Contingent work expansion. As employees have proved that they can work anywhere and still be productive, we will see a rapid expansion in contingent workers. These workers are essential for flexible organizations looking to expand their current output with highly skilled workers during busy or uncertain periods. Contingent workers will continue to provide a strategic approach to an organization, its employees, and shareholders.


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 Carl Oliveri.

Carl Oliveri is the Chief Revenue Officer of Robin, the first workplace platform that puts people before places. With 20+ years of experience selling innovative SaaS products, Oliveri is responsible for all activities that generate revenue including GTM strategy, sales, marketing, pricing, and revenue management. Prior to joining Robin, he served in senior sales and customer success leadership roles with leading SaaS companies including PayScale (acquired by Francisco Partners), Kenexa, and IBM.


Thank you for making time to visit with us about the topic of our time. Can you please tell us about one or two life experiences that most shaped who you are today?

I graduated with an undergraduate in Finance, got a finance job, and realized I wasn’t going to be happy crunching numbers. I fell into a sales role, and although I was pretty good, I still knew it wasn’t going to be my passion. My boss asked me to help some newer salespeople, and that is where I stumbled on my passion. I realized really quickly that I got a ton of energy and excitement helping people grow their skill sets and careers.

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?

What’s going to be the same, I believe, is the need for organizations to help employees balance their personal and professional lives. I think COVID and this move to hybrid work is something that companies have missed over the years. Given the Great Resignation, companies genuinely understand now that if you don’t help employees balance their professional and personal lives, somebody else will.

Technology will be different in the future of the workplace and will undoubtedly change rapidly. The Metaverse is an example, where instead of sitting in a conference room, you may be attending meetings in the office or your home but feel like you’re in the office with your peers and customers.

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

Being deliberate about building culture and evolving the employee experience to be more forward-thinking will help future-proof companies. Organizations have to focus on development and assisting employees in upskilling/reskilling. Pre-pandemic, we were above full employment, and it was still genuinely hard to go out and hire people. Now it’s exceedingly tough. Helping employees develop their talents and reskilling will be vital. As a result, people will be much more loyal to you as a company.

Most companies are now competing for talent all over the world, versus just in your local region. The sooner you operate as a company in that fashion, the better off and the more future-proof you’ll be.

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?

Every company has gaps that need filling. Our job as leaders is to match the needs of the organization and match that with the needs of the employees. You can’t just go out and hire to fill gaps you have any longer. It is the employer’s responsibility to provide the foundation for reskilling to help develop fresh and new skills. Offering employees the tools they need to build the foundation for their careers will provide a competitive edge within the market. The sooner you help employees level up, the better off employers will be to fill the gaps in their organization.

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

Most companies have figured out that their employees can work from anywhere and still be productive. There are specific industries where that’s not quite the case, but in most sectors, your employees can be productive anywhere. Organizations need to give them options on how to make the most of their workweek. In the end, employees know how to be the most productive, and allowing them to choose where they work gives them the confidence and flexibility to succeed. Employers need to start asking questions about how to support them best. Do they need quiet areas? Do they need to be around people they want to collaborate with? Putting that kind of control in the employee’s hands has to happen.

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?

Being more deliberate about those water cooler-type conversations that used to happen when everybody was in the office. Employers need to get more intentional now that employees work both in the office and at home. Still, I believe society will suffer if you don’t have those types of interactions, whether personal or professional. Working from home can make individuals become even less visible and connected. It can limit informal mentoring and networking that are necessary for career progression. With the use of technology and location of work, employers need to be more intentional about initiating interactions. The conversations that would happen at the spur of the moment are much more difficult now that employers are working both at home or in the office, and figuring out how to do it no matter where an employee chooses to work is critical.

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

Many companies thought productivity would take a considerable hit when everybody went into lockdown. They soon realized that employees were just as, and in many cases, more productive. This opens the door for employee flexibility and having a voice in how or where they work. That in itself gives me a whole bunch of hope for where we’re headed for the future of work.

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?

I don’t think companies paid much attention to mental health before the pandemic, even though it has always been a problem. COVID highlighted these issues and put mental health in the spotlight. The companies that I see succeed are the ones who prioritize mental health and recognize that they’re not afraid to talk about it or offer resources to help people cope. Organizations can create specific programs or office solutions to help with workplace stress or other mental health issues, such as designing meditation rooms and designated spaces in the office for people to get that mindfulness time.

