Carl Oliveri of Robin: “Lead with Emotional Intelligence”

Lead with Emotional Intelligence — A strong company culture starts with its executive team. Managers need to lead with empathy as they plan for the transition to hybrid/flexible working models following a year of remote work. Businesses should establish a feedback loop so they can refine their workplace model over time, based on employee needs and preferences. […]

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Lead with Emotional Intelligence — A strong company culture starts with its executive team. Managers need to lead with empathy as they plan for the transition to hybrid/flexible working models following a year of remote work. Businesses should establish a feedback loop so they can refine their workplace model over time, based on employee needs and preferences.


As a part of my series about about how leaders can create a “fantastic work culture”, I had the pleasure of interviewing 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 so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

It has been an interesting journey, but what ultimately brought me to this career path was trial and error. After completing my undergraduate degree in finance, I quickly realized that it wasn’t going to be my long-term career. Despite my introverted personality, I decided a sales role may be a better fit for my skill set.

I excelled as a salesperson but found that my “rush” didn’t come from closing a big deal. It wasn’t until I started managing a team that I really began to hit my stride. The opportunity to educate junior employees and help them achieve their professional goals was where I found the most satisfaction in my career. To this day, helping people develop, both professionally and personally, is where I’m most fulfilled. It’s also why I love what I do.

Can you share the most interesting story that happened to you since you began leading your company?

Well, this is an easy one — the COVID-19 pandemic. I had the same reaction as many executives when the pandemic first hit: “Oh shit!” As a provider of workplace software, there was an added layer of complexity to the questions facing Robin’s leadership team. With state mandates and emergency orders forcing many companies to make a massive transition to remote work, we saw a new narrative emerging around the workplace shaped by messages like, “The office is dead” and “The office is a ghost town.” We even witnessed executives of large technology companies, like Twitter CEO Jack Dorsey, tell employees they don’t ever have to return to the office. Despite all of these public announcements and sentiments, it was interesting to see how many people were actually still using the office on a day-to-day basis. Watching this issue evolve with the transition into flexible/hybrid work now is the most interesting thing I’ve ever experienced in my career.

Are you working on any exciting projects now? How do you think that will help people?

We’re currently working on different ways that allow people to check into the office in a seamless, touchless, quick and joyful way.

Ok, let’s jump to the main part of our interview. According to this study cited in Forbes, more than half of the US workforce is unhappy. Why do you think that number is so high?

This is a question of leadership versus management. If C-level executives are managing with honesty and transparency, people will inherently feel connected to the company’s bigger, broader culture which will result in enhanced productivity and alignment within the organization. This will be more important than ever as organizations transition back to an office-centric or hybrid work model. As productivity levels continue to be a major concern, the natural inclination for leaders who see a drop is to revert back to what they know. We saw it with WeWork, Netflix, and Goldman Sachs when their CEOs openly criticized remote workers, even going so far as to say that the people working from home weren’t engaged.

The workplace has changed forever, whether employers want to acknowledge it or not. Most industries, most notably tech workers, can accomplish 95% of their work tasks remotely and don’t want to give up work-life balance or return to a lengthy commute without a compelling reason from their company’s leadership team. Empathy and transparency are key to building a happy workforce.

Based on your experience or research, how do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?

If leaders don’t get a better grip on how to keep people engaged, an unhappy workforce will negatively impact all three.

I hate to see employee health and well-being listed last in this sentence as it’s one of the biggest pieces to ensuring a happy workforce. Overall employee health in the U.S. isn’t good with studies finding that the accelerated productivity of U.S. workers has come at the expense of employee happiness over the last few years. Questions around whether companies care about employees will continue to snowball with the transition back to in-person work.

Can you share 5 things that managers and executives should be doing to improve their company work culture? Can you give a personal story or example for each?

Lead with Emotional Intelligence — A strong company culture starts with its executive team. Managers need to lead with empathy as they plan for the transition to hybrid/flexible working models following a year of remote work. Businesses should establish a feedback loop so they can refine their workplace model over time, based on employee needs and preferences.

Establish a Workplace Department — Despite having the common strategic goal of enhancing the employee experience, IT, HR, and Facilities teams have traditionally operated in siloes. The accelerated integration of online and in-person workplaces over the past year has changed all of that. As we enter a trial period for how hybrid offices could impact company culture, establishing a workplace department should be a top priority for leaders looking to eliminate friction and attract workers back to the office.

Create a tech-enabled employee experience — The post-pandemic office presents complex challenges that technology is uniquely suited to solve. One of the biggest challenges facing managers today will be creating a seamless hybrid work environment that delivers a cohesive experience for employees regardless of location. In order to do this, companies will need tight integrations with their full hybrid tech stack including building access, meeting spaces, desks, and workspaces.

Enhanced communication and transparency — The key to building and maintaining a happy and productive workforce is communication. As employees start to return to the office, executives should consider technology’s ability to remove friction from the office employee experience. Implementing tools like interactive office maps can empower employees to make autonomous decisions about how, where, and when they’ll be returning to the office and what their post-pandemic workspace will look like, mitigating employee stress and optimizing productivity.

No Such Thing as a Perfect RTO Strategy — There’s no one-size-fits-all approach to the new world of hybrid work. Organizations should be treating this transition as a months-long process and make informed decisions driven by employee feedback.

It’s very nice to suggest ideas, but it seems like we have to “change the culture regarding work culture.” What can we do as a society to make a broader change in the US workforce’s work culture?

Every study I’ve looked at has shown the U.S. culture over the last 10 years has without a doubt increased productivity but those gains came at the expense of employee happiness. While the average American worker commutes 26 mins each way, the number of people who traveled more than an hour and a half each way has increased by 31% making the average American work week 47 hours. To put it into perspective, on average an American employee puts 260 more hours into work every year than British workers and 499 hours more than French citizens.

We have to start working smarter, not harder! U.S. employers need to recognize that people have a life outside of work they have to balance. Giving employees the autonomy to pick where and how they work will be critical moving forward. It’s not feasible for American workers to keep on at the same pace; productivity will suffer, people will start to burnout, and, overall, corporate culture will need to evolve to create a more fulfilling experience for workers.

How would you describe your leadership or management style? Can you give us a few examples?

I would describe my management style as empathetic and direct. I am a very service-oriented person and view my role as CRO as one centered on balancing the needs of an organization with the needs of its employees. I make sure people understand where that balance lies and try to help people find the right role within our organization.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My father has had a huge influence on me, both personally and professionally. However, I will always be grateful for my first sales manager ever, Patrick Garrity.

Patrick had a work ethic unlike anyone else and taught me the discipline of always being organized and on top of everything. Every time Patrick got promoted or moved to another part of the organization, I would follow him. Under his leadership, I was able to get a 360-degree view of different departments and roles which is what eventually led me to become Robin’s CRO.

How have you used your success to bring goodness to the world?

I love mentoring and being a sounding board for people. Whether it’s colleagues, family, or friends, helping people take skills from work and translate them into personal life or helping to coach them in different ways. I really enjoy being a part of that development outside of my role. One of the ways I do this is by volunteering time with Venture Lane, a program that helps early-stage CEOs and founders develop go-to-market strategies.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

One of my favorite quotes that has 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.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

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 these fantastic insights. We wish you continued success!

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