Hiring for Remote-First Success

As a cofounder of Stelligent, I was deeply involved in building the company as a remote-first organization designed for success in a distributed environment. Hiring was central to this effort: from the initial screening to the final offer, every step of the process was carefully designed to identify candidates with exceptional technical expertise and the autonomy to excel in a remote setting. However, the process didn’t always go smoothly, and there were important lessons learned along the way.

Early Career Lessons

Earlier in my career, I joined an elite consulting firm called Number Six Software as employee number 12. Within a year, transitioning from a large enterprise of 100,000 employees to a small company was a refreshing and distinct experience. Number Six was run by two highly technical co-founders who had bootstrapped the business, and its reputation for object-oriented programming expertise was well-earned. The hiring process there was intense and included multiple interviews plus a presentation to the entire team.

Despite the rigor, I secured a position that felt like joining the Navy SEALs of software engineering. A few years after Rob Daly sold his stake in Number Six, the two of us started a new venture that eventually became Stelligent Systems, LLC. Stelligent focused on DevOps Automation and Continuous Delivery on AWS for enterprise customers. This company was also bootstrapped and was successfully sold in 2017–18.

The Challenges of Bootstrapping

Bootstrapping often means juggling roles: sales, marketing, delivery, and operations—all in the same day. While exciting, it’s easy to feel stretched too thin. In the early stages, I made what would become legendary hires based on personal and professional relationships. But when it came time to hire from a larger pool, I lacked a structured system to evaluate and onboard new candidates. Under pressure, I made a hiring mistake that a small company couldn’t easily absorb. Rob urged me to build more robust systems—an important reminder that people problems often stem from flawed processes.

Creating a Rigorous Hiring Process

Inspired by experiences at Number Six and insights from one of Stelligent’s customers, we developed a hiring system to maintain an exceptionally high bar. The goal was to attract and retain experts in a specialized field.

1. Technical Screening

Candidates began with a phone screen conducted by a senior engineer, focused on evaluating both technical knowledge and communication skills.

2. Remote Pairing

Successful candidates then advanced to a live remote pairing session with an engineer, where they collaborated on a coding or configuration exercise based on real-world scenarios—avoiding contrived puzzles or abstract challenges. While this stage was particularly intense and provided valuable insights, it could also be difficult to evaluate consistently. To address this, the process was refined to focus on presenting candidates with flawed code. Their task was to identify the errors, explain them, and improve the code—an approach that better aligned with practical problem-solving and critical thinking skills.

3. Real-World Mini-Project

If the pairing session went well, candidates tackled a simple but open-ended project:

Write code in a language or configuration management platform of your choice that provisions an environment on Linux or Windows. Configure a web server displaying a static HTML page with the words “Automation for the People.” Provide a single command that launches this environment, and commit all code to a public version-control repository along with usage instructions.

Some candidates sought far more detailed instructions, but strong performers excelled in navigating the ambiguity. The challenge was intentionally open-ended, with no single "correct" solution, and it wasn’t designed to trick anyone. The evaluation emphasized simplicity, clarity, and the ability to effectively communicate both the approach and the practical application of the solution. This approach helped identify engineers who were self-directed, resourceful, and creative—essential traits for thriving in a remote environment.

4. Live Presentation

Finally, candidates presented their completed project—or a topic of their choice—to a panel of engineers. This stage went beyond showcasing technical skills; it evaluated their ability to articulate ideas clearly and respond to real-time feedback—critical competencies in a remote-first culture.

As the company expanded, the hiring process often involved multiple team members collaborating to assess a single candidate. This collective approach fostered a sense of shared ownership in hiring decisions and helped maintain consistently high quality standards. However, as the hiring volume increased, the lead time between initial contact and a final decision became unacceptably long—reaching around 45 days at one point. Recognizing this bottleneck, the process was streamlined to reduce delays while preserving the rigor and thoroughness essential to identifying top talent.

Why the Investment Paid Off

Involving a dozen people in the interview process may seem excessive, but in a small, remote-first organization, even a single bad hire can have significant cultural and financial consequences. Rigorous screening for technical autonomy and cultural alignment helped mitigate these risks and strengthen the company’s foundational culture. However, the process wasn’t entirely fail-safe; some hires still failed to embody the deeper cultural values, highlighting the importance of ongoing vigilance. This lesson became even more apparent to me during my experience hiring at AWS, where the stakes and expectations were even higher.

Building and Maintaining a Strong Remote Culture

Hiring is only the first step. Truly remote-first organizations must consistently invest in onboarding, communication, and collaboration practices. However, following the 2018 acquisition, we made some missteps that eroded certain aspects of the remote-first culture that we'd originally cultivated. While these were regrettable, they also underscored the importance of intentional processes and continued vigilance to keep a remote culture strong.

Over time, Stelligent published lessons on scaling remote teams, from effective new-hire onboarding to keeping distributed groups cohesive and productive. See Hiring and Onboarding Employees in a Remote-First World, 5 Practical Tips for Making Remote Work Successful, and Lessons Learned: Work Remotely and Effectively.

Final Thoughts

A remote-first company doesn’t just materialize—it must be carefully designed and constantly nurtured. By placing significant effort into hiring, Stelligent was able to maintain high technical standards and foster an environment where everyone could collaborate from anywhere.

Yet even the best systems can falter if leaders lose sight of the core principles that built those systems in the first place. Have you implemented mechanisms that support robust remote hiring and culture?