From Microsoft Dynamics to HubSpot - Unifying Four Lines of Business on One Revenue Engine

The Challenge

With four distinct sales motions in play, the issue wasn’t vision; it was execution at scale. 

Growth ran into three friction points: fragmented processes, slow time-to-change, and limited capabilities inside Hilldrup's current instance of Dynamics:

• Process fit vs. tool limits: Their residential moving business depended on a high-touch, ~30-step journey, while account-based teams needed separate pipelines for acquisition and project tracking. Beyond the cost and time to implementation issues, Dynamics handled these complex workflows inconsistently. 
  
  
• System sprawl: Critical steps lived in their various platforms (Quotes2Go, Yembo, CallRail, Podium, and Calendly) making orchestration and attribution hard.
  
  
• Data & alignment: Legacy data required cleanup to trust automation, and decision cycles slowed as multiple stakeholders weighed in. 
  
  

The real challenge was creative problem-solving; taking the complexities of multiple business lines and diverse stakeholder needs, then architecting a unified solution that HubSpot could seamlessly execute.

— William Collins, Fractional CMO, Hilldrup

The Solution

The HubSpot solution architecture was defined by William Collins (Fractional CMO, Chief Outsiders) in partnership with Troy Gibson (Fractional CTO), and the build, integration, and enablement was executed by Diamond HubSpot Partner Orange Marketing.

The HubSpot Footprint

The implementation required a comprehensive HubSpot stack to address each aspect of Hilldrup's specific operations:

• Sales Hub Enterprise to support complex multi-pipeline sales motions across each business segment with advanced automation and reporting capabilities
  
  
• Marketing Hub Professional to automate the complex, multi-touch customer journeys and nurture leads through extended decision cycles without manual intervention
  
  
• Content Hub Professional to create and manage landing pages and forms for quote requests ensuring consistent brand experience and lead capture optimization
  
  
• Data Hub Professional to unify data from 5+ disconnected systems into one source of truth, eliminating manual data entry and providing end-to-end transparency across business lines  

Each hub addresses Hilldrup's core challenges: unifying fragmented processes, enabling consistent customer experiences, providing transparency, and facilitating rapid adaptation as the business scales.

Data Hub Pro was the glue. It enabled seamless data flow between systems, eliminating manual data entry and ensuring sales teams had complete customer visibility across all touchpoints.

— Kirill Ougarov, RevOps Director, Orange Marketing

The Configuration

The technical implementation focused on six core components that would unify Hilldrup's fragmented operations:

• Multi-pipeline architecture by line of business:
  Eliminates the confusion of mixing acquisition prospects with ongoing project management, giving sales teams clear sight into their specific responsibilities.
  
  
• Sequences + Meeting Scheduler in HubSpot:
  Consolidates scheduling (migrating off Calendly) and enables 1:1 Sales Sequences for improved organization and reporting.
  
  
• Forms & Landing Pages:
  Enables streamlined intake for quote requests and multi-step customer journeys.
  
  
• Custom Objects:
  Captures Hilldrup's unique business processes (moves, storage, logistics) in structured data, enabling accurate reporting and automated workflows that match how teams actually work.
  
  
• Workflow Automation (~30 touchpoints for Residential):
  Automates reminders, proposals, non-response follow-ups, and cross-pipeline handoffs while maintaining high email deliverability through personalized 1:1 sequences instead of bulk emails.
  
  
• Key Integrations via Data Hub Pro: Connects Quotes2Go, Yembo, Podium (reviews/SMS), and CallRail (call tracking), with the call center's initial process now running through HubSpot.

The Orange Marketing team (with Kirill Ougarov, RevOps Director, leading the technical build and Rebecca Gonzalez, CEO, managing coordination and onboarding) translated the architecture into functional pipelines, properties, workflows, and integrations before delivering multi-team training to ensure stakeholder adoption.

