Social responsibility accountability. This next generation will increasingly demand their employers are responsible and sustainable. At Imprint Engine this looks like investing in sustainably made products as well as products from minority-owned and woman-owned businesses.


When it comes to designing the future of work, one size fits none. Discovering success isn’t about a hybrid model or offering remote work options. Individuals and organizations are looking for more freedom. The freedom to choose the work model that makes the most sense. The freedom to choose their own values. And the freedom to pursue what matters most. We reached out to successful leaders and thought leaders across all industries to glean their insights and predictions about how to create a future that works.

As a part of our interview series called “How Employers and Employees are Reworking Work Together,” we had the pleasure to interview Caleb Gilbertson.

Caleb Gilbertson is the CEO and a founding partner of Imprint Engine. As an innovative entrepreneur, he’s helped hundreds of businesses, from startups to well established companies, become more efficient. His focus on technology helps to evolve all departments in an organization and his expertise ranges from e-commerce and software development to advertising and growth hacking. And he’s fueled by creating seamless user experiences and strong, healthy organizations.


Thank you for making time to visit with us about the topic of our time. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today.

My first job out of high school was working in the graphics department at a promotional product supply company. I had no direct job experience at this point, but I convinced the owner to give me a shot. About six months into the job I realized the company had a very poor website and I pitched the owner on allowing me to spend half of my time learning how to improve it. A few months later, we had a brand new website. I spent the next several years building websites and learning everything I could about digital marketing and software development. I also spent a lot of time designing marketing collateral and brokering print/promo products to help bring in additional cash. Fast forward a few years and I joined a company called Renters Warehouse. I eventually became their CTO and applied what I had learned to help scale the brand from three locations to 30+ in a few years. In 2012, my friend Travis Veit, who knew me for years as a nerdy entrepreneur, approached me with an idea to start a company in the industry I started in — promotional product supplies. Travis is an amazing creative producer and supply chain expert. He saw the vision for what we could build together as a team. From there Imprint Engine was born and in the past ten years we have grown the company from two employees and 62,000 dollars in revenue its first year to 55 employees and 13M dollars in revenue last year.

Let’s zoom out. What do you predict will be the same about work, the workforce and the workplace 10–15 years from now? What do you predict will be different?

While there are many changes happening in the workplace, I think some elements that we’ve seen evolve in the past couple of years will remain the same. For instance:

  • Employees will continue to demand more from their employers. More flexible hours, better benefits, work from home capabilities, awesome employee engagement/reward and recognition and more. Companies are seeing how difficult it is to retain top quality employees and this will continue as the younger generations enter the workforce and have higher expectations about flexibility, fulfillment and rewards.
  • People will continue to move from job to job much more frequently than historical standards. Gone are the days when people would get a great job out of college and stay for 5–10 years feeling fortunate to be employed. Everyone is looking for more opportunity and growth, and they have less patience to get there than ever before. I only see this becoming more true over the next 5–10 years.

However, there will be changes that come over the next decade.

  • We will see the demise of the traditional 9 to 5 workday and 5-day work week. We’re already seeing some movement in that direction, but I think in 10–15 years things will look drastically different. As more tools become available to effectively manage workload, communication, and productivity, we’ll all be able to accomplish more in less hours, and people will expect more flexible schedules as a result.
  • I anticipate that people will regularly hold more than one job at a time. We’re already seeing the culture of the “side hustle,” but I think this will evolve into more people having multiple jobs at the same time as opposed to a “job” and a “side hustle.” The aforementioned flexibility in work schedules and remote work capabilities will allow those who want to work more to have diverse income streams from multiple jobs.

What advice would you offer to employers who want to future-proof their organizations?

Treat your employees like your most important asset, because they are. At Imprint Engine, we’re highly focused on creating a positive experience for our employees, because not only do we want to create an employee-focused culture, but we realize from a professional perspective that it’s good business. It’s much more cost effective to recruit, train, and retain top quality talent than it is to be caught in a cycle of constant turnover.

