C-suite career advice: Christopher Cabrera, Xactly

What are the three skills or abilities you look for in prospective candidates? "I value a candidate who is quick on their feet, someone who is creative and a risk taker."

Name: Christopher Cabrera

Company: Xactly

Job Title: Founder and CEO

Location: San Jose, California

Christopher Cabrera founded Sales Performance Management (SPM) company Xactly in 2005. Since then, he has led the company from startup to IPO and now private equity, while amassing major customers from Salesforce to Louis Vuitton to Hyatt. Cabrera is a known expert on SPM, compensation, commission, and employee motivation. Prior to founding Xactly, Cabrera was SVP of operations at Callidus Software, where he acquired 100+ customers, grew annual revenues, and led a successful IPO. He authored Game The Plan and co-authored Xactly Sales Compensation for Dummies. He holds a B.S. and M.A. in business administration from the University of Southern California and Santa Clara University, respectively. He was recognised by USC as Alumni Entrepreneur of the Year.


What was the most valuable piece of career advice that you received? I didn't start Xactly until I was 37 years old, so for the majority of my career, I had a boss — someone who I looked to for direction. When I became a first time CEO I remember always asking my board what they thought. One day one of my board members took me to lunch and said: "You are the CEO. You tell us what to do, don't ask us." From that moment on, I felt empowered to be the boss and became a stronger leader as a result -- stepping into the role without leaning too heavily on the board. I often think of that advice before my board meetings to remind me to take charge.

What was the worst piece of business advice that you received? An advisor once told me to choose my VC's based on the highest valuation alone, regardless of whether I believed they were going to be strong partners. He was fond of saying "All the value of a VC is in the check and all VC money is green". At the time, I didn't think about the long-term effects. I didn't look at investment partnerships as a marriage, which they are, because you may work with those organisations and people for 10+ years. I got lucky and got some great VC's when I started, but there were a couple that I picked on valuation alone. I ended up regretting this in the long run as those funds ran out of money and were not there when I needed them.

What advice would you give to someone starting their career in IT? Follow your heart and not your wallet. One of the biggest mistakes people make early in their careers is trying to maximise their income, rather than maximise their learnings — follow the opportunities that offer the most room for growth and development. Sometimes a backward step, or sideways step will open up five steps forward in the long run.

Did you always want to work in IT? I always knew I wanted to start a business and run a business. I had some early experiences in non-tech and realised quickly that that was not where I wanted to spend my time. The technology fields were always more exciting and constantly changing. I felt they offered more options to learn and be a part of something different.

What was your first job in IT? My first technology job was at Silicon Graphics -- a computer hardware and software company that was pivotal in rendering three-dimensional images on computers. It was an extremely exciting company that allowed our customers to do some really cool stuff like the graphics for Jurassic Park and Forest Gump. I started as a telesales rep in the early 90's and have been in enterprise software ever since, leading sales teams and scaling companies.

What are some common misconceptions about working in IT? A common misconception is that you have be a technologist to be successful. Of course, there are a lot of smart and technical people in the industry with great ideas, but sometimes there is a need for someone entrepreneurial who has the business acumen to turn their ideas into a real business that adds value. 

What tips would you give to someone aiming for a C-level position? Find great mentors to help you learn along the way, and don't stop at one mentor — find a few people who work in different areas of business so you can build a wide range of learnings.

What are your career ambitions and have you reached them yet? My ambitions today are less about personal success and more about seeing how big we can make the company. I also really enjoy inspiring the next generation of leaders. I get great satisfaction from mentoring our young employees and seeing their careers blossom.

Do you have a good work- life balance in your current role? It is difficult for any passionate, dedicated CEO to maintain a work-life balance. Luckily for me, however, my daughter works with me at Xactly. Aside from that, I make an effort to be completely unplugged during my time away from work. That way, I can truly decompress and make the most of my time out of the office.

What, if anything, would you change about the route your career path has taken? I've been extremely blessed throughout my career. I have no regrets, but, if I could go back in time, I would have founded Xactly earlier.

Which would you recommend: A coding boot camp or a computer science degree? Why choose? Do both. I am a big fan of people getting formal degrees. I think the degree programmes offer so many things in addition to the knowledge. They offer great opportunities to build networks and they force candidates to show incredible perseverance — which I love. That said, there is nothing like the experience of just learning the nuts and bolts of coding.

How important are specific certifications? Specific certifications can be a great resume builder but in my opinion, real work experience and a desire to learn are the best assets a candidate can have.

What are the three skills or abilities you look for in prospective candidates? I value a candidate who is quick on their feet, someone who is creative and a risk taker. I also pay close attention to someone's potential -- I believe in investing in people who will learn, grow, and build a career at Xactly. 

What would put you off a candidate? Nothing is more important than the desire to learn and reinvent oneself. When that doesn't come through during an interview, or the candidate appears to be a know-it-all, it can be a sign that someone isn't open to learning and I find that off putting. Better to be a learn-it-all!

What are the most common mistakes made by candidates in an interview? How can those mistakes be avoided? I'm a sales guy so, ask for the sale. I'm amazed how many people don't end an interview at least asking how they did and if I think they would be a good fit. You won't get it if you don't ask for it!

Do you think it is better to have technical or business skills - or a mix of both? I don't think there is a right or wrong answer. Whether you are technically savvy, a business aficionado, or a mix of both, play to your strengths. I think that the best skill is learning how to use your strengths to your advantage, while also being able to identify and continually improve upon your weaknesses. The goal is to get both. Figure out where you are weak and go get that experience.

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