Winners of Wealthtech: Angela Pecoraro


This is the eighth article in our Winners of WealthTech series, where I interview people who have made their mark in wealth management technology with a track record of innovation and success.

My previous interviews have been wildly popular, so there will be no stopping this series in 2018! Check out the previous interviews with Eric Clarke, CEO of Orion AdvisorBill Capuzzi, CEO of Apex ClearingLori Hardwick, President of Advisor Innovation LabsCheryl Nash, President of Fiserv Investment ServicesStuart DePina, President of Envestnet | TamaracBill Crager, President of Envestnet and Aaron Klein, CEO of Riskalyze.

I am pleased to present this interview with the CEO of financial technology firm Advicent, Angela Pecoraro.  Advicent, based in Wisconsin, promoted Pecoraro to CEO last April from her previous position as president and chief operating officer.

In her role as company president, Pecoraro was responsible for spearheading global strategy for Advicent’s client engagement and client experience programs. Advicent is primarily known for their financial planning software, NaviPlan, which had been focused on the HNW/UHNW segment, but has since been expanded to support clients with a wide variety of planning needs.

Pecoraro is the first woman to hold the CEO post in the company’s history.  The firm changed its name from Zywave Financial Solutions to Advicent in 2014.

Could you give me an overview of what brought you to Advicent?

I have celebrated about 16 years in financial services technology. The company that I worked for purchased EISI several years ago. I had been with that business for a long time and I had started to expand my role upon that acquisition to serve additional areas in that business to include what is known today as Advicent.

What caused you to take this role as opposed to going to another company?

I have grown up with technology, I started at that company as a front-line customer support representative as well as a product trainer and I have an insatiable interest in business and learning. Throughout my career I have taken any and all opportunities to learn; the business, the technology, the customer, and the market. I find it to be very interesting, very fun and fulfilling. That allowed me the opportunity  to serve over different areas of management and grow in my responsibilities as the company continued to grow. As I became more advanced in my career and more senior in my role, I continued to take on those responsibilities and serve the company at a wider and higher level, transitioning more into a strategic leadership position.

A few years ago I was identified as a succession plan for Advicent’s CEO, and took an opportunity at a senior executive level to span many different areas of the business. Prior to becoming the CEO, I served as the chief operating officer, and almost every year or 18 months the definition of that role evolved. Wherever the business needed leadership, or transformation, or a new lens, I had the opportunity to lead those functions. Over that four year period I served as our leader over project management, sales, marketing, and professional services support. It evolved depending on the needs of the business. In April 2017, it made sense for me to achieve the objective that was set forth for me in the career planning model that we had, and I was named CEO.

What advice do you have for COO’s looking to get into a CEO role?

I think it goes back to the learning aspect. No matter what role you’re serving in an organization or what your title is, there is still more to learn. Learning and growing is continuous, especially in the Fintech or Wealthtech space. It is very dynamic right now. There are so many different technology providers, and so much happening within the markets that we serve that there should be no shortage of opportunity to learn and grow. The more value you can provide to the organization by having a broad spectrum of knowledge, the better suited you are to serve the business as a whole. Every business is different; the size, the focus of the chief operating officer, it varies. I would encourage anyone in a senior position to define what those roles need to be, recommend how they should evolve that role to the business, not via path of participant in the role. Oftentimes I dismiss my title altogether and I think more about the business. I often joke that you can call me whatever you want, but this is where we’re going to provide the most value to the business.

It seems that each generation changes jobs more quickly, why is it that you’ve stayed at the same company for so long?

Two things; the business today is not the business that I started with 16 years ago, by way of product, leadership, ownership, you name it. The only similarity is it resides in the same city. The second thing is, I didn’t look at it as a career ladder that I was climbing, it was more of a jungle gym with different levels of complexity, areas that are interesting, and they all bring the whole company together. I’ve had lateral moves, upward mobility as well, but I never looked at it that way. I was trying to see the entire business and play on the entire jungle gym.

When I have career pathing discussions, or have the privilege to serve as a mentor, it’s one of the talk tracks that I use a lot. A lot of people think that if they’re doing a good job in their current role, and they don’t get a promotion, that it’s somewhat of a failure. If instead they move over to the side, and learn more about the business, they’re actually going to become more valuable than a senior director or a VP in their current discipline. It’s something interesting they need to think about, and really chart a course for themselves. Everyone’s path on that jungle gym can be so different, but so rewarding and so impactful to the business. You can have your expertise, but the goal would be to build multiple layers of expertise over multiple disciplines so that you can understand the complexity of the business and make good business decisions that will inevitably touch multiple areas of the business. Understanding those areas has served me quite well, and I’m not the expert in all of the areas that I’ve led, but fundamentally there are things that are transferable no matter what department you’re leading.

