SKY TEAM
Kendall Bolt
Kendall is the CEO of SKY and a passionate advocate for helping families achieve clarity, confidence, and peace of mind in their financial lives. He brings a unique blend of institutional finance experience, military leadership, and a deep personal commitment to service. Before joining SKY, Kendall advised Fortune 500 and privately held companies as an investment banker at Bank of America Securities, where he led mergers & acquisitions, IPOs, and capital raises across the industrial and infrastructure sectors. His career began as a U.S. Navy Surface Warfare Officer, where he served in multiple leadership roles and developed the values that continue to guide his work today.
Kendall holds a B.S. in Economics from the United States Naval Academy, where he was the captain of the baseball team. Clients value his thoughtful, disciplined approach and his ability to simplify complex financial decisions. He’s known for listening closely, putting clients’ goals first, and building lasting relationships rooted in trust.
Kendall lives in Fairfield, Connecticut with his wife Madison, their son Hudson, and daughters Marlowe and Demi. He enjoys coaching youth baseball on the weekends and attending local events with his family.
Robert Bingham
Bob is the Founder and Chief Investment Officer of SKY. He has forty years of experience managing equity and fixed income portfolios for individuals, families, businesses and charitable organizations. Prior to founding SKY in March of 2005, he was a Senior Vice President with UBS Financial Services and its predecessor, PaineWebber.
Bob holds a BA in Mathematics and Economics from Middlebury College. He is a Chartered Financial Analyst and a member of the New York Society of Security Analysts and the CFA Institute. He serves on the finance committee of St. Albans Church in Simsbury, CT., on the Board of Visitors for the McLean Hospital and has been active in the Simsbury Land Trust. In his free time, he enjoys fly fishing, skiing and golf.
John Wright
John worked previously at Fox-Pitt, Kelton where he advised institutional investors on their investments in the financial services sector. John has over forty years of experience in this sector, first at Keefe, Bruyette & Woods, and then as an analyst and hedge fund manager at George Weiss Associates.
John holds an MBA from Dartmouth’s Tuck School of Business and received his BA in Economics and French from Middlebury College. Previously, he served as a board member of the 10th Mountain Division Foundation in Denver, CO, the Bank of Virginia in Richmond, VA., the Investment Committee of the Hartford Foundation for Public Giving, and the First Church of Christ in Simsbury, CT where he was a Church Elder and Treasurer.
Catherine Mullen
Catherine Mullen has always been drawn to the places where disciplines intersect. She came to finance with a biology degree from Williams College and a long-standing love of economics, history, and human behavior. In time, she discovered that investing sits at the convergence of all of them. Understanding a portfolio means understanding markets, industries, global events, and the people navigating them. For Catherine, that challenge is what makes the work fun.
As a Wealth Advisor at SKY Investment Group in Hartford, Connecticut, she has spent the past decade building relationships grounded in trust, patience, and care. She frequently serves as the central point of contact for families during major life transitions, particularly women stepping into independent wealth management for the first time. Catherine brings an “old school” dedication to every interaction, relying on precise, handwritten notes to ensure every detail, goal, and unspoken concern gets remembered and addressed. More than anything, she wants clients to feel supported and empowered to make decisions about their own money.
Growing up in Farmington, Connecticut, Catherine and her siblings received U.S. Savings Bonds each birthday from their grandparents. Twenty-some years later, those small, steady gifts had grown into something real. Time, she learned, is one of the most powerful forces in finance.
Family is the heart of Catherine’s life. A twin and aunt to six nieces and nephews, she is the designated family birthday cake baker, a tradition that blends her creative side with her love for celebrating family milestones. Outside the office, she stays active running, skiing, and playing golf.
Tyler Waterman
Tyler Waterman still remembers the moment he first understood what money really meant. He spotted a Sega Genesis in a magazine for $200, and was certain he just needed to scrape together $2.00 from his coin jar. His parents gently corrected him. What followed was his first real lesson in discipline, patience, and the space between wanting something and having the follow-through required to earn it.
That early memory informs the way Tyler works today. As a Wealth Advisor and Director of Research at SKY Investment Group in Hartford, Connecticut, he spends his days building financial plans tailored to each client’s vision and helping them navigate decisions with confidence.
Tyler uses every resource available to him to stay well informed on the companies SKY invests in, takes pride in helping clients become knowledgeable savers and prudent spenders, and works diligently to answer the questions that sit heaviest: whether they’ve saved enough to support the family they’ve built, and whether their children will be capable stewards of the wealth being passed to them. Behind the scenes, he researches individual holdings, conducts deep analysis, and leads SKY’s weekly investment committee to ensure every portfolio stays aligned with client goals.
