The Scalability Trap: Finding Benefits Partners to Grow with You

Throughout my career, I have gravitated toward the ‘build’ phase, which is that pivotal transformation where a company scales rapidly. I often think of it as my ‘Mary Poppins’ streak; I tend to join organizations to help build solid internal structures that scale, and then move on to my next challenge when the company transitions to its next phase.

My focus has always been on transforming organized chaos into high-functioning operational rigor. However, I’ve observed that even the most capable People teams can be undermined by the Scalability Trap. This is when organizations outgrow legacy partners because those vendors lack the agility to keep pace with rapid expansion and transformation—yet they keep the vendor.

Selecting benefits partners, or any technology or service, shouldn’t only be a reactive effort to solve your current challenges. Instead, it requires vetting a partner’s workflows to ensure they can support multiple thousands of employees as effectively as they do hundreds. Ultimately, my goal as an HR leader is to build a seamless system where my teams aren’t bogged down by administrative friction. I build my processes, and my vendor partnerships, to enable them to focus on doing their best work.

Why We Settle for Legacy Vendors: Fear of the Unknown

When faced with the pressures of a transformative phase or tough vendor decision, the easiest thing for a leader to do is to default to their comfort zone. It’s important not to mistake ‘easy’ with complacency: I recognize, from my background in psychology, that our brains are hardwired to perceive the unknown as a threat. This creates a natural bias toward the status quo. Folks often approach complex organizational changes with the same level of caution we’d use in a far more urgent scenario, making it difficult to weigh options objectively.

Often, the path of least resistance is simply to repeat what you’ve done before; whether that means keeping a legacy provider you’ve outgrown or bringing in a vendor just because you’re familiar with them. It’s a repeat history cycle that prioritizes familiarity over the real needs of the future state of your business. This is exactly how companies fall into the Scalability Trap: by solving for the immediate fire with a “brand name”, they inadvertently tether themselves to a partner that lacks the operational rigor to grow with them. 

While the “safe” decisions might’ve been made without question previously, we’ve seen the role of an HR leader evolve significantly over the last decade. We’re no longer stuck in the back room like HR teams of media stereotypes; we are in a position where the broader C-suite is truly listening. We’ve proved ourselves time and time again with the unprecedented challenges of the past 5 years such as the COVID-19 pandemic, remote work, and the proliferation of AI tools. We’re better positioned than ever before to make changes and have the support of our organization behind us, and because of that we’re seeing more HR leaders stick their neck out. 

The HR leaders and CHROs of the future have the confidence to say: I can make things better, I can create something new, and I can try something different. That shift in HR strategy directly applies to leaders reshaping how they think about benefits. We’re done with accepting the status quo and we’re willing to work with modern benefits vendors to execute that vision.

Selecting the Right Benefits Partners for Scale

Identifying Red Flags in Current & Potential Vendors

In my experience, the first sign a partnership is failing isn’t always a major error or meltdown; it’s the realization that the market is moving faster than your vendor. You start to notice a delay in the data, and maybe you’re even spending your own time pulling information and trends, and realize that what you have isn’t going to meet your current, and especially future, needs. You cannot afford to have benefits partners who have a “set it and forget it” kind of ethos. A partner who acts as a middleman rather than an extension of your team quickly becomes a liability when you’re trying to scale.

Other red flags are often found in day to day interactions, or even in how the vendor has built their technology and processes. Clunky, old tools and unresponsiveness creates friction for your teams and employees that takes their focus away from their core responsibilities: it’s a headache for everyone involved. If you give partners feedback and the response is a flat, “Nope, we just don’t do that,” they likely lack the agility required for that next, transformative phase in your business. 

Positive Indicators in Vendor Selection

When you are evaluating if a partner can handle that jump from hundreds to multiple thousands of employees, look for a true thought leadership partner. The “green flags” are found in their DNA: are they proactive with data, and are they pushing you to think ahead of the next compliance change or renewal cycle? That will make all the difference in future-proofing your business.

The one non-negotiable I look for is a partner that is on your side of the table. In a self-funded model, this means they aren’t just reporting claims, they are providing a strategic roadmap and making adjustments every year to improve the plan without creating a huge cost increase. A truly scalable partner doesn’t only manage your benefits—they provide the insight and flexibility that allows your organization to stay focused on its people and goals.

Building a People-First Engine that Scales

I believe that the role of an HR or benefits leader is to put a structure in place that a company can afford, and that is deeply meaningful to its employees. Scaling isn’t just about software; it’s about creating an environment where the employee experience is so seamless that people aren’t spending their day dealing with whether a benefit went through.

I’ve seen how this works firsthand when building benefits from scratch. At one of my previous companies, we used surveys to ensure our benefits actually reflected what our population wanted; whether that was 401k matching or support for fertility programs. When employees feel heard and cared for, they can spend 100% of their energy on their roles. Future proofing is about creating that engine that will live long after the initial build phase is over.

If there’s one truth I have learned from leading these transformations, it’s that change is a constant. The world of work is incredibly unpredictable, and we cannot control the hurdles that come our way. However, we can control the partners we choose to have in our corner. 

Choosing those partners isn’t just about the challenges you face today. Avoiding the Scalability Trap means moving out of your comfort zone of legacy providers and finding partners who are truly agile. With that right mindset and willingness to push boundaries, HR leaders can be the executive that moves the business forward and onto the next phase of growth.