Onboarding Matrix
Pre-work for Session 3 | Prepared: 2026-02-17
Summary (3 sentences for Danny)
Getting a landlord from sign-up to “my tenants are using this” is the single highest-leverage moment in the customer lifecycle — if it takes more than a week, they drift. This matrix breaks onboarding into four customer segments with step-by-step checklists, timelines, and clear ownership (what Danny does, what the system does, and what the customer does themselves). The goal is to hit first value — a real tenant conversation handled by the AI — within 48 hours for small landlords and within 7 days for larger operators, because every day of delay is a day they could decide it is not worth the effort.
Customer Segments
Based on the ICP from the lead tiers playbook and the packaging matrix tier definitions, there are four distinct onboarding profiles:
| Segment | Example | Properties | Tech Comfort | Key Need | Onboarding Style |
|---|---|---|---|---|---|
| Solo Landlord | Sarah, 4 HMOs (25 rooms) in Birmingham, manages everything herself, uses WhatsApp and spreadsheets | 5—25 | Medium — uses apps daily but not “tech-savvy” | Get the AI answering tenant messages ASAP, stop being the bottleneck | Guided self-serve with one setup call |
| Growing Portfolio | James, 30—60 properties across Leeds, has one part-time admin, uses Arthur for lettings but hates the maintenance workflow | 25—60 | Medium-High — comfortable with dashboards, CSV uploads | Import existing portfolio efficiently, prove AI quality before trusting it with tenants | Assisted onboarding with hands-on CSV import and test phase |
| Small Letting Agency | Horizon Lets, 60—100 managed properties, 3 staff, existing vendor relationships, needs team access | 60—100 | High — uses multiple software tools already | Team setup, vendor migration, compliance reporting from day one | Dedicated onboarding sessions, phased rollout |
| Enterprise Operator | CityNest Group, 150—500+ properties, build-to-rent or large HMO chain, has IT team, wants white-label and BYOAK | 100—500+ | Very High — has procurement process, IT requirements | Custom branding, API integration, data migration from existing PMS | Project-managed onboarding with dedicated account manager |
The Onboarding Journey
Segment: Solo Landlord (Starter tier)
Timeline target: Sign-up to first tenant conversation in 48 hours
| Step | Task | Owner | Timeline | Done When |
|---|---|---|---|---|
| 1. Welcome | Account created, welcome email sent with login link and “what to expect” guide | System (auto) | Immediate | Email received, customer has logged into dashboard |
| 2. Orientation call | 15-minute video call: walk through dashboard, explain the onboarding steps, answer questions | Danny | Within 24 hours of sign-up | Customer understands the dashboard layout and the next steps |
| 3. Property import | Customer adds properties manually via dashboard (for <10 properties) OR fills in the Envo CSV template and emails it to Danny | Customer + Danny (if CSV) | Day 1—2 | All properties visible in the dashboard with correct addresses and types |
| 4. Tenant import | Customer adds tenants manually OR uses CSV template. Danny assists with CSV formatting and E.164 phone number conversion | Customer + Danny (if CSV) | Day 1—2 | All tenants linked to correct properties with valid phone numbers |
| 5. Document upload | Customer uploads key property documents (house rules, appliance manuals, boiler instructions). Danny explains the “visible to AI” toggle | Customer (guided by Danny) | Day 2—3 | At least 1—2 documents per property uploaded and marked as AI-visible |
| 6. Vendor setup | Customer adds their regular tradespeople (name, phone, email, trade). Danny shows the vendor assignment flow | Customer (guided by Danny) | Day 2—3 | At least 2—3 vendors loaded with correct trades |
| 7. Channel configuration | Enable web chat link for tenants. WhatsApp shared number configured (Starter tier). Danny explains which channels are available | Danny + System | Day 2—3 | Tenant-facing chat URL is live; WhatsApp routing is active |
| 8. Test conversation | Danny and customer run a live test: send a message as a “tenant” via web chat and/or WhatsApp, watch the AI respond, see the issue appear on the dashboard | Danny + Customer | Day 2—3 | Customer has witnessed a full end-to-end conversation and issue creation |
| 9. Tenant notification | Welcome SMS/WhatsApp sent to all tenants with: how to contact, property confirmation, landlord name | System (triggered by Danny) | Day 3 | All tenants have received their welcome message |
| 10. Go-live | System is live — tenants can now reach the AI. Danny confirms everything is working | Danny (confirmation) | Day 3 | First real tenant message received and handled |
| 11. Day-3 check-in | Quick call or message: any issues? Review the first conversations on the dashboard. Troubleshoot anything unexpected | Danny | Day 3—4 | Customer is comfortable and has reviewed at least 3 real conversations |
| 12. Week-1 review | 15-minute call: review issue volume, AI accuracy, any tenant feedback. Discuss vendor assignment if issues have come in | Danny | Day 7 | Customer confirms they are happy, or issues are escalated for resolution |
Segment: Growing Portfolio (Starter/Professional tier)
Timeline target: Sign-up to first tenant conversation in 5 days. Fully live on all properties in 10 days.