If you think about when we were in high school, you had guidance counselors to help with any issues that occurred. Bringing innovative solutions such as corporate and career counselors’ roles will improve employee wellbeing. It is essential to get experts in and make them full-time staff so their employees always have a resource that they can talk to about how they’re coping and what’s stressing them out. Having that type of staff is a concept that many companies should consider.

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? How do company cultures need to evolve?

Our job as executives is to match the organization’s needs with the needs of the people. If you are not considering the needs of your people first and foremost, there’s going to be a huge disconnect. That in itself is the Great Resignation. People are leaving organizations, and compensation has changed due to global competition. There’s been so much pressure on companies to keep employees happy. It goes so much deeper than that. I believe executives need to recognize and consider the employee’s needs or desires and the skill sets to succeed in the future. Above all, these necessities have to come first and foremost.

What are your “Top 5 Trends To Track In the Future of Work?”

  1. Hybrid work and employee productivity metrics.

Increasingly, we will see organizations utilize products to measure how and when employees use the office. Forward-looking information allows companies to prepare for the changes in the future and adjust their workplaces accordingly. The data and analytics gathered enable employers to identify or anticipate employee needs and address them faster with appropriate tools or programs.

2. Hiring and training for resilience.

We have seen organizations globally experience a disruption in the workforce unlike any other. Navigating through continued uncertainty is the new reality for corporate leaders. The 9–5 workweek in the office is long gone, and the past year has tested employer resilience to the new hybrid or flexible work model. Employers will need to remain resilient to the changes ahead and the needs of employees in the workplace. As we transition to a new way of work, employers will need to listen to and learn the needs of employees to adapt to the ever-changing office. They also need to help employees build resilience and cope with the pressure of balancing personal and professional lives.

3. Reskilling/upskilling the workforce.

As the skills gap continues to widen, it is the responsibility of the employer to empower employees with new skills to grow both professionally and personally. Upskilling or reskilling employees provides a competitive edge with the market that allows employees to gain valuable insights needed for current work and the future. Closing the skills gap is beneficial for the employees and creates a more productive workforce.

4. Contingent work expansion.

As employees have proved that they can work anywhere and still be productive, we will see a rapid expansion in contingent workers. These workers are essential for flexible organizations looking to expand their current output with highly skilled workers during busy or uncertain periods. Contingent workers will continue to provide a strategic approach to an organization, its employees, and shareholders.

5. Inclusivity.

Although COVID created a shift in the attitudes of the workplace, the situation also created opportunities to address inclusion. Providing flexibility in how people work allows employers to hire outside of their typical regional area or look to a broader talent pool. Aside from hiring, we will see more organizations embrace shared identity or interests groups. These groups can be helpful for employees and employers to gather critical insights, recommend solutions, and be an essential aid in recruiting, mentoring, and retention. Diversity, Equity, and Inclusion (DEI) is a crucial strategy for organizations as we look to the future.

What’s your favorite “Life Lesson Quote”? And how has this quote shaped your perspective?

One of my favorite quotes that have recently become even more relevant in my life is from Ben Franklin: “Tell me, and I will forget, teach me, and I will remember, involve me, and I will learn.” I didn’t realize until a few years ago that I have a learning disability which made this resonate with me even more. As the quote says, it’s easy for me to forget things when I’m just being told, but my biggest growth moments have come through participation.

A James Barrie quote has also reverberated within all aspects of my life, “Life is a long lesson in humility.” Staying humble and always recognizing that I’m never the smartest person in the room has always been important to me. I will always learn more lessons from the uber-talented people working in my organization than I’ll ever be able to share with them. Listening well and being able to connect with others is critical to gaining knowledge at work.

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?

If I could inspire one movement, it would be teaching kids at a very young age the art and discipline of self-love. So much of what’s wrong with the world comes from insecurities driven by a culture of constant comparison, an unattainable need to be perfect, and ultimately not knowing how to handle it. We see this play out in manager-employee relationships all the time, with many leaders hyper-focusing on weaknesses when they should be focused on building on an employees’ strengths. I would love to inspire a movement that would eradicate this generation’s fear of embracing their imperfections.

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