In the early days of a company, culture is shaped by proximity: shared desks, late nights, and the push and pull of turning ideas into reality. Decisions are made quickly and everyone knows each other by name. But as you scale – especially as a remote-oriented organization – that sense of connection can quietly fade. Suddenly you realize you can’t attend every onboarding, celebrate every milestone, or even recognize every face on a Zoom call.
That moment should give you pause. If not, you’re missing a red flag.
At Appfire we went from a small team to almost 800 people on multiple continents. Our ‘remote-first’ approach lets people ‘work where they wake up’, but also brings a new set of leadership challenges. In a world defined by volatility, uncertainty, complexity and ambiguity (VUCA), the old playbook of hallway conversations and impromptu lunches doesn’t cut it. Staying connected and relevant requires purposeful, adaptable systems for communication, empathy, and trust.
Here’s what I’ve learned (often the hard way): What works for 50 people absolutely breaks the bank with 800. Here are four principles I rely on to keep our culture intact as we grow, no matter how turbulent or complex the environment.
Communicate consistently to anchor the culture
When you can’t rely on physical presence, leadership communication becomes your presence. In my first month at Appfire, I started recording bi-weekly Loom videos: short, informal updates on everything from key board meeting information to customer feedback, industry trends, and what keeps me up at night. They are deliberately unpolished. The point is authenticity, not production value.
But it’s not just about me talking to people. Company-wide meetings – virtual or otherwise – are essential for transparency and alignment. Change the format: one month, an unscripted Q&A; the next, a complete focus on product milestones or wins. Routine is good, but predictability can cause apathy. Variety keeps people engaged and shows that leadership is present, listening and investing, even across different time zones.
In VUCA environments, these touchpoints become cultural anchors, holding the ship in place when the water gets rough.
Lead with empathy, especially through change
Growth brings change: new processes, shifting priorities, new faces. This can cause friction, especially if people feel overlooked or misunderstood. Empathy is not just a ‘soft skill’; it is an important prerequisite for leadership, especially in uncertain or ambiguous circumstances.
You don’t need every answer, but you do need to listen – really listen. Ask questions. Make it clear that you are aware of the daily realities that people face, whether it is your tenth or your 900th employee. Empathy creates psychological safety and unlocks collaboration and innovation, even as the ground shifts beneath us.
And in a globally distributed, remote workforce, empathy means respecting differences: work styles, time zones, communication preferences. Flexibility and inclusivity are not advantages; they are strategic imperatives in a complex world.
Assume a positive intention and try to understand it first
As companies grow, silos form. Communication takes place via Slack, Zoom or email: easy recipes for misinterpretation. My standard? Assume a positive intention. When something doesn’t make sense, I encourage teams to seek understanding first, not just to be understood.
This mindset is a buffer against the ambiguity that naturally creeps in as organizations grow and evolve. It is especially critical during moments of change: new tools, changing strategies, reorganizations. Curiosity over judgment promotes better cooperation, healthier conflict, and ultimately stronger relationships.
As a leader you must model this. It sets the tone for everyone, especially when things get messy.
Focus on what you can control
Let’s be honest: the world isn’t getting any easier. Markets fluctuate, technologies disrupt, geopolitics intrude. In a volatile, complex landscape, the temptation is to let yourself go into hiding or be distracted by what you cannot control. Resist it.
We cannot control the macroeconomy or global events. But we can control the quality of our products, the strength of our partnerships, the depth of our customer relationships and the authenticity of our culture. We can prioritize creating real value over chasing hype. We can stand up for each other. Grounding teams in what is controllable promotes resilience, clarity and focus, even in chaos.
Intention over scale
Scaling is not about headcount. It’s about evolving the way you lead when the old rules no longer apply. CEOs of remote-oriented, high-growth companies can’t rely on proximity or familiarity. We need to be purposeful – when it comes to communication, empathy, trust and clarity. These are not nice-to-haves. In a VUCA world they form the infrastructure of sustainable growth.
At Appfire I may never know every employee personally, but I do want every employee to feel like he or she knows me. Not through perfect videos, but through a cadence of authentic, consistent leadership. Staying connected isn’t about scale. It’s about purposeful intention in the face of complexity and uncertainty.
This is how you build a culture that scales – and survives – in a remote, unpredictable world.
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