From English teacher to B2B lead magnet: Samuel Cook's data-driven AI strategy that increased leads by 900%
Comparitech's Samuel Cook reveals how he A/B tests AI vs human email subject lines and grew B2B leads 900% with data-driven content strategy.
Samuel Cook's transition from high school English teacher to Head of B2B Strategy and Development at Comparitech wasn't typical. But his journey—driven by stress, curiosity, and a knack for turning content into conversions—offers valuable lessons for marketers navigating AI adoption in 2025.
Cook now leads B2B strategy at Comparitech, a cybersecurity review platform that provides in-depth software comparisons and security guides for business buyers. Founded in 2016 and acquired by Aura in 2022, Comparitech reaches over 700,000 monthly visitors with authoritative content covering VPNs, antivirus software, network security tools, and IT solutions.
Comparitech's unique SupportScore methodology helps B2B buyers evaluate vendor support quality—a critical factor when average software contracts span 1-3 years and wrong choices can cost hundreds of thousands of dollars.
Why an English teacher became a marketing strategist
Cook's career pivot began during his final year teaching English at Albemarle County Public Schools. "Teaching is one of the most impactful, but most stressful jobs one can have," Cook explains. "You're in a constant battle with quite literally everything around you: students, teachers, administration, technology, time."
The statistics back up his experience. Recent data shows that 55% of teachers plan to quit their current education roles earlier than originally intended, with newer teachers facing particularly high turnover rates. Cook started freelance writing on Upwork during his last teaching year, discovering he could earn comparable income with significantly less stress.
"The fact that I could get paid to do something so low-stress was incredible," he says. Cook not only replaced his teaching income within his first year of freelancing but doubled it within three years, reaching over US$100,000 annually while working just 30 hours per week.
His specialization in SEO-driven content led to a long-term freelance relationship with Comparitech, where he contributed to growing the site's organic traffic from under 30,000 to over 700,000 monthly visits by 2020.
After six years of freelancing, Cook joined MentorcliQ as Content Strategist in 2021, eventually rising to Content Director. There, he learned from marketing leaders like Gracey Cantalupo (now VP of Marketing at Aptarro) and Megan Love (now VP of Marketing at Axero Solutions), who gave him opportunities to tackle stretch projects and develop his strategic thinking.
Enricko Lukman
Running AI experiments in email subject lines
Cook's approach to AI adoption is refreshingly practical. Rather than wholesale automation, he uses AI as a testing partner and creative collaborator.
"I've been running an experiment for a few months that compares my own subject lines for our email newsletter to those created by ChatGPT," Cook reveals. The process is simple: Comparitech's Head of Data Research Bec Moody drafts email content, Cook feeds it to ChatGPT for subject line suggestions, then A/B tests AI-generated options against his own ideas.
The results? "I'm currently winning, but I don't always win those A/B tests, and that's important," Cook notes. This finding aligns with broader industry data showing that 47% of people decide whether to open an email based solely on the subject line.
His AI toolkit extends beyond email testing. Cook uses ChatGPT for ideation, research, outlining, and data analysis. Typeset helps convert content into ebooks. Microsoft Clarity's AI tool summarizes heatmaps for quick insights. Perplexity assists with rapid research queries.
Despite having "zero programming skills," Cook has also leveraged AI to build functional tools in Google Sheets—creating apps that intake and visualize Comparitech's proprietary data in easily replicable formats for his team. "AI tools have helped me formulate and build tools and processes that I couldn't have without them," he explains.
This measured approach to AI tool adoption reflects broader trends in marketing automation, where successful implementation requires balancing automation with human oversight.
"That's where experienced marketers still have a critical advantage," Cook emphasizes. "AI can't act on hunches or leverage years of industry intuition—that's still uniquely human."
The content-to-lead conversion strategy that delivered 900% growth
Cook's biggest win at Comparitech came from a deceptively simple strategy: creating valuable downloadable content for existing website visitors.
When Cook rejoined Comparitech in August 2024, the company had roughly three pieces of downloadable content generating 10-15 leads weekly. Within months of implementing his expanded content strategy (like this one below), weekly lead volume increased by 900%.
"We look to provide added value to people visiting our site, so we create additional, bonus content they can download and take with them," Cook explains. This includes cheat sheets, how-to guides, and streamlined versions of web content.
The strategy works because it captures intent data at the moment of highest engagement. Someone downloading a networking monitoring tools guide is likely in-market for that software category. A CISSP certification cheat sheet signals serious career advancement intentions from experienced IT professionals.
This approach reflects broader B2B marketing trends. Research shows that 75% of B2B purchase cycles take 4+ months and involve 6-10 decision makers. By providing immediate value through downloadable content, Comparitech builds relationships early in extended buying journeys.
How intent data drives qualified lead generation
Cook's content strategy succeeds because it captures buyer intent at critical moments. The downloadable content acts as both a lead magnet and qualification tool.
"Did they download our guide on buying networking monitor tools? Well, we know they're probably in-market to buy software for that purpose," Cook explains. This intent signal allows for more targeted follow-up sequences and sales conversations.
The approach aligns with industry data showing that 96% of consumers research products online before contacting salespeople. By positioning Comparitech's content at key research moments, Cook's team intercepts buyers when they're actively evaluating solutions.
This strategy proves particularly effective in cybersecurity, where purchase decisions involve complex technical requirements, compliance considerations, and significant budget implications. The detailed nature of Comparitech's content helps establish authority while the downloadable resources demonstrate ongoing value.
Patrecia Meliana
The biggest AI challenge: managing expectations
Despite AI's benefits, Cook identifies a critical limitation: unreliable performance on complex tasks.
"The single biggest challenge I face with AI tools is getting them to do what I want them to," Cook admits. "These tools are great, but they are still very limited in their capabilities, especially if you give them complex tasks that require a lot of heavy lifting."
Cook's solution involves task decomposition—breaking complex requests into smaller, manageable components—and maintaining realistic expectations about AI capabilities. "Sometimes you have to give up and, gasp, do stuff the manual way," Cook notes. "Sometimes you have to walk to the store instead of drive."
Data-driven decision making with human intuition
Cook's marketing philosophy centers on what he calls the "data sandwich"—data analysis at both ends with content creation in the middle.
"Let the data inform your strategy, not the other way around," Cook advises. "You look at trends, see what might be a good opportunity, create content that matches that opportunity, and then track success." This methodology guided both his 900% lead generation increase and his ongoing AI testing experiments.
However, he acknowledges the importance of experienced judgment, especially when evaluating AI outputs or identifying content opportunities. "Sometimes it's okay to break that rule. Experience means you sometimes have to act on a hunch, even when there's no data to back it up on the front end."
The future of AI-assisted marketing
Looking ahead, Cook sees AI as an enhancement tool rather than a replacement for strategic thinking. His experimental approach—testing AI outputs against human expertise—offers a model for sustainable AI integration.
As the future of AI marketing continues evolving rapidly, Cook's balanced methodology provides a practical framework for marketers seeking to harness AI benefits while maintaining strategic control.
The key insight from Cook's experience: successful AI adoption requires continuous testing, realistic expectations, and recognition that human expertise remains critical for strategic decisions and creative insight.
For marketers considering similar AI integration, Cook's framework offers a practical starting point: start with simple, measurable tests like email subject line optimization, gradually expand to more complex applications, and always maintain human oversight for strategic decisions.
