Cynthia Coker of N2M Advisory: “Go for it even if you don’t know everything about the job”

Go for it even if you don’t know everything about the job. That’s how I got my first opportunity with a tech startup. Even though they recruited me, I didn’t know anything about their product at the time but ended up being one of the most instrumental people in the company’s growth. I gained a […]

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Go for it even if you don’t know everything about the job. That’s how I got my first opportunity with a tech startup. Even though they recruited me, I didn’t know anything about their product at the time but ended up being one of the most instrumental people in the company’s growth. I gained a wealth of knowledge that continues to benefit me today and it turned out to be one of the most rewarding experiences in my career.

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

Cynthia Coker is the founder and CEO of N2M Advisory, a leading information technology services firm specializing in enterprise technology and digital transformation. She and her team lead critical digital transformation initiatives for some of the world’s leading companies including Fortune 50, mid-market, and private equity firms around the globe.

Coker is a twenty-five plus year technology industry veteran, tech startup executive and two-time CEO. Prior to N2M, she held executive positions with global technology companies such as McKesson and Oracle, and a Silicon Valley Venture Capital-Backed tech startup where she was instrumental in its fast growth, IPO, and exit. Highly skilled in scaling companies, Coker has launched innovative technology startups, led mergers and acquisitions(M&A) and turnaround initiatives for many venture capital firms and global healthcare and technology firms.

A recognized technology and digital leader, Coker served as a Director for Women in Technology International and currently serves as an advisor and board director to tech startups through organizations such as Springboard Enterprises and N2M’s own venture arm. Coker also serves on the board for N2M.

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 founded N2M over a decade ago as I was receiving requests from my peers in the San Francisco area to help vet and launch innovative healthcare technology companies as I had a strong background in healthcare. I started my career in the medical device industry leading market expansion focused on innovative cardiology devices for North American Instrument Corporation (NAMIC which was acquired by Boston Scientific). I later worked for Eli Lilly and McKesson.

While at McKesson, I was recruited by a Silicon Valley Venture Capital-Backed Tech Startup focused in the Enterprise Application Integration area to lead global alliances and market expansion. It was my experience in medical devices and tech startups that gave me real-world experience in launching new and innovative technology, as well as the skills to scale and grow companies through IPO and successful exits.

A well-known healthcare publication interviewed us and almost overnight, N2M went from advising and launching innovative tech startups for companies and venture capital firms to working with global medical devices manufacturers and pharmaceutical corporations assisting them to license and acquire innovative technology and companies. During that time, I gained a lot of experience in mergers and acquisitions(M&A).

I spent over twenty years in the Enterprise Technology space starting from my first tech startup role to leading digital and business transformation for PeopleSoft and Oracle supporting clients across industries. I was involved in cloud, SaaS, and digital adoption very early on. I had the opportunity to lead digital transformation initiatives for many Fortune 50 companies, mid-market, and private equity firms globally.

I noticed that many private equity firms weren’t focusing on technology in the due-diligence pre-acquisition process or even post-acquisition. Not only was this leaving them more vulnerable to risks it was also keeping them from gaining substantial revenue and returns. Many years ago, we started working with a leading global private equity firm overseeing risks that were identified in technology due-diligence assessments for their portfolio companies. We have been engaged with them ever since assisting with a myriad of projects including technology and cybersecurity due-diligence, Enterprise Resource Planning (ERP) software selection and implementation as well as turning around failed projects.

Today, N2M’s Private Equity practice serves leading private equity firms globally assisting with technology and cybersecurity due diligence, as well as providing post-acquisition IT advisory and implementation services with a specialization in digital transformation.

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

The way we work has fundamentally changed due to the COVID-19 pandemic. Almost all companies have had to find ways to quickly implement digital solutions to survive and create stability and agility. With private equity becoming more competitive as well, firms must find new ways to create operational efficiency and increase internal value.

Digitally transforming business operations can create efficiencies, increase the visibility of data, reduce costs, and increase returns on investment. The actual process of transformation, however, can be disruptive to business and deal flow. Consequently, the private equity sector has been reluctant to embrace digital transformation.

Another reason some firms have not been as quick to embrace digital transformation is that it is often misunderstood, and companies and boards don’t understand what digital transformation is. Digital Transformation is the use of technology to transform business operating models, such as replacing manual processes with automation enterprise wide. True Digital Transformation is an enterprise initiative to transform a non-digital company into a digital one.

