Aaron Hageman of Delivery Drivers On The Labor Shortage & The 5 Things We Must Do To Attract & Retain Great Talent

An Interview with Phil La Duke

Authority Magazine Editorial Staff
Authority Magazine
9 min readFeb 27, 2022

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Understanding and awareness of the quality of talent comes from maintaining substantial relationships and communication. Checking on individuals ensuring they are satisfied and still an asset to the company.

The pandemic has allowed people to reevaluate what they want from work. This “Great Reevaluation” has led to the “Great Resignation” which has left the US with a great big labor shortage and a supply chain crisis. What can we do to reverse this trend? What can be done to attract great talent to companies looking to hire? What must companies do to retain their great talent? If not just a paycheck, what else are employees looking for? In this interview series called “The Labor Shortage & The 5 Things We Must Do To Attract & Retain Great Talent” we are talking to successful business leaders who can share stories and ideas from their experience that can address these questions.

As a part of this interview series, we had the pleasure to interview Aaron Hageman.

Aaron Hageman is the owner and CEO of Delivery Drivers, Inc. (DDI) a third-party human resources and driver management firm specializing in the last-mile delivery and gig economy. Aaron has more than 25 years of experience in the rapidly growing gig economy.

Under Aaron’s leadership, DDI has been named an Inc. 5000 company nationally and regionally, ranked #194 in California. DDI was also named a 2021 Business Products & Services Companies to Watch by The Startup Weekly.

Thank you so much for joining us in this interview series! Our readers would like to get an idea of who you are and where you came from. Can you tell us a bit about your background? Where do you come from? What are the life experiences that most shaped your current self?

From a frustrated 1099 freelance delivery driver to CEO, I launched Delivery Drivers, Inc. — connecting independent contractors to last-mile delivery gigs nationwide. DDI is a third-party human resources and driver management firm that advocates for delivery drivers, as many of the team members were drivers themselves.

In the early 90s, I was a 1099 driver in Orange County, and interned for the District Attorney’s office in Sacramento, working on labor law cases. I have more than 25 years of experience and foresaw the explosion of the gig economy, long before Instacart or GrubHub came on the scene.

Since I launched DDI, I grew the company from a handful of contractors to over 160,000 today. Under my leadership, DDI has been named an Inc. 5000 company nationally and regionally for two years in a row. I have an outgoing and engaging personality that quickly helps boil down the complexities of the gig economy.

As a successful entrepreneur, I have built and led many different types of companies from human resource firms to sports teams, including owning the Albuquerque Sol FC for six years. My talents lie in organizational leadership, team building, and relentlessly pursuing the strategic vision while creating businesses of scale. Outside of work, I mentor and teach both students and entrepreneurs globally, and I donate my time to fighting homelessness in my hometown of Southern California.

Let’s jump right in. Some experts have warned of the “Great Resignation” as early as the 1980s and yet so many companies seem to have been completely unprepared when it finally happened. What do you think caused this disconnect? Why do you think the business world was caught by surprise?

COVID-19 caused the disconnect between companies and employees. The lockdowns in the beginning of COVID-19 forced everyone to change their lifestyles, both personally and for work. Thus, changing the mindset of how employees wanted to work. Employees wanted to have more control over their careers — the work/life balance of being able to work from home or anywhere they wanted and anytime.

Businesses were probably caught by surprise because they were stuck in the traditional work model. They thought as restrictions were lifted people would just go back to the office and work the same way before the pandemic hit. They didn’t think COVID-19 would create an evolution in people and how they saw work.

What do you think employers have to do to adapt to this new reality?

Employers need to adapt to the flexible lifestyle employees are demanding. They want a work/life balance. Employees want to feel secure in their job. To show that you are invested in their career, pay for them to take a course that benefits both you and your employee. Adapt to a non-traditional office environment by going hybrid or remote.

Based on your opinion and experience, what do you think were the main pain points that caused the great resignation? Why is so much of the workforce unhappy?

The main pain points that caused the Great Resignation involve this idea of self-awareness. When COVID-19 hit, people realized their jobs did not have the same stability as before. People wanted direct control over their opportunities and their careers. A lack of security became more aware through this time. Without this job, where does my income and identity lie? With the gig economy, people found purpose and stability in their own hands.

Many employers extoll the advantages of the entrepreneurial spirit and the possibilities of an expanded “gig economy”. But this does come with the cost of a lack of loyalty of gig workers. Is there a way to balance this? Can an employer look for single use sources of services and expect long-term loyalty? Is there a way to hire a freelancer and expect dependability and loyalty? Can you please explain what you mean?

When it comes to the gig economy, it is easy for independent contractors to pick and choose which platform they want to work on and which gig jobs they want to accept. Based on our internal driver network survey conducted last September, 47% of our driver-partners said they were on two or more gig applications simultaneously.

