A Conversation with Red Rover’s CEO, Dani O'Shaughnessey
Meet Daniel O'Shaughnessey, or Dani, as he’s affectionately known, the charismatic CEO and co-founder of Red Rover. Red Rover specializes in modern and innovative HR software solutions tailored to the K12 education market. With a passion for building effective teams and fostering a company culture that emphasizes servitude and growth, Dani stands alongside two other dedicated founders, Larry Foxx and Mike Sheldon.
In this interview, Dani shares his motivations, inspirations, and the story behind Red Rover’s inception. Rooted in strong work ethic and genuine care for people, Dani and his fellow co-founders embody purpose-driven leadership. They aim to make a meaningful impact on the Red Rover team and the K12 HR community, who stand on the front lines of service to teachers and students.
What motivates you to get out of bed in the morning?
The opportunity I get to serve a team that’s running so fast. To put a team together that loves to serve K12, that really energizes me. I’m not the smartest person in a room. I try to find great talent and put them in a place where they can use the gifts that God has given them to their fullest. That’s what I really enjoy.
Describe your life outside of work.
I’ve got a wife and four kids––an eleven, eight, five, and two-year-old. So, there are plenty of toys, diapers, complaining, and a lot of great times, too, of course. That’s my personal life right now––enjoying my family. We’ve got a great church, locally, that we’re involved in, so that keeps us busy on the weekends. I try to play Pickleball sometimes when I get a chance, but unfortunately, that’s few and far between.
Who do you admire?
Personally, a couple of pastors in my life. Church has certainly been influential [to me]. They have shared with me that life is short. James 4:14 says: ‘Life is just a vapor that appears for a little while and then vanishes away.’ So I think that’s been a guide for me to understand that no matter what happens, whether I have two, 20, or 100 years, it’s a really brief life, and impacting and being able to enjoy that with people is what’s most important.
Professionally, I’d probably say the co-founder of a company called Frontline, Michael Blackstone––[he’s] been a really great friend, father figure, and mentor to me over the past 20 years. He’s been a really great guide to me to keep myself grounded; keep myself hopefully humble and hungry. Keep myself pointed at people and not things.
Is there a character or persona you resonate with?
The persona for our company is Micahel Strahan, he’s on GMA [Good Morning America] and is a former New York Giants football player. He takes himself lightly. He’s friendly––he’s an outgoing and affable guy. [He’s someone] I think myself and co-founders would like to emulate.
Where do you find inspiration?
I love to put teams together. I love to watch people be able to work somewhere where they are able to freely use the gifts God’s given them to their fullest. If you put a painter in a room with easels and paint brushes and a canvas [it allows them] to really do their work. I love finding talent and putting them in a place or culture where they can thrive, move quickly, break things––and that’s OK. It’s awe-inspiring to me to watch people do some amazing things in my environment.
Would you describe yourself as an extrovert or introvert?
I love people! I love getting to know people––spending time with people. But I also re-energize myself by being alone. I’d probably call myself an extrovert. I really enjoy being around people, and I get more energy by being around people, certainly. They’re not draining to me. I love getting to know people’s souls––getting to know what they think, how they think. I love to learn about others.
What’s the story behind Red Rover?
It’s really about my co-founders and friends, Larry Foxx and Mike Sheldon. We started Red Rover four years ago because we think that school districts deserve more, fundamentally. That means they deserve a truly integrated HR experience. We wanted to build modern, intuitive software to simplify the lives of education professionals. Which is really coming alongside HR professionals to make their lives easier. That’s where our heart is.
We didn’t want to go and buy a bunch of companies and put them together. We think what serves the market better is building software, and building a team that can serve the customers better. We started Red Rover with the goal of really building best-in-class software solutions for mission-critical tasks in school workforce management.
How would you describe the culture at Red Rover?
We don’t talk about culture at Red Rover because culture is something you can’t change, it’s who you are. I think it’s the aggregate of the hearts of the leaders and all the people on the team; that’s the culture! So, [although] we don’t talk a lot about culture, we hopefully act out core values from our mission, and that’s how we operate and lead.
What’s the leadership style at Red Rover?
We have six core values, and we take them seriously. Certainly, servant leadership, which simply means that, in some ways, the more responsibility or the higher you go … the more people you serve, as opposed to people serving you. We can talk about that all day long, but being able to live and show that in action, that’s who Larry is, who Mike is, and who I am. Larry Foxx lives on four rubber tires in an RV. He’s just a person who doesn’t care about opulence or extra––he cares about people.
Stewardship is another core value. As a steward, you’re watching over or managing something. It’s not yours. We don’t believe we own Red Rover. And what that means for us—Mike, Larry, and I—is we want every person to feel like whatever gifts they have, they can use those to their fullest.
Transparency is another key core value that we have. To be transparent in all we do, and that requires humility because sometimes you make mistakes––many times you do things that are not the right decision. But we want to give people that freedom to make mistakes and learn from them quickly and grow. So being transparent, as much as we possibly can, about where we are, our strategy, our deficiencies, what’s working, what’s not working.
We [also] value life as greater than work. So for us, that means that your identity, my identity, shouldn’t be, ‘Wow, Dani’s a really great CEO at Red Rover!’ That will come and go. What we want people to believe in … is [who they are]. Maybe it’s a husband or a mother. Maybe you’re involved in the community, whether it’s a charity or a church. You should be known for your characteristics. That’s more important than work.
Whether you work at Wendy’s, Amazon, or Red Rover, work will come and go. Whether you like it or not, there will always be work, there has been for 6,000 years, and we just value life more than work.
What’s on the horizon for Red Rover’s future?
Right now, our mission is to build best-in-class software solutions for mission-critical tasks in school workforce management. I’ll break that down: School workforce management is the back-end administration office. So, while we don’t provide content or instruction or direct classroom technology for students, we think we’re tangential to that. What we do is support the professional on that front line that is serving the teachers and students.
Our vision is really to build great, modern, intuitive software––that’s our lane. Building out software that’s organic, and native, meaning we’re probably not looking to acquire companies to make that happen. We’re really looking to build software that can help an HR professional in K12. Building out employee records, building out a self-service portal for a teacher or employee at a school district––that’s the direction we think we can best serve the market.
What does Red Rover’s success look like?
Success means to make the lives of my employees, the team, and the customers better. It might seem simple, but that’s what success looks like to me. It’s not about a dollar amount; it’s not about an exit, a unicorn, or a billion-dollar company. Fundamentally it’s about listening to customers and myopically serving the customer. So success looks like building something they can use every day that makes their lives a whole lot easier.
