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Bobby Cooper
CX Architect & Founder of Pilr
Few leaders know customer success in the high-growth stage like Bobby Cooper. In the high-pressure space between Series A and Series C, he’s engineered retention systems that cut churn by up to 75% and helped companies grow 12x with only 3x headcount growth — turning reactive, overloaded teams into scalable growth engines.

3% to 0.7% monthly
and sustained that performance for almost a decade as the company grew from
3K to 35K customers
from $10M ARR to $250M+
At Tapcart, he scaled the business from
$3M ARR to $27M
while holding churn below 1% and preserving CX quality even through a stalled growth period.

Before “customer success” was a job title, Bobby was building it. At InsideSales.com — one of the first companies to approach go-to-market strategy scientifically — he learned under Dean Robison (Salesforce) and Ursula Llabres (Facebook), mastering impact-over-activity and balancing inbound responsiveness with proactive outreach. That foundation, paired with his obsession for using data science to predict churn, became the Pilr Model. Now, vetted AI partnerships are accelerating his foundational system —
Proof that the right system doesn’t just survive scale,
it powers it.