The Remote Work Revolution: Daniel Ramsey of MyOutDesk On Building Strong Cultures in a Digital World
An Interview With Chad Silverstein
Leaders must foster a group culture of winning, which comes from sharing values and goals for the business. When employees understand where the business is heading and why, they feel more connected to the company and its mission.
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 Daniel Ramsey.
Daniel Ramsey isn’t just building businesses, he’s engineering growth. As founder & CEO of MyOutDesk, named the Best Virtual Assistant Service for Specialists in 2024 by U.S. News, he’s spent more than 17 years transforming how 8,000+ clients reclaim their time and amplify their impact.
A career entrepreneur, Daniel has built, scaled, and sold multiple businesses, staying ahead of the curve in optimizing operations for growth. He is the founder of Ramsey Real Estate & Development Corporation, Play Park Hospitality LLC, and MyTimeIn.io., ventures that span real estate, hospitality, and innovative workforce solutions.
In 2008, he recognized a fundamental problem: business leaders were drowning in necessary administrative tasks, bogged down by routine work that kept them from focusing on high-value strategy. Determined to change that, he launched MyOutDesk — a virtual talent solution that empowers business owners to reclaim their time, streamline operations, and scale smarter. Today, MyOutDesk helps leaders address inefficiencies before they become roadblocks.
Beyond business, Daniel has a passion for service, as the Founder of MOD Movement, a nonprofit dedicated to creating lasting, global impact, around the globe.
Daniel shares his expertise with his audiences, from stage to social media, and with his best-selling book “Scaling Your Business with MOD Virtual Professionals: How to Drive Revenue, Save Time, and Create Your Dream.”
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?
Much of my beliefs and work ethic were shaped by my childhood. I grew up in Redding, California, where I learned the importance of hard work and dedication, encouraging me to become an entrepreneur. In fact, I started my first business selling candy bars when I was just 12 years old!
After studying finance at California State University Sacramento, I channeled my passion for business and entrepreneurship to run and sell several businesses before founding MyOutDesk. Today, I’ve helped thousands leverage virtual agents to streamline administrative and time-consuming tasks, freeing leaders to focus on scaling their businesses and growing profitability.
Can you share the most interesting story that happened to you since you began working with remote or hybrid teams?
We analyzed our team and their roles to gain a better and deeper understanding of their work to see what would be best: remote, hybrid, or in person. Our goal was to make sure we were providing our employees with the right tools and processes possible. We know there is value to in-person collaboration and face time, but also recognize the flexibility that remote work offers.
This segmentation helped us to better understand our job descriptions and executable work, while also looking at the burden of documentation that impacts our remote workforce. This has helped us to set up a better business model for our teams.
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?
Adding Value: Our core value at MyOutDesk is having a servant’s heart. We are constantly in service of others, whether that is through the work we do for our customers or through our non-profit, MOD Movement.
Process Oriented: We also maintain a mindset around data, growth, and scale. MyOutDesk was founded as a way to serve small and medium-sized businesses, which make up nearly all businesses in the United States, yet are often overlooked by providers. We faced a challenge early on: how to put a processing system in place so we can pass on savings to the customer. We spent the time analyzing data, growing, and scaling to create that innovation process and better serve our customers long term.
A Long-Term Mindset: Having strategic conversations, while maintaining a relationship-based and people-centric approach to our work, has helped to create a long-term mindset where we approach each task and decision with a growth mentality.
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?
MyOutDesk has been working in the virtual space since our founding in 2008, where we’ve managed virtual assistants to help companies outsource administrative tasks like email & calendar management, CRM updates, office administration, and bookkeeping. Because of this extensive background, I’ve learned that culture is not about office perks but shared goals and collaboration. It’s what you do as an organization, how you work together, and what you accomplish as a team.
What are some of the unique challenges that remote or hybrid teams face when it comes to creating a sense of connection and belonging?
Isolation can be a common problem for remote or hybrid teams, as they’re disconnected from vital interpersonal and face-to-face communication. For us, team meetings have been key to solving that problem and building connection among our employees. We start every internal meeting with personal updates, sharing what we did over the past weekend or something we are excited about at work. This helps us to know more about our teammates as people and creates a sense of pride for the work we are producing.
What tools or technologies have you found most effective in fostering communication, collaboration, and team alignment in a remote setting?
We regularly invest in software and systems to streamline remote work, working with individual departments to determine what is most needed for their teams. I am a firm believer in combining data and human behavior to inform our decisions. I do not shy away from technology or AI to train our workforce and enhance collaboration, particularly as AI will become increasingly engrained in our workplaces. However, I always ensure our technology has an overarching human element so we don’t lose that important connection.
