How to Craft a Winning Content Strategy for Your Agency with Ross Crooks

Gray MacKenzie sits down with Ross Crooks, co-founder of Column Five, to discuss how the agency built a reputation as a leader in content strategy and brand storytelling. Column Five works with tech companies, education organizations, and nonprofits to develop brand narratives that drive measurable results. In this episode, Ross shares how the agency evolved from a scrappy content shop into a full-service brand strategy firm.

From Lifestyle Blog to Content Strategy Powerhouse

Column Five’s origin story is anything but conventional. Ross and his co-founders started with a lifestyle blog in 2007-2008, originally designed to cross-promote their individual clothing businesses. When early clients like Mint.com approached them for content creation, the team recognized an untapped opportunity in data visualization and infographics - a format that barely existed as a commercial service at the time.

Being first movers in that space gave Column Five a significant competitive advantage. While other agencies were focused on traditional marketing deliverables, Ross and his team were pioneering visual content that brands could use to simplify complex data and tell compelling stories. That early bet on an emerging format defined the agency’s trajectory and attracted clients like Uber, LinkedIn, GitHub, QuickBooks, Brex, and Ramp.

Over time, the agency shifted from producing viral content pieces to building comprehensive brand strategies. Today, Column Five’s approach encompasses three key phases: understanding brand purpose and values, developing strategic frameworks, and executing content production. This evolution from execution to strategy represents a pattern that many successful agencies follow - moving upstream to deliver higher-value work.

Organizational Structure That Scales

One of the most practical takeaways from the conversation is how Column Five structures its team to support both client relationships and creative output. The agency organizes around three core roles. Account Directors manage client relationships and identify growth opportunities within existing accounts. Strategists develop brand and content strategies that align with client business objectives. Producers oversee creative execution and project management, ensuring work ships on time and on brief.

This structure creates clear ownership at every stage of the client lifecycle. Account Directors own the relationship. Strategists own the thinking. Producers own the output. When these roles are well-defined, the agency avoids the common pitfall of having one person try to manage relationships, develop strategy, and oversee production simultaneously - a model that breaks down as the agency scales.

Ross notes that Column Five serves over 100 clients annually across diverse industries. That breadth reduces client concentration risk while building cross-industry expertise that makes the team’s strategic recommendations stronger. Patterns that work in tech can be applied to education. Storytelling techniques from nonprofit work can elevate corporate brand narratives.

Scaling Challenges and Growth Strategy

At the time of recording, Column Five was anticipating 25% growth and actively hiring strategists, account directors, and video producers to support that expansion. Ross is candid about the primary constraint: finding and retaining the right people.

Recruitment and team building are where most of the growing pains show up. The agency needs people who can think strategically and execute creatively - a combination that is not easy to find. Balancing flexible staffing arrangements with dedicated team consistency remains an ongoing challenge. Contractors provide flexibility but can lack the institutional knowledge that makes client work seamless. Full-time hires provide consistency but require sustained pipeline to keep them utilized.

Ross also discusses how business development works at Column Five. The agency’s content itself serves as a primary growth driver - when you are known for producing exceptional content strategy work, that reputation generates inbound interest. M&A activity and client network effects naturally drive additional growth, with referrals from satisfied clients creating a compounding pipeline over time.

Building a Content Strategy That Works

The broader lesson from Column Five’s story is that content strategy is not just about producing more content. It starts with understanding what a brand stands for, who it serves, and what it is trying to achieve. Only then does the conversation shift to formats, channels, and production schedules.

Agencies that skip the strategy phase and jump straight to execution end up producing content that looks good but does not move the needle. The ones that invest in understanding brand purpose first create content that compounds in value - building audience trust, establishing authority, and driving business results over months and years rather than chasing short-term virality.

Resources Mentioned

• Ross Crooks on LinkedIn - Co-founder, Column Five
• Column Five - Brand strategy and content agency
• Column Five Careers - Open positions