Demo Preparation
Before scheduling demos:
- Share this evaluation framework with vendors so they can prepare relevant scenarios
- Request 2-hour demo slots (not 30-minute overviews)
- Include Marta (House Captain perspective) and Colette (Operations perspective) in demos
- Ask vendors to configure a test environment that mimics Truckee property setup
- Prepare test guest phone numbers to simulate real texting scenarios
Core Evaluation Scenarios
Test each platform with these five real-world scenarios that represent your operational model:
Context: It's 2 PM on Tuesday. Marta is on duty as House Captain. Guest texts the property number.
Guest Message: "Hi! We'd love to use the hot tub tonight. What time does it close and do we need to reserve it?"
What to Test:
- How does the message route to Marta? Automatic or manual?
- Can Marta see guest name and property details when message arrives?
- How does Marta respond? What interface does she use?
- Can Marta use saved responses for common questions?
- Does the system track message read/response times?
- Can Marta see message history with this guest?
Success Criteria: Message reaches Marta within 10 seconds, she can respond in under 60 seconds using mobile device, guest receives hospitality-appropriate language
Context: It's 11 PM on Friday. Colette is on duty. Doug (backup) should be notified if no response in 10 minutes.
Guest Message: "The master bedroom heater isn't working and it's getting really cold. We have two small kids. Can someone help?"
What to Test:
- Does message route to Colette based on schedule?
- How does the platform handle "urgent" indicators?
- Can Colette override phone silent mode if needed?
- What happens if Colette doesn't acknowledge within 10 minutes?
- How does automatic escalation to Doug work?
- Can Colette loop in maintenance vendor from the platform?
- How do you document resolution for property records?
Success Criteria: Colette receives persistent notification, can acknowledge within 2 minutes, escalation to Doug works automatically, resolution is tracked with timestamps
Context: Guest checks in tomorrow (Friday) at 4 PM. They should receive pre-arrival message at 2 PM Thursday.
Automated Message: "Welcome! We're preparing Titus House for your arrival tomorrow. Would you like us to stock your favorite beverages or arrange a private chef dinner for Saturday?"
Guest Response: "Yes! Can you stock local IPAs and arrange dinner for 8 people Saturday at 7 PM?"
What to Test:
- How do you set up automated pre-arrival messages?
- Can messages be customized per property and guest type?
- Does guest response route to appropriate team member (Quinten for chef request)?
- How do you track upsell conversion for revenue reporting?
- Can you create internal tasks from guest requests (e.g., "Stock IPAs")?
- Does the platform integrate with your booking/payment system?
Success Criteria: Automated messaging works without manual triggers, upsell requests route correctly, tasks are created automatically, revenue is trackable
Context: You're managing Truckee and Palm Springs simultaneously. Different staff on duty at each property.
Situation: Truckee guest texts about ski equipment rental. Palm Springs guest texts about golf tee times. Both arrive at 3 PM.
What to Test:
- How does the platform handle multiple properties?
- Do messages automatically route to correct property's on-duty staff?
- Can leadership view activity across all properties?
- How do you set up different schedules for different properties?
- Can staff work across properties if needed?
- How do analytics aggregate across properties vs. show individual performance?
Success Criteria: Zero cross-contamination between properties, centralized oversight without losing property-specific context, easy schedule management per location
Context: Marta's shift ends at 6 PM. Colette takes over. Active guest conversation ongoing.
Situation: Guest texted at 5:45 PM asking about dinner reservations. Conversation continues past shift change.
What to Test:
- Does Colette automatically receive new messages after 6 PM?
- Can Colette see Marta's previous conversation with guest?
- How does the guest experience the handoff? Seamless or disruptive?
- Can Marta add handoff notes for Colette about pending items?
- What happens if guest texts during the 5:55-6:05 PM transition?
- How do you manage shift swaps (Colette calls in sick, Doug covers)?
Success Criteria: Zero dropped messages during handoff, incoming House Captain has full context, guest experiences continuity, ad-hoc schedule changes are easy
Detailed Evaluation Criteria
Score each platform 1-5 on these criteria (1=Poor, 5=Excellent). Multiply by weight for total score.