Digital Transformation can be the real financial differentiator for Private Equity portfolio companies. N2M is working with leading private equity firms globally to assist in creating that competitive edge through digitization that they couldn’t get otherwise.

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?

I am not sure if there was one funniest mistake, but I have made many along the way. One of the biggest lessons I learned is to be more aware of opportunities and to make the most of them. I was recruited to work for a Silicon Valley Venture Capital-Backed Tech startup in the 1990’s. This was before Google or Facebook were even founded. I found myself going from Atlanta, Georgia working for McKesson to the heart of the tech startup scene in San Francisco and working with Venture Capital firms. It was a fascinating and exciting opportunity and time. We grew the company rapidly and sold it in three years. I was offered the opportunity to stay with the company that acquired us, and I was also offered another opportunity to live in San Francisco working for another rising startup at the time. What I didn’t realize then is all the opportunities I had and how to make the most of them. Sometimes, you need to pause and be aware of opportunities you have at hand as there is a lot to be said for timing and location.

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?

I have had many mentors including my parents who were both successful entrepreneurs to others in my career who have given me opportunities and believed in me. What I have learned is that mentors come in many forms — they can be managers, parents, role models, customers and more. N2M’s Private Equity practice has grown through the support of key partners and customers who continue to believe in us and support us today.

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?

In just a few months’ time, the COVID-19 crisis has brought about years of change in the way companies in all sectors and regions do business. Companies have had to accelerate the digitization of their customer and supply-chain interactions and of their internal operations by three to four years. To stay competitive in this new business and economic environment requires new strategies, practices — and disruption of the old way of doing business. Digitizing businesses and operations now are obviously a necessity and will bring about positive results.

Having worked in the tech startup area for years, I learned a lot about disruption. However, the path of a disrupter is not always a lucrative one. As part of its makeup, the disrupter chooses to take on established businesses, and sometimes an entire system or industry, head-to-head. The objective is to replace or displace an existing way of doing something. The success of the disruptor comes down to preparation, planning, innovation and ultimately timing. The attempt to try to disrupt something must be carefully evaluated. Timing on any transformation governs its success; it often depends on whether the market, ecosystem and customers are ready for it.

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

Go for it even if you don’t know everything about the job. That’s how I got my first opportunity with a tech startup. Even though they recruited me, I didn’t know anything about their product at the time but ended up being one of the most instrumental people in the company’s growth. I gained a wealth of knowledge that continues to benefit me today and it turned out to be one of the most rewarding experiences in my career.

Action is the key to success. I have been fortunate to launch new technologies, divisions, and companies in my career. A lot of people spend more time planning and trying to have everything perfect before they launch a product, company or whatever the venture may be. Oftentimes it is just taking the first step that keeps people from succeeding. I am a big believer in starting and doing — you will learn a lot as you go.

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

I have had experience working in one of the most male-dominated industries which is technology, and as a female founder and CEO. There are not many of us around or to network with. Only 13% of women own startups in the information technology sector in the United States. Given my experience, I believe the lack of having a network like men do in business is one of the biggest challenge’s women face. It’s much easier for men to get funding, career, and board opportunities and more due to men having greater networks than women. There are simply more men in positions to help other men.

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

There are a few books that I keep on my desk. One I refer to time and time again is “The 80/20 Rule Principle” by Richard Koch. It is based on the 80–20 rule, also known as the Pareto Principle, which is an aphorism which asserts that 80% of outcomes (or outputs) result from 20% of all causes (or inputs) for any given event. In business, a goal of the 80–20 rule is to identify inputs that are potentially the most productive and make them the priority.

I have used this principle to gauge startups and companies’ potential, identify strengths and weaknesses and uncover areas of focus for growth and to turnaround companies. I believe the 80/20 rule applies to both life and work as it helps to focus on what’s important and yields the greatest returns as well as happiness.

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. 🙂

National and corporate cybersecurity is the greatest threat facing the world economy over the next 10 years. Among all the myriad worries faced by global leaders, cybersecurity is placed above all other major concerns. These include the risk of disruption caused by income inequality and the job losses arising from technological advances; societal and ethical implications of artificial intelligence; and the impact of climate change. Cybersecurity is a systemic threat and an existential threat. N2M has been working with companies and corporate boards to increase the awareness that they must treat technology and cyber risks at the highest governance level.

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

“All that we are is the result of what we have thought.” — Buddha. I have learned that what we focus on most is what we become. Focus on failure and you will fail. Focus on what you want most and that is what you will have and become.

How can our readers follow you online?

I can be found on LinkedIn or can be reached through our company website at

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

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