Women Of The C-Suite: “Harnessing different mindsets into collaborative efforts is the true challenge of an effective leader” With Jennifer M. Wolfsberg

“Gathering different perspectives and harnessing unique mindsets into collaborative efforts is the true challenge of an effective leader…

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“Gathering different perspectives and harnessing unique mindsets into collaborative efforts is the true challenge of an effective leader. Although it takes practice and careful feedback it creates the true power of a team. Finding that special chemistry with a creative team can launch strategies in exciting and productive directions. In my opinion, cultivating this atmosphere of collaboration is the responsibility of any leader, not just female leaders. The embrace of change and flexibility is paramount so that the firm can growth and not just in revenue terms but your company nor its people should be stagnant or look the same in five years.”

I had the pleasure to interview Jennifer M. Wolfsberg, Managing Principal at Centerpoint Advisors, LLC. With over 19 years of wealth management experience Jennifer serves as Managing Principal of Centerpoint and leads the team’s communications with clients and their families. She manages the overall client and family planning needs and thrives on the synergistic coordination and collaboration of our team with our client’s other advisors and professionals, including but not limited to their CPAs, estate, divorce and corporate attorneys, and insurance professionals. Her macro view for big picture needs solidifies the complete vision that keeps high net worth families on track to achieve their goals. Jennifer founded Centerpoint Advisors, LLC alongside Richard Greene in 2006.

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I have always been intrigued by finance since I was a young teenager. I started my by journey at an early age by learning about simplistic banking and savings strategies and interest rates that allowed me to squirrel away savings from working in restaurants and later bartending throughout high school and college. I was fiercely independent and loathed the thought of relying on others for support. The true catalyst for this started at the age of fourteen and, was sparked actually primarily out of need rather than interest.

I am the youngest of four children and the only daughter in our family. I have three amazing older brothers who have always been, and continue to be, a supportive and influential in my life. Next to my husband of course, they have always been my greatest and loudest cheerleaders. There is an age differential among us ranging from eleven to seven years older and therefore, at the age of fourteen my parents decided to fulfill their long-standing dream by selling our family home and build a new home on Cape Cod. Now that the boys were out of the house and independent, the ease of relocating and uprooting me to a new high school and town seemed to them an easy transition. Perhaps not surprisingly, I did not feel the same way and I decided to make a stand. After a very difficult year commuting long distances and staying with numerous families and friends, I was fortunate enough to have my best friend’s family offer to allow me to live with them during the school week to finish my high school career with my friends, teachers, and athletic teams. I would then go to Cape Cod on the weekends to be with my parents; arriving late on Friday nights and leaving early Monday mornings to arrive on time for school. This would continue for three years until I graduated.

I attended a public high school in which I had wonderful friends and for the most part fantastically supportive educators. In fact, to this day I remain close with one teacher who served as a mentor and support system. My father and all my brothers also attended this school so there was a fun family history. A good history. As you can imagine though, I was the talk of the town for quite a while as people thought I was crazy to go through so much work to stay in our sleepy, country town. Remember this all transpired before “School Choice” programs existed and therefore, any nonresident of the town had to pay tuition to go to the school even though it was a public school. This tuition equated to a real estate tax formula. My parents were not able, nor willing to pay for the $400 per month payment and put the onus on me for the tuition. I could either find a way to make the money to pay for my tuition or move to the high school on Cape Cod. I was accountable for my choice and I thrived on the challenge. I chose to find a way to pay for my education and found a waitressing job on the weekends on Cape Cod at a small, family owned breakfast restaurant. It was one of the best, the busiest, and most chaotic places to work. It was also my entryway to financial independence. At a young age I was earning more than enough to cover my school tuition by working every Saturday and Sunday on Cape Cod to cover my tuition. While I felt the freedom of some degree of financial independence from my parents, I had to quickly learn what a checkbook was, how money orders worked, and what interest rates even were. The administrators waited every month for that check to be hand delivered and over time it was evident some of them disagreed with the decision I made. It was far too out of the box for such a small town.

To make the next step towards independence I wanted to make sure I wasn’t relying on anyone else to sign my tuition checks, so I found a lovely woman at the local savings bank who took me under her wing to helped me establish my first accounts. She helped me understand checking and saving accounts, check registers and even helped me roll coins from my waitressing tips. (For those of you of a certain age… you may remember those horrible paper wrappers before Coinstar existed!).

I know my decision was out of the ordinary, and perhaps my childhood was non-traditional, especially for that time period. I had to forgo many experiences that others had on the weekends while I worked, such as football games, the last minute get-togethers, and weekend sports practices. When Monday mornings rolled around, I would hear about the fun events or teenage drama that transpired in town over the weekend, but I never once felt like I was missing out. I never once felt bad for myself knowing that my situation was out of the norm since I was being accountable and responsible for the decision I made. And to be honest, I was probably too stubborn to give up or give in. Looking back, what I didn’t realize was how my early teenage years and my early 20’s would shape my perspective and discipline going forward in life. My financial foundation had been forged, and it was created by the many life lessons along the way that I was unknowingly navigating.