| Criteria |
Weight |
What to Look For |
Score (1-5) |
| GUEST EXPERIENCE (30% Total Weight) |
| Guest-facing language & tone |
5x |
Does messaging feel like hotel service or IT support? Is terminology hospitality-appropriate? |
___ × 5 = ___ |
| Response speed |
5x |
Can staff respond within 3 minutes? Is mobile app fast and reliable? |
___ × 5 = ___ |
| Message continuity |
3x |
Do shift changes disrupt guest experience? Is conversation history maintained? |
___ × 3 = ___ |
| No-app-required access |
3x |
Can guests text a number without downloading anything? |
___ × 3 = ___ |
| Pre/post-stay automation |
2x |
Can you automate welcome messages, checkout instructions, review requests? |
___ × 2 = ___ |
| OPERATIONAL EFFICIENCY (35% Total Weight) |
| Schedule-based routing |
5x |
Do messages automatically go to whoever's on duty without manual intervention? |
___ × 5 = ___ |
| Escalation reliability |
5x |
Does backup get notified if primary doesn't respond? Is timing configurable? |
___ × 5 = ___ |
| Multi-property management |
4x |
Can you manage 10+ properties without confusion? Property-specific schedules? |
___ × 4 = ___ |
| Mobile app quality |
4x |
Is mobile app responsive, stable, and feature-complete? Works offline? |
___ × 4 = ___ |
| Staff collaboration tools |
3x |
Can team communicate internally? Share notes? Create tasks from requests? |
___ × 3 = ___ |
| Saved responses & templates |
2x |
Can staff quickly respond to common questions with pre-written templates? |
___ × 2 = ___ |
| BUSINESS INTELLIGENCE (15% Total Weight) |
| Response time tracking |
4x |
Can you measure average response time per staff member? Property-level analytics? |
___ × 4 = ___ |
| Upsell conversion tracking |
3x |
Can you track which messages lead to additional revenue? |
___ × 3 = ___ |
| Guest sentiment analysis |
2x |
Does platform flag potentially unhappy guests? Satisfaction scoring? |
___ × 2 = ___ |
| Custom reporting |
2x |
Can you build custom reports for Board presentations? Export data easily? |
___ × 2 = ___ |
| IMPLEMENTATION & SUPPORT (20% Total Weight) |
| Setup simplicity |
4x |
Can you be operational within 2 weeks? Or does it require technical configuration? |
___ × 4 = ___ |
| Training requirements |
3x |
Can hospitality staff use it without extensive training? Intuitive interface? |
___ × 3 = ___ |
| Customer support quality |
3x |
Response time for support tickets? Phone support available? Account manager? |
___ × 3 = ___ |
| Platform reliability |
5x |
Uptime guarantees? Have there been major outages? Redundancy built in? |
___ × 5 = ___ |
| Future-proofing |
2x |
Active development roadmap? Will vendor be around in 5 years? (Avoid Opsgenie) |
___ × 2 = ___ |
| TOTAL WEIGHTED SCORE |
___ / 235 points maximum |
Scoring Interpretation
190-235 points: Excellent fit — proceed to pilot test
145-189 points: Good fit — address specific gaps before committing
100-144 points: Marginal fit — consider alternatives
Below 100: Poor fit — do not proceed
Demo Day Agenda
Structured 2-hour demo format to maximize evaluation efficiency:
0:00-0:15
Introduction & Context
- Vendor presents company background and customer base
- You present Guesthouse distributed hotel model
- Align on demo objectives and scenarios to test
0:15-0:45
Live Scenario Testing (Scenarios 1-3)
- Vendor demonstrates platform using your actual scenarios
- Test with real phone numbers, not simulated messages
- Have Marta interact with mobile app in real-time
- Focus on guest experience and response workflows
0:45-1:00
Hands-On Trial (You Drive)
- You and team test the platform directly
- Set up a test schedule with multiple staff
- Send messages and observe routing behavior
- Test mobile app responsiveness
1:00-1:30
Advanced Features & Multi-Property (Scenarios 4-5)
- Configure second property in system
- Test cross-property analytics and management
- Review escalation policies and shift handoffs
- Explore automation and integration capabilities
1:30-1:50
Analytics, Reporting & Business Case
- Review available analytics dashboards
- Understand what metrics track upsell conversion
- Discuss implementation timeline and support
- Review pricing details and contract terms
1:50-2:00
Q&A & Next Steps
- Address any gaps or concerns identified
- Discuss customer references in hospitality
- Clarify trial/pilot options
- Establish timeline for decision
Critical Questions to Ask Each Vendor
Guest Experience Questions
- "Show me what a guest sees when they receive their first message from us. Can we customize this completely?"
- "What happens if a guest texts a question at 2 AM? What automated response do they receive?"
- "How do you prevent guests from seeing 'incident #12847' or other technical terminology?"
- "Can we send photos/videos to guests? Can they send them to us?"
- "What's your typical response time from guest message to staff notification?"
Operations Questions
- "Walk me through creating a weekly rotation schedule with 5 staff members across 2 properties."
- "What happens when someone calls in sick 30 minutes before their shift? How do we reassign?"
- "If our House Captain doesn't acknowledge a message within 10 minutes, how does escalation work?"
- "Can the same staff member cover multiple properties if needed? How does that work?"
- "Show me your mobile app on both iOS and Android. What features require wifi vs cellular?"
- "How do you handle message routing if someone's phone dies or loses signal?"
