Philip Sherman

Senior Retirement Plan Consultant, Deschutes Investment Consulting, LLC

Business at a Glance

PLANADVISER: How has your retirement plan practice evolved over the past three to five years? What strategic decisions most changed your growth trajectory or client impact?

Sherman: Over the past three to five years, our practice has evolved from a traditional plan‑level consulting model into a deeper, more integrated partnership with the HR and finance teams we support. Rather than expanding by adding layers of staff or leaning on call‑center‑based service structures, we made a strategic decision to stay intentionally small, senior and hands‑on, ensuring that every client has direct access to the same experienced advisers throughout the relationship. This continuity has become one of the biggest drivers of client impact, especially as plans face increasing regulatory and operational complexity.

A second major evolution was our investment in strengthening our technical depth. Bringing an actuary in‑house fundamentally changed the level of design, testing and regulatory guidance we could provide. What once required coordinating across several outside partners can now be addressed quickly and precisely, helping clients make faster and better‑informed decisions on areas like ERISA compliance, match restructuring and nondiscrimination testing. This shift has meaningfully improved outcomes for both sponsors and participants.

Finally, we shifted our focus from helping employers simply “offer a plan” to helping them use the retirement benefit as a strategic tool for attraction, retention and employee engagement. By integrating plan design and education more closely with each organization’s mission and workforce needs, we’ve been able to deliver more intentional, measurable results. These decisions collectively accelerated our growth, strengthened client loyalty and elevated the overall impact of our advisory work.

PLANADVISER: What’s one lesson you’ve learned the hard way as a retirement plan adviser—and how has it changed your approach?

Sherman: One of the most important lessons I’ve learned the hard way is to never assume how much bandwidth an HR team has or how much operational complexity even a small plan change can create for them. Earlier in my career, I occasionally underestimated how stretched HR departments were. A recommendation that seemed simple on paper, such as a match redesign or an adjustment to automatic features, sometimes created a ripple of extra work for a two‑person HR team already juggling payroll, recruiting, onboarding and employee relations. Even well‑intended enhancements could unintentionally add stress.

That experience fundamentally reshaped my approach. Today, we evaluate every recommendation through an operational lens before we even bring it to the committee. We map out the steps HR will need to take, how payroll may be affected, the timing and what ongoing maintenance will look like six months later. We now ask questions like: Will this improve outcomes without overburdening staff? Is this sustainable for this organization? What support will HR need to implement this successfully?

This shift has made our guidance more practical, more empathetic and, ultimately, more effective. It also strengthened our philosophy of acting as a true extension of the HR team: not adding to their workload, but helping them manage it. By grounding recommendations in operational reality, we help plan sponsors make changes that actually stick and generate the participant outcomes they want, without overwhelming the people responsible for carrying them out.

PLANADVISER: What is the most complex or persistent challenge your 403(b) clients face today? How have you helped address it?

Sherman: The most persistent challenge our 403(b) clients face today is improving true retirement readiness, particularly in environments where employees are deeply mission‑driven but often underpaid, stretched thin or hesitant to prioritize their own financial well‑being. Many nonprofit employees enter the workforce later, experience more career interruptions or work in roles that historically have lower wages, all of which make long‑term savings difficult. For HR teams already balancing limited resources and high turnover, advancing retirement readiness can feel overwhelming.

We help address this by meeting organizations where they are and designing solutions that are both realistic and sustainable. We start by analyzing participant behavior—not just participation rates, but deferral patterns, missed opportunities and gaps unique to their workforce. From there, we partner with HR to implement simple, high‑impact plan features such as automatic enrollment, step‑up increases and streamlined investment menus that help employees build momentum without adding administrative burden.

Equally important is education that resonates with nonprofit employees. We deliver financial wellness programs tailored to their realities: seeing savings as self‑care, balancing service‑oriented careers with personal financial security and understanding how even small changes can meaningfully improve outcomes. Because many HR teams lack the capacity to drive this work, we position ourselves as an extension of their staff, handling communication plans, educational workshops and one‑on‑one conversations so employees receive ongoing, personalized guidance.

By simplifying the plan, easing the operational load on HR and delivering mission‑aligned education, we help 403(b) sponsors make meaningful progress toward improving retirement readiness across their workforce.

PLANADVISER: How did you build expertise in the 403(b) market, and what advice would you give advisers considering this specialization?

Sherman: I entered the 403(b) space through referrals from corporate clients who also served on nonprofit boards. Those early introductions gave me a front‑row view into a sector where retirement plans often struggled simply because HR teams were stretched thin and juggling high turnover, limited resources and competing organizational priorities. It became clear that 403(b) plans weren’t just “another plan type” and that they required a different level of support, education and empathy.

To build real expertise, I immersed myself in the nonprofit environment. I spent time understanding how each organization’s mission influenced its culture, its staffing model and its benefits philosophy. Instead of approaching 403(b) plans like 401(k)s, I learned where the operational friction points were: payroll coordination, universal availability, vendor complexity and the reality that benefits decisions often sit with people already wearing five different hats. That understanding allowed me to develop practical, mission‑aligned solutions that support compliance without overwhelming HR.

For advisers considering this specialization, my advice is simple: The technical rules matter, but relationships matter more. Nonprofits want an adviser who is patient, present and genuinely invested in their mission. You must recognize that these plans operate differently—culturally, operationally and financially—and your recommendations need to reflect that reality. When you show that you understand their challenges and are willing to act as an extension of their team, nonprofits respond with extraordinary loyalty. Stay flexible, lead with empathy and let their mission guide your approach.