| Step | Task | Owner | Timeline | Done When |
|---|---|---|---|---|
| 1. Welcome | Account created, welcome email with onboarding timeline and CSV templates attached | System (auto) | Immediate | Email received with CSV templates downloaded |
| 2. Kick-off call | 30-minute video call: understand their current setup, property types, pain points, existing tools. Plan the import approach | Danny | Within 24 hours | Danny has a clear picture of their portfolio; import plan agreed |
| 3. CSV preparation | Customer fills in property CSV and tenant CSV from their existing records. Danny available for questions on formatting, E.164 conversion, and property type mapping | Customer (Danny supports) | Day 1—3 | CSV files received by Danny, reviewed for completeness |
| 4. CSV import (batch 1) | Danny imports first batch of 10—15 properties and their tenants. Quick validation: are addresses correct? Are tenants linked properly? | Danny (admin-assisted) | Day 3—4 | Batch 1 properties and tenants visible and correct in dashboard |
| 5. Document upload | Customer uploads compliance documents (gas safety, EPC, EICR) and property-specific docs (house rules, manuals). Danny shows bulk upload and explains AI visibility | Customer (guided by Danny) | Day 3—5 | Key documents uploaded; at least gas safety and house rules per property |
| 6. Vendor setup | Customer adds existing vendor contacts. If they have many vendors, Danny provides a vendor CSV template | Customer (Danny supports) | Day 4—5 | All regular vendors loaded with correct trades and contact details |
| 7. Channel configuration | Web chat enabled. WhatsApp configured (shared or dedicated number depending on tier). Discuss voice AI if on Professional | Danny + System | Day 4—5 | Channels configured and tested |
| 8. Test phase (pilot properties) | Go live on batch 1 only. Tenants in those properties notified. Monitor for 2—3 days — review AI conversations, check accuracy, catch any issues | Danny + Customer | Day 5—7 | Pilot properties live; customer has reviewed conversations and is satisfied with AI quality |
| 9. CSV import (remaining) | Import remaining properties and tenants. Danny validates the full dataset | Danny (admin-assisted) | Day 7—8 | All properties and tenants imported and verified |
| 10. Full go-live | Tenant welcome messages sent to all remaining tenants. Full portfolio now live | System (triggered by Danny) | Day 8—10 | All tenants notified; issues flowing in from across the portfolio |
| 11. Day-3 post-launch check-in | Review first few days of full operation. Issue volume, AI accuracy, any tenant confusion or feedback | Danny | Day 10—12 | Customer is confident in the system across all properties |
| 12. Week-2 review | Deeper review: issue categories, urgency distribution, vendor assignment workflow, compliance dashboard status. Discuss upgrading tier if relevant | Danny | Day 14 | Customer confirms operational comfort; any issues escalated |
| 13. Month-1 review | Formal check-in: operational metrics, conversation volume vs cap, any feature requests, discuss moving to annual billing if applicable | Danny | Day 30 | Customer retained and engaged, or feedback captured for product |
Segment: Small Letting Agency (Professional tier)
Timeline target: Sign-up to first tenant conversation in 7 days. Fully live in 14—21 days.
