About us

Meet the team behind Ruby.

Who is Ruby?

Ruby is not just one person, but a group of us. We are a group of humans that wanted to make it easier for families who are caring for a loved one who needs support.

We promise to always use clear language that is simple to follow and to provide a place for you to find answers to your questions.

We will always respect you and your loved ones and be honest about how we work.

About Ruby

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Operating Team


Sam Bledsoe

Sam manages all things technology. He’s brilliant at understanding and communicating business requirements to technology teams, and keeps us all focused should we stray from our goals.

“I worked with my brother and my sister on managing my mom’s care and finances while her health degraded slowly, then suddenly. I build software when I have nothing else to do, and Ruby is software that will make a positive impact on the world and my life. So I’m building Ruby.”


Aaron Briggs

Aaron is in charge of both product and marketing. Said another way, he is charged with truly understanding the voice of our customer, and making sure we meet their most pressing needs.

“As an only child, I know that as my parents age it is 100% my responsibility to ensure they’re cared for and secure for the rest of their lives — a reality that became clear a few years ago with dad’s heart attack. In the years since, I’ve watched both my parents play an active role in the financial care for my grandparents; I’ve seen the frustrations and uncertainty and stress that caregiver role can create, even in tight knit loving families. I’m building Ruby to make it easier for families like mine to work together, and to give myself a tool that will make it possible for me to get involved in my parents finances early, before there’s a mess to untangle.”


Nic Discepoli

We call Nic our Swiss army knife. No matter the task, he can get it done.​

“After battling various forms of cancer since he was 25, my Dad recently received news that not much more can be done to treat his condition. As a CPA and Financial Planner, my dad has always been the one to deal with money matters in my house. My mother and sister have never enjoyed handling financial matters, so when my father passes, the responsibility will fall to me. So, I’m building Ruby as a way to allow myself to more effectively keep track of my mother’s finances and collaborate with her to ensure she is financially secure for the rest of her life. Additionally, as a financial planner my dad focuses on helping everyday- people reach financial security. Building Ruby is my way of honoring his work and bringing it into the digital world.”


Mason Frenzel

Mason is our storyteller. From brand images and copy, to product marketing and videos, he helps bring Ruby’s mission to life.

“When my grandfather passed away, my grandmother was forced to take on a lot of responsibilities that she had never had to manage before.  She worried about money a lot, and my mother did her best to help, but she lived 800 miles away. I’m building Ruby so that families like mine can enjoy the precious moments they have together just being a family, not worrying over financial stresses.”


Kristina James

Kristina is the captain of our marketing efforts. We call her a captain because her workstation is a bit like a cockpit. Lots of screens and dials, optimizing our outreach and messaging.​

“As a planner at heart, I know that the time will come that I will have to help out the people I love managing their day-to-day lives as they get older. I will be more than happy to step in and do everything I can, but it will still be a strange shift in our relationship when it happens. Whether it is my parents, my in-laws, or even my extended family, I want to be as prepared as I can to support them in any way possible. I’m building Ruby to help families everywhere with one of life’s most difficult transitions. Families can be complicated enough; if Ruby can help make someone’s life easier, I will consider this journey a success.”


Chris Roth

Chris is our COO, and keeps everything on track and moving forward. He’s passionate about culture and is deeply committed to building a strong team at Ruby.​

“After my grandfather passed away, my grandmother decided to relocate closer to my parents and eventually moved in with them. Living with my parents has meant that she has been able to turn to them for help when recovering from a health issue or with managing her finances. That said, even though they live together, it can still be difficult to keep track of everyone’s health insurance information or tax forms. I am building Ruby to make it easier for families to collaborate, whether they live under the same roof or thousands of miles away.”


Executive Management


Troy Woolley

Troy serves as our entrepreneur in residence, and is responsible for building the team and launching the product.​

“My mom is the ultimate caretaker. She’s always the one to step in during a crisis or loss, and seems to always know the right thing to do. But I know the day will come when someone will have to care for her as she has cared for so many. My sister still lives near my parents and I know the bulk of that care will fall to her. I’m building Ruby so that I can share some of that responsibility with my sister, and do my part. Our parents cared well for us, and we want to do the same in return.”


Mark Montgomery

Mark is our resident instigator. He makes sure we’re never complacent in our efforts and that we’re always trying to be better.

“I have watched both my own family and other friends and extended family struggle with issues around money and elders.  From siblings who simply cannot get along, to a lack of trust amongst family members, to outright theft of elders assets.  Ruby provides a solution to problems like these (not to mention just plain old better organization of information in a secure environment), allowing for trust, transparency, and respect for all of those involved in the care continuum.”