For us that means offering benefits like unlimited PTO, a flexible schedule with the option to work from home, fully paid health insurance, a fully stocked break room with whatever snacks and beverages they want, fun company outings that staff get to pick, a dog friendly office, gym membership credit, a cool remote workspace and social club separate from our own office, and competitive compensation. You have to constantly evaluate your compensation and benefits to stay ahead of what others are offering. It’s also crucial to show your employees that they are top of mind in your decision making process about the evolution of the company.

What do you predict will be the biggest gaps between what employers are willing to offer and what employees expect as we move forward? And what strategies would you offer about how to reconcile those gaps?

I think actual compensation will continue to be the biggest driver in decision making for employees. Benefits can be a huge lever, but I think the most significant gap will remain financial compensation and what people want/expect to make vs. what employers are willing to pay. We could also see a trend towards equity or options for roles or industries where that’s not traditionally a compensation vehicle. It could almost be a return to the days of pension plans where employees expect to have some sort of fund that takes care of them when they retire beyond the normal 401k matching and retirement plans.

Employees want to help companies grow, but they want to share in the value and growth they are contributing to. We will start to see how companies adjust to those expectations, how it will impact employee compensation in the long run, and ultimately how large a role that will play in employee retention. People used to work for companies for longer periods of time, but a large part of that could have been how they were incentivized by things like pensions. As pensions have largely gone away, we’ve seen the employee loyalty to their companies also erode, so it will be interesting to see if there’s a return to that dynamic.

We simultaneously joined a global experiment together last year called “Working From Home.” How will this experience influence the future of work?

This fundamental shift in the way we work will likely be one of the biggest legacies of the pandemic. While the technology existed to make this a reality, it took the pandemic to force companies to re-evaluate the very core of the workplace. One of the biggest challenges companies face in the shift to “work from home” is the engagement with their coworkers and with the company. This has led to our largest area of growth at Imprint Engine: employee onboarding and retention.

We’ve had an explosion of work from HR teams trying to figure out how to onboard employees, keep them engaged, and create a professional work from home environment. A few examples of this are automated employee welcome kits, where we’re able to integrate with HR platforms to automate the sending of welcome kits for new employees. By their first day of work we’re able to land a customized welcome kit containing things like company branded swag, welcome letters, HR paperwork/manuals, snacks, and home office essentials.

We also have partners sending out monthly “home office upgrade” kits with things like ring lights, headphones, desktop organizers, and other essentials to upgrade the home offices of their employees. As companies also want to maintain the camaraderie and interaction between co-workers, we’ve also sent out a lot of “Happy Hour Kits” where employees are receiving the same snacks or activities that pair with a Zoom-based activity, further fostering employee engagement. I think these HR driven employee engagement tactics will continue to become more and more essential as companies adjust to the realities of long term work from home situations.

We’ve all read the headlines about how the pandemic reshaped the workforce. What societal changes do you foresee as necessary to support a future of work that works for everyone?

I think the changes in workplace culture brought about by the pandemic are all positive for society in terms of creating a healthier work-life balance and adjusted attitudes about the prominent role that work plays in our lives. I think it places more power in the hands of employees, which is a long overdue need in a world where companies have largely controlled the narrative and set the standards.

I think the only thing we need to be wary of is the potential for work to “never end” with people working from home and the realities of Slack/email/text/Zoom creeping outside of work hours. Employees need to be able to turn it off when they aren’t in work mode, but I think that’s largely driven by the employees more than employers. We’re seeing some interesting trends globally, such as Portugal experimenting with making it illegal for bosses to contact their employees outside of work hours. It’s a fine line between productivity and demanding too much from employees, and that is a boundary that will have to be drawn over time.

What is your greatest source of optimism about the future of work?

I’m very optimistic about the role technology is going to play in improving the way we work. Things like artificial intelligence, the rise of video conferencing, tools like Slack and Calendly all allow us to accomplish more with less effort. This has the potential to lead to a much healthier work-life balance and enable people to have very successful careers that are balanced with healthy home, family, and social lives.

As mentioned above, I also think this next generation of workers are going to demand more from their employers and push for what they want instead of sitting back and accepting what is offered. This shift will hopefully lead to a more healthy and balanced power and profit dynamic between employers and employees.

