Boutique Operator 3x's Upsell Revenue with Digital Guest Journey

Boutique hospitality group Simplissimo transformed its guest experience across 200 listings by partnering with Enso Connect. Over three years, they saw a 3x increase in monthly upsell revenue, achieved 96% occupancy rate, earned a 4.89 rating and a Superhost status on Airbnb, and streamlined operations, all while enhancing their signature service.

Comprehensive Digital Guest Journey

Simplissimo implemented the Enso Connect platform, integrating seamlessly with their existing property management software, Smily (10+ year partnership) and Igloo smart locks.

Implementation Highlights

Boarding Pass Guest Portal
The centerpiece of Simplissimo's digital guest experience, prominently featured on the company's website and marketing channels.

AI-Powered Unified Inbox
Consolidating SMS, email, WhatsApp, Airbnb and Booking.com messages for complete operational control.

Smart Automation
Journey-based messaging that saves staff time for meaningful guest interactions.

Comprehensive Guidebooks
Proactive guest education covering everything from packing lists to local attractions and amenity instructions.

Strategic Upsells
Valuable add-ons including fully stocked kitchens, coffee pods, baby equipment, pet services and more.

Secure Access Management
Igloo smart lock integration enabling contactless entry and single-use contractor access.

The Results: Measurable Success Across All Metrics

Revenue Growth

Since implementing Enso Connect, upsells like early check-ins, late checkouts and on-demand services were driving incremental revenue, covering the software costs. The introduction of damage waivers in April 2025 marked a turning point, with monthly upsell revenue growing 3x. This translates to approximately $47 per listing per month in incremental revenue, demonstrating the scalable impact of their digital guest experience strategy.

Guest Satisfaction Excellence

David Hotel achieved 4.89 Superhost rating on Airbnb with remarkable guest feedback patterns:

25% of reviews explicitly praised staff responsiveness and communication quality:

• "The host is super responsive and helpful" (Bayley)

• "Phayssal provided exceptional communication" (Drew)

• "Virtual staff were responsive and helpful" (Heather)

17% of reviews specifically mentioned the seamless digital check-in process:

• "The process is digital... very easy and seamless" (Sheniah)

• "Easy and intuitive self check-in system" (Phayssal)

• "Everything is self-contained and automated, it's great" (Antoine)

With an impressive 96% occupancy rate, Simplissimo's properties showcase the powerful combination of high demand and guest satisfaction that their digital experience delivers.

Operational Efficiency

Key efficiency improvements:

• Eliminated reception congestion: Guests bypass front desk entirely

• 24/7 access capability: Seamless arrivals at any hour

• Contractor access control: Single-use digital keys for maintenance teams

• Reduced staff stress: Automated responses handle routine inquiries

Innovation Through Partnership

As a power user for four years, Simplissimo has helped shape Enso Connect's product development. Many guest-facing features were inspired by their feedback, including:

• Tiered upsell boarding passes

• Enhanced verification processes with ID check

• Apple Wallet integration and Apple Pay

• Custom field optimization for intuitive data collection

• Timed access to check-in instructions

• Multi-media guidebook capabilities

The Competitive Edge: Digital-First Hospitality

Simplissimo's approach differentiates them in Montreal's competitive hospitality market through:

Proactive Guest Education: Comprehensive guidebooks answer questions before guests ask them

Seamless Technology Integration: Every touchpoint feels natural and effortless

Maintained Hospitality Values: Automation enables staff to focus on meaningful guest interactions

Looking Forward: Scaling Success

With proven success across their Montreal portfolio, Simplissimo is expanding abroad. They are leveraging their refined digital hospitality model to establish new properties, such as two new capsule hotels (130 and 100 beds) in Singapore.

The company's vision extends beyond individual properties to become "a global standard for premium, turnkey accommodations" - a goal made achievable through their comprehensive digital infrastructure and unwavering focus on guest satisfaction.

Steal Simplissimo's Boutique Hospitality Scale Playbook

1. Technology amplifies hospitality

   Digital solutions can enhance rather than replace human touch
   
   

2. Integration is crucial
   Seamless PMS, guest management and communication, and access systems create operational excellence
   
   

3. Guest education drives satisfaction
   Proactive information sharing prevents guest questions and issues before they arise
   
   

4. Revenue opportunities exist everywhere
   Strategic upsells and damage protection tools can significantly impact bottom line
   
   

5. Continuous innovation pays
   Long-term partnerships enable product development that serves real needs

Simplissimo's journey demonstrates that boutique hospitality operators can embrace digital transformation while preserving their unique character and commitment to exceptional guest experiences. Through strategic technology adoption and operational excellence, they've created a scalable model for premium hospitality that delivers measurable results across revenue, efficiency, and guest satisfaction metrics.