As you embark on the formidable journey of scaling a business into double-digit ARR, you’re likely facing this challenge for the first time. The weight of responsibility can feel immense, touching not just your employees, but their families, your management team, investors, and yourself. While there’s no playbook to fully prepare you for this unique challenge, seeking guidance from those who’ve tread similar paths can offer invaluable insights.

Reflecting on my tenure at SendGrid, from its $30 million ARR days to its evolution into a publicly-traded entity under Twilio’s wing, I encountered numerous surprises and lessons that I’m eager to share. While every business journey is unique, I believe the lessons learned along the way can offer valuable guidance to fellow CEOs navigating their own growth trajectories.

Transitioning from startup mode to the growth stage demands a radical shift in leadership approach. The tactics that fueled early success must make way for new strategies as the company matures. Leading by example, once effective in the intimate startup setting, gives way to leading by ideas. As the CEO, your role shifts from direct interaction with every employee to inspiring through storytelling, empowering teams to align with your vision even in your physical absence.

A critical aspect of scaling beyond $10 million ARR is widening your aperture to think long-term. While early-stage concerns revolve around immediate survival and validation, growth-stage leadership necessitates multi-year planning. Employees must grasp the long-term implications of their actions, understanding that sustained growth demands foresight and strategic investment in the present.

Communication becomes paramount in orchestrating hundreds of individuals towards a common goal. Establishing the right rhythm of communication, balancing frequency with quality, is key. At SendGrid, we found a monthly cadence supplemented by major all-employee events to be effective, ensuring alignment and transparency across the organization.

As the company scales, role specialization becomes inevitable. While early-stage employees may thrive wearing multiple hats, growth demands Olympic-level expertise in specific domains. Navigating personnel switch-ups becomes essential, ensuring the right talent is in the right roles to drive the company forward.

Decision-making at scale presents its own challenges, often bogged down by interdependencies. Adopting decision-making frameworks like RAPID helps streamline the process, empowering employees to act decisively within defined parameters.

Above all, culture emerges as a steadfast anchor amidst the whirlwind of change. Scaling successfully hinges on scaling culture alongside operations. Investing in culture-building initiatives across the entire employee lifecycle, from recruitment to performance evaluation, reinforces organizational values and fosters a cohesive, empowered workforce.

Scaling a high-growth company demands foresight, adaptability, and relentless commitment to nurturing a thriving culture. Embracing change, communicating effectively, and empowering teams to think long-term are foundational to navigating the tumultuous teenage years of a company’s evolution. It’s a journey of continuous learning, evolution, and ultimately, growth.