Pamela Piccola-Fales

She’s Maximizing Marketing Efficiency at Squarespace

Squarespace may splurge on memorable Super Bowl ads, but don’t get the wrong idea: The website design software company is all about maximizing its marketing dollars. That’s due in large part to the efforts of Pamela Piccola-Fales, who joined Squarespace’s Media & Acquisition team in 2018 after earning her chops at Plated, E*TRADE, Digitas, and SAP. In 2023, Piccola-Fales was promoted to Vice President, and since then she’s been instrumental in reshaping Squarespace’s marketing measurement approach, developing actionable solutions to ensure the company’s marketing investments are tied to the most effective performance metrics. In 2024, she led a critical reevaluation of Squarespace’s attribution model results after identifying gaps in confidence that required further exploration. The effort delivered significant cost savings while increasing efficiency and driving sustainable growth — growth that’s more important than ever. In 2024, Squarespace went private, continued enlisting new customers, and released an AI-assisted website-building tool, joining the race to simplify web design.

By Audrey Goodson Kingo