I experienced let’s just say less than positive adult support and judgement at times from other parents in town and some school administrators, all the while working in a very difficult restaurant environment that was family owned and operated. Looking back, it was a lot of stress for a teenager to handle. I was one of the very few non-family employees that made it past a one-year anniversary without quitting or being fired. The intense family dynamic was often explosive and toxic at times and you never knew from week to week what type of environment you were walking into. However, through it all, they were loyal to me and I to them for many years. The patrons of the restaurant were loyal and supportive. It paid my bills and provided me financial freedom that I desperately needed. This experience unknowingly exposed me to the issues and challenges unique to a family business. I now recognize a lot of these same challenges many years later as a consultant to an array of businesses and owners across several diverse industries. It is funny the level of stress you can handle when in a clouded blend of ignorance and stubbornness.

My unique path provided me so much more in experiences than simply a good work ethic and proficiency with goal setting. Although the deepest life lessons are only recognized years later in retrospect, I think my first job and the pressure to pay a monthly bill taught me about long-term planning, budgeting, and the value of money well spent. I realized that I was willing to give a lot for something that was important to me, and I had to tune out opinions from others that would only serve to take me off course. It taught me to seek out people who were willing to help and teach me, to listen and direct me. I was jumping between two cities weekly and between school and the restaurant I was granted the opportunity to meet so many wonderful people. Working as a waitress taught me interpersonal skills and exposed me to so many personalities and social situations. I came to focus intently on customer service, and I realized the value of community. When you find those very few who extend a helping hand, you are inspired to show-up. You show up each and every time. You show up on time, with a smile on your face and with a contagious, positive energy to learn and absorb anything and everything they are willing to share.

I am so thankful and grateful for that experience and it set me on my financial path of today. I know it is part of why I love helping those in need at any age who struggle with financial education and navigating our industry. I especially love helping those that seek assistance with a passion for improvement and knowledge.

Can you share the most interesting story that happened to you since you began leading your company?

While there are wonderful success stories to share about the families we have been fortunate to work with and help over the years I would say from a leadership perspective one of the key lessons learned for me was the need to protect your team. With any business you have an ideal client profile and there are times that the service needs of a client may begin to shift outside of your nucleus or core strength.

The unwavering dedication of your team may cause them to continue to attempt to deliver their very best, yet be met with a less than positive response. The reality is over time people may no longer be a fit for your firm and honestly you for them as well. I think one of my greatest lessons is to protect the time, emotion and mental energy of your team. Without communication between you and your team, a client new or even longstanding can risk the energy, productivity and focus or your most valuable asset- your team. We understand we are not a fit for every family and only want what is best for them however, it is a leader’s job to intercept, redirect and handle these decisions.

What you can learn from this is that when a family is interviewing you for your services and expertise you as well should be doing the very same to ensure philosophy and personality alignment. We want to ensure their expectations are met and exceeded, yet we need to also confirm their expectations of us as well. Thoughts surrounding service needs and market returns should be discussed to ensure you are on the same page so as to not cause frustration for either party.

Early on in your career you are trying to be everything to everyone, employees, colleagues and clients however, you need to stay true to is your value system overall and understand the goals you are set out to achieve. You cannot do that while trying to appease the masses.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I first transitioned from trading to directly working for the partners at the Buffalo firm I was eager to show my level of productivity and energy. Our portfolio management team was a team of five to six people and I was learning all the client relationships and service needs while still assisting as the liaison in trading and portfolio management.

I would work late, study and do anything I could to help Katherine and the team. I would often pop into her office to provide her with unsolicited updates on my work, client contact, projects and status of next steps. Some of this would also result in me running into difficulties and stopping points that I would need guidance on as I was trying to move forward.

I remember clearly the day that she pulled me into her office and while she was supportive to a point, she wanted to instill in me words to live by if I was going to work with her. I thought for sure I was getting fired of course.

These quotes to this day ring true and I laugh now at my lack of experience and perspective given where I was in my career at that time, understandably so. I also understood over time as I began to balance client needs with leading a team how basic, yet necessary these simple themes were and lessons I learned just from that one, poignant meeting. There are always exceptions to the rule however, it taught me to be more independent and strategic and that yes I may make mistakes but it is how we learn and with research and strong overview for my actions and decision making she would support me but it had best be well thought out.

Consolidate your questions!” Unless I could not move forward on a project without her assistance everything must be consolidated, organized and addressed within minutes of stepping into her office. The pop-in or quick question was not welcomed.