Our collective mental health and wellbeing are now considered collateral as we consider the future of work. What innovative strategies do you see employers offering to help improve and optimize their employee’s mental health and wellbeing?

We’re seeing a very genuine focus on the mental health and wellbeing of employees from our forward thinking clients, who are mid-large tech companies based in San Francisco. I think these clients represent the thought leaders in this space and are ahead of the curve in recognizing the value of addressing this issue.

My hope is that traditional companies will eventually follow suit. For example, we’ve got clients who are sending monthly care packages to their employees to help make their home office environments more calm and relaxing, including things like herb gardens, desktop zen gardens, scent diffusers, candles, humidifiers, and other items. I’ve seen others offering free mental health counseling, gym memberships, massages, and other similar programs under their compensation packages.

It seems like there’s a new headline every day. ‘The Great Resignation’. ‘The Great Reconfiguration’. And now the ‘Great Reevaluation’. What are the most important messages leaders need to hear from these headlines? How do company cultures need to evolve?

I think the message is loud and clear: We’re seeing a fundamental shift in the employee/employer relationship. Anyone who isn’t hyper focused on changing to keep up with these trends is going to lose a lot of great people and put their company at risk.

Company cultures need to evolve to become much more employee-centric and start to think of a balance towards sharing more of their profits with their employees. It seems clear that people are willing to work hard, they just want the work they do to benefit them personally, not just the company they work for. Companies who understand this and make changes in their compensation thought process to react to that will be the winners.

Let’s get more specific. What are your “Top 5 Trends To Track In the Future of Work?”

  1. Invest in engaging ways to reach employees at home. With the rise of work from home and a future filled with hybrid work options employers will need to find and embrace meaningful ways to connect with their employees from a distance. HR departments in particular need to proactively seek ways to engage, interact and keep teams connected to their companies. From on-boarding to team building, to custom-branded kits, — items arriving on the doorstep that can help improve the stay-at-home office environment and create camaraderie with employees will pay off in the long run and help greatly with employee retention.
  2. Prioritize work-life balance for employees. We’ll see companies invest in benefits that support a work-life balance. From unlimited vacation, to gym memberships to four-day work weeks, employees are looking to enjoy life outside of work and companies are going to need to embrace this to attract and retain top talent.
  3. The demise of the 9 to 5 and the increase in the “side hustle.” Similar to the point above, the new workforce is looking for something different than the traditional 9–5 work week. With hybrid and work from home business models becoming both inevitable and sustainable, the next trend in this model will be a shift to when work is done and the ability and desire to do more than one job
  4. Continued investment and growth in digital spaces. With the increasing options for tech advancements, and the ability to work from anywhere, we’ll continue to see a wide variety of ways companies will depend on tech to connect with their employees and how employees interact with each other.
  5. Social responsibility accountability. This next generation will increasingly demand their employers are responsible and sustainable. At Imprint Engine this looks like investing in sustainably made products as well as products from minority-owned and woman-owned businesses.

I keep quotes on my desk and on scraps of paper to stay inspired. What’s your favorite “Life Lesson Quote”? And how has this quote shaped your perspective?

“Inspiration is perishable.” This comes from one of my favorite books, “Rework” by Jason Fried. Everyone has great ideas, but having the inspiration and the ability to execute on those ideas is harder to come by. You never know when that inspiration will come and when it does you need to take advantage of those moments to accomplish things that could otherwise take a long time to make happen.

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, she, or they might just see this if we tag them.

Tim Ferris. His book, “The 4-Hour Workweek” was one of the first books that made an impact on my mentality in regards to how to build a business and think differently about how to approach solving problems, taking risks and looking at the world with a new perspective.

Our readers often like to continue the conversation with our featured interviewees. How can they best connect with you and stay current on what you’re discovering?

Follow me on Twitter @CalebGilbertson and LinkedIn https://www.linkedin.com/in/calebgilbertson/

Thank you for sharing your insights and predictions. We appreciate the gift of your time and wish you continued success and good health.