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RoostUp: Pipedrive to HubSpot Migration

The Client

RoostUp is Boston's leading coliving brand, founded in 2016 by Mario Ricciardelli. They offer fully furnished private rooms in shared homes across Dorchester, Mattapan, and Cambridge, with all-inclusive pricing covering rent, utilities, WiFi, cleaning, and laundry. With 2,000+ residents served and a 4.9-star rating across 252+ reviews, RoostUp has built a serious operation.

Mario is an operational genius. His team runs a sophisticated sales pipeline with multiple pipeline stages, custom deal tracking, lead routing, automated nurture sequences, and integrations across multiple platforms. This wasn't a simple CRM swap.


The Problem

RoostUp had outgrown Pipedrive. Their existing setup was complex: multiple pipeline stages (Lead, Scheduled, Showing, Application, Deposit, Closed Won), automated task management, lead scoring, and integrations with their website, Google Ads, and third-party tools like The Coop for contact deduplication.

They'd already tried another vendor. Before coming to Lock and Quay, Mario hired a different team to handle the migration. The result? Cookie-cutter automation that ignored the nuances of RoostUp's actual workflow. They didn't take the time to understand how the business operated. They just applied templates and automated whatever they could, with no real consideration for the operational complexity underneath.

Mario needed a partner who would actually sit down, understand his business, and build a system that worked for his team, not against them.


The Approach

Lock and Quay's approach started with deep discovery.

Phase 1: Mapping the As-Is

Before touching HubSpot, we mapped RoostUp's entire existing process in detail. Using collaborative Miro boards, we documented: