Paid Media Marketing Evolution Timeline

Strategic Approach

Channel Diversification & Optimization

Paid Search: Aggressively scaled Google and Bing Ads, focusing on high-intent keywords and competitor research. Focused on driving efficiency, volume, and improving our funnel from leads, MQLs, to SALs resulting in 3x growth year over year, every year.

Paid Social: Expanded presence on LinkedIn and Meta tailoring creative and audience segmentation to reach founders and finance leaders. Leveraged retargeting and lookalike audiences to build trust with prospects for full-funnel coverage.

Newsletters & Sponsorships: Partnered with high-reach startup and finance newsletters to capture attention where founders already engage. Achieved a 12x return on Acquired Podcast.

Out-of-Home: Piloted targeted OOH campaigns in San Francisco to reinforce digital messaging, build trust, and drive conversions.

Data-Driven Experimentation

Adopted a high-velocity testing culture: new channels, creative formats, messaging with PMM, landing pages, and new offers were A/B tested weekly.

Leveraged data for granular audience segmentation and personalized messaging, increasing relevance and conversion rates.

Infrastructure & Collaboration

Consolidated campaign measurement and reporting into a unified dashboard, enabling real-time optimization and cross-channel attribution1.

Worked cross-functionally with product, sales, and analytics to ensure alignment and maximize impact of campaigns.

Budget Management & ROI Focus

Managed a mid-7 figure budget, reallocating spend dynamically based on channel performance to maximize efficiency of pipeline to spend, revenue to spend, and payback period.

Prioritized channels and campaigns that drove both high volume and high-quality leads, optimizing for retention rates, customer CAC and LTV, and payback period.

Execution Highlights

Iterative Keyword & Audience Expansion: Regularly refine and refresh Search and targeting to capture new demand and outpace competitors.

Creative Testing: Launched dozens of ad creatives per week, optimizing for click-through and conversion rates.

Landing Page Personalization: Developed segmented landing pages for different industries and company sizes, improving lead quality. Specifically had success in building out landing pages for Search.

OOH + Digital Synergy: Synchronized OOH placements with digital campaigns in SF to create max lift. Our Gong calls held evidence that OOH was working.

Results

Revenue Growth: Paid marketing-driven revenue grew from $3M to $25M.

Lead Quality & Volume: Achieved significant increases in both lead volume and quality, supporting Pilot’s expansion into the broader SMB market.

Efficiency Gains: Improved cost per acquisition through continuous optimization and channel reallocation.

Brand Awareness: OOH and newsletter sponsorships contributed to a measurable uptick in brand recognition among target audiences.

Key Takeaways

Channel Mix Matters: Diversifying beyond search and social—into newsletters and OOH—amplified reach and impact.

Experiment Relentlessly: High-tempo testing and rapid iteration were crucial to finding what worked at scale.

Data Is the Foundation: Unified measurement and granular audience segmentation enabled smarter decisions and better results.

Cross-Functional Alignment: Close collaboration across marketing, sales, and product ensured that paid efforts translated into real business growth.

Conclusion

Jer’s leadership as Growth Marketing Lead at Pilot.com demonstrates how a data-driven, experimental, and multi-channel approach can unlock exponential growth in a competitive B2B landscape. By scaling paid marketing from $3M to $25M, Jer helped position Pilot.com as a category leader and fintech unicorn.