| Step | Task | Owner | Timeline | Done When |
|---|---|---|---|---|
| 1. Welcome | Account created, welcome email with onboarding plan document and CSV templates | System (auto) | Immediate | Email received; key stakeholders identified |
| 2. Kick-off call (extended) | 45-minute video call with the decision-maker AND the team members who will use the dashboard daily. Understand their current workflow, tools, vendor relationships, compliance pain points | Danny | Within 48 hours | Clear understanding of team structure, current tools, and data sources; onboarding plan agreed with milestones |
| 3. Team setup | Create team member accounts. Assign roles (owner, manager, viewer). Walk team through dashboard access and permissions | Danny + Customer | Day 1—3 | All team members have accounts and understand their access level |
| 4. Data preparation | Customer extracts property and tenant data from existing systems (Arthur, spreadsheets, etc.). Danny provides CSV templates and assists with data mapping from their current format | Customer + Danny | Day 2—5 | Clean CSV files ready for import, validated by Danny |
| 5. Bulk import | Danny imports full property and tenant dataset. Validation step: customer reviews imported data in dashboard for accuracy | Danny (admin-assisted) | Day 5—6 | All properties and tenants imported; customer has verified a sample |
| 6. Document migration | Bulk upload of compliance documents. Set expiry dates. Upload property-specific documents for AI. Prioritise properties with highest tenant volume | Customer + Danny | Day 5—8 | All compliance documents uploaded with expiry dates; AI-visible docs for at least top 20 properties |
| 7. Vendor migration | Import full vendor directory. Set preferred vendors per property or area. Configure vendor notification preferences | Customer + Danny | Day 6—8 | All vendors loaded; preferred vendor lists configured |
| 8. Channel configuration | Dedicated WhatsApp number setup. Voice AI configuration (if included). Web chat link generated. Email channel setup if applicable | Danny + System | Day 7—9 | All channels tested and confirmed working |
| 9. Workflow training | 1-hour training session for the team: issue management workflow, vendor assignment, compliance monitoring, notification settings. Record the session for future reference | Danny | Day 8—10 | Team can independently manage issues, assign vendors, and navigate the dashboard |
| 10. Pilot rollout | Go live on a subset of properties (20—30). Monitor closely for 3—5 days | Danny + Customer | Day 10—14 | Pilot running smoothly; team comfortable with daily operations |
| 11. Full rollout | Tenant notifications sent for remaining properties. Full portfolio live | System + Danny | Day 14—17 | All tenants notified; full portfolio active |
| 12. Post-launch support | Daily check-ins for first week of full operation. Danny reviews conversations, issue handling, and flags anything unusual | Danny | Day 17—21 | Stable operation; team handling issues independently |
| 13. Week-3 review | Formal review: operational metrics, team feedback, compliance dashboard, reporting needs, conversation volume vs plan | Danny | Day 21 | Customer confirmed happy; support moves to standard cadence |
| 14. Month-1 business review | Review against success criteria agreed at kick-off. Discuss ROI, time savings, feature requests, and contract terms | Danny | Day 30 | Customer retained; annual billing discussed if applicable |
Segment: Enterprise Operator (Enterprise tier)
Timeline target: Sign-up to pilot in 14 days. Fully live in 30—45 days.
