Case study

Rebuilding the conversion funnel through a PLG-to-sales pivot at Pingboard

~$8M ARR HR Tech, acquired by Workleap in December 2023. VP of Marketing, 2022–2023, Austin, TX.

Category HR Tech, product-led → sales-assisted Role VP of Marketing Team Three

Situation

Pingboard was mid-pivot — moving from a low-ACV, product-led growth motion to a higher-ACV, sales-assisted one. That meant marketing couldn't simply optimize one funnel; it had to own demand creation and capture across both self-serve/product-led and sales-led paths at the same time, with a team of three.

Strategy

Andrew led demand generation through the transition, rebuilding the free-to-paid conversion funnel to work for the higher-intent, higher-ACV buyer the company was now pursuing, while keeping the existing self-serve funnel functioning.

Results

Helped deliver 26% revenue growth year-over-year, with a sub-12-month payback period.
170% lift in free trial-to-paid conversion rate.
38% increase in high-intent leads.
Pingboard was acquired by Workleap in December 2023.

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