top of page
  • Writer's pictureJay Judas

Tier One Interview: Dakota Brizendine

This month, Jay sits down with life insurance industry rising star, Dakota Brizendine, Managing Director and Head of New Org at Commonwealth Financial Group. The pair discuss integrating life insurance into financial planning and wealth management, recruiting, and retaining female talent and what her career has meant for her family.

JAY: For months, I have been hearing from different people in our industry about rising star, Dakota Brizendine from Burlington, Vermont. Even one of my neighbors who is a coworker of yours cornered me in our association’s gym and said, “You really ought to interview Dakota because she is definitely top tier.” You seem to have a significant fan club, Dakota, and as I have come to know you, I can say that it is well-earned.

First, I don’t know if the term ‘rising star’ is accurate because this gives the false impression that you have suddenly become successful. The truth is that you have been working hard and grinding it out in the career system for over ten years and it has paid off. Let’s start by hearing about your firm, Commonwealth Financial Group, and your role on the leadership team.

Dakota Brizendine of Commonwealth Financial Group

DAKOTA: Thank you for including me in the Tier One Interview Series, Jay. I have been looking forward to this. Commonwealth Financial Group is a comprehensive financial planning firm that was first established in the Boston area in 1857 and is still going strong over 165 years later. CFG supports its advisors through each stage in business actualization, from the progression of starting a practice, to building a business that an advisor owns and not just operates. I am the Head of New Org, which means I'm responsible for recruiting and developing new advisors to CFG.

Over my time at the firm, I have become passionate about the transformational growth that can occur in our business. I'm a firm believer that in 10 years our industry will look vastly different to what it did just 10 years go. Because of this, a focus on purpose and culture will be more important than ever for both our clients and our advisors. As a result, a lot of my work is on how we can continue to push the envelope in both of those areas and deliver the best possible experience to our advisors and clients. This can be accomplished by inspiring elite performance and thought leadership throughout the organization and using principles of design to fulfill the business, learning and wellness goals of my division.

JAY: You have one of the most inspirational back stories of anyone I have interviewed for this series. To say that you did not grow up with a silver spoon in your mouth is an understatement. However, as a young adult you made a decision to learn more about how to change your financial circumstances that laid the foundation for where you are today.

Can you tell me about your parents, your upbringing and how you got to where you are today in the life insurance industry?

Dakota Brizendine speaking at LAMP

DAKOTA: I grew up in a pretty challenging financial situation. I often joke that my parents started at negative 50 and managed to get us to zero, which I am incredibly grateful for. That said, we faced constant financial struggles throughout my childhood, which made me acutely aware of the profound impact that financial education can have on one's life. Despite our limited resources, my parents always instilled in me an abundance mindset. That belief helped me understand that, by being focused, I could have a significant impact on my circumstances.

When I turned 18, I made the conscious choice to meet with a financial planner, and it was a pivotal moment in my life. For the first time, I felt empowered and equipped with a clear plan to achieve success. Balancing the responsibilities of being a young parent, I pursued a business education while raising my young children. At the age of 22, I entered the industry by joining Northwestern Mutual. I worked tirelessly, pounding the pavement and leveraging my connections in the small community of Burlington, Vermont, where I am based, to build my practice.

Through a series of transitions, I eventually found myself at MassMutual and finally Commonwealth Financial Group. It was there that I fully embraced the concept of comprehensive financial planning and not just financial planning as a product. Recognizing that my clients' needs extended beyond only life insurance, I focused on providing holistic solutions that addressed all aspects of their financial well-being.

JAY: Today, you have a portfolio of over 500 clients, and this has led you to expanding your team to help you both provide on-going care of these clients, manage the continuing opportunities they bring as well as to foster new relationships. You recruited other female advisors to your team and have a phenomenal 100% retention rate with your recruits. In our industry, we have a shortage of women and people of color in client-facing roles. How do you recruit women and then help ensure their success?

DAKOTA: I believe that leadership involves recognizing the untapped potential in others. When it comes to women in our industry, I make it a point to try to see more in them than they see in themselves. This perspective has been a cornerstone of my strategy for attracting women to our business.

Often, a lack of confidence often holds women back from pursuing careers like ours, as they sometimes question if they have what it takes. I make a concerted effort to communicate my unwavering confidence, conviction, and vision for their future at every opportunity. I also firmly believe that representation plays a pivotal role in attracting individuals to our field.

As a woman in a leadership position, I serve as an example to other women, showing them that success is possible. Personally, as a mother of two, I understand the demands of motherhood can sometimes discourage women from pursuing careers like ours, making them feel like they can't fully commit. However, I genuinely believe that our profession offers an ideal lifestyle where you can have it all. It provides the opportunity to make a profound impact on clients' lives, enjoy autonomy and freedom, and still have the flexibility to be present for important family moments. If I want to attend my kids' basketball game at 3 PM, I have the freedom to do so, all while earning a substantial income. This flexibility and earning potential make our industry particularly appealing to women.

At its core, I view our role as advisors to be one of relationship management. Women naturally excel in these roles and environments and an advisor role leverages their innate strengths. My strategy for recruiting and attracting women to our business is not that complex – it revolves around helping them recognize their potential. By providing this support and encouragement, I help them gain the confidence they need to take the leap into our industry.

