Join the Cypress Team
We believe in the power of relationships. With our clients and team members, we foster genuine connections that fuel success and create a supportive, collaborative environment. Your unique talents are valued, and your aspirations are supported as we work together to shape the financial future of our clients and community.
Named Florida's #1 Best Company to Work For
MEDIUM COMPANY CATEGORY
This recognition reflects the voices and experiences of our employees and the culture we’ve built together, one rooted in trust, collaboration, and a genuine commitment to one another.
At Cypress, relationships come first. We believe that applies not only to how we serve our clients and communities, but to how we support one another. As we celebrate 30 years, we’re proud that our greatest strength continues to be our people. We’re committed to creating a place where talented people can build meaningful careers, grow personally and professionally, and find purpose in the work they do.
“At Cypress Bank & Trust, employee experience isn’t just a department—it’s our philosophy. We don’t define our culture through HR; we define it through how we care for our internal clients—our team. We hold ourselves to the same thoughtful standards internally as we do with our external clients, because we believe that when our people thrive, our business does too.”
Jeri Castrillon
Vice President & Director of Employee Experience
What You Can Expect
FROM OUR CYPRESS TEAM
Collaboration & Support
We believe in teamwork, where every voice is heard and every contribution counts.
Room to Grow
Whether you’re just starting out or looking to advance, we provide the resources and opportunities you need to achieve your career goals.
Work-Life Balance
Your personal life matters. We offer flexibility and support to help you maintain a healthy balance.
Empowerment
We give you the tools and encouragement to succeed in your career, knowing that your growth contributes to our collective success.
A Culture of Connection and Growth
At Cypress, we foster a vibrant and supportive environment where teamwork and personal growth go hand in hand. Our culture is built on meaningful connections, innovation, and a shared commitment to well-being.
PERSONAL CONNECTIONS
We get to know our clients and team members on a personal level, fostering a culture of belonging and respect.
ENGAGING ENVIRONMENT
We embrace innovation and encourage you to share your ideas, creating a dynamic workplace where you can thrive and make an impact.
EMPLOYEE WELL-BEING
We offer competitive benefits, professional development opportunities, and a focus on work-life balance to support your overall well-being.
FUN & FULFILLING
At Cypress, we believe work should be enjoyable. We combine hard work with a positive, fun atmosphere that makes every day rewarding.
Our Team Members’ Stories
TESTIMONIAL
Ken Thompson, Senior Trust Executive, Senior Vice President
Raphael Lima, Associate Portfolio Manager
Current Job Openings
EXPLORE OPPORTUNITIES WITH CYPRESS
Ready to take the next step in your career? Explore our job openings and discover how you can thrive as part of a team that’s committed to your success.
Cypress Bank & Trust complies with federal and state disability laws and makes reasonable accommodations for applicants and employees with disabilities. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or to receive other benefits and privileges of employment, please contact EmployeeExperienceDepartment@cypressbanktrust.com
Our Guiding Values
Community
Cypress will always prioritize building connections and fostering community growth.
Client-Centricity
Our commitment to client-centricity ensures your financial well-being is our top priority.
Accountability
At Cypress, accountability is not just a buzzword; it’s our guiding principle.
Clarity
Transparency and clarity go hand in hand at Cypress.
Integrity
Integrity is the cornerstone of every decision we make.
Dedication
With unwavering dedication, we strive to exceed your expectations every day.
Building Careers and Community
At Cypress Bank & Trust, we’re deeply rooted in the communities we serve. We believe in giving back and making a positive impact alongside our clients and colleagues.
VOLUNTEER INITIATIVES
Our team actively participates in community service, with dedicated volunteer hours supporting local causes.
PARTNERSHIPS WITH NON-PROFITS
We proudly partner with organizations that align with our mission and values.
EMPLOYEE INVOLVEMENT
We encourage our employees to engage in community initiatives, empowering you to make an impact both inside and outside the office.
Cypress in the Community
MEDIA, EVENTS, & NEWS
Thirty years of growth begins with strong roots. At Cypress Bank & Trust, those roots are relationships.
This cypress bonsai tree, generously gifted by Stephen Heuston and the Heuston Legal team in honor of our 30th anniversary, serves as a meaningful reminder that lasting growth is built over time. Like the roots of a tree, relationships provide the strength, stability, and support needed to flourish for generations.
As we celebrate this milestone, we`re grateful for the many relationships that have helped Cypress grow over the past 30 years and look forward to continuing that legacy for years to come.
Oct 7
Cypress team members from across Florida came together to attend the Estate Planning Council of Northeast Florida, where they heard from former FBI Special Agent Toni Chrabot on the critical topic of protecting clients` and families` personal information.
The discussion explored risk management, digital security strategies, and the importance of proactive planning in an increasingly complex environment.
Representing Cypress Bank & Trust were John Moore, June Lundy, Christina Morelli, Tony Azqueta, and Raphael Lima. While they serve clients in different markets across the state, opportunities like this bring our team together to learn, share perspectives, and strengthen the knowledge we bring to the families and businesses we serve.
Oct 6
Thirty years is more than a milestone. It`s a reflection of the relationships, trust, and community support that have guided Cypress Bank & Trust since 1996.
Our anniversary celebration brought together clients, shareholders, team members, and community partners to commemorate this special occasion.
Thank you to 28 North Gastropub for helping create an exceptional experience for our guests, and to Groundswell Startups for the incredible custom skateboard featuring our 30-Year Anniversary logo. The gift was both unexpected and meaningful, symbolizing creativity, entrepreneurship, and the strong partnerships that make our community unique.
