Leah Sylvester

Executive Partner | President - Retirement Plans, Shepherd Financial

Business at a Glance as of 12/31/24

• Location: Carmel, Indiana
• How many retirement plan assets do you have under advisement? $2.6B
• What is your median plan size (in assets)? $10.7M
• How many plans do you have under administration? 63
• How many participants in total do you serve? 28,080
• Parent firm: Not applicable

PLANADVISER: How is your team unique in the marketplace? How do you differentiate yourself from others?

Sylvester: What makes our team unique is how truly collaborative we are—both in how we support our clients and how we show up for one another. We take a team-based approach that emphasizes community, care and connection, creating an environment where everyone feels support and empowered to do their best work. We’re intentional about our culture, and it shows up in the way we engage with each other and our clients.

We intentionally hire individuals with diverse backgrounds and perspectives, but there’s a common thread across our team: empathy, a commitment to quality and a shared passion for helping others. This extends beyond technical expertise—we approach each client relationship with a deep sense of responsibility to do what’s right.

Above all, we never stay stagnant—what we accomplished last year is never good enough. We’re constantly evolving, looking for new ways to communicate, educate and add value. Whether it’s improving our technology, refining our processes or deepening the conversations we have with plan sponsors and participants, we remain focused on growing to meet the moment.

PLANADVISER: What challenges do you think the retirement plan industry faces, and what role do you have in addressing and confronting those challenges?

Sylvester: The retirement plan industry is facing a perfect storm of complexity, constant change and constrained resources. Regulations are evolving faster than ever, yet many plan sponsors lack the time or internal expertise to keep up. At the same time, our industry faces a growing talent gap—fewer young professionals are entering the retirement space, posing a long-term risk to both innovation and client service.

We’re also at a pivotal moment with technology, particularly artificial intelligence. There’s tremendous potential for AI to streamline processes, improve participant outcomes and create efficiencies—but only if leveraged thoughtfully and ethically. We need to view it as a tool for progress, not something to fear.

My role is to help cut through the noise. That means staying ahead of legislative and industry changes, coaching our team to deliver proactive guidance and fostering an environment where new ideas and talent can thrive. I am also committed to giving back to the profession—through mentoring, offering internship opportunities and helping cultivate the next generation of retirement plan advisors. It’s one way we can ensure our industry continues to grow stronger, smarter and more inclusive.

PLANADVISER: What type of plan sponsor is your typical client (location, size, industry, design elements, etc.)? Please describe your average service model and deliverables.

Sylvester: My typical client is an Indiana-based organization with 250 to 1,000 employees and between $10 million and $500 million in plan assets. I work with a wide variety of industries—including manufacturing, health care, education and professional services—and often serve as an extension of their HR or finance team. Many of our clients value a strategic, consultative partner to help navigate the complexities of plan management while keeping their employees engaged and informed.

Our service model is structured and proactive, anchored by regular committee meetings that serve as comprehensive review and planning sessions. These meetings include regulatory updates, plan design evaluations, fiduciary training, cybersecurity and provider oversight, cost benchmarking and participant engagement strategies. We also guide clients through regulatory updates like SECURE 2.0, compliance testing and the Form 5500 process. Our team also conducts QDIA and IPS reviews, monitors investments and keeps clients on track with a compliance calendar and timely reminders.

Participant outcomes are a key focus—we provide personalized education, employee wellness resources, financial wellness surveys and customized communication strategies to help employees make informed decisions about their financial futures.

Ultimately, we bring structure, clarity and care to every part of the retirement plan so our clients can focus on running their business while knowing their plan is in good hands.

PLANADVISER: What are three of the most important issues your plan sponsor clients face with their company retirement plans? What actions do you take to assist them in overcoming those issues?

Sylvester: Three of the most important issues our plan sponsor clients face are keeping up with regulatory changes, engaging employees effectively and designing a plan that balances generosity with cost-efficiency.

Regulatory shifts—like SECURE 2.0—can be overwhelming, especially for HR teams juggling multiple priorities. We simplify complex legislation into clear, actionable steps and stay ahead of changes so our clients are always prepared.

Employee engagement is another challenge. Sponsors want their employees to see the value of their retirement plan, but it’s tough to reach a multi-generational workforce with different needs and preferences. We develop custom education strategies that meet employees where they are—whether via on-site sessions, one-on-one meetings or digital resources.

Lastly, many sponsors struggle to design a plan that’s competitive while sustainable. We provide benchmarking, tailored plan design recommendations and strategic guidance to align plan goals with broader organizational objectives—whether that’s improving retention, boosting participation or enhancing retirement readiness.

We see ourselves as problem-solvers and partners—here to make life easier for our clients while improving outcomes for their employees.

PLANADVISER: What’s your favorite book or podcast?

Sylvester: When I’m reading, it’s usually to unwind—so I gravitate toward light, feel-good stories with a little romance and humor. Abby Jimenez and Emily Henry are two of my favorite authors. Their books are the perfect escape at the end of a busy day: smart, funny and heartwarming, without being too heavy. It’s nice to step out of the world of plan design and compliance for a bit and just enjoy a great story.