A Tale of Two Startups: What I Learned About Hiring

This newsletter is based on my Linkedin carousel series called "A Tale of Two Startups". You may access the carousel here.

In the fast-paced world of startups, assembling the right team can be the difference between success and failure. As the COO of two venture-backed SaaS companies with vastly different outcomes, I’ve experienced firsthand how hiring practices shape the fate of a company. One startup was successfully acquired, while the other struggled and failed. Through these experiences, I learned crucial lessons about the role of hiring in building a high-performing team and sustaining company growth.

Here’s what I discovered about the power of great job descriptions, structured hiring processes, personality assessments, and the importance of standardizing hiring practices.

1. It All Starts with a Great Job Description

Acquired Startup:
We invested time in creating detailed job descriptions that resonated with candidates. Each description was designed to speak directly to the people we wanted to hire, making them feel like the role was tailored for them. This approach attracted top talent who aligned with our company’s needs and culture.

Failed Startup:
The failed startup didn’t fully document job descriptions. We often hired without clarity on what the role entailed, leading to mismatched expectations and underperformance.

Lesson: A well-crafted job description is the foundation of successful hiring. Candidates should read a job posting and feel that it was written specifically for them. Clarity in expectations attracts the right people and sets them up for success from day one.

2. Assembling a Great Team Requires a Formal Process

Acquired Startup:
We followed a well-defined process for vetting candidates. This included multiple interview stages, scorecards, and input from several team members. The structured process helped reduce bias and ensured that candidates were evaluated thoroughly.

Failed Startup:
Hiring decisions in the failed startup were often based on friend referrals and gut feelings. Without a formal vetting process, we missed critical red flags, which led to poor hiring decisions.

Lesson: A formal hiring process is essential for assembling a high-performing team. Involving multiple team members in the process helps catch things you might miss and reduces the likelihood of hiring based on bias or incomplete information.

3. Personality Assessments Are Key to Designing Roles and Evaluating Fit

Acquired Startup:
We used personality assessments to design roles and evaluate candidates for fit. This ensured that the people we hired not only had the necessary skills but were also a good match for the company’s culture and the specific demands of their roles.

Failed Startup:
The failed startup didn’t use personality assessments during hiring. As a result, we often ended up with employees who weren’t a good fit for the roles they were hired for, leading to poor performance and high turnover.

Lesson: Hiring without personality assessments is like flying blind. These tools provide valuable insight into how a candidate will fit into the team and the role. They help prevent mismatches and ensure that new hires are set up for long-term success.

4. Standardizing Hiring Practices Keeps the Bar High

Acquired Startup:
We implemented Topgrading to standardize our hiring process across the company. This method ensured that every candidate was evaluated against the same high standards, and it helped us maintain a consistent quality of hires across all departments.

Failed Startup:
Each manager at the failed startup used their own approach to hiring, leading to inconsistent results. This lack of standardization allowed poor hires to slip through, negatively impacting culture and productivity.

Lesson: Standardizing your hiring practices ensures that the bar remains high for every candidate. Without consistency, you run the risk of letting bad hires through the door, which can poison your company’s culture and undermine productivity.

What Can We Learn?

Hiring is one of the most critical factors in a startup’s success or failure. From crafting detailed job descriptions to implementing formal hiring processes, personality assessments, and standardized practices, every step of the hiring journey plays a crucial role in building a successful team.

If you want to create a high-performing company, it starts with hiring the right people—and that requires thoughtful, intentional processes. Take the time to invest in your hiring strategy, and you’ll build a team that can take your business to new heights.