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.
“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
Roth or Traditional? It`s one of the most common questions in retirement planning - and the answer isn`t the same for everyone.
Check out what our own Sascha Rizzo, CFA, CFP, Senior Vice President and Senior Portfolio Manager, has to say about it in this month`s Orlando Business Journal.
Jun 29
Meet George Rivera, the newest member of our team, joining us as a Commercial Banking Associate in our Maitland office.
With over a decade of banking experience in Central Florida, George has built his career from the ground up. From his start as a Teller to roles in platform banking and commercial lending, he brings a deep understanding of what it takes to serve clients well.
What sets George apart is his commitment to building real relationships with the businesses he works with. He takes the time to listen, understand, and deliver solutions that make a difference.
Outside the office, George is a family man who enjoys spending time with his wife and son, hitting the bowling lanes, and supporting his wife`s growing plant business.
We`re proud to have George on the Cypress team.
Jun 25
Six months down. Six months of opportunity ahead. Your Cypress Bank & Trust advisor is here to help you navigate the ups and downs and make sure your finances stay on track.
Here`s your mid-year reset:
• Money In, Money Out: Review your income and expenses. Cut what`s not serving you and redirect it toward what matters.
• Emergency Fund: Is it still covering 3–6 months of essentials? If not, now`s the time to top it off.
• Investments: Check your portfolio allocation. Market shifts may have moved you away from your target mix.
• Retirement Contributions: Are you on pace to max out your 401(k) or IRA this year? Small increases now add up.
• Tax Planning: Don`t wait until December. Consider harvesting losses, adjusting withholdings, or maximizing deductions while you still have time.
• Estate & Insurance: Life changes fast. Make sure your beneficiaries, coverage, and documents reflect where you are today.
A mid-year check-in doesn`t have to be complicated — it just has to happen. Your advisor is ready when you are.
Jun 22
Happy Father`s Day to the dads, grandfathers, mentors, and father figures who show up every single day.
Your guidance, patience, and quiet strength shape the people around you in ways that last a lifetime. At Cypress Bank & Trust, we see it firsthand - in the clients building legacies for their families and the team members who lead by example, both at work and at home.
Today, we celebrate you.
Jun 21
June 19th is a day of reflection, celebration, and renewed purpose.
Juneteenth marks one of the most important moments in our nation`s history and a reminder that freedom and justice require continuous commitment. At Cypress Bank & Trust, we`re proud to serve communities across Florida that are rich in diversity, culture, and resilience.
Today, we celebrate the progress made and recommit to the work ahead.
Jun 19
Summer in Florida calls for one thing - iced coffee on repeat.
Whether you`re fueling a Monday morning or powering through a Friday afternoon, the Cypress Bank & Trust team runs on it. Bonus points if it comes from a local spot.
What`s your go-to iced coffee order? Drop it below.
Jun 18
Congratulations to our very own Luis Barrios on being accepted into Leadership Winter Park`s 37th Class.
Leadership Winter Park is a highly selective program that brings together professionals who are committed to strengthening the community and making a lasting impact. Being chosen for this program is a reflection of the kind of leader Luis already is.
At Cypress Bank & Trust, community involvement isn`t just something we encourage. It`s who we are. We`re proud to have Luis representing our team and look forward to seeing the great things ahead.
Jun 17
Proud to be recognized as one of the Orlando Business Journal`s 2026 Best Places to Work.
At Cypress Bank & Trust, our culture is built on trust, collaboration, and a shared commitment to excellence. This recognition is a reflection of the incredible team behind everything we do.
Thank you to every member of the Cypress Bank & Trust family for making this possible.
Jun 15
Living in Florida means knowing that hurricane season is starting right now in the month of June. So, the best time to prepare is before you need to.
A few reminders from the Cypress Bank & Trust team:
• Set up online and mobile banking now - so you`re ready if branches are temporarily closed.
• Store copies of financial records, insurance documents, and estate plans in a secure digital location.
• Make sure your emergency fund is liquid and easily accessible.
Our team is here year-round - before, during, and after the storm. If you have questions about protecting your finances this hurricane season, reach out to us directly.
Jun 13
Cypress Bank & Trust was back in Gainesville for the 2026 UF Advisor Network Gator Gathering, and it did not disappoint.
As a proud sponsor of this year`s event at the Straughn Professional Development Center, our team spent the day connecting with advisors, sharing insights, and building relationships across the financial community.
Sascha Rizzo`s presentation, "Giant Mindless Robot," was a standout, exploring the generational forces shaping today`s stock market.
Thank you to the UF Advisor Network for another incredible event.
See you next year, Gator Nation.
Jun 11
Urgent wire requests, last-minute changes to payment instructions, and emails that appear to come from someone you trust are all signs of one of the most costly scams in banking today - wire fraud.
Wire fraud is one of the most costly scams affecting individuals and businesses today. Once a wire transfer is sent, it`s nearly impossible to recover.
Before you act on any payment request, pause and verify:
• Confirm wire instructions by calling a known, trusted number - not the one in the email.
• Be cautious of any last-minute changes to account or routing details.
• If something feels off, slow down. Urgency is a scammer`s favorite tool.
At Cypress Bank & Trust, protecting your assets is part of how we do business.
Jun 8
Choosing a bank is more than choosing where to keep your money; it`s choosing who you trust with your financial future.
The right bank takes the time to understand your story, whether that means growing your business, planning for your family, or making everyday financial decisions with confidence. It`s a relationship built on trust, not transactions.
Check out what our own Max Jasmund, Commercial Banking Associate, has to say about why that kind of partnership makes all the difference in this month`s Orlando Business Journal.
Jun 5