| Step | Task | Owner | Timeline | Done When |
|---|---|---|---|---|
| 1. Contract and scoping | Signed contract. Scoping document: property count, data sources, integration requirements, branding needs, BYOAK setup, SSO requirements, compliance needs | Danny + Customer | Pre-onboarding | SOW signed; technical requirements documented |
| 2. Welcome and onboarding plan | Detailed onboarding project plan shared with milestones, responsibilities (RACI), and timeline. Dedicated Slack/Teams channel created | Danny | Day 1 | Customer has reviewed and approved the onboarding plan |
| 3. Technical setup | BYOAK configuration: customer provides their Twilio, SendGrid, and/or LLM API keys. Custom domain setup. SSO configuration if required | Danny + Customer IT | Day 1—7 | All API keys configured and tested; custom domain resolving |
| 4. Branding configuration | Custom logo, colour palette, email templates, and SMS sender ID applied. “Powered by Envo” removed if contracted. Customer approves branding | Danny + Customer | Day 3—7 | Customer has signed off on the branded tenant experience |
| 5. Team setup | Create all team member accounts. Configure role hierarchy. Set up SSO if applicable. Training schedule agreed | Danny + Customer | Day 3—7 | All users provisioned; SSO working if applicable |
| 6. Data migration | Full property and tenant data migration from existing PMS. May involve API integration or bulk CSV processing. Data validation and reconciliation | Danny + Customer IT | Day 5—14 | All properties and tenants migrated; reconciliation report reviewed and approved |
| 7. Document migration | Bulk compliance document upload. AI-visible document processing for all properties. Priority given to highest-volume properties | Danny + Customer | Day 7—14 | All compliance documents uploaded; AI knowledge base populated |
| 8. Vendor migration | Full vendor directory import. Preferred vendor mapping by area and trade. Vendor notification preferences configured | Danny + Customer | Day 7—14 | Vendor directory complete and verified |
| 9. Channel configuration | Dedicated WhatsApp number(s), voice line(s), web chat, email channel — all under customer branding. BYOAK channels tested end-to-end | Danny + Customer IT | Day 10—14 | All channels live and branded; end-to-end test passed |
| 10. Team training | Multiple training sessions by role: operations team (issue management), compliance team (document tracking), management (reporting and analytics). Sessions recorded | Danny | Day 12—16 | All team members trained; training materials delivered |
| 11. Pilot rollout | Go live on 20—30 properties. Dedicated monitoring. Daily stand-up with customer during pilot | Danny + Customer | Day 14—21 | Pilot stable; key metrics reviewed daily |
| 12. Iterate and refine | Adjust AI behaviour, emergency keywords, vendor workflows, reporting based on pilot learnings | Danny + Customer | Day 21—28 | All pilot issues resolved; customer approves full rollout |
| 13. Full rollout (phased) | Roll out in batches of 50—100 properties. Tenant notifications sent per batch. Monitor each batch for 2—3 days before the next | Danny + Customer | Day 28—45 | All properties live; system stable under full load |
| 14. Hypercare period | Dedicated support for 2 weeks post-full-launch. Priority response times. Weekly business reviews | Danny | Day 45—60 | System stable; operational cadence established |
| 15. Handoff to BAU | Transition from onboarding to ongoing account management. Quarterly business reviews scheduled | Danny | Day 60 | Customer operating independently; QBR schedule confirmed |
Time-to-Value Targets
Industry benchmarks suggest SaaS customers who do not see value within 1—3 days are significantly more likely to churn. For Envo, “first value” means the customer witnesses a real tenant conversation handled by the AI without their intervention — this is the “aha moment.”
| Segment | Sign-up to First Value | Sign-up to Fully Live | Key Milestone (First Value Event) |
|---|---|---|---|
| Solo Landlord | 48 hours | 3—5 days | First real tenant message handled by AI, visible on dashboard |
| Growing Portfolio | 5 days | 10—14 days | First tenant issue auto-created from a real conversation on a pilot property |
| Small Letting Agency | 7 days | 14—21 days | Team member sees and manages a real issue from AI conversation on pilot properties |
| Enterprise Operator | 14 days | 30—45 days | Pilot properties running under customer branding; team using dashboard independently |
Critical insight: The test conversation (step 8 for Solo Landlord) is the make-or-break moment. If the customer sees the AI respond intelligently to a realistic tenant message and the issue appear on their dashboard, they are sold. If the test conversation is clunky, inaccurate, or fails — they lose confidence immediately. Danny should rehearse this with realistic scenarios before every onboarding call.
Onboarding Resources Needed
These are the materials and tools Danny needs to deliver onboarding consistently. Prioritised by what is needed for the first 10 customers.
| Resource | Purpose | Priority | Exists? |
|---|---|---|---|
| Property CSV template | Standardised format for bulk property import (address, postcode, type, units) | P1 — Critical | Partially (format defined in Onboarding spec, needs a downloadable .csv file with headers and example rows) |
| Tenant CSV template | Standardised format for bulk tenant import (property_address, name, phone, email, room_number) | P1 — Critical | Partially (format defined, needs downloadable template with E.164 phone examples) |
| Welcome email sequence | Automated emails: welcome (day 0), “ready for your setup call?” (day 1), “your tenants are live” (go-live day), “how’s it going?” (day 7) | P1 — Critical | No |
| Onboarding checklist (customer-facing) | One-page PDF or web page: “Here’s what we’ll do together to get you live” — steps, timeline, what we need from you | P1 — Critical | No |
| E.164 phone number guide | Short guide explaining UK phone number formatting (+44…) with common examples. Landlords will not know what E.164 means | P1 — Critical | No |
| Test conversation script | Pre-written realistic tenant messages Danny can use during the test conversation step (boiler issue, damp report, “where’s the stopcock?”, emergency gas leak) | P1 — Critical | Partially (demo script exists, needs a separate lightweight version for onboarding) |
| Video walkthrough: dashboard tour | 5-minute video showing the dashboard: properties, tenants, issues, documents, settings. Customer can re-watch after the setup call | P2 — High | No |
| Video walkthrough: tenant experience | 2-minute video showing what the tenant sees: sending a WhatsApp message, AI responding, issue created. Useful for landlords to share with tenants | P2 — High | No |
| Vendor CSV template | Standardised format for bulk vendor import (name, phone, email, trade, notes) | P2 — High | No |
| Tenant welcome message template | The actual SMS/WhatsApp message tenants receive. Should be reviewable/customisable by the landlord before sending | P2 — High | Partially (logic exists in system, but not exposed for landlord review/customisation) |
| “How to report an issue” tenant guide | Simple one-pager (digital) that landlords can share with tenants: “Text this number, call this number, or use this link” | P2 — High | No |
| Document upload guide | Short guide: what documents to upload, what “visible to AI” means, how to set expiry dates, which documents matter most | P2 — High | No |
| FAQ document | Common questions from onboarding: “What happens if a tenant isn’t in the system?”, “What if the AI gets it wrong?”, “How do I add a new property?” | P3 — Medium | No |
| Onboarding feedback survey | Short survey (3—5 questions) sent after go-live: how was the setup experience? What could be better? Would you recommend Envo? | P3 — Medium | No |
| Video walkthrough: vendor assignment | 2-minute video showing vendor assignment, secure link, accept/decline flow | P3 — Medium | No |
| Data migration guide (from Arthur/Fixflo) | Instructions for exporting data from common competitor tools and mapping it to Envo’s CSV format | P4 — Future | No |
| API onboarding documentation | For Enterprise customers integrating via API | P4 — Future (not built yet) | No |
Who Does What
This RACI-style matrix clarifies responsibilities across all onboarding tasks.
