Remote-First Culture: Building a Company Without Walls
Stelligent Systems LLC was launched during the Great Recession in late 2008 with a vision to revolutionize software development and delivery. Without a detailed roadmap or a significant safety net, we began our journey. From those uncertain early days, we established core principles of flexibility, autonomy, and innovation—values that now form the foundation of a remote-first culture. This post explores our shift from an onsite consultancy to a fully remote-first company and the lessons learned along the way.
From Onsite to Remote-First: Embracing Flexibility
In our early years, we operated as a traditional consultancy, often flying weekly to customer sites across Maryland, Georgia, California, and even as far as China and Australia for extended engagements. While this approach helped build trust and strengthen relationships with customers, it placed a significant strain on our team—especially those balancing family responsibilities.
Even then, we relied heavily on cloud-based tools like Google Workspace (known over time as Google Apps for Your Domain, G Suite, and Google Suite) and Harvest for time tracking and invoicing. This early adoption of cloud tools sparked a simple yet transformative question: Why not run our entire business in the cloud?
From the outset, we adopted SaaS tools to streamline internal operations, including QuickBooks Online for accounting, Expensify for expense tracking, JIRA for project management, TriNet for HR and payroll, and later Slack for communication. At the same time, we were leveraging AWS to deliver scalable, innovative solutions for several customers. In 2013, we made a bold decision to focus exclusively on AWS for all customer engagements. This decision wasn’t just technical—it was cultural. By fully aligning with AWS, we didn’t just simplify our offerings; we embraced a partner that shared our core values of innovation and scalability.
This evolution also marked a shift in our operating model. We transitioned away from traditional weekly onsite engagements to adopt a remote-first approach. While we still often kicked off engagements in person and maintained relationships through periodic onsite check-ins every 4–6 weeks, most of our collaboration became virtual. Some customers were initially hesitant, but most quickly recognized the benefits of this model: greater flexibility, improved efficiency, and access to a broader, more diverse talent pool.
Building a Remote-First Culture
Transitioning to remote-first required more than just tools—it demanded intentional strategies to foster a thriving culture. Here’s what worked for us:
1. Hiring for Remote-First Success: Our hiring process prioritized technical skills and the ability to thrive in a remote-first setting. Candidates went through a rigorous process that included technical screenings, real-world coding challenges, and collaboration on a small project. Finalists presented their work in a live demo, proving they could work autonomously while contributing collaboratively. By the time we were 20 people, around half the company often participated in evaluating a single candidate, ensuring the high bar wasn’t just a principle but a practice.
2. Annual and Small-Scale Gatherings: AWS re:Invent became our de facto company reunion, reinforcing our commitment to learning by requiring active AWS certifications for attendance. Later, we launched StelliCON—an annual gathering for alignment, learning, and celebrating our unique culture. These moments weren’t just about connection; they solidified our shared mission.
3. Intentional Mentorship: Every new hire was paired with a buddy/mentor for their first 100 days, guided by a detailed onboarding checklist. This mix of structure and human connection ensured smooth transitions and accelerated their ability to contribute meaningfully.
4. Asynchronous Workflows: “If it’s only in your head, it doesn’t exist.” Documentation was our mantra, enabling autonomy and minimizing bottlenecks. From onboarding checklists to code reviews, we externalized knowledge to empower teams.
Tools and Practices for Remote Success
Our remote-first approach was supported by a thoughtfully chosen stack of tools, refined through experimentation and iteration. We explored many SaaS options across different categories to find what worked best for our team. Over time, some predominant tools emerged:
- Collaboration: GoToMeeting for virtual meetings, Slack for quick communication, and JIRA for tracking work became staples in our workflow.
- Knowledge Sharing: Confluence, Google Drive (Docs, Slides, and Sheets), and GitHub became our go-to platforms for maintaining single sources of truth.
- Informal Communication: To foster camaraderie and replicate the "water cooler" experience, we relied on tools like Sococo to create a sense of shared virtual space.
While these tools were pivotal, our willingness to explore and adapt new solutions ensured that we could continuously improve how we worked together remotely.
When I joined AWS in 2021, I was drawn to its culture of innovation, autonomy, and customer obsession—principles I had embraced throughout my career. Amazon’s Leadership Principles, particularly long-term thinking, felt like a natural extension of the values we had cultivated while building Stelligent.
In 2023, Amazon’s decision to implement a return-to-office mandate felt like a step backward. Trust, flexibility, and autonomy—the principles that had driven Stelligent’s success—seemed to be replaced with a model less aligned with the evolving realities of modern work. That said, I recognize the immense challenges of managing an organization on Amazon’s scale. Unlike a 75-person company, Amazon faces complexities like real estate investments, early-career mentoring, cultural perceptions, and the logistical hurdles of a global workforce—problems without simple solutions. I don’t envy the difficulty of making such a decision.
At Stelligent, we chose to be remote-first rather than remote-only, though we didn’t always fully achieve that ideal. Our goal was to strike a balance, fostering flexibility while maintaining meaningful in-person collaboration.
Ultimately, this experience underscored a critical lesson for me: resilience in today’s business landscape requires more than technological innovation. It demands an organizational mindset willing to adapt to the changing nature of work. Autonomy, trust, and flexibility aren’t just cultural ideals—they are competitive advantages in a rapidly shifting world.
Key Takeaways for Building a Remote-First Business
- Do Interesting Work: Culture isn’t about perks; it’s about purpose. By taking on work that mattered—pushing boundaries and delivering tangible impact—we attracted top talent driven by the opportunity to solve complex problems for customers.
- Foster Intentional Connections: Strong relationships don’t happen by accident. Combining virtual collaboration with periodic in-person gatherings helped us align, build trust, and strengthen bonds.
- Empower Teams with Autonomy: Autonomy starts with clarity. We prioritized documentation, mentorship, and shared systems to enable our teams to operate independently and confidently.
- Invest in Tools and Systems: The right tools remove friction and amplify focus. By adopting SaaS solutions early, we built a foundation for seamless collaboration and scalability.
Resources for Remote-First Success
- GitLab's Guide to All-Remote - I love that GitLab shares its culture openly with the world.
- Remote: Office Not Required by Jason Fried and David Heinemeier Hansson
- The Year Without Pants by Scott Berkun
Building a remote-first business isn’t just about tools or policies—it’s about trust, intentionality, and shared purpose. The lessons we learned at Stelligent remain just as relevant today as they were during our early days.
I’d love to hear how your organization is navigating the future of work. Are you leaning into flexibility or doubling down on traditional models?