Transforming mySidewalk into a SaaS Workflow Platform

The Situation

As market conditions shifted in response to the 2020 COVID pandemic, mySidewalk's growth faltered. With a user base heavily concentrated in public health, the overnight redirection of resources highlighted underlying growth challenges across mySidewalk's market segments. Without this key vertical, the brand struggled to acquire new customers and navigate churn.

Our Insight

Our research quickly identified that mySidewalk’s packaging and messaging reinforced point solutions, making it difficult for customers to grasp the full value of the platform beyond, instead, valuing the published deliverables. To adapt to changing conditions, mySidewalk needed to evolve beyond one-off point solutions and reposition itself as a scalable, subscription-based data storytelling platform.

The Solution

To drive sustainable growth, mySidewalk needed a systematic approach to communicate its offering, improve sales efficiency, and scale its business. Over multiple quarters, we executed a strategic transformation:

• Repositioned the brand as a SaaS workflow solution, shifting from deliverables-based sales to a recurring subscription model.
• Redesigned packaging and pricing around three core offerings (Explorer, Builder, Accelerator) to align with customer workflows.
• Developed a systematic value framework to clearly articulate how customers derive repeatable value from data storytelling.
• Built a structured solutions model that simplified quoting, reduced complexity, and improved scalability.
• Streamlined contract configurations to mitigate risk, enhance efficiency, and ensure consistency in sales and renewals.

The Impact

By shifting from point solutions to a true SaaS workflow platform, mySidewalk built a scalable foundation that strengthened its market position and unlocked new growth levers:

• 50% faster sales cycles, reducing time-to-close from 190 to 86 days.
• 15% improvement in net retention, reducing churn and increasing contract expansion potential through a "bill of materials" approach.
• 20% increase in total addressable market and average annual contract value (ACV), raising ACV to $23K.

This transformation not only stabilized mySidewalk’s business but positioned it for long-term, scalable growth in an evolving market.