Instrument — TI/99 4A. I was so excited to start coding and using the computer. Since most of my siblings were older and out of the house, my parents asked me if I wanted to go to two summer camps at the University. I chose volleyball and computer camp. At the computer camp, there were lots of kids — all boys except for two girls. It was hard to be a girl interested in technology. By college, I was only taking software classes and not computer science. But my first job out of college, I was on a computer eight hours a day running a production department for a publishing house. Over my career, I kept landing in new fields with new technology and new problems to solve. I always saw technology as a way to make things more efficient and better. I fell into cybersecurity because with technology solutions also comes risks and responsibilities. And I wanted to help people understand the technology but use it in a way that was safe and didn’t compromise the organization. My unique story about how I landed in cybersecurity was because of a long history of different jobs and industries that showed me the benefits and pitfalls of technology, and I wanted to help solve some of the inherent risks that I kept seeing.

Can you share the most interesting story that happened to you since you began at your company?

I was working with a large potential client. We had several meetings and had attended a conference or two together. I was attempting to sell this organization services that I offered. The head administrator got to know me well enough that he said, “This is what I want and need.” Though I told him it wasn’t in the marketplace, I asked more about what he was looking for and we developed a scope. Over time, I agreed to build a product that he would fund. I then went one step more, informing him that I wanted to own the Intellectual Property. He said, “Sure, the organization was not interested in that.” And we started a great relationship — both getting what we needed.

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?

When I was younger I worked for a company that was family-owned. As I got to know my colleagues, I found myself conversing with others who had been talking negatively about the lack of skill set in other employees. What I hadn’t realized was how many family members were in this company, all with different last names — sons, daughters, nieces, grandparents. What I learned was never talk bad about another employee. Always assume that people are friends or related. Remember that the person with the title might not be the most powerful person in the company — a title is just a title.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

At one point I had built a very lucrative company with continued sales and contracts in the 1 to 2 million range. I decided to sell the company, but had never been through the process. Looking back, I had chosen the wrong representative to find a buyer and broker the deal. When the ink was signed, I started working with the new owners to transition the business. Within 2 days I realized that they would never be able to run the company successfully and had misrepresented their skills. I tried to get the deal reversed but it was too late — I trained the new owners, handed over the reins, and watched a very successful company dissolve within months. The majority of the sale was on a buy-out over time, and I lost almost all of the sale. It was a very expensive lesson to learn.

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 about that?

I know it’s a typical answer but my parents are a large part of who I am. My father was a veteran of WWII and his values and focus on God, family, and country gave me a very solid background. He was also a lifer at General Electric and was very proud of me as I ventured into the entrepreneurial world and began shaping my own future — one very different from his path. My mother showed me that helping has no limits. You help and volunteer wherever and whenever you can. When you see a problem, you were given talents to help solve it. So it’s your responsibility to do that. One story in particular was around building a covered dock at our lake cabin. We did all the work ourselves. We had to carefully float and drag lumber to the dock area, organize supplies in a limited space, watch the weather and timing because it was late fall. We had to lift and nail, support and brace, shingle and cover. It was a large project that we did in only a few days. What I reflect upon is that I was an integral part of the team. I did as much work on the project as my older brothers did. My dad never saw me as a “girl” that could do “girl” things. He saw me as capable, and I stepped up to the role. I have carried that attitude and philosophy into my career. I didn’t think I should be held back because of my age, or gender. I thought if I worked hard and learned the material that I could do it. I learned that from my father — ironically a man from a much older generation.

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

The definition of insanity is doing the same thing over and over again and expecting a different result. Attributed to Albert Einstein.

I love this quote because it calls into question all actions. We have control over our actions and the results are really determined by us. It’s the opposite of destiny. While many people fell into complacency and entered the general idea of insanity — I strove to break out of this mold.

Ok super. Thank you for all that. Let’s now shift to the main focus of our interview. We’d love to learn a bit about your company. What is the pain point that your company is helping to address?

Decreasing cybersecurity risk and preventing breaches through empowering employees with skills and knowledge in cyber security and other compliance areas.

What do you think makes your company stand out? Can you share a story?

