Pros
A mission worth believing in. Exceptionally talented and dedicated coworkers. Opportunities to solve challenging and meaningful problems. Teams that genuinely care about customers despite the obstacles placed in front of them.
Cons
Human Interest has a mission I genuinely believe in, which is what makes watching it undermine itself so frustrating. The company has hired incredibly talented people across Account Management and Operations. Many of them care deeply about helping customers and want to build something exceptional. Unfortunately, the organization's incentives consistently work against those goals. From a leadership perspective, the company's greatest challenge wasn't talent—it was priorities. If you want to understand Human Interest's culture, don't read the values. Follow the incentives. The company invests heavily in acquiring customers and partnerships while consistently underinvesting in the teams responsible for keeping them. Sales is rewarded for closing business. "Onboarding" is, in practice, an extension of Sales. The organization is heavily incentivized to move customers through the pipeline as quickly as possible, and when implementation teams are compensated like revenue organizations, they naturally optimize for speed rather than customer readiness. That isn't a criticism of the people doing the work. It's the predictable outcome of how the organization is designed. The result is equally predictable. Customers are often promised an experience that the post-sales organization simply isn't given the resources to deliver. Those customers then arrive in Support and Account Management requiring significantly more guidance than they should, and the customer-facing teams are expected to absorb the operational debt created upstream. Meanwhile, the organizations responsible for retaining customers and protecting long-term revenue are asked to do more with less. The imbalance in investment is difficult to ignore. Customer-facing teams routinely operate with fewer resources, increasing workloads, and constant pressure to compensate for decisions they had little ability to influence. What was most disappointing was that many of these issues were foreseeable. Leaders closest to customers repeatedly identified risks, surfaced operational concerns, and offered practical solutions. Too often, those perspectives were overshadowed by short-term revenue objectives. The executive leadership of the revenue organization deserves particular attention because much of the company's organizational dysfunction originates there. There appeared to be far greater value placed on blanket agreement than experience and expertise. Leaders who challenged assumptions with operational experience, customer insight, or data often had less influence than those willing to reinforce existing narratives. That leadership dynamic has consequences. It becomes increasingly difficult to solve root causes when raising them is viewed as resistance rather than leadership. As a result, many of the same operational problems continue to resurface while customer-facing teams are left managing the consequences. The Human Resources organization was equally disappointing. In my experience, it was the least effective HR team I've worked with. For an organization of this size, the resources, guidance, and leadership support provided by HR were surprisingly immature. Managers were often given simplistic frameworks and training that fell well short of the complexity of the situations they were expected to navigate. Rather than serving as a strategic partner, HR frequently delegated significant responsibilities to frontline leaders while providing limited practical support. Even more frustrating was the inconsistency in priorities. Managers were expected to spend significant time documenting and coaching relatively minor issues, while much more serious organizational concerns were often minimized or dismissed. It created the impression that process was valued more than judgment. Perhaps most concerning, managers were frequently expected to communicate difficult messages or enforce expectations that HR itself was unwilling to clearly state in its own documentation, guidance, or employee-facing resources. Instead of providing clarity and organizational alignment, HR often left frontline leaders carrying those conversations alone, creating unnecessary inconsistency and eroding trust between employees and managers. The irony is that Human Interest has everything it needs to succeed: a meaningful mission, talented employees, and a product that solves a real problem. What it lacks is leadership willing to invest in customer success with the same intensity it invests in customer acquisition. The company doesn't have a customer problem. It has an alignment problem. Until executive leadership—particularly within the revenue organization—begins valuing long-term customer outcomes as much as quarterly growth metrics, I believe the same patterns will continue.