Tyler grew up in Simsbury, Connecticut, where he still lives today with his wife and two sons. You can usually find him outdoors playing baseball, fishing, kayaking, or paddleboarding, and he is always up for a good round of golf, hockey, or paddle tennis. On the weekends, Tyler loves rolling up his sleeves for home improvement and landscaping projects around the house. Tyler holds his undergraduate degree from Worcester Polytechnic Institute.
RJ Pye
RJ Pye has been thinking about investments since he was 12 years old, when he and his grandfather used to sit together and pick stocks. That early experience left something with him: the conviction that investing is not purely a technical exercise, but a deeply human one, capable of changing the shape of a family’s life.
As a Wealth Advisor and Head Trader at SKY Investment Group in Hartford, Connecticut, RJ brings that conviction to the families he works with every day. He joined SKY as an intern in 2019, and has grown into his current role overseeing both the firm’s trading and every aspect of his client relationships. He enjoys finding the right investment solutions for each client, firmly believing that there’s an opportunity for any interest and a strategy that reflects each client’s unique goals. For RJ, trust is the foundation of good advice, and he works to make every client feel calm, steady, and optimistic about what lies ahead.
What RJ finds most fulfilling is the quality relationships that take shape. Over time, what begins as a professional engagement becomes something closer. Clients share what they are working toward, what keeps them up at night, and what they hope to leave behind. That trust, he believes, is the most important thing any advisor can earn.
RJ grew up in Chester, Connecticut, and earned his undergraduate degree from the University of Connecticut. Outside the office, he can be found on the slopes, fishing, or traveling with his family and friends.
Bonnie Brooks
Bonnie has over thirty years of experience in the financial industry, specializing in client service. Prior to joining SKY, she worked at UBS Financial Services in various positions including Operations Manager, Administrative Manager and Stock Option Administrator. At SKY, her primary responsibilities include addressing clients’ operational needs by coordinating with external custodians. Bonnie’s other interests include visiting family throughout New England, experimenting with new recipes and spending time with her rescue dog.
Kayce Barrett
Kayce joined SKY from Aetna where she worked for 14 years. Prior to working at Aetna, she worked at UBS Financial Services where she was an Account Administrator. She has 30 years of Project Management and Operational experience in the Software, Finance, and Healthcare industries.
Margaret Hubbard
Peggy has been a part of SKY since its inception in 2005. Prior to joining the firm, she spent nine years with UBS Financial Services. At SKY, she oversees the management and maintenance of the firm’s data, systems, and administrative platform.
She earned her BA in Mathematical Sciences from Connecticut College. Peggy has also served as a board member and treasurer for a local daycare center, and more recently, as treasurer for a local high school’s Safe Graduation party.
Anabela Andrade
Ana joined the SKY team in 2019. In her current role, she supports data and system maintenance as well as client management.
Before entering the investment management industry, Ana spent over 20 years in retail, including a decade as the store manager of the successful Country Curtains location in Avon, Connecticut.
She holds a certification in Travel and Tourism from the Morse School of Business in Hartford, Connecticut, and is fluent in Portuguese.
Lauren Bettencourt
Lauren joined SKY full-time in May 2023. She holds a B.S. in Business Administration with a major in Finance from the University of Rhode Island. Prior to her full-time role, Lauren interned at SKY during the summer and continued working part-time throughout her senior year. She supports the firm’s data and systems operations, including daily processing, reconciliation, and trading activities, and also contributes to SKY’s investment research.
William Newman
Bill joined SKY after twenty years with a multi-faceted family business. Bill has extensive experience in “family office” issues, including tax, investment, residency, real estate, generational and asset transition matters. Bill has served on the boards of the Noah Webster House/West Hartford Historical Society and the Park Road Playhouse. Bill graduated from Connecticut College with a BA in American Studies and Twentieth Century History.
Kent Zahner
James Pierlioni
Tyler Horner
Tyler joined Sky Investment Group in 2026, supporting the firm’s investment management and client service operations. He works closely with the team on portfolio administration, investment-related projects, and day-to-day client account needs.
Tyler earned his bachelor’s degree in Finance from Central Connecticut State University. Prior to joining Sky Investment Group, he gained experience in both banking and financial services, developing a strong foundation in client service and wealth management. He has also passed the SIE and Series 7 examinations.
Outside of work, Tyler enjoys working out, running, golfing, and spending time with friends and family. He is also an avid Chicago Bears fan.
James Barrett
Jim was formerly with UBS Financial Services before starting his IT consulting firm, JBIT Consulting. Jim has over twenty years of investment industry and technology platform experience and has helped SKY with technology-related matters since its inception in 2005.
Lauren Bettencourt
Why Choose SKY?
At SKY, we believe that you are best served by having an investment manager who knows you personally, listens to your concerns, and tailors your portfolio to meet your specific financial needs.
- SKY is privately held.
- We invest directly in stocks and bonds usually avoiding hedge funds and mutual funds.
- Our compensation is based on a percentage of assets managed, not on sales commissions.
- We pride ourselves on customer service.
