Skylight Leadership Spotlight: Chief Operating Officer Trisha Rutherford


April 8, 2021

At Skylight Financial Group, we are fortunate to have incredible leadership to motivate us to be our best selves. We sat down with Chief Operating Officer Trisha Rutherford to better understand her leadership style and how she got to where she is today, in part due to the people and experiences she has encountered throughout her life. 

Tell us a bit about how you started out in your career and the progression of your role at Skylight…

“This is all I have ever known. I started in 2003, while in college, as the front desk receptionist for a MassMutual firm in Cincinnati. My roles quickly escalated into recruiting, new business, client services, and many different operational positions over the years.

I was first introduced to a leadership role in 2006 when I was promoted to Business Manager. Once the Ohio statewide merge of several MassMutual firms under Skylight Financial Group happened in 2017, I moved into the Director of Operations/Human Resources position. This position finally led me to the chief operating officer role when Dan Brennan retired in 2019.

I had many adaptive roles that allowed me to understand different parts of the business. Each position I have had throughout the years continues to help me grow into the leader I am today. I push myself to grow as the firm continues to grow, and I am more than excited about the future.”

What is your favorite part about being COO?

“One of my favorite parts of being COO of Skylight is working with everyone who makes up our firm.  Our team is amazing, always willing to help, and holds the same vision, drive, and passion. If there is an idea or opportunity that presents itself, I know I have an entire team backing me and providing the support needed to make it a reality.”

What is one of the biggest lessons you have learned through your position as a leader?

“I was the oldest growing up, so I was taught to always lead by example. Now I may be younger than some, but I still have an entire team looking at me as the role model. Even though I learned that lesson young, it became more prevalent when I took on a management role. I now know that in order to expect the best of someone, I have to be the best of myself as well.”

Who do you look up to for inspiration when it comes to leadership?

“I look up to my dad when it comes to leadership because we have many similarities in our work and personal life. My dad was also the oldest growing up with high expectations placed on him as a child, personal life, and career. He was always the go-to growing up, and I find myself being that person in my personal and work life as well.

I like being the person someone first thinks of when they are in trouble or need something, just like my dad was for me. Whenever I doubt myself or have fear in my ability, I always think back to “what would dad do?” He is constantly the voice of reason and is steady during times of panic, which he has instilled in me.”

How do you keep the firm motivated despite obstacles?

“One of the key motivators I emphasize at Skylight is making sure people understand that they are surrounded by others who care about who they are as a person, and not just as an associate. We have a strong culture, and we are a part of something bigger than just our jobs. We are family.

Another way I try to motivate people is by pushing them to do their best and have the confidence that I see in them. These conversations can be uncomfortable, but I genuinely believe it helps them create a natural motivation from within them to do things differently.”

What do you think the most important attributes of being a successful leader are?

“I believe the most important attributes of a leader are love, honesty, transparency, and really listening.

First and foremost, I always want people to know I am coming from a place of love. Whether I am having a good or bad conversation with someone, I show love and respect for them and the work that they are doing.

As a leader, you’ll inevitably have to have difficult conversations with people, but it is crucial to stay honest no matter what. If you don’t have trust, you have nothing.

Transparency is critical through the good, the bad, and the ugly as a leader. They need to see you fall short and rise again. They need to see your good days and your bad days to know you are human too. They need to watch you process situations, live by example, and celebrate the wins.  

Last but not least, never forget to listen—to your people, your industry, and yourself. You never will know where you are needed if you do not listen to what people are or aren’t saying.”  

In what ways do you strive to continually develop as a leader?

“I am constantly developing as a leader because I continue to do self-reflections by debriefing my day and reaching out for input from the team and people outside of the industry. I also strongly believe in pushing myself to constantly learn something new—I always have higher expectations for myself than anyone else in the room.

I am also continuously trying to work on my own mindset so my team can get the best of me. This can be difficult because I am not only the COO, but a wife, mom, daughter, and much more! As a leader, I have to be balanced in all of those aspects because it will reflect on my role if I lack in one.”

Who were your most influential mentors leading up to you becoming COO?

“I have to give credit where credit is due and say, Dan Brennan. He told me hard things that no one else would say that have molded me into who I am and who I want to be. I always come out of a conversation with him with a lesson learned, even when I didn’t want to admit it. Even though the way we lead may differ, the reasons for what we do are the same. He believed in me more than I believed in myself through the transition process.”

Thanks for sharing, Trisha!