Douglas J. O'Brien

Situation. An expanding product portfolio across multiple regions depended on legacy paid programs that had stopped performing. At the same time, buyer discovery was moving into AI search and communities where the brand had little presence.

Action. I took ownership of global paid digital across search, display, CTV, LinkedIn, Reddit, Quora, retargeting, and third-party media. I cut spend from underperforming programs and launched Reddit, Quora, and CTV. I also piloted ChatGPT Ads, built a review-platform strategy for visibility in LLM and ChatGPT results, and led a full YouTube channel overhaul from scope through vendor delivery.

Result. In 2024, digital met a pipeline commitment raised 25% year over year. In 2025, influenced pipeline grew 83% to $463M across 3,262 deals, with touchpoints up 186% and Q4 coming in as the strongest quarter at $130M. 2026 pipeline commitment was met in the first 8 months, despite reduced martech capability and budget uncertainty. Three years, rising goals, consistent delivery.

Situation. Enterprise cybersecurity has a long sales cycle and a buying committee that generic demand generation struggles to reach. The company needed to concentrate spend on accounts showing real intent, connect advertising to pipeline and revenue, and give sales a reliable signal for when to engage.

Action. I used 6sense intent and predictive data to identify in-market accounts, prioritize them, and run targeted advertising before a sales conversation began. I tracked accounts reached, accounts engaged, marketing-qualified accounts, opportunities, and wins. That connected advertising influence to pipeline and revenue rather than clicks alone.

Result. Across 2.5 years, advertising influenced 1,498 opportunities and contributed to $1.16B in pipeline. Of those opportunities, 203 had closed won to date, generating $24.0M in ad-influenced revenue, while a substantial share of the remaining pipeline was still active. The program recorded more than 950,000 target-account touches, engaged 70% of reached accounts, and qualified roughly 32,000 as marketing-qualified accounts. Q3 2024 was the strongest quarter, with 462 ad-influenced opportunities, 59 closed-won deals, and $11M in revenue. Against roughly $35K in tracked ad spend, the return on ad-influenced revenue was nearly 700×.

Situation. A two-person team was responsible for running paid digital across eleven channels and three global regions, covering multiple products and target verticals. Ad review cycles were slow, journey management was largely manual, and internal handoffs were eating time the team didn't have.

Action. Implemented Windsor.ai connectors to centralize cross-channel data and cut ad review cycles by two thirds, putting real-time performance monitoring across every active channel in one place. Built artifacts to support quick access and sharing. Created journey automations in 6Sense and HubSpot for target account lists across distinct buying motions, multiple products, and several verticals, so the right message reached the right account at the right funnel stage with minimal manual intervention between touches. Used AI to templatize briefs and SDR handoff docs, standardizing the process and freeing the team to focus on what moved pipeline.

Result. The efficiency gains compounded in ways that went beyond time savings. By centralizing data and automating the heaviest manual work, optimization cycles that had been weekly became daily without adding hours to the week. In fact, total time spent on ad review dropped by two thirds from a baseline of 4.5 hours weekly. Campaign support tasks that averaged 50 minutes each came down to 15, and internal reporting time fell by 70%, recovering roughly 3 hours a week that went back into strategy. All told, the team reclaimed an estimated 24 hours per month, close to three full workdays, reinvested directly into optimization and growth. When third-party channel volume grew by 35%, the team absorbed it with minimal disruption. The infrastructure built to run lean made expansion feel routine rather than stressful.

Situation. The business needed to move upmarket, but paid digital spend was not aligned with target-account value. At the same time, a new PAM solution needed an efficient route into the installed customer base.

Action. I owned demand generation strategy and budget for assigned product groups, rebuilt the program around ABM, and concentrated paid spend on accounts with higher target ACV. For the PAM launch, I chose a focused campaign to the installed base instead of a broad new-logo push.

Result. The new approach cut CAC by more than 20% in one quarter. The PAM soft launch reached 1.73M potential billable endpoints and generated $675K in bookings in six weeks.