Skip links

Interview: Mike Fitzsimmons
Co-Founder and CEO of Crosschq

Failure is a bad word. When you are trying to disrupt the status quo, the term failure is irrelevant. And success cannot be measured by anyone but the disruptor.


March 2, 2020 –
Mike Fitzsimmons has a long history of creating companies that disrupt the status quo to create change that benefits consumers and businesses alike. Born out of his frustration with bad hires, Mike co-founded Crosschq to pioneer a new category for talent acquisition that harnesses the power of people to help companies better source, match and retain the best people. With a mission to build better businesses, Crosschq takes a talent-first approach that prioritizes trust and transparency, minimizes bias and protects privacy.

Prior to Crosschq, Mike founded and was CEO at Connekt, Inc., and Delivery Agent, an interactive commerce company acquired by Hillair Capital in 2016. His corporate business expertise, from finance and sales to technology and development, have made him a thought-leader for entrepreneurs and sought-after expert for CNBC, CNN, Bloomberg, New York Times and Forbes.

Mike’s partnered with top companies like Comcast, CBS, Fox, Disney, HBO, Sony, Amazon, LG and PayPal and successfully raised over $200M in capital from financial and strategic investors. He’s received multiple awards, including Inc. 500 Fastest Growing Media Company, Ernst & Young Entrepreneur of the Year Finalist and Deloitte & Touche Fast 50 Silicon Valley.

Where did the idea for Crosschq come from?
I was really tired of making bad hires.

What does your typical day look like and how do you make it productive?
As a start-up founder and CEO, every day is very different, but I always start and end my day with a clean inbox. I also take time each morning to catch up on global and industry news before I hit the ground running and I make time every day for some sort of exercise.

In regards to maximizing productivity, one technique I use is to set recurring weekly time blocks to focus on things that I deem are mission critical. For example, on Mondays, I focus on Sales, Tuesdays: Customer Success; Wednesdays: Product & Technology; Thursdays: Recruiting and Team Building; Fridays: General Strategy and Weekly KPI. This system allows me to have time solely dedicated to reviewing, exploring and improving various areas of the business. It’s easy to get distracted, so having a comfort zone of 45 minutes on my calendar for a deep dive every day on a specific topic is essential.

How do you bring ideas to life?
For me, new ideas have three categories: 1) Immediately actionable 2) Actionable 3) Everything else. If I deem an idea to be immediately actionable, I rally the troops, get buy in and get to work. If it falls into bucket 2, I incorporate it into our regular innovation schedule and prioritize it as such. In bucket 3, it ends up in my notebook for a rainy day. I have a lot of filled pages in my notebook.

What’s one trend that excites you?
Right now I am all about the Future of Work. There’s a fascinating thing happening with the definition of work and how, where and by who it gets done; and I am especially interested in the remote work phenomenon we are experiencing. I remember when I started my career and you were expected to arrive at 8am to a generic office building and sit in your cubicle until 5pm. The landscape is completely different today, with the rise of gig workers and more companies being open to remote work and flexible schedules. This trend is still early, but it is truly fascinating and fun to watch the Future of Work unfold before our eyes.

What is one habit of yours that makes you more productive as an entrepreneur?
Efficiency with my time. Time is our most precious personal commodity, and besides being a CEO, I am also a husband and father who doesn’t want to spend all my time working. This efficiency allows me to be more productive during the work day. I make it a habit to not waste it on things that aren’t going to yield results, and that includes no long meetings or phone calls that tend to go nowhere.

What advice wold you give your younger self?
I had an early mentor that told me my priority should be, in this order: investors, customers and employees, and I believed him! I was young and impressionable, and his ideology was reflective of that time. But that advice is so very wrong now. I only wish I had a greater appreciation for people earlier in life and understood the true power that comes from putting people in the right place to achieve the best possible outcomes.

Tell us something that’s true that almost nobody agrees with you on.
Klay Thompson is better James Harden.

As an entrepreneur, what is the one thing you do over and recommend everyone else do?
I analyze everything, all the time. It is the only way that I can identify signals in what I am trying to accomplish, and it helps me determine if I need to adjust our adjust our strategy to make sure we are on the path to solving the problem we set out to solve. I also use data to help me establish a framework for success and to get it right in terms of KPIs. I believe it is crucial for success to monitor and measure your business, even at an early stage, with frequency.

What is one strategy that has helped you grow your business?
With Crosschq, we learned that our early customers were huge evangelists and lovers of our product. The HR industry tends to have a high degree of trust with peers, so we put together a customer advisory board which converts our most active customers into active evangelists of the product to create awareness and help drive demand with new customers. We are all looking for authentic marketing messages and the ability to have people who are users and believers in the product effectively marketing it on our behalf has been extraordinarily effective in generating new customers.

What is one failure you had as an entrepreneur, and how did you overcome it?
As an entrepreneur you fail daily. That’s just a Monday for me. I have started companies that have worked and not worked, and you pick your chin up and move on to the next great idea.

However, one of the most painful “failures” in my career was hiring a senior executive at my last company that looked great on paper, had stellar references and seemed on the surface to be the right fit for our needs. This single hire nearly derailed the entire business and was the poster child of a “mis-hire.” We were able to recover somewhat after they were fired, but the business was never the same. Pete and I were so shaken by this experience that we decided we wanted to help companies avoid “bad hires” and therein the idea for Crosschq was born.

What is one business idea that you’re willing to give away to our readers?
Fix the services industry. It is getting left behind in this robust economy and rise of tech workers. There just isn’t enough talent out there to do mission critical jobs like plumbing or fixing cars and those needs aren’t going away. I think there is a massive opportunity here that will be wide open for innovation over the next decade.

What is the best $100 you recently spent? What and why?
I recently purchased “Traversing the Traction Gap” for several of my team members. This is the Bible for anyone interested in building a B2B SaaS company. I believe it will help my team better understand and align with our core mission and will be a key to our ultimate success in winning this market.

What is one piece of software or a web service that helps you be productive?
We are Slack addicts at Crosschq. Part of it is that we have a distributed workforce, so it allows us to easily communicate without having to be in the next desk over. We use it for everything from managing our workflow to phone calls and as a tool for acknowledging and celebrating the great work of our team.

What is the one book that you recommend our community should read and why?
As a general book for entrepreneurs, I wholeheartedly recommend The Hard Thing About Hard Things. Ben Horowitz’s book is a must for anyone with an inkling of desire to start a company, and you learn a ton from his own experiences and journey. For leaders, Bill Walsh’s book, The Score Takes Care of Itself is also a winner.

What is your favorite quote?
“All You Need is a Chip and a Chair” is a great quote from poker player Jack Straus. This is particularly relevant for early stage entrepreneurs because if you’re not at the table, you can’t win.

Key Learnings:

  • The Future of Work is going to be fascinating. New tools, new ways of working (remote, gig, flexible schedules) will help foster and bring about innovations we cannot even imagine. Bring the popcorn, the show is just starting.
  • Bad hires suck.
  • Get your customers to help market your business. If you add value to them, they will want to add value to you.
  • Failure is a bad word. When you are trying to disrupt the status quo, the term failure is irrelevant. And success cannot be measured by anyone but the disruptor.
  • All’s fair in technology and basketball.