“Don’t come to me with a problem unless you have a solution.”

“Remember with more money and title comes greater responsibility and accountability”

What do you think makes your company stand out? Can you share a story?

Customization of planning, facilitating collaboration with external advisors, follow-up, and determined, unwavering problem solving.

Are you working on any exciting new projects now? How do you think that will help people?


We’re working on a project right now to teach financial literacy to children between the ages of 12–17 through one-on-one meetings, videos, and school presentations. Financial literacy has been removed from so many schools and it is really a shame. Tuitions are going up, and financial education is going down, setting even the brightest students up for potential failure. They may be destined to carry heavy student debt that they don’t understand. Few children these days are even exposed to cash transactions, so they are completely unaware of spending trade-offs. I’m excited about this project. It’s a big undertaking but I know that it can have a big impact in the long run by providing these children the tools to make smarter decisions. With increasing frequency, we are asked by our clients to meet with their children to engage them more in understanding the fundamentals, from day-to-day financial experiences to the larger investment landscape. Our most recent meeting was even with a 10-year-old whose favorite show is Shark Tank. He wanted to learn more about investing and the difference between private and public equity. It was a fantastic meeting.


On an internal strategic level we are working on multi-level mentorship across team members and engagement for broader team participation. We have been hiring over the last two years and our strategic vision for helping clients and their families relies on the inspiration, education and advancement of our people. Each team member has something to share with one another which will not only enhance and advance their own career path but will also have a positive impact on the client experience.

What advice would you give to other female leaders to help their team to thrive?

Transitioning from the mind-set of being task-oriented to vision creator is truly one of my greatest personal challenges. It is important that over time you begin to shift your focus from task-oriented, day to day work to designing strategy and creating longer-term vision for your team. Allow THEM to create the process. Your hope is that you hired the right talented, curious and innovative people that have the skills and desire to create. A well prepared and motivated team will want you to step back after you have set the goals to allow them to formulate the plan to achieve those objectives. Some leaders, myself included, have to consciously work to avoid getting mired in the details. This is the eternal struggle that a leader has. The balance of trusting in the small steps in order to look up and navigate the path towards the future. You are constantly trying to maintain the quality of work that brought you the success that you achieved to this point however; micromanaging is not an adaptable structure that supports efficient scalability of a company. Above all, giving team members autonomy (with accountability) fosters team work and greater employee engagement. At the same time, it can also be the defining moment where you can identify your weakest areas that need to be addressed.

I even use this same philosophy when talking with clients about the unrealistic nature of trying to continue to manage their family wealth, investment, finances, tax and estate needs the same way they have 20, 10 or even 2 years ago. It becomes impossible to work alone as the complexities of their daily lives grow with everchanging demands, including career development, family responsibilities and often elder care issues. Clients do best when they acknowledge their comprehensive family needs, and seek wide-ranging professional support, counsel and assistance.

What advice would you give to other female leaders about the best way to manage a large team?

Give team members that autonomy and confidence to tackle problems and inefficiency head on. Inspire individuals to identify problems and engage with other team members to generate unique solutions for frustrating topics that may affects multiple people or departments. When a service, work flow or procedure is constantly delivering a negative result we often find ourselves in a frustrating merry-go-round if it is not disruptive enough to halt the day-to-day operations. Rather than tear down the process and fix it, we may continue to tolerate it and work around it. This is a mistake that we need to be on guard for. It can be drain on efficiency, and a source of frustration or errors in the long term. Individuals must be empowered to make changes for the long term benefit of the team, and confident that their efforts will be recognized and supported.

The challenge is to align complementary yet differing personalities for true collaboration. You want to cultivate an atmosphere that does not silence or mute any thought or possible solution Sometimes it is the person with the least experience on a topic that provides a fresh perspective.

Gathering different perspectives and harnessing unique mindsets into collaborative efforts is the true challenge of an effective leader. Although it takes practice and careful feedback it creates the true power of a team. Finding that special chemistry with a creative team can launch strategies in exciting and productive directions. In my opinion, cultivating this atmosphere of collaboration is the responsibility of any leader, not just female leaders. The embrace of change and flexibility is paramount so that the firm can growth and not just in revenue terms but your company nor its people should be stagnant or look the same in five years.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I started my finance career as a trader at one of the largest independent advisory firms in Buffalo, NY. I was then offered an opportunity to join the partners group and work directly under a woman one of the owners and active managing principals of the firm. She truly served as a mentor to me at a key time early in my career and personal development. The culture at the firm itself also had a tremendously positive impact on my growth. The alignment and timing of where I was in the learning curve was simply perfect for the experience I was about to encounter over the next four years. I would later come to realize what a true rarity the company’s design was, where women represented more than half the firm. Specifically, each advisory team had one senior female who managed portfolios and lead client relationships. While each of these women had different personalities, investment styles and roles on their team, each was very supportive of the next generation. My boss and mentor, Katherine, was not only managing portfolios and meeting with clients, but she was also running the day-to-day operations of the firm and all department heads reported to her.