To partner with independent contractors, businesses need to think of what sets them apart from other platforms, how are they putting the solopreneur first. Ultimately, what it always comes down to is perks and money. Start prioritizing the driver’s earnings and time and in return they will be loyal to your business to where you can depend on them.

It has been said that “people don’t quit jobs, they quit bosses”. How do you think this has been true during the Great Resignation? Can you explain what you mean?

It’s absolutely true, there has been a shift in the traditional workforce mindset by the younger generations. Look at Gen Z, they grew up on social media, watching people make money as influencers and YouTube stars. They grew up with the mentality that they can be their own boss, control their own careers, and have the work/life balance the traditional working model didn’t allow.

On the flip side you have some millennials who in the beginning of the pandemic had to manage working from home and childcare. Employees asked their employers to be flexible with their schedules and have empathy for their work from home situations. Employers found this difficult to hold employees accountable and as COVID-19 restrictions were loosened, some businesses were requiring employees to go back to the traditional work model. This clashed with the work/life balance many found during lockdown. Making employees rethink their employer and find a career with someone who shared their same values.

I am fond of saying, “If it’s fun they charge admission. But you get a paycheck for working here.” Obviously, I am being facetious, but not entirely. Every job has its frustrations and there will be times when every job will aggravate employees. How important is it that employees enjoy their jobs?

We’ve come to the core of the matter here. As our employees go, so do our companies. But what does “enjoyment” really mean? I would offer that it’s more than the actual work we do. It is on us as leaders to create a great work environment that has opportunities for employees to have autonomy, learn something new, and while aligning the company purpose and vision. When we get all of these ingredients together, everyone looks forward to the workday.

How do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?

These are the fundamentals, but I think it all starts with turnover. When we lose experienced staff, we lose the ability to service our customers well and turnover in our ranks soon leads to turnover within our customer base. The dominos that fall naturally lead to lower profitability as we fight to replace the team members and customers!

An often-lost piece of this conversation is the negative impact on your employees who are still around. The unhappy customers unleash their complaints on your remaining staff while they are then overworked from being short staffed and training new team members. It’s a lot to deal with and can feed the downward spiral.

What are a few things that employers, managers and executives can do to ensure that workers enjoy their jobs?

ASK them. Too often employers assume they know what their employees want. Not only are the demographics of the workforce changing, but our existing employees, many of whom we’ve known for years… have needs that are evolving. For example, it is not the same dealing with health matters and sickness in 2022. Nor is parenting the same during Coronavirus times. We have to evolve our benefits package to serve our evolving employees.

Can you share a few things that employers, managers and executives should be doing to improve their company work culture?

The first thing to do is create a system to communicate regularly with your employees about culture. Be open, honest and trusting in this process and regularly solicit feedback during these changing times. Find out what’s working, what’s not, and what’s missing.

Covid shook up our mentality around personal health and work-life-balance. So, one thing we’ve been doing at DDI is reviewing our programs to support these topics. We’ve been reviewing our benefits programs, remote and hybrid working scenarios, and making sure our employees are aware of and have access to mental health resources.

Okay, wonderful. Here is the main question of our interview. What are your “5 things employers should do to attract and retain top talent during the labor shortage?” (Please share a story or example for each.)

With the labor shortage, the concept of attracting and retaining great talent is top priority. A company’s culture can depict an introduction to what goes on behind the scenes. This is visualized through an online footprint like Glassdoor and Clearly Rated, which can portray a company’s image.

Social media presence is crucial in the modern digital space. Businesses must actively and authentically stay up to date with industry trends across social platforms like LinkedIn, Instagram, etc.

Another way to attract and retain is to offer growth and education. By promoting within an organization and advancing careers with educational programs and incentivizing goals.

A platform of attracting and retaining talent can make or break a company. Knowing when to use a digital platform, print or a combination of both. Retaining quality talent comes from understanding the needs of the different talents and offering those perk solutions. Allow each talent to be their own solo-preneur with benefits that help their self-growth, as they provide partnership assistance.

Lastly, understanding and awareness of the quality of talent comes from maintaining substantial relationships and communication. Checking on individuals ensuring they are satisfied and still an asset to the company.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

I will go with Sir Richard Branson. In addition to his philosophy on taking care of employees that is in alignment with our conversation today… I’m a big space nerd and have to know what space flight was like!!

Our readers often like to follow our interview subjects’ careers. How can they further follow your work online?

They can follow me on LinkedIn and Instagram. Delivery Drivers, Inc. can be found on our main website and various social media platforms of LinkedIn, Instagram, Facebook and Twitter.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this. We wish you continued success and good health.

Thank you for your time! If you have any questions on the gig economy, being an independent contractor or partnering with us at DDI, please feel free to contact us at sales@ddiwork.com

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Authority Magazine
Authority Magazine

Published in Authority Magazine

In-depth Interviews with Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

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