Meet the Experts: Stephen Daddio

Stephen Daddio

Sales Consultant

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1. What do you find most unique about working at October Three? 

What stands out most to me is the level of expertise and collaboration within the company. Having the opportunity to work directly with some incredibly talented actuaries and retirement professionals is something you don't find everywhere. October Three takes a very consultative approach, and I appreciate that we're not just offering a product. We're helping solve complex problems and develop creative retirement strategies for businesses and their owners.

2. How did you get into this industry? 

I actually graduated from the University of Arizona with a degree in Classical Piano, so my path into the retirement industry wasn't exactly traditional! I started working in retirement services in 2019 on the defined contribution side of the business. Over time, I became increasingly interested in the more technical aspects of retirement planning, particularly how business owners can use retirement plans for tax efficiency and long-term wealth accumulation. That curiosity ultimately led me to October Three and the world of Cash Balance plans.

3. What's one project or achievement you're particularly proud of? 

One thing I'm particularly proud of is helping expand awareness of Cash Balance plans among financial advisors and business owners. It's rewarding to introduce someone to a strategy they may not have previously considered and show them how it can make a meaningful difference in their financial picture. Being able to take a complex concept, simplify it, and help turn it into an actionable solution is one of my favorite parts of the job.

4. What's one thing you wish others could know about your role? 

There's a lot more education and problem-solving involved than people might expect from a sales role. Every business has a different ownership structure, employee demographic, and financial objective, so there's rarely a one-size-fits-all solution. A significant part of my day involves working alongside financial advisors, CPAs, and our actuaries to understand those unique circumstances and help determine which retirement strategy makes the most sense.

5. What's a book, podcast, or other resource you'd recommend to others, and why? 

I'd recommend How to Win Friends and Influence People by Dale Carnegie. While it's often considered a classic business book, I think its lessons extend well beyond sales. It reinforces the importance of listening, understanding different perspectives, and building genuine relationships. Those skills are valuable in just about any professional or personal setting.

6. What's a skill or hobby you have outside of work? Have you applied any lessons or knowledge from your skills or hobbies in your role at October Three?  

Outside of work, I've played classical piano for most of my life, and I also enjoy staying active through the gym and pickleball. Studying piano taught me a tremendous amount about discipline, preparation, and attention to detail. When you're learning a difficult piece of music, you have to break it into smaller sections, understand how everything fits together, and consistently work toward the finished product. I think that translates surprisingly well to my role at October Three, especially when explaining complex retirement strategies in a way that's easier for advisors and their clients to understand.