Adaptability is part of the job for Chris Cabrera at Xactly Corp.

Keep your promises

For many years, Xactly only supported a single language in its offerings. But as demand outside the U.S. began to grow, additional languages were added into the mix. It proved to be an enormous undertaking and deadlines began to be threatened.

“I can remember being in some meetings where the engineering team was highlighting, ‘Hey, this is more work than we thought. Looks like we’re going to miss this deadline we set,’” Cabrera says. “It would have been no big deal and probably wouldn’t have mattered that much to the customers if we had said, ‘Hey, guess what, we’re going to miss on this by two months.’ We could have gone on doing our business.”

Instead, the feeling in the room amongst team members was that doing so would have represented a failure to keep a promise.

“We’ve put a stake in the ground,” he says. “We’ve told our customer we’re going to deliver by this date. So even if it’s going to cost us a little bit of money and make our lives a little uncomfortable, come hell or high water, we’re going to hit that date. We rearranged some things so we could afford it and we doubled down our engineering efforts. Lo and behold, we made the deadline and delivered. Every one of those decisions matters.”

The tricky part for some companies is managing the needs of the customers and the ability to grow the business with the resources on hand and what those resources are capable of providing. When there is disagreement on the latter, it can quickly lead to tension.

“You have to create an environment and culture where it’s safe to tell the truth,” Cabrera says. “It’s safe to tell management not what they want to hear, but what’s real. That’s a tough culture to create. I think as much as possible, you root out politics. You root out people caring more about hierarchies than the truth. We’ve done a good job of that by not killing the messenger because you don’t like the message.”

Incentives have proven to be helpful in this area. The key to their success is setting them across multiple departments or areas of the company.

“It creates this teamwork and cohesion for wanting to help out other groups,” Cabrera says. “If they just do their own little silo and their one group does well and the other three don’t, we don’t all win. It’s this notion that we all live together.”

Cabrera isn’t afraid to add resources, including new hires, to help the company perform at its best. But he takes a measured approach to such decisions.

“We don’t just go back to the till and throw another $2 million of loss on the books,” he says. “We say let’s do this so it fits into our overall plan of getting the company to profitability while maintaining these very nice and appropriate growth rates.”

Be willing to change

One area where Cabrera has become a little bit less conservative when it comes to operating the business is with hiring and internal advancement. The change came about when he underestimated the drive and desire of the millennials that the company had hired.

At the time, the expectation was that you would start at Xactly as an inside sales rep and stay in that job for four or five years before moving up. It was a path that Cabrera himself had followed in the early days of his career.

“These younger folks were so driven and energized and they wanted to be recognized amongst their peers for achieving things more quickly than this five-year thing,” he says. “So we changed the sales force.”

New levels were created and new opportunities to earn more money, more shares and more responsibility.

“It gave us an opportunity to take these super smart millennials that were so driven and create a track for them where they could keep seeing success in a shorter window,” he says.

And it was another opportunity for Cabrera to demonstrate his willingness to reinvent his leadership style when a new approach is needed.

“If you are self-aware and you have great mentors and coaches and people who are not sycophants, but are comfortable telling you your weaknesses, you create that environment,” he says. “You can change and be open to addressing opportunities to improve and reinvent yourself every step of the way.” ●


  • Focus on what’s really important in your business.
  • Don’t backtrack on your promises.
  • Be willing to reinvent yourself.

The Cabrera File

NAME: Christopher W. Cabrera
TITLE: founder and CEO
COMPANY: Xactly Corp.

Born: Framingham, Massachusetts

Education: Bachelor’s degree in business, University of Southern California; MBA, Santa Clara University. I went through the entrepreneur program at USC and was recognized as the 2011 Entrepreneur of the Year.

What was your first job? My first job was the San Francisco Chronicle and I only did that for about eight months and then I moved to the San Jose Mercury News and I did that for five years. The paper route was how I made money all through high school.

Who has been the most influential person in your life? My father, Eduardo, who passed away about three years ago. He didn’t get to see the IPO at Xactly, but he would have loved it.

What did you learn from your father? He was a serial entrepreneur in the years when you didn’t raise money and do the venture capital thing to grow your business. Everything I learned about how to sell and how to treat people and how to build teams I learned from him.

Every summer, I was always at his office working. He was president of his own company. He treated everybody the same in the sense that, whether it was the janitor or another CEO.

He treated people respectfully and never talked down to them. He always wanted to get to know them and learn about them. He was the kind of guy who would give you his last dollar if you needed it. He didn’t play any politics with his team. What rubbed off on me was to create these apolitical environments as much as you possibly can. I don’t care what your title is. I just want to know what you think and what your feelings are.