Broker Check


Jason Lettenberger, CFBS


(262) 432-7204


Jason Lettenberger, CFBS
Milwaukee, Wisconsin

  • Small Business and Family Financial Representative
  • Massachusetts Mutual Life Insurance Company (MassMutual) 2019 Top of the Council Qualifier (recognizes top 125)
  • MassMutual’s Agents Association Committee Chair

Helping You Make the Appropriate Financial Decisions, Based on What Matters to You.

“Asking hard questions gets people talking about subjects they’ve been avoiding or haven’t even considered, Jason says.”  “It’s an important aspect of helping people arrive at good financial decisions for them, and it’s guided me since the day I started as a financial representative.”

If there is a conventional path to becoming a financial representative, Jason didn’t follow it. He went to technical school to build a working skillset, but discovered what really drove him was his entrepreneurial mindset. “At 23 years old, I shifted gears and partnered in a mortgage company,” Jason recalls, “and over several years helped build a thriving business. Then 2008 hit me with two life-changing events: the premature birth of twins and the biggest mortgage crisis in history.”

That double-dose of reality changed Jason’s family and his business. It also fueled his willingness to outwork anyone. A financial industry veteran recognized Jason’s potential and recruited him. “I’ve been fortunate to have great mentors and supportive family and friends,” he says. “I put pride and joy into what I do, and it’s no secret that I work best with people who like and trust me. That’s how I have built my practice organically, almost entirely by referrals. Everyone on my team is up front with clients about being hands-on. It’s about being transparent.”

One area Jason emphasizes with clients is risk management. “It can take different forms depending on whether a business needs to protect the contributions of key individuals, fund a buy/sell arrangement or develop strategies for business succession to the next generation. It’s not that different with families, and my help comes from a position of experience and understanding. You have kids? So do I. You have a budget? Me, too. But do you have a strategy for retirement, and do you have life insurance? I do. So does my wife. So do my kids! I can create a custom strategy to help you get where you want to be. After the hard work is done, I can only suggest what you should do. My role is to help you make the best decisions for you, based on what matters to you.”

Jason is pictured here with his wife and twin boys. 

Jason Lettenberger is a registered representative of and offers securities through MML Investors Services, LLC. Member SIPC 10401 Innovation Drive, Suite 125, Wauwatosa WI  53226  (414) 615 4850. Lettenberger Financial Group is not an affiliate or subsidiary of MML Investors Services, LLC, or its affiliated companies.

Sharon Staley-Smith

Executive Assistant



What do you enjoy most about the financial services industry?

I truly enjoy helping individuals and families be in control of how they manage the money that they’ve worked so hard to earn.  Developing a personal game plan based upon their own unique goals, allows them to make informed, timely, and adaptive decisions.  Then, when life throws them a “curve ball”, they can continue to sleep at night, knowing that we are navigating the journey proactively and have a strong support team.


What do you think are the best skills that you bring to your job?

I enjoy helping put others at ease and have a love for problem solving. I am committed to helping others feel comfortable and confident, regardless of where they may be in their financial journey.  I have seen too many avoid reaching out for help because they don’t know how to ask, or where to begin. Or, they are embarrassed because they “should have done so many things sooner.” We are not in the business of judging.  We are in the business of helping.


What are you most passionate about professionally?

I’m passionate about empowering others through education, tools and support to accomplish goals beyond their expectations. 


Who are your greatest influences or role models?

I admire anyone who has overcome life’s obstacles and still maintained a positive energy.


What inspires or motivates you?

Any challenge!


What are you happiest doing when you’re not working?

I love being outdoors – walking, hiking, skiing, water sports, or just relaxing.  Being outside – regardless of the weather - is good for the soul.  I also find huge joy in volunteering for my church, charitable organizations and my local community.