Michael Fitzsimmons, of Crosschq: “Trust the Process”

by Jerome Knyszewski
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Michael Fitzsimmons Crosschq

Michael Fitzsimmons is the co-founder and CEO of Crosschq.

As an executive, Michael Fitzsimmons applies his “long history of creating companies that disrupt the status quo to create change that benefits consumers and businesses alike.”

With Crosschq, Michael Fitzsimmons wanted to “pioneer a new category for talent acquisition that harnesses the power of people.”

Michael Fitzsimmons believes that this power can “help companies better source, match and retain the best people.”

Together, Michael Fitzsimmons and Crosschq take a “talent-first approach that prioritizes trust and transparency, minimizes bias and protects privacy.”

Both the company and Michael Fitzsimmons pursue their mission “to build better and more diverse businesses.”

Before starting Crosschq, Michael Fitzsimmons “founded and was CEO at advanced advertising company, Connekt, Inc., and Delivery Agent, an interactive commerce company.”

Throughout his career, Michael Fitzsimmons has amassed a wealth of knowledge, experience, and expertise. He has worked “from finance and sales to technology and development.”

Thanks to his success and experience, Michael Fitzsimmons has become a “thought-leader for entrepreneurs and sought-after expert for CNBC, CNN, Bloomberg, New York Times and Forbes.”

Michael Fitzsimmons has also “partnered with top companies like Comcast, CBS, Fox, Disney, HBO, Sony, Amazon, LG and Paypal.”

Likewise, Michael Fitzsimmons has “successfully raised over $200M in capital from financial and strategic investors.”

Check out more interviews with successful executives here.

Once I started asking the questions, I quickly realized there was a massive opportunity to re-define this $75B industry.

Jerome Knyszewski: Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Michael Fitzsimmons: I am the CEO and Co-Founder of Crosschq, a company that has been built to fundamentally level the playing field for job seekers by redefining how companies source and screen the best talent. This is my third entrepreneurial venture, having founded Advanced TV Advertising Company, Connekt, Inc. and Interactive Commerce Company, Delivery Agent. Through these experiences I have hired over 1,500 employees and have learned the critical lessons as to how important talent is to achieving success. That said, I have also learned how unfair and riddled with bias our current hiring tools and processes are and am determined to fix it.

Jerome Knyszewski: What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

Michael Fitzsimmons: Like many entrepreneurs, the business opportunity for Crosschq was directly born out of a series of personal experiences. Specifically, as a CEO, I was just plain frustrated. I spent too much time and too much money with fancy recruiting firms only to have them consistently place talent into my organization that turned out to be destructive to culture and productivity.

Those experiences are what got me thinking how does this keep happening? Where are the tools? Once I started asking the questions, I quickly realized there was a massive opportunity to re-define this $75B industry.

Jerome Knyszewski: Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Michael Fitzsimmons: Starting a company is hard. Anyone that tells you otherwise is just not being truthful. The job is riddled with rejection, especially in the early years. Whether investors, customers, partnerships and even hiring, you should expect to hear Ten “NO’s” for every “YES”. It’s easy to say you’re committed and that you’ll persevere, but in practice, you have to be around people who support the mission to achieve those things. Those people come from three sources:

  • Your teammates. If they’re confident and have your back, you’re confident.
  • Your customers. If they’re excited of your vision and mission, then you’ll be able to get through the tough times. It is amazing how much this helps.
  • Your family and friends. You need to have that foundation to be in the game in the first place. Without that you’re dead in the water.

And in that last category is my co-founder, Pete Goettner. He’s a huge part of what keeps me going. He is the OG in our company and is an awesome ying to my yang. I’m really lucky to have found someone like Pete (aka The GOAT.)

Jerome Knyszewski: So, how are things going today? How did your grit and resilience lead to your eventual success?

Michael Fitzsimmons: As a team, we’ve gotten through COVID and been growing rapidly through the pandemic. We’ve also been super productive in a remote environment.

Our customers are happy. We now service 125 high growth companies and have an off the charts NPS rating of 86.

On the investment side, we were substantially oversubscribed in our last round and are proud to have Bessemer Ventures, GGV and Tiger and Slack and SAP in our corner.

Starting a company is hard.

Jerome Knyszewski: Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

Michael Fitzsimmons: One of our team meetings was Zoom bombed by a friend in Amsterdam and none of us quite knew how to get this person off the call. This “guest” was under the influence and would not stop talking. It also happened to be the first day of another employee and I didn’t want her to think this is how we run things!

We eventually wrapped up the call, but the lesson here is to lock down your Zoom calls (especially when you’re trying to impress new employees!) None of us predicted this would happen but we did have a good laugh afterward.

A good idea without talent is just an idea; but a good idea with talent can change the world.

Jerome Knyszewski: Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading My Company”? Please share a story or an example for each.

Michael Fitzsimmons:

  1. Overhire early. A good idea without talent is just an idea; but a good idea with talent can change the world.
  2. You don’t have to be perfect early. You don’t have to make execute to perfection in the early stages. As long as you’re focused on the right foundational things, the numbers will come.
  3. Don’t spend on money on dumb things. At the top of that list would be conferences and fancy offices but I disagree with Cuban…swag is good.
  4. Trust the process. In my early years I put so much pressure on myself because I thought this was going to be the only shot to create a transformational company. We don’t often times equate patience with startups but a little pacing will go a long way.
  5. Fail fast. When something isn’t working, rapidly identify that and take immediate action.

Jerome Knyszewski: How can our readers further follow you online?

Michael Fitzsimmons: They can follow me on Twitter and LinkedIn.

Jerome Knyszewski: This was very inspiring. Thank you so much for the time you spent with this!


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