For our virtual assistants, we’ve invested in a specific and streamlined onboarding system with a 360-degree company overview. As a core differentiator, this has helped us to reduce lift on the client, while guaranteeing an assistant’s success. Similarly, having the smooth onboarding process and investing in that upfront has helped to reduce turnover and lessen mistakes later.
What role does leadership play in building and sustaining a strong company culture in a remote or hybrid work environment?
Leaders must foster a group culture of winning, which comes from sharing values and goals for the business. When employees understand where the business is heading and why, they feel more connected to the company and its mission.
This is particularly important with employees, or in my case virtual agents, who are remote and completing more administrative tasks. These tasks are vitally important, but without understanding the larger goals, they can feel unnecessary and monotonous to the employee. By including them in the larger strategy, they can see how their role impacts business success.
What advice would you give to leaders who are struggling to maintain employee engagement and motivation in a fully remote workforce?
Focusing on and investing in philanthropic causes — specifically causes that impact your employees directly — help to boost employee morale and engagement. At MyOutDesk, being of service is a core value, which led to us starting the MOD Movement to serve underprivileged communities, both in the United States and abroad. Through this non-profit, we’ve been able to build homes and hospitals in the Philippines, helped teens build a personal roadmap to achievement, and built shelter for senior citizens.
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.
Onboard Remote Workers Like Any Other Employee: We’ve invested heavily in building our onboarding structure, which allows us to quickly bring employees up to speed and jump on tasks sooner. By putting in the time and effort to create strong remote trainings, employees have the confidence to complete their work or ask another remote colleague for support.
Overcommunicate and Document the Role: Overcommunicate and overexplain work and assignments with remote employees. Because the workforce is remote, it’s harder to just tap your shoulder and ask for guidance; a water cooler moment becomes a 15-minute Zoom call. However, being available to answer questions and work with your team is monumental to getting the task done.
Remote work also forces structure that accelerates growth. When working in person, (tribal knowledge) historical knowledge is often shared verbally or in passing between employees. When working remotely, that knowledge must be documented to properly train teams.
Play, Pause, Do: I love to implement a “Play, Pause, Do” method with my remote employees, in which every procedure in our playbook has an accompanying video with written instructions. When employees need a refresher or want to check their work, they can simply go back to this video and complete the task as expected.
Rhythms and Cadences Inside the Business: I regularly jump on Teams and Zoom meetings with my teams to help better manage our hybrid and blended workforce and create a steady flow of check-ins. Through this, I’ve seen compound leverage in our remote employees to help them feel comfortable asking questions with both each other and our leadership team. This also helps to streamline that onboarding process, as when a new employee joins, they have time set up already to meet with the team.
Employ Technology to Manage the Remote Team: Finally, we leverage technology like MyTimeIn, a time and productivity tracking system, to help us understand where our teams’ time is going and how we can best support them to complete their tasks in a timely manner.
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?
We host an internal conference each year, where we bring team members together to meet in person and collaborate. We share company updates, give away prizes, and focus on building community among our remote teams.
Beyond the conference, we always have opportunities for remote team members to come into the office and meet their coworkers. That in-person communication and connection matters, and we want to ensure it is always on the table for consideration.
Finally, we have a strong company values, expectations, and onboarding process, and have updated these policies to work for our remote teams.
How do you strike the balance between flexibility (one of the main benefits of remote work) and ensuring accountability and productivity?
We use a variety of technologies, such as MyTimeIn.io and Scoreboard, to help track time and productivity. We also implement morning huddles, weekly check-ins, monthly results reflection meetings, and quarterly goal-setting meetings to ensure we are meeting those goals and remaining accountable as a workforce.
What trends or innovations in remote work are you most excited about, and how do you see them shaping the future of workplace culture?
Leveraging Virtual assistants will be key to driving business growth. I’m excited to see businesses continue to leverage this remote workforce to improve productivity and efficiency, ultimately scaling their business in the process. Rather than requiring all employees to be in the office 5 days a week, companies can look to employ and integrate virtual agents quickly and efficiently.
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?
Our employees are the ones serving and interacting with our customers daily, whether that is internal at MyOutDesk or through our virtual assistants. By focusing on the needs of our employees and fostering a strong culture, our employees feel empowered to meet and surpass the needs of our 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. 🙂
A new business landscape calls for new models of both entrepreneurship and remote work. Entrepreneurs need a new guidebook for an increasingly competitive and precarious business environment. Embracing these new working methods and tapping into virtual agents can drastically improve work cultures.
How can our readers further follow you online?
You can visit us at https://www.myoutdesk.com/ or follow me on YouTube (@danielramsey_) or LinkedIn (@thedanielramsey).
This was great. Thank you so much for the time you spent sharing with us.
The Remote Work Revolution: Daniel Ramsey of MyOutDesk 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.