We`re grateful to everyone who has been part of our story and look forward to continuing to grow together for years to come.
#Cypress30Years #CypressBankTrust #TheCypressWay #TeamCypress
Oct 5
Our Cypress Tree is Growing! Please join us in welcoming Jenifer McQuillen, who is joining our Lakeland team as a Client Support Specialist.
Jenifer brings more than 10 years of experience in the legal field, with expertise in probate and estate matters, corporate documentation, and legal administration. Throughout her career, she has partnered closely with attorneys, clients, CPAs, financial advisors, and other professionals, earning a reputation for her attention to detail, organization, and commitment to exceptional client service.
Her experience, professionalism, and relationship-focused approach make her a valuable addition to Cypress, and we look forward to the contributions she will make to our Lakeland team and the clients we serve.
Welcome to the Cypress family, Jenifer!
#WelcomeToCypress #CypressBankTrust #TheCypressWay #TeamCypress #GrowingStrongRoots
Oct 2
Columbus Day is just around the corner, and Cypress Bank & Trust will remain open and available to our clients and community. We look forward to welcoming you and continuing to provide the personalized service and trusted guidance that define the Cypress experience.
Sep 30
We`re honored to be nominated for the 2026 Best of Winter Park by the Winter Park Chamber of Commerce. This recognition reflects the relationships we`ve built with our clients, community partners, and neighbors throughout Central Florida.
If we`ve made a positive impact on your financial journey, we`d be honored to have your vote. Voting is open through October 16, with one vote per day permitted. Vote here: https://www.winterpark.org/best-of-winter-park/
Thank you for being part of our story.
#CypressBankTrust #TheCypressWay #TeamCypress
Sep 29
A great day on the course and even better conversations.
Cypress Bank & Trust recently welcomed community partners to Pointe West Country Club for a golf mixer focused on building relationships, sharing perspectives, and exploring opportunities to better serve clients throughout Florida.
Representing Cypress were Brian Skarbek, Senior Investment Officer, Senior Vice President, and Owen Straub, Commercial Banker, Assistant Vice President, who connected with fellow professionals and discussed opportunities to strengthen business relationships across our markets.
Strong partnerships create stronger communities, and we`re grateful for opportunities to connect beyond the workplace.
#CypressBankTrust #CommunityPartners #BusinessRelationships #FloridaBusiness #TheCypressWay #RelationshipBanking
Sep 25
We`re honored to be featured in Brevard Business News, where our President & CEO, Dana Kilborne, shares the story of Cypress Bank & Trust`s continued growth, our people-first culture, and the journey that has shaped our organization over the past 30 years.
The feature highlights what has remained constant throughout our growth: a commitment to building meaningful relationships, serving our clients with excellence, and investing in the people who make Cypress what it is today.
Read the full article: https://acrobat.adobe.com/link/spaces/urn:aaid:sc:US:f1d84aad-5231-4121-81ac-db2323445a39
Sep 23
A legacy isn`t just what you leave behind. It`s the security you provide today.
September is Life Insurance Awareness Month, a reminder that protecting the people who matter most is an important part of any financial plan.
While many people spend time preparing for retirement, building wealth, or creating an estate plan, life insurance is often overlooked. The right coverage can help provide financial security and peace of mind for those you love.
A conversation today can make a meaningful difference tomorrow.
#LifeInsuranceAwarenessMonth #LegacyPlanning #FinancialSecurity
Sep 18
Grow Your Career with Cypress Bank & Trust
As Florida`s #1 Best Company to Work For in the medium category, we foster a culture where people are valued, supported, and empowered to succeed. Here, you`ll work alongside talented professionals who are committed to delivering exceptional service, strengthening our communities, and helping clients achieve their financial goals.
Whether you`re looking to grow your expertise, build meaningful relationships, or make a lasting impact, you`ll find opportunity, collaboration, and purpose at Cypress.
Ready to join our team? Explore current opportunities and discover where your future can take root.
https://cypressbanktrust.com/careers/#job-openings
Sep 17
Who`s your banker? At Cypress, we believe every client should know theirs.
Our Maitland team brings deep banking expertise, strong local connections, and a commitment to helping individuals, families, and businesses throughout Central Florida achieve their financial goals. They understand that great banking is built on personal relationships, trusted advice, and being accessible when clients need them most.
As we celebrate our 30th anniversary, we`re proud to recognize the dedicated professionals who help make Cypress Bank & Trust a trusted financial partner throughout the Orlando area and beyond.
These are the faces of the bankers who serve our clients and community every day. They know that exceptional banking starts with knowing your clients, understanding their goals, and providing thoughtful guidance through every stage of their financial journey.
Learn more: https://cypressbanktrust.com/maitland/
Sep 16
Our Cypress Tree Is Growing!
Please join us in welcoming Chad Fiedor, Commercial Banking Associate, to our Palm Beach team.
A South Florida native, Chad brings a strong background in finance, research, and operations. He began his career in corporate finance before serving as a Summer Analyst at a hedge fund, where he focused on equity research. Most recently, he supported the operations of an early-stage startup through a single-family office in West Palm Beach.
Chad earned his degree in Finance from Florida State University and is passionate about helping businesses across South Florida achieve their growth objectives. We`re excited to have him on the team and look forward to the impact he will make for our clients and communities.
#TeamCypress #CypressBankTrust #BestPlacestoWork
Sep 15
