C-suite career advice: Ray Kruck, Tugboat Logic

What was the most valuable piece of career advice that you received? “Build a foundation of solid career relationships with people who can trust you and who you can empower to be successful as well.”

Tugboat Logic

Name: Ray Kruck

Company: Tugboat Logic

Job Title: CEO

Location: Burlingame

Ray Kruck has a 24+ year enterprise security career with executive leadership roles in Corporate Development, Marketing and Sales at several leading firms, including Check Point Software, Proofpoint, Websense, and Voltage Security. In 2011, Kruck co-founded Nexgate with a breakthrough platform to help brands discover, monitor and secure their brands social presence. Nexgate was acquired by Proofpoint (NASDAQ: PFPT) as their largest acquisition in 2014. Kruck enjoys mentoring other startup ventures with his participation as an Associate in Canada’s leading technology venture mentorship program - Creative Destruction Lab. In 2017, Kruck founded and became CEO of Tugboat Logic Inc, a security assurance platform that leverages advanced technology and embedded guidance to automate and simplify security management. Tugboat Logic helps clients prove compliance and transact more effectively. 

What was the most valuable piece of career advice that you received? Build a foundation of solid career relationships with people who can trust you and who you can empower to be successful as well. Develop your personal brand. I learned that early on when I worked at Checkpoint Software.  

What was the worst piece of business advice that you received? The worst advice I’ve received was from a CEO. He told me every work relationship was either someone that was going to help me up, or that I needed to step around in order to move forward.  He felt that the only way you move forward is by stepping on or around people and that he had to look for an advantage or an angle in everything.

What advice would you give to someone starting their career in IT/tech? If you have the chance, your first job out of college should be with a large company. It'll show you a good infrastructure around in terms of learning opportunities and space. Typically, a big company with resources gives employees time, space and educational opportunities to be able to figure out their role and get assimilated. It also gives you a chance to build trusted relationships over time, your career and your brand within a larger organisation. Big companies can afford to make mistakes, there's lots of room to make try new things and the company won't fail as a result in most cases. One of the takeaways from a large company dynamic can be with not to do from a strategy point of view or what not to do at a personal management point of view.

Did you always want to work in IT/tech? No, I started off in a family car business in Toronto fresh out of college with my MBA. The first job I had was running a car dealership with 55 employees and over $60M in revenue. I was only 22 years old was supposed to be running this very established legacy business. It was terrifying pressure, but I learned how to manage people very quickly, and be a good judge of character—it was more dog eat dog than the tech world is.

What was your first job in IT/tech? My first role in tech was BD at Check Point Software.

What are some common misconceptions about working in IT/tech? Some people think it's easy and you just need to say something clever or be smart in some kind of ethereal way and have a few insights. And some people do succeed that way. It also isn't true that you need to be a coder or a geek. I'm sort of a geek, but in a different way. I like technology for technology's sake, but I don't know how to code a single line of code.

I've met tons of successful leaders, executive leaders and even CEOs who don't have a technology background, but they have an openness to learn and be curious – I think that's the key to success.       

What tips would you give to someone aiming for a c-level position? Pick an executive that you admire at some level, whether that’s how they carry themselves or how they manage other people, find some executive that you feel you can emulate and build that relationship. I've done this before. If it’s not someone in your direct reporting line, then find ways to empower them to make them or their team successful. I think CEOs like to promote those who can carry their own and are competent in their own, but also have a positive impact on others around them. That's a truly magical person you want to keep and promote likely within your organisation.

What are your career ambitions and have you reached them yet? Yes, I think my ambition was always to run my own company. When I left the car business and came down here, I had to start all over again and switch industries. I did work at a big company, learned from others and built my networks up over time. I've had the opportunity to run my own company now four times over, which I consider to be really fortunate. 

Do you have a good work life balance in your current role? It's really hard. I think I do find work life balance and make sure I take time out for my family. Your partner and your families all have to understand what you're signing up for. Especially if you're a founder of the company. I've seen lots of relationships struggle because it can really be all consuming.

What, if anything, would you change about the route your career path has taken? I think I would have just started a little bit earlier. I find it's generally a young person's game. When you have success later in life, you realise just how many hours it takes to be successful and how much energy you have to put into it. And I wish I'd had this success maybe 10 years earlier where I'd have more energy to work a hundred hours a week consistently, which is kind of what you have to do to be a startup CEO.

Which would you recommend: A coding bootcamp or a computer science degree? If you are a software engineer, my vote is that you go towards the bootcamp versus a four-year computer science degree. I say that now in 2021, because I think to get started, there's no need to know how all of the core underpinnings of tech are built. You can sort of rely on the knowledge and hard work of many other platform players that have now productised and packaged. Six or twelve months of a bootcamp can get you direct knowledge of how these apps are built and work with each other.

How important are specific certifications? I think certifications are important. I think you can get those in abbreviated forms, like one or two-week short courses versus longer attestations. They actually definitely pay dividends for certain certifications in terms of being able to extract a higher compensation for yourself and faster advancement.

What are the three skills or abilities you look for in prospective candidates? Number one, I look for the basic competencies and ask myself, can they likely perform that function? How fast are they going to ramp up? How much hand holding will they need? How quickly are they going to understand the type of business that we're in or the vertical market we're in?

Number two is creativity and decision making. I really want to home in on how they think and how they make decisions. And there's ways you can ask that in an interview that kind of get them to kind of bring that forward.

Third, I look for a spark and whether this person has some curiosity. You can see in the way they talk to you and answer your questions if they want to lean in and learn more.

What would put you off a candidate? A lack of enthusiasm or curiosity for the candidate’s potential role. You want candidates to have some appreciation for why they're building what they're building. They should have a curiosity around that.

What are the most common mistakes made by candidates in an interview? How can those mistakes be avoided? I think storytelling is the most important thing. It doesn't matter what role it is; I've seen some people do a really awful job being able to tell their own story. I tell young college kids or graduates that they need to learn how to tell their own story and highlight what you're good at, with an example.

Number two is failure to ask questions during the interview. When I say, “okay, do you have any questions for me?” And they go, “no, not really.” I'm like, really? You don't have any questions? You're going to join a company!

In order to avoid this, candidates should always be prepared to ask questions that help both them and the interviewer figure out if they’re a good fit for the company. The best questions to ask as an interviewee are: what makes a person successful in this role? What's your vision of success for this per person in this role?  

Do you think it is better to have technical or business skills – or a mix of both? I think a mix is always important, a little bit of balance, even for a software engineer. Even those who work in highly technical roles should have some appreciation the business side—the big picture mission and vision of the company.