Could you give me an example?

The most basic example is leading a high-performing team. You need to chart a path, have a vision of where you’re going, set clear objectives on how you’re going to get there. Align your team and give them the tools and support that they need, hire great people. Those are all the elements and foundational groundwork that needs to be laid. The semantics and the details of what makes a great support team will play themselves out as you build that team. The basics are there and that’s necessary no matter what area of the business you’re in.

You mentioned that you’ve been in the same city all this time, did that play a part in your decision?

Absolutely. I’ve been very fortunate to have built a nice career and be happy with the work that I do. I was able to stay near my family, have a support system, and raise children in an environment that I’m comfortable with. It has also been an evolution of multiple companies over time, so I celebrate that I have been fortunate to work for a very entrepreneurial, incubator startup company, all the way through to a global firm that serves international organizations at the very highest level, and everything in between. Not the type of thing you hear a lot about in the Midwest, particularly not in Milwaukee.

Milwaukee, Wisconsin is a smaller market, we’re not known for technology — the leaders in this area are working hard to change that perception — but we’re definitely a smaller market. We’re not Silicon Valley, we’re not New York City. I’m proud of the fact that we’ve been able to build a couple of strong technology companies in this area in a market that people don’t know a lot about.

In your personal life, what has become most important to you over the past few years?

My family is always the most important. My health and everyone’s health around me. I’ve been privileged to have three beautiful, healthy children and see them grow up a bit, and I’m excited to see them continue to grow and flourish. I married my highschool sweetheart, so we’ve been able to create a wonderful life for ourselves and have great careers. As I mentioned both of us were born and raised in the Milwaukee area so we’ve had the privilege of being near all of our family members and to raise our children in an environment that allows us to be close to them and have that support.

Is there anything that has become less important to you over the past few years?

Not caring as much about what people think, having more confidence, which I think comes with maturity and experience. I want to make the right decision and there may be naysayers, but the right decision is the right decision. I also care less when people say something can’t be done. At work we often talk about what’s possible. Not everything is possible, but there usually is something that we can do.

When you say you care less about things that are impossible, is that in your personal life or in business?

Both, I think that’s just how I approach things in all aspects of my life. We’re going to be challenged in our lives in a number of different ways but high expectations for ourselves and very aggressive goals both in business and in life is important. Progress is key, having a vision is key, and also understanding what’s acceptable. Making tradeoffs is okay, but understanding what success looks like, or what happiness truly is; if you get close to that, you’re in good shape.

Having started at this firm in 2002 and working your way up to CEO, how do you stay motivated?

I am motivated by surrounding myself with people who are going to challenge the status quo, who are willing to put in the extra effort. Those who are willing to try new things, and look at new ways of conducting business.

Building a company that is very team-oriented, collaborative, and trusting, that’s my number one motivator. The second one is the markets that we serve. I guarantee you that Advicent today will not look the same as Advicent tomorrow. We are going to evolve and transform this business based on the needs of our market, and as you’re well aware, the needs of our market are very intense, dynamic, and exciting. There’s a lot of great macro-economic things happening, new technology being introduced, clients, you name it, it’s all going on at the same time. That’s a dynamic that I thrive in and that I welcome. If we were in an environment that was not growing, I would not be happy. But there’s no shortage of opportunity in this business, and that’s very motivating to me.

Is there something that you believe that other people might say is crazy?

There are a few principles that have come up throughout my career and have guided me. The first is that you won’t get anything unless you ask for it. Whether that is a new relationship with a new client, a promotion, a favor, feedback, you’re not going to get it unless you ask for it.

Another principle that I live by is to be careful how you treat people on the way up the corporate ladder because you will see them as you come down that ladder. Understanding where real work gets done, respecting the value that everyone in the organization provides, and respecting that everyone has earned their seat at the table.