| Task | Self-Serve (Customer) | Assisted (Danny) | Automated (System) |
|---|---|---|---|
| Sign up / account creation | Fills in form | — | Creates org, auth user, sends welcome email |
| Orientation / kick-off call | Attends, asks questions | Leads the call, explains steps | — |
| Property entry (manual, <10) | Adds properties via dashboard | Available for questions | Validates addresses, deduplicates |
| Property import (CSV, 10+) | Prepares CSV from their records | Validates CSV, runs import, troubleshoots errors | Processes CSV, commits valid rows, returns errors |
| Tenant entry (manual) | Adds tenants via dashboard | Available for questions | Validates phone numbers (E.164), links to property |
| Tenant import (CSV) | Prepares CSV | Validates, runs import | Processes CSV, validates phones, links to properties |
| Document upload | Uploads files, sets expiry dates, toggles AI visibility | Explains what to upload and why | Stores files, triggers AI extraction pipeline, indexes for RAG |
| Vendor setup | Adds vendors with trade and contact details | Shows the workflow, assists if many vendors | Stores vendor records, enables assignment |
| Channel configuration | — (not customer-facing yet) | Configures WhatsApp, voice, web chat | Routes channels, verifies connectivity |
| Test conversation | Participates, watches the AI | Leads the test, explains what is happening | AI responds, creates issue, displays on dashboard |
| Tenant notification | Reviews welcome message before sending | Triggers the send, monitors delivery | Sends SMS/WhatsApp to all tenants |
| Go-live confirmation | Confirms they are ready | Gives the green light, monitors first hours | System is live — tenants can now reach AI |
| Post-launch check-ins | Shares feedback, flags issues | Proactively contacts, reviews conversations | — |
| Team setup (Professional+) | Invites team members | Explains roles and permissions | Creates accounts, assigns roles |
| Branding (Enterprise) | Provides logo, colours, approves templates | Applies branding configuration | Renders branded experience |
| BYOAK setup (Enterprise) | Provides API keys | Configures keys in system | Tests connectivity, routes via customer’s accounts |
Risk Points
Where customers drop off or onboarding stalls — and what to do about it.
| Risk | Impact | Mitigation |
|---|---|---|
| Customer never prepares the CSV | Onboarding stalls at step 3; momentum lost | Danny sends the CSV template pre-filled with 2—3 example rows. Offer to do a screen-share where they fill it in together. Set a firm deadline (“Let’s aim to have this by Thursday so we can go live next week”) |
| Phone numbers in wrong format | Tenant import fails; customer gets frustrated by errors | Provide a clear E.164 guide with UK examples. Build a phone number formatter into the CSV import tool (auto-convert 07xxx to +447xxx). Danny pre-validates CSVs before import |
| AI gives a poor answer during test conversation | Customer loses confidence in the entire product | Rehearse the test conversation with known-good scenarios. Ensure property documents are uploaded and indexed BEFORE the test. Have fallback scenarios ready. If it fails, acknowledge it honestly and show the correct behaviour |
| Tenants confused by welcome message | Tenants ignore the message or contact the landlord directly instead | Let the landlord review and approve the welcome message before sending. Include clear instructions: “Reply to this number to report any issues.” Consider having the landlord personally introduce Envo to tenants first (via their own WhatsApp group) |
| Low tenant adoption in first week | Customer sees no value because tenants are not using the system | Set expectations: “Not every tenant will use it immediately. But the first time someone texts at 11pm and gets an instant response, word spreads.” Track and share the first successful conversation as a win |
| Document upload feels like too much work | Customer skips it, AI knowledge base is empty, tenant Q&A quality is poor | Prioritise: “Start with house rules and one appliance manual per property. You can add more later.” Frame it as optional for launch but valuable for reducing repeat questions |
| Customer has no vendors yet | Vendor assignment step is irrelevant; customer questions the product’s value | Frame vendor setup as optional for launch. “Issues will still be created and you can manage them yourself. Add vendors when you’re ready.” The core value is AI intake, not vendor dispatch |
| Existing tool migration friction | Customer uses Arthur/Fixflo and exporting data is difficult | Danny helps with data extraction. Build export guides for common tools. For early customers, offer to do the data mapping manually |
| Decision-maker delegates onboarding to a junior team member | The person doing setup does not understand the product vision; setup is half-hearted | Always include the decision-maker in at least the kick-off call and the test conversation. They need to see the “aha moment” personally |
| Time gap between sign-up and go-live | The longer it takes, the more likely the customer forgets, gets busy, or loses interest | Danny should batch onboarding steps into as few sessions as possible. Ideal: one setup call that covers steps 2—8 in a single sitting for Solo Landlords. Momentum is everything |
| Customer’s tenants do not speak English as first language | AI conversations may be confusing for non-native English speakers | Set expectations that multilingual support is on the roadmap. The AI currently handles simple English well. For properties with non-English-speaking tenants, suggest starting with web chat (where tenants can take their time) rather than voice |
| System downtime or bugs during onboarding | Catastrophic for first impressions | Danny to always test the system before any onboarding call. Have a backup plan: “If anything is down, we reschedule within 24 hours.” Prioritise stability over features for early customers |
Success Metrics
How we measure whether onboarding is working — both for individual customers and for the process overall.
