The Remote Work Revolution: Rob Levin of WorkBetterNow On Building Strong Cultures in a Digital World
An Interview With Chad Silverstein
We build in social elements that encourage people to know one another beyond their professional roles. In addition, we do social activities such as meditation and yoga classes as well as fun stuff like talent shows.
The remote work revolution has transformed how we think about work, but it has also raised important questions about maintaining culture and connection in a virtual world. To explore this important topic, we are interviewing Rob Levin, Co-Founder and Chairman of WorkBetterNow.
Rob Levin is a serial entrepreneur with over 30 years of experience helping small and midsize businesses (SMBs) run their businesses better. In 2018, he co-founded WorkBetterNow (WBN), a game-changing venture that provides US-based small and midsize businesses (SMBs) with high-performing talent from Latin America. WBN has empowered hundreds of businesses to thrive in the face of the talent crisis.
Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
My journey to founding WorkBetterNow was shaped by over 30 years of working with small and midsize businesses (SMBs). Early on in my career, I ran several companies. Eventually, I launched the New York Enterprise Report, a media company serving business owners, where I had a front-row seat to the many challenges business owners face — especially when it comes to hiring and talent retention. As I scaled my own businesses, I saw how difficult it was to find top talent, and I personally experienced the game-changing impact of hiring a remote executive assistant. That moment led to the creation of WorkBetterNow, where we help SMBs access high-performing remote professionals who become integral parts of their teams.
Can you share the most interesting story that happened to you since you began working with remote or hybrid teams?
One of the biggest eye-openers was seeing how a single strategic hire transformed my business and my life. I’ll never forget when I hired my first assistant, who worked remotely from El Salvador. Within weeks, I realized I had been wasting enormous amounts of time on tasks that weren’t in my unique ability. That assistant didn’t just make my life easier — she helped me scale my businesses more effectively. (By the way, she is now the General Manager of WBN). Since then, I’ve watched hundreds of SMBs have similar breakthroughs when they bring on the right remote talent.
You are a successful leader in the remote workspace. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
- Curiosity — I was always interested in how successful business owners did things, not just what they did. This led me to starting The New York Enterprise Report, a media company to help business owners better run their organizations. We uncovered and shared these best practices. Even though I sold the company over 10 years ago, I still get people telling me they refer to the stacks of magazines sitting at the side of their desks.
- Perfectionist — Now, hear me out on this one. I want to blow away someone’s expectations. In a business setting, I want my company’s clients to say “WOW” during their entire experience. So, our processes and procedures are designed to do just that. However, we know that perfection is not realistic all of the time, so our core value is the “pursuit of excellence”.
- Empathy — I have a really good understanding of our clients and our talent. I have shared that understanding with the WBN team, and they have done an amazing job of meeting both stakeholder groups’ needs.
Let’s now dive into the focus of our interview. When the shift to remote work became widespread, what was the biggest challenge you faced in maintaining a strong workplace culture? How did you address it?
When it comes to remote, we were remote from Day 1, which I suppose gave us a head start because we didn’t have to make changes to adapt to remote. Everything was designed for a remote environment.
For us, it started with deciding to have a culture by design. My partner, Andrew Cohen, and I agreed on our first core value (which creates the expectations for the culture) on the day we decided to start the business. That core value was “talent comes first”, which has a double meaning.
First, it means that we put our WBN Certified Professionals “in front of our clients”. The idea there is that if we take care of our talent, they will take care of our clients.
Second, it means that we really care about the WBN team. Making WBN a great place to work is a priority for us.
Over time, we added 5 other core values and we use them when making hiring, promotion, firing, etc., decisions.
In addition, we employ many tactics that help by addressing the human side of work, including:
- Weekly all-team meeting. One of the things we do in each meeting is a team member will tell us about their personal life.
- Recognition program — Our W Awards recognizes people when they do something exceptional and in alignment with our core values.
- Fun activities — talent shows, meditation and yoga classes, virtual happy hours, etc.
What are some of the unique challenges that remote or hybrid teams face when it comes to creating a sense of connection and belonging?
As you can imagine, it can be challenging to build connections and have a sense of belonging in remote and hybrid environments. It is easy to underestimate the benefit of the water cooler. That said, there a number of things that companies can do to mitigate these challenges.
- Overcommunicate, particularly things like company updates/news, new hires (and leavers) as well as processes.
- Make data and other information easy to find and well-organized.
- Share personal information during meetings. For example, in our weekly meetings, one of our team members spends 5–10 minutes telling the team about their background, family, hobbies, etc.
- Provide for digital personal get togethers — at WBN we have virtual happy hours, yoga sessions and talent shows.