The third, which I don’t think is anything crazy, is telling it like it is. In my experience, you can fall into a trap of communicating at a very surface level — not being very honest, not being very direct. Business is too dynamic for that. We’re all trying to be successful, there is not time to beat around the bush. It is important that the industry and the people you’re dealing with know where you stand, what you’re trying to do with your business, what you’re trying to do with your life, so that you have a right to ask them the same questions. That’s how I approach business and I think it has helped me establish stronger relationships with clients and people that I work with. Everyone knows where I stand, and I expect the same type of feedback coming back to me.

How do you determine if someone would be a good fit at Advicent?

We definitely want a diverse group of people. Diversity in thinking, background, talent, capability, personality, tenure, even in teams and groups. We also want people who think about what is possible, who see a roadblock as an opportunity, and are motivated by working through that. We want people who trust one another. We spend so much time with our coworkers, they become like our second family. If we can’t trust the people we work with, we’re not going to get a lot of work done. Those who are willing to admit their faults, provide feedback to their coworkers, and leave their title at the door.

How do you measure if someone is trusting before you hire them?

We participate in the standard interviewing process we make sure they are open to providing and receiving feedback. Someone that is open to having a dynamic work environment and who understands that the world is changing rapidly and we are a software company. Therefore we must remain very agile and dynamic. Their job description today may evolve tomorrow, and “tomorrow” may literally mean tomorrow. Someone who is easygoing and trusts in the direction that we’re headed in, and moves towards that direction. There are some interview questions, some interactions that we leverage to registers that, and look at culture fit as well. They can learn anything, but if they’re not a culture fit that puts us behind a little bit.

Are there certain interview questions you have that determine if the candidate would fit into your culture?

We do a lot of situational interviewing, and request the participant to present a story or an example to demonstrate how they would navigate that situation. We also want them to draw parallels to roles they’ve had in the past and how they might leverage those skills. As I work with leaders I talk a lot about is although you might be interviewing someone for a position today, you should really be interviewing them for the position they will have in their second or third role in the business. That’s when they’ll start making a career impact for themselves and for the business. We’ve changed so much and we’re still growing, so we need the type of person who may start as a tech support person, evolve to a business analyst, or maybe a quality assurance analyst. Someone who can move throughout the organization and leverage their knowledge of the market, the customer and product and apply it in a number of capacities. Not everyone supports that, some people have a good sense of where they want to be in an organization, and that’s okay but we need to know that. We need to create a culture of people who by and large want to move throughout the organization and create value for themselves and for the business.

What is your morning routine?

It has evolved over time, and once you have children you are required to become a morning person, so I am. I wake up very early, around 4:30 and I hit the gym. That is the only 30-45 minutes of my day that are for me. Then I go home, get dressed, get all the kids including a neighbor onto their respective school buses. I try to stop for breakfast on my way to the office, then hit the ground running at about 8:30. I also check my email and my calendar while I’m on the treadmill to make sure I’m prepared as I walk in the office.

Who do you think of when you hear the word “successful”?

I know in your previous articles people have identified certain individuals, but I see what success looks like to different people and it has helped me define what it means to me. Success comes in a variety of different shapes and sizes, titles, accomplishments, and I’ve used that to inform myself. I know that people define success differently, whether it’s by work-life balance, or a particular title, more time with their kids, early retirement, and so on. Those are the type of things I think about when I think of successful people.

For instance, I said I married my high school sweetheart. He began a career as a police officer, as an intern, at the age of 19. He has had a successful career of over 25 years and is able to retire at an early age. He didn’t climb the corporate ladder, he remained a front line police officer. Yet he remained safe, healthy, and achieved that 25 years which is coming up soon for him. He can have a choice, and have the things he wants in life. That, to me, is success. I can give you a number of examples both professionally and personally, but success to me comes from people’s happiness. Whatever happiness is to them, defines their success.

What bad advice do you hear most often?

When a mentor or a manager is having a conversation about someone’s career and is pigeon-holing them into a path that may be logical, but is not exploring the idea that there are alternatives. Someone in a particular role or expertise might make quite the dark horse candidate for a role in another area of the business. Not providing them that advice is a detriment to that individual and to the business, as is making assumptions for them.

I like to take the time to make changes, for example, when a position is recently vacated, or two teams are merging. I’d rather stop and consider the next step than blindly proceed the way we always have. I think the best leaders slow down, think about what works well, and apply the best of everything.

Is there a behavior or belief you have recently adopted or changed?

