Our Team
Our team is committed to delivering unparalleled customer service by crafting tailored solutions for each client. Our fusion of experience and innovation, traditional values and advanced technology, positions us as the ideal blend of tradition and modernity.
Ann Rash
VP of Strategic Transition
Ann Rash is Vice President of Strategic Partnerships at Headwaters. She has a Business Management Degree from Johnson and Wales University. After managing several restaurants across New England, Ann returned to school to earn an additional Bachelorโs Degree in Paralegal Studies. As a Paralegal, Ann specialized in workersโ compensation defense and was an expert in recovering funds for clients from the NH Second Injury Fund. On the defense side, Ann assisted insurance companies and self-insured employers to mitigate exposure and defend against workersโ compensation claims.
For the past 15 years Ann has been assisting clients with their marketing needs and developing custom marketing and advertising plans for high end clients. She has worked with event professionals to increase their targeted outreach and expand brand awareness. Ann is a seasoned professional who is exceptional at bringing valuable insight to any discussion with passion and enthusiasm. Annโs passion is customer service which allows her to help doctors with goals for their practice and provide options for successful transitions.
Ann and her family have recently relocated to Florida, where they can enjoy the sunshine and boating and biking year round. Growing up in New England, she is a huge hockey fan and is often seen cheering on her Boston Bruins.
Bailey Jones
Executive Director of Communications
Carrie Naroian
VP of Practice Strategy
Carrie Naroian is Vice President of Strategic Partnerships at Headwaters. She attended the University of Louisville and began her career in Human Resources for a top Fortune 500 company. After enjoying many years in HR and personally connecting with over 350 employees daily, Carrie did an about face and began a new and challenging career path in sales & marketing, where she has spent the last 20 years. What prompted her to make that change and what she enjoys most is really getting to know her clients, their business and making that personal connection.
Carrie was born in New England, but has lived in various parts of the country โ making her home in Alabama, Kentucky (you know where she always was that first Saturday in May) and in Colorado before making her way back to the coast of Massachusetts with her family where she enjoys the beach, trail riding and all that living on the coast has to offer. In typical New England fashion, sheโs a die-hard New England sports fan, but when it comes to college football, you will find her cheering on her sonโs team: Texas A&M.
Dominick Ricciardi
Mergers and Acquisitions Consultant
Dominick Ricciardi joins Headwaters Transitions with over 20 years of sales experience and a deep background in both dental financing and dental technology. A native New Yorker, Dominick has assisted hundreds of dentists in all areas of the start-up and acquisition process.
Dominickโs intimate knowledge of the dental landscape comes from many years working in technology sales for a Fortune 500 Dental Distribution company. His diverse experience also includes recent years spent as a VP of Business Development at one of the largest dental financing companies while also serving as sales team lead for an up-and-coming dental technology start-up.
A transparent, client-focused approach makes him a trusted resource throughout the transition process. Dominick resides in Westchester, NY with his wife and son and enjoys basketball, the Adirondacks, and Floridaโs Treasure Coast.
Jennifer Sims, CPA
Executive Vice President of Valuation Services
After earning her Bachelorโs degree in Business Administration and Accounting from Baylor University, Jennifer became a licensed Certified Public Accountant. She began her career in public accounting as an auditor of financial service companies before finding her true passion in the dental industry. For over ten years, Jennifer served as a practice manager and accountant in the dental field, where she discovered a passion for developing businesses, mentoring staff, and driving practice growth through operational efficiency.
Jenniferโs deep understanding of both dentistry and finance allows her to deliver expert valuation services tailored to the needs of dental professionals. Her faith is the most important thing in her life, shaping how she leads, serves, and approaches every relationshipโwith integrity, compassion, and a desire to make a meaningful impact. She thrives in team environments, values collaboration, and brings an enthusiastic, team-spirited energy to every endeavor.
Now living in Colorado, Jennifer finds joy in family life, serving her church, traveling with friends and family, and soaking in as many live sporting events as possible. She is especially proud to have supported her husband throughout his 27-year military career, a journey that strengthened her sense of purpose, gratitude, and resilience.
John Burnett
Mergers and Acquisitions Consultant
John has over two decades of experience in the dental industry and brings a unique blend of
expertise to his clients. Early in his career, John honed his skills as a Digital Technology
Specialist and quickly became recognized as one of the top reps in the country for a Fortune 500
dental distributor. This led to serving as an Area Sales Manager working exclusively with DSOs
and group practices to implement enterprise-level practice management and imaging systems.
Born and raised in Iowa, John graduated from Iowa University and later moved to Chicago to
build his career. Now residing in St. Petersburg, Florida, he enjoys staying active through
workouts, playing guitar, and attending live music events in the sunny weather.