Scaling Questions
- "We plan to operate 10 properties within 18 months. How does pricing scale?"
- "Can we set different service level standards per property? (e.g., 5-min response for flagship, 15-min for others)"
- "How do analytics aggregate across properties while showing individual performance?"
- "What does implementation look like for property #2 vs property #1?"
- "Do you have customers managing 10+ locations successfully? Can we speak with them?"
Business Intelligence Questions
- "Show me how you track upsell revenue generated through messaging."
- "What guest satisfaction metrics can we measure? NPS? Sentiment analysis?"
- "Can we export data for Board presentations? What format?"
- "How do you identify patterns? (e.g., 'hot tub questions spike on Fridays')"
- "What API access do we have for custom reporting?"
Implementation Questions
- "What's your realistic timeline from contract signature to first guest message?"
- "Who handles setup? Do you do it or do we?"
- "What training do you provide? Is it included in pricing?"
- "What support do you offer during first 90 days? After that?"
- "What's your platform uptime guarantee? SLA for critical issues?"
- "Have you had major outages? How long to resolve?"
Commercial Questions
- "What's included in the quoted price? What costs extra?"
- "Are message volumes unlimited or is there a per-message charge?"
- "What's your contract term? Annual or monthly?"
- "Do you offer pilot/trial pricing for first property?"
- "What happens to our data if we leave? Export capabilities?"
- "Who are your investors? How long have you been profitable?"
Post-Demo Evaluation Process
Within 24 Hours of Each Demo
- Complete scoring matrix while impressions are fresh
- Document concerns — any functionality that didn't work as expected
- List follow-up questions for vendor
- Gather team feedback — Marta's usability perspective, Colette's operational view
- Calculate weighted score and compare to threshold (190+ points)
After All Demos Complete (Week 2)
- Compare final scores side-by-side
- Request customer references from top 2 platforms — speak with hospitality customers managing 5+ properties
- Negotiate pilot terms with finalist — 30-day trial at Truckee with option to expand
- Review contracts — especially data ownership, export rights, termination clauses
- Make decision and schedule implementation kickoff
Pilot Test Protocol (30 Days)
Once you select a platform, test it in production at Truckee before scaling:
Week 1-2: Initial Setup & Training
- Platform configured with Truckee property and 5 team members
- All staff trained and comfortable using mobile app
- Test messaging with 10 friendly guests (friends/family bookings)
- Troubleshoot any routing or notification issues
- Target: 95% of messages reach correct staff within 10 seconds
Week 3-4: Full Production Testing
- Use platform for all guest communications (10+ paying guests)
- Test escalation policies with intentional non-responses
- Track response times and guest satisfaction
- Measure upsell conversion vs. phone/email baseline
- Target: 90% guest satisfaction, average response under 5 minutes, zero dropped messages
End of Week 4: Go/No-Go Decision
- Review metrics vs. success criteria
- Gather staff feedback on usability
- Assess guest experience (reviews, direct feedback)
- Calculate ROI based on upsells generated
- Decision: Roll out to all properties or switch platforms
Key Metrics to Track During Pilot
- Response Time: Average time from guest message to staff response (Target: <5 minutes)
- Resolution Time: Time from initial request to issue resolved (Target: <30 minutes for standard requests)
- Upsell Conversion: Percentage of pre-arrival messages resulting in add-on purchases (Target: >15%)
- Staff Adoption: Percentage of team actively using platform vs. defaulting to phone (Target: >90%)
- Guest Satisfaction: NPS or satisfaction score from messaging interactions (Target: >8/10)
- System Reliability: Message delivery success rate (Target: 100%)
Decision Matrix Summary
Recommended Demo Sequence
- Week 1 Monday: HelloShift demo (establish hospitality baseline)
- Week 1 Wednesday: Canary demo (compare hospitality alternatives)
- Week 1 Friday: Internal debrief — decide if hospitality platforms meet needs or if you need technical flexibility
- Week 2 Monday: PagerDuty demo (if technical flexibility needed)
- Week 2 Wednesday: Zenduty demo (budget-conscious technical alternative)
- Week 2 Friday: Final comparison and finalist selection
- Week 3: Reference calls with 2-3 customers from finalist platform
- Week 4: Negotiate pilot terms and finalize contract
- Week 5-8: 30-day pilot test at Truckee
- Week 9: Go/no-go decision and rollout plan for remaining properties
Final Reminder
The distributed hotel model is new. Most platforms — whether hospitality or technical — weren't designed specifically for your hub-and-spoke approach. The right platform is the one that adapts most easily to your unique operational model while maintaining the guest experience standards that justify your premium pricing.
If in doubt after demos, trust this principle: Guest-facing polish beats technical flexibility. You can work around feature limitations, but you can't easily rebrand a technical platform to feel like luxury hospitality.