I haven’t changed anything, but there is something I’ve elevated more than I ever expected. As the CEO, dealing with transparency and making sure that everyone in the company understood where we were and where we were going. Something that I have changed is my availability, maintaining good communication with the entire team on a regular basis. Staying accessible and varying the ways I interact with different teams across the business to build trust and a culture that I expect of everyone and that I also demonstrate. Demonstrating to the rest of the leadership team that this is the expectation, that we’re going all in together and we’re not looking back. Some people opted out, but that is one of the elevated beliefs that I put in place.

What would your close friends say you are exceptionally good at?

I hope they would say that I’m fair and pragmatic. That I look at all sides of an issue and weigh the pros and cons to make a fair business decision. They would also say that I’m a pretty intense businessperson. The inner workings of a business, the leverages we can pull if necessary, behind the scenes things. I’m a data person. It’s a necessary evil that we need to rely on, and make sure we understand the business from a numbers perspective.

Do you have a favorite failure that you learned the most from?

My favorite failures come by way of interactions. I tend to learn the most when I’m interacting with people, if I had ineffective communication, or I set the wrong tone. Whether it’s clients or team members, I learn the most by interacting with them. Of course over the last 16 years we’ve introduced new products to the market, new pricing, which may or may not have worked. People say to “fail fast”, and learn from your mistakes as quickly as possible. A failure is a learning opportunity so long as you don’t repeat it. You have to let the people around you fail too. If you know the answer and it’s a low-risk situation, you have to let them roll with it and grow from it. Let them feel a little bit of pain, because nothing you tell them can be better than learning from a mistake they made. Biting my tongue is hard sometimes, but it’s important.

Is there a book that you’ve gifted most often?

I don’t typically gift books, but I do refer to them. One book that I refer to quite often is a bit dated but has a framework that has served both myself and the company well is The Heart of Change by Dan Cohen. It’s a great framework for people to use around a transformation they might be embarking on and really leading organizational change. Particularly when the changed leader doesn’t have the positional authority to make that change happen but has to leverage influence. Thinking what type of business you want to be running tomorrow rather than at one point in time.

Do you have a favorite app that makes you more efficient?

Yes, primarily in my personal life. We use a family calendar tool so everyone can log in and schedule their different activities, called Cozi. I tend to use a lot of sport apps for all the different sports my kids are in. One in particular is called TeamSnap, and I get to watch both my boys play baseball. I can watch the game live and see when one of my sons is up to bat, if he gets an out, all of those things. When I travel for business it pains me to be missing their games but this is a nice bridge for that gap. I can talk to my children about their performance on the team, and celebrate their wins when I’m away.

Is there anyone who was your biggest influence growing up?

From a business perspective it would be my father. He managed a car dealership for over 30 years through the 70s and 80s when it was a tough business to support a family with before special interest rates. He built that business based on trust, in an industry where there isn’t a lot of trust, in a small neighborhood in Milwaukee. He had such a following, and sold cars to people for multiple generations. I had the privilege of working alongside him early in my career, and I learned a lot about people. No matter who you work for, it always boils down to the trusting relationship you have with your customers. That was a lot of fun, I learned a lot of healthy negotiation skills from him. It was long hours but it was fun. If you’re too serious too often you’ll burn out.

Is there a quote that you live by that might be different than your principles?

I don’t know who this quote is from but I use it a lot when thinking about my own approach; “Leaders make people believe in them, but great leaders make people believe in themselves”. It’s stuck with me, maybe from college or high school, and I try to think about it when working with people. It’s never, ever, ever about the leader. It’s about the rest of the team.

Looking back on your career, is there a message you would send yourself at 25, at 35, and would the message be different?

I would tell my 25 year old self to have more fun, I was a bit too serious. I should have traveled more, I was buried in my job trying to be an adult. At 35 I should have had a lot more confidence. But overall I would tell myself, “You got this, don’t overthink it. There’s nothing you can’t learn so go after it”. Don’t be reckless, but what’s the worst thing that could happen? A lot of positions over the years have been changed or eliminated, but there’s always a place for a top performer.

Finally, do you have a favorite movie or documentary?

“A Few Good Men”, that’s my favorite movie.



The Wealth Tech Today blog is published by Craig Iskowitz, founder and CEO of Ezra Group, a boutique consulting firm that caters to banks, broker-dealers, RIA’s, asset managers and the leading vendors in the surrounding #fintech space. He can be reached at