Drip7 was founded because a company needed to create behavior change around cybersecurity in their organization. The products available were not satisfying their needs. Drip7 addresses the growing issue of cybersecurity education. There is a 3-part perfect storm that is creating opportunity for criminals. 1. Cloud computing is here to stay and on the rise. 2. COVID-19 sent workers home with new routines and processes. 3. There are now more Millennials in the workforce than Baby Boomers. Combine these three things with the statistic that 90 percent of all cyber breaches can be traced to human error. We must change the way we look at cybersecurity and empower people with knowledge for the current interconnected world. Drip7 stands out because it’s bringing an empowering message to an industry focused on fear and guilt. Last year, I spoke with the head of a security department — a CISO. When I told him what I was working on, he asked if his organization of 65,000 people could be part of our early adopters. When I asked him why, his answer was simple. “It’s about time that someone fixed this problem in the industry. I think you have it.”

Are you working on any exciting new projects now? How do you think that will help people?

Yes, Drip7 is a new project. Drip7 is an innovative implementation of technology that stemmed from its parent company, Stronger International. It’s a microlearning platform that addresses the need for a more gamified, mobile solution to training around cybersecurity and compliance areas. It’s designed to be flexible and creates retention of information by spreading the desired learning out over time. Drip7 empowers people with knowledge that is critical for their personal use, the organization’s use, and for the community.

Let’s zoom out a bit and talk in more broad terms. Are you currently satisfied with the status quo regarding women in Tech? What specific changes do you think are needed to change the status quo?

I am a big proponent of getting more women into the technology field. Our world is dominated by technology and computers, and yet, the people designing how the computers work in terms of AI, blockchain, and security are all primarily men. Women need to help create the solutions that will make this world a better place — and technology in all its forms can be the tool to make that happen. There needs to be opportunities for women to learn more innovative implementations for technology and take leadership roles. I am a female entrepreneur in technology and have observed that a significant gender gap remains among both investment administrators at venture capital firms and recipients of venture capital funding.

In 2019, 2.8% of capital funding went to women-led startups, an all time record. However in 2020, this number fell back to 2.3%. According to the Harvard Kennedy School of Business, “The gender gap in venture capital can lead to major disparities in the tech sector and beyond, given that venture capitalists play a critical gatekeeping role in deciding whose ideas, products, and innovations get a chance to shape our modern economy and society.” More support and funding needs to be available to female technology founders.

In your opinion, what are the biggest challenges faced by women in Tech that aren’t typically faced by their male counterparts? What would you suggest to address this?

I already mentioned the disparity in funding for entrepreneurs. Women also face challenges in being perceived as an expert in the technology space. There was a time when the pronoun for a doctor might have been a male pronoun. Now, that pronoun’s context is likely female — for the first time in history, women make up the majority of students in US Medical schools. This shift has yet to happen in technology. Currently, only 20 percent of computer science professionals are women — a number that has decreased since the 1980’s. We need to create a path and provide acceptance — in both education and the workforce — for women to have both a career and a family is essential. Women also need to feel supported and have access to mentors to help them throughout their career.

What would you advise to another tech leader who initially went through years of successive growth, but has now reached a standstill. From your experience do you have any general advice about how to boost growth or sales and “restart their engines”?

Understand the difference between want and need. There are things that need to be done and things you want to be done. Balance your home, physical, and work life. Being centered is critical to being sharp and able to handle many situations. Cybersecurity is an ever changing and highly stressful field. Balance is key. Also remember that it’s the journey not the destination.

In your specific industry what methods have you found to be most effective in order to find and attract the right customers? Can you share any stories or examples?

I believe there are different customers for different stages of a company. At the early stages of a company, all customers are wanted. But as a company grows, the right customer becomes more apparent. The key areas that must match are: 1. The company’s service or product needs to solve the pain point for the customer 2. The price to service level balance must be met. If price is the key factor then the customer service might be lacking. If customer service is essential then the price will have to include those costs. 3. The culture and values are a match. When these 3 areas align, a company will have a customer for a very long time.

Based on your experience, can you share 3 or 4 strategies to give your customers the best possible user experience and customer service?

1. Listen to the customer. The culture of the US is to talk and be heard. I have found that the best way to understand a customer and make a real connection is to actively listen. Write it down. Hear it. Reiterate what they are saying so you get it right. Listen to how they are saying it and what they are saying.
2. Be accessible. We have customers that want to hear from us through email only. Others that have a 30 minute meeting scheduled every week. As an owner, I take every call and put that person into my phone. When I am in a meeting, I can see who is calling me. I give my personal cell to key clients because I want them to know if they have an issue, they always have a direct line to the top.
3. Adapt to the client. One of the areas of “Blue Ocean” in the cybersecurity education sector is customization — be able to offer a client a customized solution quickly and easily. In today’s world, no one wants a generic off the shelf solution. Make it fit the customer’s business.