JAY: The other day, I was speaking with Mike Moran, CFG’s Head of Brokerage, and he told me that your success in recruiting and retaining women to our industry is something he has not seen before. That is so wonderful to hear, Dakota. Since we are discussing sustainability in terms of your recruiting and teams, I believe this extends to other areas of Commonwealth Financial Group where technology and proper governance play a key role. Fill me in on how these benefit both CFG’s clients and the organization’s team.

DAKOTA: We are trailblazing in an industry that's typically behind the curve. Our team is constantly delivering new ideas, methods, and innovations while building on strong fundamentals from the past to increase value to our advisors and clients. CFG understands that the advisor is our client, too, and the firm has operationally structured resources to provide exceptional client experience. For example, we have an advisory board composed of our top 25 advisors who actively participate in shaping the firm’s future and contribute to their unique perspectives and ideas.

Team from Commonwealth Financial Group

Our commitment to technology and innovation is evident in our refined systems, prospecting management, sales funnels, planning experience and the ways we’ve used technology to streamline our production process. This means less time spent on tedious tasks and more time focused on thought leadership, strategy development, and delivering the best ideas in our field.

As you mentioned, Jay, sustainable growth is a core focus at CFG. We prioritize layered leadership and co-elevation, which is leading without pre-established authority, and this allows us to make long-term network investments and recruit talented individuals who align with our verticals. You made an observation when we spoke a couple of weeks ago that the team at CFG is skilled at storytelling and maintaining a tight point of view. That’s true and it helps us drive sustainable growth and make a meaningful impact in the lives of our clients who, again, are both our advisors and their planning clients.

This would not be possible without longevity in the role of the advisor. Increased retention is another key aspect in sustainable growth. We believe in building strong relationships through shared experiences. CFG invests in the development of our advisors, providing them with resources and opportunities for personal enrichment. This focus on relationship building and advisor development fosters loyalty and creates a positive and fulfilling work environment.

JAY: Most of my interviewees are already where they will end up in terms of their career. You are definitely not. Today, at a relatively young age, you are already on the leadership team of a highly successful career brokerage. What do you think you will achieve as you look ahead?

DAKOTA: I read a book called "Infinite Game" by Simon Sinek, and it helped solidify a framework for something I've always felt. Rather than having a specific end goal, my driving force is expanding my impact. I thrive on finding new ways to grow and increase that impact.

I simply love the game itself and wherever it takes me. As long as I can continue to play, generate ideas, iterate, and take risks, I'll be fulfilled.

My entrepreneurial spirit leads me to being a thought leader, generating visionary ideas, and embracing the risks and rewards that come with them.

JAY: I have to interject with the answer you gave to this question in our pre-interview as you are obviously being modest today. I asked you where you see yourself in your career in the future and you replied with, “I don’t know for sure, but I always see my name at the top of an org chart.” That is the best answer to a question I think I have had to anything asked in a Tier One Interview. Being focused on ‘where’ and not ‘what’ is incredibly astute, and I hope it serves as an example to others in our industry.

Fortunately, you are not working all the time. You and your husband, Owen, have two children, ages 10 and 12, and live on some acreage adjacent to a lake in Vermont. I am going to take a wild guess and imagine that your family is very active in its free time. Am I right?

DAKOTA: You’re absolutely correct! A couple of years ago, we moved to North Hero, Vermont, to a beautiful six-acre property on Lake Champlain. During the summers, we embrace the outdoors and enjoy various activities. Both of my kids are involved in sports, and we spend a lot of time on the lake. We have a boat and love our time on the water. Quality family time is important to me, and I invest in activities that will create lasting memories for my kids. Boating has been a fantastic way for us to spend our summers together.

In the winter, we love going to the mountains for snowboarding, and my hope is that our kids will continue to join us in these adventures well into their adulthood. Last year, instead of a typical vacation, we embarked on a family road trip. We packed up our dog, the two kids, and set off in my husband's off-roading truck, equipped with a rooftop tent. Over the course of two weeks, we drove across the country, exploring South Dakota, Montana, Wyoming, Utah, Colorado, and more. It was an epic journey that created incredible memories for everyone. Now, the kids are eagerly asking when our next adventure will be.

JAY: I am excited to see where your career takes you, Dakota. This has been a treat! Let’s finish the interview with the famous restaurant question. I know your husband is a chef and you and he are major foodies so this should be easy. Without naming a steakhouse or a steak dish, tell me about some spots I should try and what I should order while I am there.

DAKOTA: It’s been a pleasure speaking with you as well and thank you, again, for the opportunity to be featured on Tier One. Let me share two awesome spots, including one from our recent trip to Miami and one from Vermont.

We had an outstanding meal at Contessa in Miami’s Design District. This place has it all: a stunning vibe and incredible food. Don't skip the squash carpaccio—it's delicate and delicious!

If you ever find yourself in Vermont, be sure to seek out Pizzeria IDA in Burlington. It's a hidden gem that offers a unique dining experience. They are unmatched in their quality of ingredients and the exceptional flavors they deliver really set this place apart. Make sure to try their ‘square pie’ it is a must-have.

Dakota Brezendine is a registered representative of and offers securities and investment advisory services through MML Investors Services, LLC. Member SIPC. Supervisory office: 101 Federal Street, Suite 800, Boston, MA 02110 Tel: 617-439-4389.


Since its inception, Life Insurance Strategies Group has solely focused on the individual high net worth life insurance market. We do not sell products. This allows us to offer unbiased, pragmatic advice. Visit us at


bottom of page