I recently went one on one with Craig Hinkley, CEO of WhiteHat Security. Craig joined WhiteHat Security as CEO in early 2015, bringing more than 20 years of executive leadership in the technology sector to this role. Prior to joining WhiteHat Security, Craig served as vice president and general manager of the LogLogic business unit for TIBCO Software. In that role, he was responsible for global field sales and operations, client technical services, engineering, research and development, product design, and product management. Before TIBCO, Craig served as the general manager at Hewlett-Packard for the HP networking business in the Americas. Earlier in his career, Craig held positions at Cisco Systems Inc. and Bank of America. 

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?

Craig: I had an unconventional route to the CEO position as I started on the customer side inside large IT organizations. I began my career as a technical engineer and expert in telecommunications and networking before being promoted to executing and managing the largest IT outsourcing contract for a tier-1 US-based financial institution. I moved across to the technology side when I joined Hewlett-Packard to help them build their enterprise networking business. My career from then was centered on expanding my functional responsibilities and experience to take on General Manager roles until ultimately joining WhiteHat Security over five years ago as my first CEO position. Over my nearly 30-year career, I have had many challenges, setbacks, and failures, while also several successes and triumphs. I am a subscriber to the philosophy that we learn more from our failures and challenges than we do from our successes. For it is in our failures that we learn humility, vulnerability, and most of all, perspective. I find that when a person has faced and overcome major personal or professional adversity there is a sense of calm during “normal” crisis because of the perspective gained from overcoming such deep and challenging situations.

To give a recent example of a setback and challenge of mine would be during my first year as CEO at WhiteHat. If you had asked me back in 2015 what percentage of my leadership skills from my previous roles applied to my new CEO position and what percentage were new skills I thought I needed to learn to be an effective CEO, I would have given you an 80/20 split. That is, 80% are transferable and 20% were the new skills I would need to learn. I was completely wrong. It was the complete opposite with only about 20% of my skills being transferable and 80% being the new skills I had to learn.

One of the most significant things I had to learn was to be my true self as a leader and learn new CEO skills versus what I did, which was to wear the “costume” of how I thought a CEO should act and behave.

Adam: What are the best leadership lessons you have learned over the course of your career?

Craig: Over my career the three lessons I have learned are:

Lead from within. It is a confidence that comes from knowing who you are; what you stand for; and what you believe. It is also knowing that you will fail, but you will also learn from failure and recover quickly. An inspiration that emanates from your vision and passion. A leadership approach that “pulls” people toward you versus trying to “push” them along. A style of leadership that creates the space that allows your team to move toward you.

Circle of Dignity. This is about defining: What do I stand for as a person and as a leader; what are my values; and what are traits that people would use to describe me and that I want them to use to describe me at the end of my life. These are the things that I would never compromise - no matter what.

My “Circle of Dignity” is defined as:

• Caring - Give freely to others; be there to help

• Optimistic/Positive Energy - It is an infectious, active, and forceful positive energy

• Committed/Perseverance - Bring effort and dogged determination to push through to achieve the goal.

To support and maintain my “circle of dignity,” I cultivate and develop the following personality traits:

• Be true to myself

• Be vulnerable

• Be authentic

Knowing who you are as a leader in terms of what you enjoy, what your strengths are; and where you want to spend your time, effort, and energy. What that means for me is that I know I am not a start-up leader. I’m not your $0 to $10M or $0 to $20M leader. I am not an entrepreneur in that sense, and I accept that. I know I am a turnaround, transformation and growth leader who leverages “Value Creation & Value Extraction” models to redefine and reposition a business for success.

Adam: In your experience, what are the key steps to growing and scaling your business?

Craig: As a CEO we have three priorities or main responsibilities. The three priorities of a CEO are: 1) Fund the Business; 2) Set the Vision; and 3) Build the Team. Using a plane analogy, I would describe this as:

• Fund the Business: It is about raising capital to create the runway for the business to take-off and operate. Then continuing to raise capital to fuel the plane to sustain the flight.

• Set the Vision: As the Captain of the aircraft we must set the destination. To set the vision of where you are going. To define and be able to announce to the crew and the passengers what the vision of the company is. Where will the company be in five years? The purpose is to set general direction of where you are heading, knowing that the vision will change over time – and therefore, making course corrections as you learn. Like the flaps on the wings of a plane, we will constantly be making minor corrections and adjustments, and if we encounter a storm or bad turbulence ahead, make changes. But one thing is for sure, this plane does not have an autopilot. We are always on. We are always actively flying the plane.

• Build the Team: We can’t do this alone. We can’t fly this plane alone. We need a great set of co-pilots and flight crew. We are responsible for recruiting, training, and developing the team that is going to help you fly, service and support the plane and the flight path we are on. Our job is to continue to support, challenge and grow that team to be the best team for the flight we are on together. There may be times we need to swap out a leader. As the plane is soaring and reaching for new heights, sometimes a leader will go horizontal as they can’t keep up the leadership growth trajectory. Jettisoning a leader is one of the hardest things we ever must do, but it is often necessary.