Implementation

To translate the architecture into day-to-day execution, Orange Marketing rolled out HubSpot in phases: sequencing discovery, launches, and training around each group’s readiness.

Our work was herding multiple teams into alignment; getting everyone in the room, scheduling training, and keeping momentum so the build could actually ship.

— Rebecca Gonzalez, CEO, Orange Marketing

How the rollout unfolded:

The implementation was sequenced strategically over 12 weeks, with each phase building on the previous one to ensure smooth adoption across Hilldrup's diverse teams:

• Discovery & Architecture
  William finalized pipeline logic and stage definitions; Orange Marketing interviewed stakeholder teams to reconcile requirements with on-the-ground selling.
  
  
• Logistics first
  Multiple Logistics sub-teams were launched together under a designated Hilldrup team leader.
  
  
• Employee Mobility

Created a single pipeline with customized properties to support corporate, government and military employee relocation, and new account acquisition strategy.

• Residential Moving next 
  The heaviest lift: integrations with Quotes2Go and Yembo, plus the call center (which moved to the Philippines during the project) were organized. Hilldrup's residential high-touch journey was rebuilt in HubSpot; the call center’s initial process now runs through HubSpot.
  
  
• Workplace Solutions
  Pipelines finalized with incremental go-lives as the teams were ready
  
  
• Handover & Warranty 
  Hilldrup fully established HubSpot; Orange Marketing transitioned from implementation to warranty, then to paid documentation, troubleshooting, and optimization.

Adoption & Enablement

To ensure teams could execute consistently from day one, enablement focused on these areas:

• Onboarding: An expansive team of Sales Hub Enterprise users and Marketing Hub Enterprise users were trained.
  
  
• Deliverability-first automation: HubSpot's Enterprise capability was set to trigger Sequences from Workflows (1:1 email) instead of bulk marketing sends.
  
  
• Data quality: Legacy records were migrated from Microsoft Dynamics 365 to ensure trustworthy automation.
  
  
• Messaging channels: Reviews/SMS support via Podium established (with an additional SMS tool also referenced in the transcripts).

Results

Faster time-to-value and scalable, data-visible workflows set in motion and teams trained:

• Time & Cost Avoidance: By selecting HubSpot over extending Microsoft Dynamics 365, Hilldrup avoided the quoted ~6-month timeline and hundreds of thousands of dollars for marketing automation in Dynamics. Total implementation and training time was approximately 12 weeks at a fraction of the cost.
  
  
• Operational Unification: Four lines of business now run on one CRM platform (HubSpot), with Logistics and Employee Relocation actively using pipelines, and their new call center operating in HubSpot.
  
  
• Automation at Scale (Residential): ~30 orchestrated touchpoints now run automatically in HubSpot (reminders, proposals, reviews, non-response triggers), reducing manual follow-up and stabilizing handoffs.
  
  
• Scheduling Consolidation: Calendly → HubSpot Meeting Scheduler, tightening attribution and reducing tool sprawl. Significantly enhanced scheduling, surveys, call tracking, reviews, etc.
  
  
• Visibility & Control: With Data Hub Professional and custom objects, data now flows from integrated systems into HubSpot, giving leaders oversight that was impossible in the old approach.
  
  
• Partnership Extended: Hilldrup extended Orange Marketing’s engagement beyond initial timelines for documentation, troubleshooting, and continued optimization.

Orange Marketing has gone above and beyond at every turn. We knew from the start that getting our complex data and workflows fully optimized would take time beyond the initial launch, which is why we've extended our partnership with them.

— William Collins, Fractional CMO, Hilldrup

Bottom Line

Hilldrup traded a slow, costly expansion of Microsoft Dynamics 365 for a unified HubSpot stack that’s already running pipelines for Logistics and Employee Relocation, powering the call center, and automating numerous touchpoints. The move compressed time-to-value, simplified tooling, and created the data foundation to measure what matters as adoption deepens, exactly the trajectory a multi-line, high-complexity business needs.