Chris Cabrera of Xactly: Optimal Performance Before High Pressure Moments; How To Relieve Stress, Clear Your Head, and Prepare Yourself For High Stakes Business Encounters

Parveen Panwar, Mr. Activated
Authority Magazine
Published in
12 min readOct 1, 2020


Part of that preparation is to do your homework. Know who you are meeting with and what makes them tick. With such a huge network on LinkedIn, you can usually find someone who knows the person/people you are meeting with. Get to know what their likes and dislikes are.

As a part of our series about “Optimal Performance Before High Pressure Moments”, I had the pleasure of interviewing Chris Cabrera.

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.

Thank you so much for joining us in this interview series! Before we dive into the main focus of our interview, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I grew up on a dairy farm in Massachusetts, where I learned countless lessons that have unwittingly served me in my career. For example, as the fourth of five kids, I learned that I had to fight for everything, including dinner. But what I love about the big family I grew up in is that we could have heated debates all day, and then go back to being normal. It made me comfortable with being super open and communicative with my executive team, and very receptive to employees speaking up and sharing their ideas and feedback from all levels of the organization.

What or who inspired you to pursue your career as an entrepreneur or business leader? We’d love to hear the story.

My dad — he was a serial entrepreneur, and every single summer as I was growing up, I worked at his companies. Much of what I have learned about how to treat people and how to build teams I learned from him. He was president of his own company, but treated everybody the same, whether it was the janitor or another CEO. He never talked down to anyone and always wanted to learn about people and get to know them personally. On the day before Thanksgiving, we’d deliver frozen turkeys to each one of his employees. He was the kind of guy who would give away his last dollar if someone needed it.

None of us can achieve success without some help along the way. Was there a particular person who you feel gave you the most help or encouragement to be who you are today? Can you share a story about that?

My wife, Marla, has given me tremendous support throughout my career. I stand by the adage, “Behind every successful man is a strong woman.” Countless times when I have been unable to see something, she has provided clarity — in fact, I credit her with the company’s name, Xactly. Years ago, when I was grappling with the challenge of what to call our new venture, she asked me, “What is this new company going to do?” I replied: “Pay exactly the right amount at the exactly the right time.” And she said, “Why don’t you call it Exactly?” We dropped the “e” in the end, but the name stuck. Our mission has since expanded far beyond compensation to encompass planning, managing, compensating and analyzing sales performance, but the exactness and precision of our data remains the foundation of everything we do.

Can you share the funniest or most interesting mistake that occurred to you in the course of your career? What lesson or take away did you learn from that?

Early on in my career, I had a tendency to want to personally jump in and get involved if an employee was worked up about an issue with a colleague. It was rooted in caring about each individual person at the company and wanting to create harmony, but I realized I was becoming part of the problem. Much of the time, the issues were petty, and the energy we spent on them gave credibility to the drama and didn’t move the ball forward. My take-away lesson was to stay above the drama and to focus instead on the bigger picture — on fostering a broader culture of caring for one another, our customers and our community. My executive team and I put a lot of time and effort into building and living Xactly’s core values of Customer Focus, Accountability, Respect, and Excellence. Today, our culture thrives because our people truly believe in, and live out, those values.

The road to success is hard and requires tremendous dedication. This question is obviously a big one, but what advice would you give to a young person who aspires to follow in your footsteps and emulate your success?

One of my mantras throughout my career has been to constantly reinvent myself as a person, an employee, and a leader; to embrace new obstacles as opportunities to grow and evolve. I would urge a young person interested in following this path to shift their perspective to see career setbacks (which will inevitably happen) as chances to level-up. Part of reinvention for me is constantly challenging myself to think about what I could do differently, and do better. I believe that kind of flexibility and openness to change is vital to success in any industry.

Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

When I was just starting in my career, all the leadership talk was about Steve Jobs. Having gone to high school in Silicon Valley, I remember reading a book on how he started Apple. The story made a great impression on me. Like all leaders, there are good and bad traits. On the one hand, I was surprised and disappointed to learn how he treated some of his employees and family members, but on the other hand, I was struck by his determination. The stories of how he started the company and did whatever it took to get it off the ground really resonated with me. His total belief in success and conviction in the face of massive amounts of naysayers was inspirational.

Can you share your favorite “Life Lesson Quote”? Why does that resonate with you so much?

Growing up my father often cited a quote from JFK (originally from the bible) that “to whom much is given, much is expected”. I think about that quote often (it’s on a bench we put next to his grave) as it reminds me that there are always many less fortunate people who need help. It is the reason I created the XactlyOne Foundation and put 1% of the company in it. It’s the reason we do so much as a company philanthropically which is a major part of our corporate culture.

What are some of the most interesting or exciting projects you are working on now? How do you think that might help people?

Our primary focus this year has been on helping companies adapt to the disruption caused by Covid-19 and its economic fallout. When a company is at financial risk, they need their sales team to meet their numbers more urgently than ever. That’s where we come in, working with sales organizations to pivot their strategies quickly under pressure, using data and AI to set reps up for success despite new obstacles. At the beginning of the pandemic, we made one of our core products, AlignStar, free to help companies adjust their sales territories given the rapid market changes that were taking place. Since then, we’ve consistently rolled out new products to further support businesses amid the uncertainty, including Xactly Forecasting, which helps sales leaders improve the accuracy of their forecasts and in turn, decrease economic risk to keep the business afloat during a time when every dime counts.

OK, thank you for all of that. Let’s now shift to the core focus of our interview. As a business leader, you likely often face high stakes situations that involve a lot of pressure. Most of us tend to wither in the face of such pressure and stress. Can you share with our readers 3 or 4 strategies that you use to cope with the burden of stress?

I have always focused on not letting the highs get me too high, nor the lows get me too low. So I try to approach high stress situations by recognizing that no matter what the end result, I will be fine. I am not a devoutly religious person, but I do have strong faith. I have always believed in the adage that “everything happens for a reason”. When things haven’t gone the way I wanted, I tell myself this is part of a bigger plan and will probably be better in the long run. A good example of this is at one point when Xactly was a much smaller business, we were in a dialog to sell the company. It was very stressful as it seemed the weight of the world was on my shoulders. The ramifications were so big (I thought) financially for me and for the employees. The deal fell through and rather than fall to pieces I remember saying, “There is a bigger plan here. This was not the right time to sell the company”. A few years later, we did sell the company for hundreds of millions of dollars more than that first attempt. I chuckled with some of the execs and said can you believe we almost sold for so little!

Aside from being able to deal with the burden of stress, can you share with our readers 3 or 4 strategies that you use to optimize your mind for peak performance before high pressure, high stress situations?

1. The other way that I de-stress a situation is by being overly prepared. When I am stressed about a meeting and go in knowing that there is no scenario I can’t handle, the stress seems to melt away.

2. Part of that preparation is to do your homework. Know who you are meeting with and what makes them tick. With such a huge network on LinkedIn, you can usually find someone who knows the person/people you are meeting with. Get to know what their likes and dislikes are.

3. Sounds obvious, but I make sure I am well rested before any type of big meeting. I want to be on my game and I don’t want to be tired.

4. I know it is old-school, but I like to look the part. If I am having an important meeting, I wear a favorite suit and tie. I feel more confident when I am sharply dressed. And nothing is worse than showing up and being under dressed. Of course, in the age of COVID, a collared shirt is about as dressed up as I get!

Do you use any special or particular breathing techniques, meditations or visualizations to help optimize yourself? If you do, we’d love to hear about it.

I am big into visualizations. I remember in my youth, sports coaches would always make a big deal of visualizing each play over and over. I try to visualize meetings, all-hands, off-sites, even board meetings. I play over and over how I will present something and what questions I will get and how I will respond.