As you likely know, this HBR article demonstrates that studies have shown that retaining customers can be far more lucrative than finding new ones. Do you use any specific initiatives to limit customer attrition or customer churn? Can you share some of your advice from your experience about how to limit customer churn?

1. Onboarding is a critical part of a customer experience. They have made the decision to purchase your product or service and want to have a good experience. Assist them with having an efficient, clear experience and meet the desired expectations.
2. Put people first. Treat your employees with respect and they will treat the customer with respect. In life, when we feel belittled and put down, we often turn to the person or animal that is beneath us in hierarchy and take out our frustrations on them. Respect and loyalty are earned. When a company has that as a value, it translates to how they interact with their customers.
3. Put yourself in the customer’s shoes. What would you want to see to get a problem resolved or to solve an issue. What would make a problem go away for you if you were a customer. Put yourself in your customers shoes and stop creating excuses, create solutions

Here is the main question of our discussion. Based on your experience and success, what are the five most important things one should know in order to create a very successful tech company? Please share a story or an example for each.

1. Hire the right people. A company is only as good as its people. Very few companies can be successful with just one person. Hire the right people to compliment you. Don’t be afraid to hire people better than you are. Early in my career, I had the opportunity to hire an assistant manager who was clearly more qualified than I was. I did not hire that person, and although we remained friends, I always regretted that decision. Later as I was growing a company I had the choice to hire younger people, older people, skilled people, unskilled people. What I have learned is that hard work and attitude cannot be taught. And ethics and loyalty are part of a person’s nature, not something that can be taught. I hire for ethics. If I can’t trust them, I can’t work and grow with them.
2. Work Hard. I believe the majority of people could do any job. 90 percent of jobs out there the average worker could do. What they lack is support, training, and confidence. My first job out of college, I became the production manager of a publishing house. I was hired quickly to produce a national magazine and send it to the press in 10 days. They had lost an employee, and I needed to fill those shoes. We did not have the internet as a resource like we do today. So I bought books and called friends. I asked questions and read at night. I learned what I needed to to get the job done. I worked hard and that will always pay off.
3. Keep Learning. The technology world is changing every day. Literally, applications and processes that were followed just 5 years ago are gone. As a leader and someone who is going to create a lasting company, continued learning is critical. Listen to podcasts, read or listen to books, talk to a variety of people, meet with mentors, take classes, sign up for volunteer opportunities, take on new projects. Learning is a lifelong skill. Those who understand that the world is continually changing will be okay with uncertainty, thrive when not knowing all the answers, and be able to teach the next generation through a wide range of experiences.
4. Create a Network. Everyone has a network of people they know. For entrepreneurs, their network of people needs to be wide. Take time to talk to, text, or email people to keep them in your loop. Post on social media to keep your name relevant to the people you know. Networks provide employees, jobs, advice, support, connections, and education. I had the opportunity to become a Tory Burch Fellow. One of the valuable lessons I learned while participating in that year long program was that I was not alone. I was surrounded by dozens of other women who were building companies, learning, and growing just as I was. They are part of my network now and they make the journey better. You don’t create something alone. Be connected. It will pay off in multiple ways.
5. Listen to the customer. Drip7 was created based on listening to a customer. They needed to solve a specific problem and couldn’t find the right solution in the marketplace. Listening teaches you more than talking. Learn to listen actively by writing things down and repeating key things back to the other person.

Wonderful. We are nearly done. Here are the final “meaty” questions of our discussion. You are a person of enormous 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. :-)

Support a woman to get involved with technology. Whether it’s a relative or a friend, support women of all ages to get more involved in learning about business and technology. Our whole world is dependent on technology, and women need to be involved in the creation of the new solutions that will help solve our world’s problems. Ask a young woman about a career in technology.

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them :-)

I would love to have breakfast with Thai Lee. She is the co-owner of SHI. Drip7 is a product distributed by SHI, and I am an admirer of how she created and grew the company. She is the picture of what makes the United States a unique place — a woman in tech who was an immigrant to the United States. When I see that she did it, I know it’s possible for other women too.

Thank you so much for this. This was very inspirational, and we wish you only continued success!