Adam: What do you believe are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

Craig: Acknowledging we are on a journey and that leadership growth is about progress and not perfection. I strive to have awareness of how I show up as a leader during the day and to work on these leadership qualities that I know helped get me to where I am today, but will not help me be successful in the current and newer roles I want to have. I strive to make today’s version of me as a person and a leader better than yesterday, and I commit to do the work needed to make tomorrow’s version of me better than today.

Be vulnerable. Your leaders and your company want to know they work for someone who makes mistakes and therefore allows them to strive and push themselves knowing too that they may fall short. We often talk about these qualities as “soft skills,” but at a recent Simon Sinek virtual seminar I heard him refer to them as “Human-Skills”. My advice: show people your human-skills.

Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?

Craig: Every situation is unique. Every leader is unique. We each have our own set of experiences, skills and capabilities that make us who we are as entrepreneurs, executives, or civic leaders. Therefore, offering advice or tips would be done without context of all the great things that make you the leader you are. My singular best tip for all leaders is … get a coach and/or surround yourself with mentors. Find a common community of leaders who, like you, want to grow and develop themselves, and then engage each other in real, open and engaging dialogue on all the issues, challenges and obstacles in your way of being a successful leader. Listen and learn from them. World class athletes have coaches, so why shouldn’t we?

Adam: What is your best advice on building, leading, and managing teams?

Craig: Build an environment that allows your leaders the opportunity to grow, to fail and to learn from that failure. One of the skills I had to learn in building a constructive leadership environment was to create the space that the leaders could move into and expand their leadership. I am an energetic and outgoing leader, so it is easy for me to have that energy and enthusiasm occupy any and all available space. What I had to learn was to not speak, and by doing so, allow that vacuum to exist. I also had to hold that space open so the leaders around me felt safe that they could lean into and fill the space up with their leadership. 

Understand that not everyone will make it. Some leaders will not have the leadership bandwidth to grow as the business grows. While these are difficult decisions to make, it is important for the overall health of the leadership team to make those changes as soon as possible, providing the outgoing leader with the level of dignity and respect they deserve. As I was struggling with a leadership decision a mentor of mine quoted to me the following saying that I use when faced with these decisions: “I wish I had waited three more months before letting that leader go, said no CEO ever.”

As a leader, focus on business needs and the outcomes you want. Allow your leaders the opportunity to define the decisions and paths needed to get there. Their plan and path will ultimately be more effective than any approach you outline as a leader because it is their will that is based upon their collective set of skills, experiences, strengths, and weaknesses. Your will is based upon your set of skills, experiences, strengths and weaknesses, which are inherently different than your leadership teams, and therefore, given that context, your plan that leverages your skills, experiences, strengths and weaknesses will be the wrong path for your leadership team who have a completely different set.

Adam: What are your best tips on the topics of sales, marketing, and branding?

Craig: In today’s digital world, how successful your company is at extracting value from your clients in the form of revenue is more a function of how multiple parts of the organization work together versus the performance of the sales organization as a standalone component. The revenue function in today’s modern organization is more analogous to an engine where all of the functions that are part of delivering high-quality revenue are cylinders that need to be connected, synchronized and aligned to perform at their collective best. The planning and discussion on revenue is no longer merely a discussion on the quality of the sales organization, but rather a broader discussion on the quality of all the functions that make up the revenue engine.

A major factor in building a repeatable and predictable revenue engine lies in the ruthless application of a sales methodology – e.g. MEDDIC; Sandler, etc. Whatever sales process is best for your team, market, industry – select it and adopt it. The true power of a sales process is not the process itself but the rigor, discipline, and commitment to the sales methodology you have chosen to use. The power and effect of a sales process is in the passion and commitment to the methodology not the merely the methodology itself. Whether your company has a CRO or these functions report to different executives, I believe they must be considered, discussed, and planned as one connected system—as part of one connected revenue engine

Adam: What are your most important tips for leaders on the topic of cybersecurity?

Craig: Continue to evolve your cybersecurity capabilities. The threat actors are evolving their skills and techniques for finding ways to attack and exploit human and technology weaknesses of an organization. 

Knowing where to start and what to do is often the hardest for companies because the attack surface is almost always larger than you have human or technology capital to deploy to mitigate or remediate. Therefore, my recommendation is to use a risk-based approach to understanding what the operational, reputational, customer, capital risks are to the business and applying the resources to mitigate the largest cybersecurity risks facing the company.

Adam: What is the single best piece of advice you have ever received?

Craig: You are never not the CEO. Understand the power that the position holds, and that people will always assess what you say through that lens. You may be an open and engaging leader who truly appreciates active discussion, debate and decision making. The tough part is realizing that when you speak there is often a perceived sense of finality to what you are saying. One way to combat that is to be overt in your communication styles and the intent of the discussion upfront but realize even in that situation you still have the risk that people take what you say as the final word. So, perhaps wait and hold your thoughts, and speak last as often as you can. 

The other great piece of advice I received, and I am working to operationalize in my own leadership DNA, is to truly be a servant leader it is my responsibility to understand how to connect, communicate, and lead my leaders in the way that motivates and inspires them.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

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