Taylor Roa, Head of People & Talent at January, shares how a nine-year-old Series B company achieved something virtually unheard of in startup culture: zero layoffs through every market cycle while maintaining sustainable growth. As January approaches their hockey stick growth moment after years of disciplined scaling, Taylor reveals how they’re reinventing their hiring approach to double their team size while preserving the cultural elements that drove their success. His framework for building lean, efficient teams through AI-powered recruiting and intentional culture evolution offers a blueprint for sustainable scaling without the typical startup growing pains.

Topics Discussed

• Building sustainable growth cultures that survive market downturns without layoffs
• Creating writing-first cultures that enable async collaboration and thoughtful decision-making
• Developing outbound recruiting strategies for companies without strong brand awareness
• Implementing AI tools across people operations to increase team efficiency by 50-200%
• Managing cultural evolution during controlled growth phases rather than hypergrowth
• Building people functions that amplify founder strengths instead of fixing cultural problems
• Designing lean team structures that can scale to IPO with plateau headcount models
• Creating hiring processes that prioritize exceptional talent over rapid volume scaling

Lessons For People Leaders

Choose Your Founder Before Building Culture

Rather than trying to change or fix company culture, Taylor emphasizes selecting founders whose core values align with your people philosophy. He recommends conducting root cause analysis on previous workplace tensions to identify whether conflicts stemmed from value misalignment or strategic disagreements. Ask founders directly about their expectations for the people function and how they want to partner with you. This approach prevents the notorious tension between HR leaders and CEOs by ensuring alignment before joining.

Amplify Cultural Strengths Instead of Building From Scratch

At companies with established cultures like January’s nine-year foundation, the people function’s role shifts from building culture to understanding what works and amplifying key elements. Taylor identifies the most important cultural differentiators that contributed to success, then helps leadership become “maniacal, repetitive, and unwavering” about reinforcing these elements. This requires studying the founder’s natural leadership style and extending their best qualities throughout the organization while softening sharp edges.

Embrace Cultural Evolution Instead of Preservation

Taylor reframes the common question of “how to preserve culture during scaling” by acknowledging that doubling headcount inevitably changes culture through new personalities and perspectives. Instead of fighting this natural evolution, he focuses on identifying the simplest list of unique elements that drove success and remaining open to how culture evolves at scale. Leadership must consistently reinforce core differentiators while allowing organic cultural development.

Build Outbound Recruiting Systems for Brand-Unknown Companies

January transformed from relying on inbound applications to building an intensive outbound search function, giving them control over talent bar and pipeline diversity. Without marketing team or brand awareness, they created custom sourcing strategies using AI tools like Juicebox and custom GPTs to optimize messaging based on response rates. This approach enables selective hiring for companies that can’t rely on employer brand to attract top talent.

Deploy AI Tools as Competitive Necessity

Taylor positions AI adoption as career-critical, stating that companies banning AI tools provide “the best reason to quit your job.” His team implements AI across all recruiting functions: Granola for automated interview transcription and scorecard creation, custom GPTs for hiring strategy development, and AI-powered sourcing tools. Team members report working 50-200% faster in specific areas, making AI proficiency essential for resume competitiveness in the next two years.

Design Lean Growth Models That Plateau Strategically

January’s founder explicitly aims to plateau headcount at 250-300 employees while continuing business growth, enabled by AI and efficiency tools. This model challenges the traditional startup mentality of hiring for every problem and instead focuses on finding the most exceptional people who align with rigorous, truth-seeking culture. Taylor manages this by treating each hire as precious, investing extraordinary effort in outbound search to ensure every addition maintains cultural and performance standards.

Focus on Relationship Building in First 90 Days

For new people leaders, Taylor prioritizes trust-building with stakeholders over immediate system implementation. He acknowledges that people operations involves working with leaders who each have different expectations, making relationship building crucial for success. New people leaders should align upfront on priorities and focus areas, as most initiatives require more work than stakeholders realize and explaining this complexity requires established trust.