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Rich Oakes of GigSmart Tells Us about Smart Hiring Solution during the Global Crisis

kokou adzo



Rich Oakes GigSmart

First of all, how are you and your family doing in these COVID-19 times?

Rich Oakes: Like most Americans, it is safe to say we have gone a little stir crazy during this crisis. With that being said, we are all healthy, and we’ve had the opportunity to spend more time together and connect. We have also had the opportunity to build stronger relationships with our neighbors. Cul-de-sac parties with each family hanging in their respective driveways have given us a great sense of community with our neighbors over the last 6 months.

Tell us about you, your career, how you joined GigSmart.

Rich Oakes: I spent the early days of my career building successful high growth sales and marketing teams across multiple industries. In my role before GigSmart, I was a Sr. Executive within a national auto finance company. We scaled the family-owned business significantly and secured a very successful transaction with a well-known Wall Street Private Equity group. After a few years of retirement, the same family had the vision to create GigSmart. I immediately fell in love with the idea and agreed to join GigSmart to help bring the product to market and scale the company up across the US.  

How does GigSmart innovate?

Rich Oakes: At GigSmart, innovation comes from many places. User feedback creates an environment where the product and development team faces challenging wants, needs, and customer recommendations to problem solve. Our internal GigSmart team frequently comes up with recommendations to innovate based on data and trends we see in the marketplace. We also have many ideas being generated by GigSmart management, not focusing on where the market is today, but where the market is going tomorrow. This forward-thinking and dreaming drives innovation as well.

How the coronavirus pandemic affects your business, and how are you coping?

Rich Oakes: GigSmart works across many industries allowing businesses and residential users to source and hires the workers they need to fill shifts and complete projects. Although some industries have been adversely impacted by this crisis (catering, events, restaurants, hospitality), other industries have experienced significant growth (warehouse, grocery, e-commerce, food delivery). Despite the challenging economic conditions, GigSmart has focused on assisting essential businesses to keep the supply chain open for our local communities by providing the labor they need. We are fortunate to have been able to grow our business in the midst of these challenging times. 

Did you have to make difficult choices, and what are the lessons learned?

Rich Oakes: Whether we are facing a global crisis or pushing forward to the “new normal,” entrepreneurs always have to make difficult choices. What is the most efficient use of capital? What paths should we use to raise additional capital? What is the proper time to add headcount, increase payroll? What kind of culture do we want to create? Do we grow organically or utilize partnerships to assist in fueling growth? Which market segments will accept our product/service most efficiently? I just recently read a statistic that said approximately 90% of startups fail. Regardless of this current crisis, entrepreneurs need to wake up ready to make difficult choices. The odds of success are not in our favor. We only beat the odds through effective execution.  

How do you deal with stress and anxiety? How do you project yourself and GigSmart in the future?

Rich Oakes: I personally deal with stress and anxiety by leaning on my entrepreneur peer group. These are very successful people that have navigated most entrepreneurial challenges that we face daily. Having a small group of peers who have fought the entrepreneurial fight and have been successful is critical for business owners. Healthy eating also keeps me grounded when stress and anxiety are increasing in the business. Last but not least, don’t underestimate the value of unplugging for three or four hours early in the morning. On Sunday mornings, I usually take a hike deep in the Rocky Mountains. No cell service. No Slack. No email. It is a great time to get exercise and experience some quiet time.

Who are your competitors? And how do you plan to stay in the game?

Rich Oakes: I always tell our team that our number one competitor is our prospect, our customer’s past habits. Sourcing talent through temp agencies and job boards hasn’t changed in decades. It is slow. It is expensive. Most use those resources because that is what they have always done, not because it is fast and efficient.

Our platform sources labor faster, and we are the most cost-efficient solution on the market today. On a daily basis, we are talking with businesses across the US explaining there is a better way, changing the behavior and habit of our clients’ one business at a time.

Your final thoughts?

Rich Oakes: I was running my own business when we experienced the horrific tragedy of September 11th. I was a senior executive at a national finance company when the 2008 financial crisis hit. 2020 has been a very challenging year. Creating and scaling a business sounds great, but it’s hard work, and unfortunately, occasionally, crisis strikes, creating more waves and hurdles along the way. The biggest thing an entrepreneur needs is a commitment to the process and to surround himself/herself with others who are committed to the process, from capital partners to key associates. A committed team will find a way through hard work and many business pivots to be successful.

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Kokou Adzo is the editor and author of He is passionate about business and tech, and brings you the latest Startup news and information. He graduated from university of Siena (Italy) and Rennes (France) in Communications and Political Science with a Master's Degree. He manages the editorial operations at

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