Melissa Preisler​

Melissa makes sure we manage our money wisely. Very very wisely.​

“My aging Aunt has a great many health issues and currently lives alone in a town nowhere near family. She lives in an area where it will be near impossible to sell her house anytime soon and without doing so, she will not have the funds she needs to move and secure independent or assisted living.  I am currently trying to assist her in creating a plan for that point in time, but it is not easy being so far away, and with her not understanding why I need access to the things I do.  I am excited about what Ruby is poised to bring to the table. I believe it will be extremely valuable in providing a systematic structure for working through this process and in its ability to bring peace of mind to all parties involved.”


Katie Williams

Katie gets things done. Whether planning board meetings or keeping our scrum team organized, she always picks up where others leave off.

“When my grandmother’s health began to decline, it fell to my mother to handle her healthcare decisions and financial responsibilities. Thanks to years of missing paperwork, a shady reverse mortgage, and my grandmother’s failing mental health, I watched my mother wade through a mess she was not prepared to handle. It finally became so overwhelming that she handed the estate over to the bank and walked away from the decision making. I’m building Ruby to create a simpler process and help other families avoid the heartache my mother endured.”


Advisory Board


Bruce Bowman

Bruce Bowman is the President of KaBOOM!, a national non-profit organization dedicated to ensuring that all kids get a childhood filled with the balanced and active play needed to thrive. Prior to KaBOOM! he was with Wild Oats Markets, Inc. During his six years at Wild Oats he served in the capacity of SVP of Operations and SVP of Business Development. He came to Wild Oats in 2001 from Ben & Jerry’s Ice Cream where he was their COO for six years. Prior to the snack food industry, he was a mechanical engineer and flight test engineer in the aerospace industry with Pratt & Whitney Aircraft and General Dynamics.


Tamara Clemmons

Tamara Baxt Clemmons has extensive experience in marketing and product management in the entertainment, telecommunications, fintech and SaaS industries. Most recently, she has managed small business outreach campaigns on behalf of clients in fintech, including Mastercard. Early in her career, Tamara held a marketing role at Oxygen Media during the first years of the network’s launch, followed by work at Comcast. More recently, she managed a digital marketing agency that built customer engagement campaigns for clients in the television, music, book publishing, ticketing and wine industries.


Drea Groeschel

With more than 15 years in consumer goods marketing, creative product development, and manufacturing, Drea Groeschel brings a diverse background of operational management to her entrepreneurial endeavors. In California, she worked as the production coordinator for U.S. based clothing manufacturer American Apparel. Groeschel then moved to Tennessee and led the founding team at The Jaeckle Center. In 2011, Groeschel became the CEO of FlashPoint Candle. In early 2018, Groeschel founded her latest company, Beautiac.


Cindy Kent

Cindy Kent is a healthcare veteran with 20+ years in the industry. She is currently the President & General Manager for the 3M Infection Prevention Division. Cindy has global operational P&L responsibilities, including the development of the strategic and annual operating plans, as well as resource allocation across research and development, clinical, manufacturing and commercial functions. Cindy is a member of the Health Care Business Group’s Global Operating Committee as well as a member of 3M’s Executive Leadership Conference—the company’s top 100 executives.


Bo Spessard

As a seasoned SAAS operator with 20+ years of legal, finance and operational background, Bo brings his knowledge and experience to help investors/founders/owners scale their operations and grow their businesses. From HR to culture and legal to strategic investments/acquisitions/partnerships, Bo draws on his decade plus of running Emma, one of Nashville’s most successful SAAS technology companies, to help operators/owners/investors grow and scale their companies.


Mello Thompson

Mello Thompson is an award-winning optician and passionate business owner. As the President, owner, and licensed dispensing optician of Image Optical for nearly 30 years, Thompson has achieved unparalleled success in her field. Mello is an avid art collector, residential real estate investor and grassroots community organizer. Thompson helped lead the West End Business Association, alongside fellow business owners in the West End/Midtown Corridor.


Leonora Williamson

Leonora Williamson is a strategist, investor, foodie, mom, and executive coach-in-training. She studied at Princeton University and earned her MBA from Harvard Business School. She started her career in investment banking (J.P. Morgan) and management consulting (the Boston Consulting Group). She then spent close to a decade at the Estee Lauder Companies. In 2008 she moved from the northeast to Chattanooga, TN where she served as a founding partner of the JumpFund, an angel fund investing in female entrepreneurs in the southeast, worked for SIGNiX (digital signatures) and most importantly, raised her two daughters. She is a passionate volunteer, having served on multiple community boards. Leonora now calls Nashville home and doesn’t foresee ever leaving!

Be the first to use Ruby.

When Ruby launches in Summer 2019, be one of the first to start using it to care for your loved one. Enter your email address to be notified for early access to Ruby.