Do you have a special technique to develop a strong focus, and clear away distractions?

For me clearing away distractions is about having my house in order. If I have personal things going on that I am worried about it becomes very distracting to me getting the job done. This is where having a great partner (my wife) is very handy. I never have to worry about the kids or the house because I know it’s in good hands. This has always allowed me to stay laser focused on what I need to get done for the business. Don’t get me wrong, I’m not a chauvinist, I pull my weight at home, but I’m able to tailor my responsibilities around my work schedule.

We all know the importance of good habits. How have habits played a role in your success? Can you share some success habits that have helped you in your journey?

I have always considered myself a curious, coachable person. I’m constantly seeking out ways to improve my knowledge and skill set. This has proven to be the single most important factor in my success. Since founding Xactly in 2005 I have seen so many other founders start their companies and ultimately be removed from the helm as the business outgrew them. It has always been obvious to me that the skills required to take Xactly from zero to $20 million were different from the skills that I’d need to take the company from $20 million to $100 million and so on. Often, people think that they need to know everything in their roles to be successful. I think it’s far more important to adopt an attitude of being a learn-it-all instead. My advice: make it a habit to continuously seek out new knowledge and work on your professional development. It all goes back to reinvention.

What is the best way to develop great habits for optimal performance? How can one stop bad habits?

The best way to stop bad habits, is by admitting you have them. Then asking your friends, family and/or co-workers to help you fix them. Years ago I used to say “um” a lot. I asked everyone on my team to stop me and point out every time I said it. It got so annoying, I was forced to make a change. This is another area where mentors come in handy. You need to have mentors in your life who will give you honest feedback. People who will tell you when you need to change some behavior. Sometimes we have a blind spot without realizing it.

As a business leader, you likely experience times when you are in a state of Flow. Flow has been described as a pleasurable mental state that occurs when you do something that you are skilled at, that is challenging, and that is meaningful. Can you share some ideas from your experience about how we can achieve a state of Flow more often in our lives?

I think the first step is to overcome our culture’s glorification of “busy.” People seem to relish in how busy they are, often to their own detriment. It has become commonplace for people to mistakenly work their lives away thinking that they are winning — then later regret that they didn’t take more time to enjoy a minute or two outside, away from the noise, relaxing. Over the years I’ve come to realize the power of quiet reflection. Some of my best business decisions happen at our family ranch, just sitting in nature and listening to the birds.

Ok, we are nearly done. You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

We need to normalize the idea of vulnerability as a sign of strength and foster a stronger culture of mental health in the workplace. This mission has always been important to me, but it’s on my mind today more than ever given the psychological toll of Covid-19 and everything else going on in the world, from racial injustices to natural disasters. Business leaders need to get comfortable showing their vulnerability and giving employees the space and support they need to express themselves. This can take many forms. Cut the small talk and ask your people how they’re really doing. Give them permission to answer that question honestly, and be honest with them in return. Close your business for a mental health day (and if you can, do so on a regular basis) — if wellness days are made optional, many employees won’t feel comfortable to ask for them, or to go fully offline when they do. I’ve given employees an extra day off each month since March to focus on recharging. It’s also important to lead by example in setting and honoring personal boundaries: that may look like declining a Friday afternoon meeting that can wait until Monday, or letting your team know that you are muting Slack notifications to take an uninterrupted break.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we both tag them :-)

The Pope

How can our readers further follow your work online?

They can keep up to date on all things Xactly on our website and blog. They can also read my Forbes column for broader business leadership perspective and advice.

Thank you for these really excellent insights, and we greatly appreciate the time you spent with this. We wish you continued success.



Parveen Panwar, Mr. Activated
Authority Magazine

Entrepreneur, angel investor and syndicated columnist, as well as a yoga, holistic health, breathwork and meditation enthusiast. Unlock the deepest powers