Kaile Vierstra
Practice Marketing Manager
Kaile Vierstra has a long background in quality customer service, marketing and office management. She firmly believes that people do business with people they like- and is positive that youโll like doing business with Headwaters.
Coming from a sports background, she is highly goal-oriented and applies this to her work with Headwaters. Often the first point of contact as the Practice Marketing Manager, Kaile strives to display company values and build relationships in every interaction- from sending basic documents to discussing potential practices. Kaile is excited to be part of the HPT team and to assist in making everything run smoothly to better help our clients.
Kaile graduated from Western Kentucky University โ Go Tops! โ and her love of racing and riding mountain bikes brought her to Colorado Springs. She has since fallen in love with the community and lack of humidity. When not in the office, youโll find her in North Cheyenne Canon Park on her mountain bike, rock climbing or trying to tire her Rhodesian ridgeback Stratton.
Kenny To
Business Valuation Specialist
Kenny, a proud Colorado Springs native, is a finance pro whoโs been happily sucked into the world of Excel, and he brings a unique blend of analytical expertise and client-focused advisory experience to his work in finance. Whether it’s digging into financial statement analysis, crafting financial models, or presenting insights to various stakeholders, he loves every part of the process.
A graduate of the University of Colorado, Colorado Springs, Kenny earned his degree in Finance and a minor in Information Systems, graduating Summa Cum Laude. Kennyโs strength lies in his relentless curiosity, always digging deeper to uncover insights and opportunities others might miss.
When heโs not crunching numbers, you can find Kenny geeking out over sports, lifting heavy things in the gym, plotting his next travel adventure, or getting lost in a good book (probably something finance related, but hey, a guyโs gotta have fun too).
Kim McCleskey
VP of Sales
Kim has worked in dentistry for the last 30 years. She spent those early years managing and leading large dental practices. Kim eventually served as Director of Operations overseeing multiple dental practices and specialized in the pre- and post-acquisition process, until forming her own company, True North Dental Solutions. At True North, Kim focused on practice start-ups, practice management, and continued consulting through the pre- and post-acquisition process. Kim went on to merge her company with the Avitus Group to start Avitus Dental Management Solutions, a full service dental consulting firm to include building a successful in-house virtual dental billing company.
Kim is a Certified Professional Business Coach and holds memberships with ADMC, DEN, and AADOM. Kimโs strengths are found in Leadership, Business Development, Business Transition, Startups, and Team Development.
Kim is married and has two grown children. She loves to run, hike, and to spend time with family and friends, and a day is not complete without reading a good book! One of her greatest accomplishments is co-founding a nonprofit with her husband, David, where they Educate, Encourage, and Empower indigenous pastors and church leaders through a literacy program in Uganda, East Africa.
Mark Frazzini
Vice President โ Valuations
Mark completed two bachelorโs degrees in Finance and International Business from New Mexico State University, and later a masterโs degree in Finance from Arizona State University. He has experience helping small business owners plan and prepare for retirement while at Vanguard. Mark has also prepared the financial reports for mutual fund products while at BNP Paribas, helping them establish their domestic financial services division.
Mark incorporates an analytical and forward looking approach in his work. Collaboration and communication are a part of his core principles he implements throughout the valuation process. Outside of work, Mark loves checking out local cafes, going to stand up comedy shows and sharing his playlists with anyone who will listen.
Jess Williams
Business Valuation Specialist
Jess has grown up in the dental industry for nearly his entire life. His grandfather, father, uncle, two cousins and younger brother are all either retired dentists, currently practicing, in dental school or applying. While similarly immersed in dentistry as his family, Jess approaches it from a different angle. He has completed his bachelorโs degree in Accounting from Baylor University. He has experience helping mid-sized firms through the auditing process as an audit intern with Erst and Young. Jess now uses his experiences with both business and dentistry at Headwaters to help set up doctors for a successful retirement and practice sale.
Outside of work, Jess loves to rock climb, mountain bike, and snowboard. He also loves to read various types of novels, poetry, and documentaries as well as some occasional writing.
Todd Sheets
Headwaters Managing Broker
Todd was born and raised in Columbus, Ohio. He is a military veteran, having served in the Air Force and the Air National Guard as an Air Traffic Controller for the states of Ohio, Colorado and finally Texas. After the conclusion of his military service, Todd settled in the Dallas-Fort Worth Metroplex and began his career in sales and leadership. Over the next couple of decades, he co-founded and solely financed a dental sales organization that was purchased and integrated by a Fortune 500 Dental Distribution Company. During Toddโs 12 years with that distributor, he led various teams in dental technology, dental software, and veterinary software sales. After exiting the distributor in mid-2019, Todd has been involved in dental practice transitions.
Todd resides in Mansfield, Texas with his wife and six rescue animals which is a great passion they share. He and his wife have been blessed with two beautiful daughters. His hobbies include playing basketball, guitar, and college football.