What tools or technologies have you found most effective in fostering communication, collaboration, and team alignment in a remote setting?
We use a number of tools for communication and collaborating:
- Office 365, including Teams for chat and calls (video and audio) and Sharepoint/OneDrive for files.
- As part of this, all files/data are stored in the cloud.
- Some people, including myself, use Planner for managing projects and tasks.
- We use AI notetakers so we can be more present during meetings.
- As we run on EOS, we use L10s (structured weekly meetings) to go over KPIs, make sure our projects are on track, and discuss issues.
What role does leadership play in building and sustaining a strong company culture in a remote or hybrid work environment?
It is up to leadership to set the culture, lead by example and encourage others to embrace the culture and make it come alive. That means setting clear expectations, celebrating wins, and making sure employees feel heard and valued. It is also on leadership to set the tone by fixing culture violations when they occur.
What advice would you give to leaders who are struggling to maintain employee engagement and motivation in a fully remote workforce?
Create programs that encourage engagement. That is everything from regular meetings (company-wide, departmental, 1:1s) to recognition systems to fun stuff like I mentioned above.
Of course, this only works if you have the right people on the bus. This includes everything from hiring motivated people who are excited by your mission and can thrive in a remote environment (not everyone can) to taking quick action when discovering that someone is not a good fit.
Ok, let’s explore actionable insights. Based on your experience, can you share “5 Strategies to Build a Strong Workplace Culture in a Remote Work Environment”? If you can, please include examples or stories for each.
- It starts with having a mission and vision that excites the team. Then, core values that provide a guide as to how we work.
- Overcommunicate expectations and feedback, and be consistent in communication.
- Ensure every team member understands their responsibilities and how they tie to our mission and goals.
- Celebrate achievements.
- Offer learning and growth opportunities.
How do you address potential feelings of isolation or disconnection that employees may experience in a remote work environment?
We build in social elements that encourage people to know one another beyond their professional roles. In addition, we do social activities such as meditation and yoga classes as well as fun stuff like talent shows.
Can you share an example of a remote work initiative, policy, or program that you implemented which had a significant positive impact on your team?
Our W Awards program, where team members nominate each other for going above and beyond, has been a massive success. (Here is how we do it: https://www.workbetternow.com/blog/how-workbetternow-recognizes-its-remote-team)
How do you strike the balance between flexibility (one of the main benefits of remote work) and ensuring accountability and productivity?
We focus on outcomes rather than on managing time. Our KPIs and structured check-ins ensure employees have some flexibility while staying accountable for their work.
What trends or innovations in remote work are you most excited about, and how do you see them shaping the future of workplace culture?
There is so much to be excited about with respect to AI. For starters, along with automation, AI can handle many tasks on its own, freeing the human workforce to focus on higher-impact activities and increasing productivity.
In addition, with remote-based training now accessible to companies of any size, there is a huge opportunity for upskilling, which is a win/win. The workforce gets new skills, which enables career progression. The company gets new capabilities, which it needs to keep up with the increasing pace of change in business.
In your opinion, how does building a strong culture in a remote work environment impact not just employees, but also customers, clients, and the company’s overall performance?
A strong culture leads to engaged employees, which translates into better customer experiences and higher retention rates. When employees are motivated and aligned with a company’s mission, performance and profitability soar. As Danny Meyer once said to me, take care of your people, and they will take care of your clients.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people through better remote work cultures, what would that be? You never know what your idea can trigger. 🙂
To borrow from the name of my podcast, I am indeed trying to start a movement called Great Talent Great Business. It starts with the employers creating a great, productive place to work with many of the things we have discussed, including a powerful mission and impactful values. Then creating an environment where people can thrive… clarity in communications, tools that are effective that the workforce is trained on using and measuring results, not time sitting in front of a computer. Then add continuous learning, meaningful recognition and throw in some fun… If you had mentioned this to me 10 years ago, I wouldn’t have been sure if it would work… But I can tell you we are living this now at WorkBetterNow, and it is awesome.
How can our readers further follow you online?
Connect with me on LinkedIn: https://www.linkedin.com/in/robertslevin/.
This was great. Thank you so much for the time you spent sharing with us.
About the Interviewer: Chad Silverstein is a seasoned entrepreneur and Thought Leader with over 25 years of business experience. He has founded, operated, and exited multiple companies and now builds into a handful of high impact CEOs. Chad has launched multiple online communities, including a recent leadership development platform, and also serves as a strategic advisor for Authority Magazine’s thought-leader incubator program.
To learn more and connect with Chad visit: chadsilverstein.io
The Remote Work Revolution: Rob Levin of WorkBetterNow On Building Strong Cultures in a Digital… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.