Sheryl O’Connor
CEO and Co-founder, WealthConductor
Age: 63
Industry experience: 30 years
Sheryl O’Connor got her start with financial technology back in the 1990s. A schoolteacher at the time, O’Connor decided to apply to MassMutual’s bootcamp to learn computer programming for Y2K projects. After spending time at MassMutual and The Hartford, O’Connor co-founded an asset management firm with her husband in 2006. Working with financial advisers and their clients, O’Connor saw that the industry needed a fintech platform to help with retirement planning.
A Denver-based adviser, Phil Lubinski, approached O’Connor about creating a platform focused on retirement income. Together they built IncomeConductor and began offering it in 2017 through the fintech firm, WealthConductor, co-founded by Lubinski, O’Connor and her son, Tom.
The Hartford-based fintech recently launched its first strategic advisory board, bringing on industry executives who have worked at Bank of New York Mellon, JPMorgan Chase and other financial firms.
Q: Why did you create IncomeConductor?
A: For the past few decades, the financial services industry has really been focused on helping individuals save and invest their money, both in 401(k) plans and in individual accounts. But we saw, with 10,000 baby boomers reaching 65 every single day just in the U.S., that there was going to be a huge demand for retirement income planning services and the technology to support it. Most technology in the marketplace today is based on a systematic withdrawal approach. That worked for our parents and grandparents really well. But today’s baby boomers are living much longer, and they don’t have pensions, so they’re relying on their savings as their sole source of income beyond Social Security.
We use a very different approach called time segmentation. It was first developed by my partner, Phil Lubinski. It gives individuals a customized, written plan that gives them the assurance that they won’t run out of money before they die. That plan can then be managed across large 30-, 40-, even 50-year retirement horizons to ensure that adjustments can be made, and they can continue their income stream regardless of what happens with the market or taxes or changes to their individual spending needs.
Q: Can community banks and credit unions use the platform?
A: Absolutely. Right now, we service mostly the independent broker-dealer space and the [registered investment adviser]. We work with LPL Financial Services, and they provide advisory services through banks and credit unions. Using IncomeConductor in a strategy that clients really love gives them a competitive edge, and it makes it very easy for them to work with a very diverse population. Typically, the tools advisers use for financial planning right now are very complex and very cumbersome. With IncomeConductor, the adviser and the client can create the plan together dynamically. It’s a very intuitive, easy-to-use software, and the client can see the impact of different assumptions immediately using the software in the meeting with the adviser.
The other thing about this strategy that really fits well with the bank and credit union population is that the strategy works beautifully with the mass-affluent client. These are people who have saved anywhere from $100,000 through maybe $1.5 million to $2 million. That really represents the bulk of not only the baby boomers as a group but also the typical clientele for the bank or the credit union advisory customer. It serves a wide swath of that population, not just the typical high net-worth client.
Q: Why did you decide to launch an advisory board?
A: All the surveys show that having mentorship and advisory support can really help a company grow much more quickly. Depending on a company’s size, their maturity and how far along they are in their growth cycle, advisory boards can have different goals. Since our company is only three years old, our advisory board has two goals. The first is to help us develop the business, and they do that through introducing us to executive-level decision-makers and larger adviser groups that could become customers. Then the second thing is to help us raise capital to accelerate our growth.
We’ve been really fortunate that we’ve been approached by these folks rather than us going out and looking for them, because they think what we’re doing is so needed in the world right now, and they love the software and the team. Besides that, they come from some of the top firms in the industry: Bank of New York Mellon, JPMorgan, Nationwide, 3D Asset Management.
The nice part is that they all bring a lot of experience, but they all bring different skill sets. Some of them worked in sales and marketing, so they’re very astute at the sales and marketing strategies. Some of them worked in technology, some of them were C-level, so they know from an infrastructure standpoint how the various entities of financial services work together.
Q: What are your goals for IncomeConductor?
A: We’d like to be the premiere and preferred retirement income technology in the market. We are specializing only in retirement distribution, so it is a real niche specialty. We’ve decided to take that specialty and go deep rather than go wide and provide a vast number of services on both the accumulation and the distribution side.
Our software is also unique in that it can be applied to different countries and different retirement structures. We do have advisers using it in Canada and Australia. Our plans are to move beyond those countries into Europe and South America as well.
Q: What has been your experience as a woman CEO of a fintech?
A: It’s one of those areas that women have not had a huge presence in. And financial services as a whole – you don’t see a whole lot of women leaders on boards or in C-suites in financial services. But that’s changing. I was lucky enough to be involved with a global competition called “Female Founders in Tech,” and it’s put on by a group down in New York called Quesnay. They had female founders like myself that were leading or had founded financial technology companies all around the world apply for this. And I won, which was great, but what was really nice to see was that there was so much support.
There’s a span of women who are stepping up and saying, “I can do this. I have a great idea. I can put together a team. I can build this technology, and I can market it and do some good out there in the world.” And we’re getting recognition and support from very, very large firms. It’s going to take a while until you see 50 percent of a board as female members, but we’re getting there.
O’Connor’s Five Favorite Travel Destinations
- The Maldives
- Fiji
- Australia
- Egypt
- Spain





