The Unsung Heroes of Startups:

Over our work supporting hiring and team building with early stage startups over the past 5 years has us working hand in hand with many Chief of Staff type roles. These close collaborations led to my co-creating an intimate cohort program for folks to collaborate and learn in community. We just wrapped up our first 3 month cohort and it was really amazing. This piece is dedicated to the to the early stage Startup People and Operations Leaders who have graciously let me into their worlds.

While they often join our organizations and elevate us all upwards - if we don’t invest in their continued learning and growth - they can become the ceiling of the organization too.

In the fast-paced world of startups, the roles of Chief of Staff, Chief Operations Officer, Operations Manager, and Head of People are often cloaked in complex titles. Yet, these positions, which we can collectively refer to as People and Operations Leaders, often serve as the linchpin that can make or break a business.

Through numerous interviews with candidates from startups that failed—whether through abrupt shutdowns, slow declines, or fire-sale acquisitions—a striking pattern has emerged. Many of these leaders pointed to a common theme: a lack of focus on HR, People, and internal culture played a significant role in their organization’s downfall. The issues often started earlier but went unaddressed, until it was too late.

Why "People" Challenges Are So Tricky

Unlike more quantifiable aspects of a business, like sales or marketing metrics, "people" challenges are less exact and harder to measure. For example, when implementing a new paid family leave plan, the long-term impact is difficult to forecast. This uncertainty often results in such issues being pushed to the "tomorrow" pile—a place where they often languish indefinitely.

To address these challenges, startups frequently hire Operations pros who are not only organized and capable of executing strategies but also adept at handling complex problems. These leaders often step into multiple roles, running departments until they are sufficiently operational to justify hiring more specialized leaders. They become the go-to individuals when employees face issues or when something about the business feels off.

The Multifaceted Role of People and Operations Leaders

Although these generalists excel in many areas, managing "people" functions is particularly challenging. They must serve as the bridge between individual contributors and the executive team, keeping a finger on the pulse of the organization, and addressing issues before they escalate. They also need to build buy-in with the CEO, solve problems that only they foresee, and manage change effectively.

In our recent cohort of People and Operations Leaders, several key insights emerged:

1. Early Detection of Cultural Challenges: These leaders are often the first to sense cultural issues before they become significant problems. Their insights, while frequently accurate, are not always taken at face value by leadership, which wastes important time.

2. Storytelling and Influence: They need to be the company’s best storytellers, using their narrative skills to build support and drive change across multiple levels of the organization.

3. Change Management: Managing change effectively is perhaps their most critical role. They are tasked with steering the organization through transitions and ensuring that changes are adopted smoothly. It’s hard to think of an initiative worth doing that doesn’t require some adjustment to our behavior and way of thinking.

4. The Loneliness of the Role: This function can be isolating. People and Operations Leaders invest heavily in the well-being of their teams, often neglecting their own needs and support.

One surprising revelation from our sessions was the immense value participants gained from simply discussing their challenges and sharing experiences. While expert-led sessions were beneficial, the true magic happened during open discussions where leaders explored their issues, brainstormed solutions, and offered support to one another.

Looking Ahead

The impact of these leaders is profound, as evidenced by a total transformation in one of the businesses represented in our cohort as a result of supporting and empowering this function. This underscores the critical importance of the People and Operations function and the need for robust support systems.

Our next cohort will commence this fall. If you're a startup operations leader or a Chief of Staff, consider joining us to gain insights, share experiences, and strengthen the vital role of People and Operations Leaders in your organization. [Details and registration link]

PS - Reading this and realizing you need a dynamic leader in your business? Let’s chat - we have a strong candidate pool of startup pros who are ready for their next impactful role as an organizational change leader.