Jenny Dwyer
Vice President of Business Development,
5by5: A Change Agency
From two internships in the music industry in Nashville, TN to working for 5by5, a full service digital marketing agency, Jenny has a lot of experience and even more wisdom to share.
Elon Graduation Year
Live Oak Communications Position
Account Executive (2007 - 2010)
Jenny's Company History
A Q&A with Jenny Dwyer
How did your internships in college, both of which in the music industry, prepare you for a post-grad career? What skills did you learn in those roles that were important for your success following graduation?
​
My internships in the music industry during college were a whirlwind —
glamorous, exciting, and the perfect introduction to Nashville, a city I’ve
since come to adore. Those roles were not only a launchpad for what would
become my community here, but they were also a ton of fun. I got a taste of
the fast-paced, high-energy world that Nashville is known for, and I loved
every minute of it.
But as I dove deeper into the grind, I started to realize something important:
while the glamour and excitement were real, the long-term climb up that
ladder wasn’t for me. It taught me what I wanted my career to look like and,
just as importantly, what I didn’t want. Those internships were a pivotal
experience, pushing me to trust my instincts, build resilience, and
understand the balance between chasing dreams and maintaining long-term happiness. Ultimately, they helped me find the right path—one that keeps me grounded in a city I love, doing work that excites me without sacrificing the work-life balance that I value.
What is your favorite campaign that you have had the chance to work on with 5by5?
​
One of my favorite campaigns I’ve had the chance to shepherd into the agency (I am sales so I don’t do the work) - has been with Charity:Water, specifically the recent project promoting their new Lab Experience in Franklin. Charity:Water has always been a dream client for us—a “we made it” client that we’ve admired since the early days of building our prospect lists. Being able
to partner with them for this campaign has truly been a highlight.
The Lab Experience is a unique, immersive journey where visitors can learn firsthand about the innovative, life-changing work Charity:Water does to provide clean water to communities in need. It’s an interactive, educational space that brings their mission to life in an unforgettable way. We’re incredibly proud of the campaign and the impact it’s had.
Check out the video below to see the Lab Experience in action:
​
What kind of challenges do you face in your role and how do you navigate them?​
One of the biggest challenges I face in my role is navigating what I can
and cannot control in a crowded and price-driven marketing landscape.
With so many agencies offering similar solutions, it can be tough to
differentiate ourselves, especially when budgets vary widely.
On top of that, this year has brought its own set of hurdles—
the sales cycle has been slow and unpredictable, with accounts
slipping through the cracks due to unexpected funding cuts or
leadership changes. We’ve come close to landing big accounts, only
to come in second after long RFP processes.
​
To navigate these challenges, I focus on showing, not just telling,
what makes us different. I highlight the amazing work our team is
doing and bring in the experts during sales conversations to build
trust and instill confidence. I’ve also learned that when it
comes to things I cannot control, I’ve gotta just let it go and remind
myself what matters most.
Ultimately, I feel incredibly fortunate to work at a company that is made up of a team of change makers serving change makers, and when you love what you do and the people you work with, maintaining energy for growth comes a lot easier.
Can you describe a typical day in your current role as the Vice President of Business Development for 5by5?
A typical day in my role as Vice President of Business Development
for 5by5 starts with the usual morning hustle —
getting my kids off to school and grabbing my first
cup of coffee before heading into the office.
Once I'm settled in, my day is usually a mix of internal and external
meetings, where we discuss sales opportunities and
keep them moving forward.
Since I’m the only one fully dedicated to sales, I’m
involved in every step of the process—from
initial inquiry all the way through negotiation and
onboarding our team. It’s a role that really
leans on my project management skills, as I juggle multiple moving pieces and timelines.
​
The best part of it all? I get to do this alongside my best friends. This company has become my community, the people I do life with, and I’m incredibly grateful to be part of a team that is made up of change makers serving change makers. It’s a lot of hard work, but it’s also a ton of fun, and every day brings something new. I love seeing things come together and knowing we’re making an impact.
What is the most rewarding part of your job and why?
​
The most rewarding part of my job is closing business and contributing to the growth of a company I truly care about. It's incredibly fulfilling to play a small part in a change maker’s journey, helping them optimize their impact. I’m not just “selling” a service; I see myself as a guide in our prospective clients’ journey, helping them navigate the next right step for their business. I treat every interaction as an opportunity to be a consultant and educator. I start by
listening—leading with curiosity—to help clients crystallize their needs and define what success looks like, which includes identifying the right partner to amplify their impact. If that’s 5by5, fantastic. If not, that’s okay too.
Another huge reward for me is the people I work with and the culture we've built here at 5by5. I love being part of a team that’s committed to making a difference and creating an environment where collaboration thrives. While many might assume I lead a sales team, the truth is that our success isn’t about scaling a team but about bringing in the right leaders and experts at the right
time. The people our clients will actually be working with become a key part of the sales process, building trust and confidence right from the start—often tipping the scales in our direction. That’s the real secret sauce, and it’s what makes our work so rewarding.
I’m incredibly grateful to be part of a team that is made up of change makers serving change makers.
If you could give one piece of career advice to a Live Oak student about to graduate and enter the workforce, what would it be?
1. Trust your gut – The road ahead might not always be a straight path,
and you’ll face unexpected twists and challenges. But your instincts are
often your best guide. Don’t be afraid to take risks,
ask questions, and lean into opportunities to learn and grow.
2. Ask for feedback – I’ve always said that feedback is my
superpower. I’ve worked hard to strengthen my ability to receive and
act on feedback, even when it’s tough or ego-bruising. It’s
essential for growth, and the more open you are to it, the faster you’ll improve.
3. Remember that your career (God willing) is a long journey – You don’t need to have it all figured out right away, but you do need to take care of yourself every step of the way. Success isn’t just about climbing the ladder—it’s about finding a role and a company that align with your values and passions. Surround yourself with people who inspire and challenge you, and make sure you prioritize your well-being along the way.
​
4. Lead with strategy first, if you plan to be a marketer, but also make sure your strategy is actionable. Be decisive - your clients aren't paying you to hand them big ideas and not provide the discernment of what they SHOULD be doing based on their constraints and reality (rather than all they COULD be doing). And chart a clear path for the client to unlock their budget to you to run with. Ultimately, clients pay the right and best agencies to tell them what to do (and why), and then execute and report on the impact metrics that truly drive growth. This is not an idea economy - it is an impact economy.
"Jenny, and her sister Lynn, were inaugural members of Live Oak when we launched the agency in 2007. During her tenure at Live Oak, she served on several client accounts including EarthShare NC, the Durham Arts Council, and Pro Feet sports socks. She was a fireball AE who always raised the bar for our work and made a difference for our clients. I remember when she landed her first agency job in Nashville, she wrote to tell me what a seamless transition it was and how prepared she felt to handle client management because of her work in Live Oak. She wrote, 'The family feel here is much like how I felt on my Pro Feet client team my last semester with Live Oak, and having that is really special.' Jenny always approached her work with energy and excitement.
There was no doubt in mind she would be a change maker in her professional life."
Lee Bush
Founding Faculty Advisor, Live Oak Communications
Inaugural Photo of Live Oak Communications, 2007