Authentic &


Matt Douglas, Founder and CEO of Sincere Corporation

Why “Second-Job” Employees are a Smart Investment

I’ve always been very active in hiring at my company. Over the years, I have accumulated some best practices and learned how to spot talent. One of the things I’m most proud of is the team I’ve put together. It’s a mix of more seasoned folks, and a few younger “millennials.”  And one thing I’ve noticed is that I’ve hit the ball out of the park by hiring people who are in their second job out of college. Across our organization, we’ve hired these relatively inexperienced employees, and they have blossomed into some of the most productive and strong leaders in our organization. Is this is a coincidence? I don’t think so — in fact, it’s something I stumbled upon that I think makes a lot of sense for most organizations. Let’s take a closer look at why second-job employees are a really smart investment:

1) They are equipped with basic training and work experience in an office setting.

Employees with one job under their belt have already learned some of the essentials about working at a company. They have experience at how to navigate the nuances of daily interactions with coworkers. They understand the importance of personal accountability and know how organizations balance the needs of an individual AND the needs of the team. They know the basics of how human resources and payroll works, and don’t ask simplistic questions. Typically, these employees are more likely to have the technical ability needed to successfully communicate in a 21st century workplace (i.e. video conferencing, screen-sharing, instant messaging, etc.), but — more importantly — they have an understanding of when it’s appropriate to send an email, instant message, or (gasp!) pick up the phone and actually talk to someone. Employees with one job under their belt are often able to hit the ground running because they can acclimate to the company and make contributions more quickly. In fact, I often feel like the second-job employees we hire have worked at Punchbowl for ages and am genuinely surprised when I’m reminded that they have only been with the company for a few months.

2) They are moldable and still willing to learn.

I value experience a lot, but I prefer to hire people who are smart and able to learn. Several times in my career I’ve hired someone with experience over someone less experienced who appeared smart. When I look back at those decisions, more often than not the person with experience didn’t live up to their resume. Now that I’ve hired dozens and dozens of people, I know I strongly prefer a second-job employee who will be moldable and is still willing to learn. We’ve all worked with “old dogs” who aren’t able to learn new tricks. Frankly, it’s hard to correct a person who has developed bad habits over a long career. In contrast, a second-job hire is more likely to be open to new ideas and still bring things they have learned to the table. These kinds of people recognize that they don’t have all of the answers, but yet they still bring a set of experiences with them to the table. That combination can be very helpful, especially at a smaller organization or group.

One of the characteristics I look for in new hires is people who are naturally curious. More often than not, the most curious potential employees are those who have had a taste of the corporate life and want to understand how to best approach a problem or market. These days, most second-job employees come equipped with an understanding of new technology, sometimes even pushing the envelope on our own internal knowledge. I’ve noticed that second-job employees tend to listen before they speak in their initial days with the company and then carefully suggest new solutions to existing problems. We love when an employee shows us a new service or technology, and more often than not it’s a second-job employee. The amalgam of a second-job employee’s ideas with a forward-looking organization is very productive.

3) They cost less

Simply put, the total cost to hire a second-job employee is typically less than someone who has years and years of experience. This is like buying a value stock: you’re “investing” in the asset because you believe the future cash flows of that asset will far exceed the money spent to acquire the asset. Economics aside, the direct salary and benefits to hire a second-job employee are right in the sweet spot for a growing company. Those with a few jobs under their belt will have more experience and have higher salary expectations. On the benefits side, I would be remiss if I didn’t mention that many second-job employees don’t require benefits at all (because they are covered under someone else’s plan). Although that’s not a factor in our decision-making process because we cover 100% of an employees benefits, the reality is that it does lower the cost for the company. Finally, second-job employees usually don’t have high expectations when it comes to bonuses or stock options, which can effectively lower the cost too.

Some people might argue with me: why not just hire freshly-minted college grads and save even more money? I would argue that the cost of time and resources to train someone who hasn’t held a corporate job will outweigh any cost savings. I would much rather hire someone that already passed through the “filter” of another company. It’s a step of validation for a candidate that is hard to value. Give me a second-job employee over a college grad any day, and I think I’ll get better return on the investment.

CONCLUSION: Our current Director of Marketing is a second-job employee. Our Director of Analytics & Data is also a second-job employee. And they have both been with the organization for 6+ years. They have brought infectious energy, seasoned perspectives, and a wealth of new ideas to the company. When the stars align and you have an open position, I believe it’s a smart investment to hire people who have only one job under their belt and I now actively seek those kinds of candidates. What do you think? Have you had success hiring people as a second-job employee?

©2024 Matt Douglas