Katherine made it look easy, but I learned how she invested and dedicated extremely long hours of work and logged miles of travel. I was in awe of her dedication, her professionalism and focus. I was her biggest fan. I was also absolutely terrified of her as she had a very low tolerance for wasted time and energy. She also had incredibly high expectations for her direct team and for the firm overall. She was on the front lines of final hiring and firing and while I was excited and honored to be recommended to her team I was also extremely intimidated at the thought of working under her. I am so happy to say that we still talk, and we laugh about the many one-liners she would say to me that still echo in my mind I smile when a bit inside when I use those same one-liners with my team to this day. And now, I have a completely different level of respect and perspective for what she achieved since I am running a team as well.

Now more than ever I have the highest regard for her given the incredible amount of stress, responsibility and accountability that rested daily on her shoulders behind the scenes. Running portfolios, client needs and a team was just one portion of her day while strategic planning and departmental and employee dynamics was a hidden and consistent undercurrent humming in the background. While most on her direct team knew she was dealing with many issues behind closed doors, until I became an owner I was never really able to appreciate how much she balanced to maintain success. Until you experience it firsthand as a leader or founder no one truly understands that everything defaults to you, for better or for worse. As a leader or as an owner, you are the last stop and on the front line for any client or business-related successes or failures associated with the decisions you and your team are making at any moment of the day. I feel incredibly fortunate to have had that opportunity to grow and learn with Katherine and to maintain this relationship for so long over the years. She was the first to congratulate me when we established Centerpoint.

How have you used your success to bring goodness to the world?

With the success we have been fortunate to experience at Centerpoint, we feel it is important to give back and provide some pro bono planning services when appropriate to many NextGen clients or family and friends of existing clients who do not have a financial planning resource or who do not have the ability to pay for such services. The interesting thing is that those who have limited funds need the counseling and guidance most. With limited income, savings and investable assets the room for error or loss is significantly diminished. If their asset allocation is perhaps too aggressive or they are not maintaining a suitable savings level, the relative risk to that client is exponentially higher. Beyond investments, we may be able to find opportunities for savings, for instance a high interest rate credit card or school loans that should be consolidated or refinanced. Each and every dollar counts and the compounding of interest or a poor purchase decision can affect their credit and follow them for years.

We also have integrated a program of giving in our firm in which we provide paid time off to each employee to volunteer at a charitable organization of their choice. It has been extremely successful, and frankly, it is fun to see each team member’s choice. We all have special passions so it has allowed for team members to showcase their individual personalities, and for the entire office to learn more about local organizations.

You are a person of great influence. If you could inspire a movement that would bring the most amounts of good to the most amounts of people, what would that be? You never know what your idea can trigger. 🙂

I would love to inspire a movement that would make people feel more comfortable speaking honestly and authentically about their finances and the challenges they have. With the exposure to social media and the incessant posting of unrealistic goals, expectations and lifestyles we see, there is an overwhelming desire for perfection through instant gratification with not enough praise for hard work. Unfortunately, this leads to people putting on a facade when it comes to their finances, and foolish spending while trying to keep up with the perceived status quo. It leads to great anxiety among social groups and is a problem that transcends generations, gender, and income levels. Everyone is feeling the stress of maxed out schedules, career burnout, and financial fear but no one is talking about it. I think a movement that encouraged honesty in this way would be a breath of fresh air and would help so many.

While our focus is on wealth management, that goal encompasses a considerable amount of planning and information as it touches nearly every aspect of a person’s life in some way. Money represents something very different to each individual. For some it represents security, while for some its freedom. Some see money simply as a tool to get from one day to another, while in others it causes great angst and stress. Think about how money plays a role not just in education expenses and retirement, but also in assisting elderly parents that are running low on funds, home expenses, healthcare, special needs children, medical costs and treatments that may not be covered. We are honored and proud of the fact that our clients entrust us with the most intimate issues that they and their families are dealing with however, we all need to remember that each family has their own personal challenges behind closed doors. While we celebrate wonderful successes, we always remember there everyone lives also lives with great heartache. Mental health, addiction, divorce and chronic illnesses are among some of the difficult, but common issues that range universally across all levels of education and income. I want to inspire a more advanced, comprehensive platform for planning services for clients and their families to relieve at least a fraction of their worry. I love recapturing time for clients, relieving stress and providing education surrounding topics that answer questions to their specific needs.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

There are so many great quotes that I have heard over the years that based just on the timing of them had a large impact on my views of our team, clients and personal growth.

“What got you here will not get you there.”

How can our readers follow you on social media?

Twitter: @Centerpoint_Now


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