| Metric | Target | How to Measure |
|---|---|---|
| Time to first value (first real tenant conversation) | Solo: 48 hrs, Growing: 5 days, Agency: 7 days, Enterprise: 14 days | Timestamp of first non-test tenant message minus account creation date |
| Time to fully live (all properties active) | Solo: 5 days, Growing: 14 days, Agency: 21 days, Enterprise: 45 days | Date all tenant welcome messages sent minus account creation date |
| Onboarding completion rate | >85% of sign-ups reach fully-live status | Count of fully-live customers / count of sign-ups (exclude disqualified) |
| Onboarding drop-off step | No single step loses more than 10% of customers | Track where customers stall or abandon; review weekly |
| First-week tenant adoption | >30% of tenants send at least one message in week 1 | Unique tenants with messages / total tenants imported, in first 7 days post-notification |
| First-week AI accuracy | >90% of AI conversations rated “acceptable” or better by landlord | Danny spot-checks conversations during week-1 review; customer rates in check-in |
| 7-day retention | >95% of customers still active 7 days after go-live | Dashboard login within 7 days of go-live |
| 30-day retention | >85% of customers still active 30 days after go-live | Dashboard login and at least one issue managed within days 21—30 |
| Customer satisfaction (onboarding) | NPS >50 or satisfaction >4/5 | Post-onboarding survey sent after week-1 review |
| Danny’s time per onboarding | Solo: <2 hrs, Growing: <5 hrs, Agency: <10 hrs, Enterprise: <20 hrs | Danny tracks time spent per customer during first 3 months; optimise from there |
Open Questions for Session
These need discussion and decisions before we onboard the first customers:
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Who does what — Danny vs the engineering team? The current onboarding spec says “admin-assisted CSV import” — is Danny doing the import, or does he collect the CSV and hand it to the engineering team? The answer determines Danny’s workload and whether we need admin tooling in the dashboard for CSV upload.
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Self-service CSV upload timeline? The onboarding spec lists self-service CSV upload as a future enhancement. For the first 10 customers, admin-assisted is fine. But when do we need this in the product? If Danny is doing 5+ onboardings per week, it becomes a bottleneck fast.
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Tenant notification approval flow? Do landlords get to see and approve the welcome message before it goes to tenants? Some will want to tweak the wording. Others will want to warn tenants personally first. What is the default process?
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What happens if a landlord wants to go live on just 2—3 properties first? Is partial rollout supported in the system, or is it all-or-nothing per organisation? Phased rollout is important for Growing Portfolio and Agency segments.
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Test conversation environment? Do we have a sandbox/demo mode where the customer can test without it affecting real tenant data? Or is the test conversation done on their real, imported properties? The latter is better (it proves the system works with their data) but needs careful handling.
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Document AI pipeline readiness? The capability map says the auto-extraction pipeline is “actively being built.” Is it ready for onboarding? If a customer uploads a house rules PDF, will the AI be able to answer questions from it by go-live? This is critical for the test conversation step.
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Channel readiness at onboarding? The biggest gap to “real product” is deployment and channel integrations (E-007, E-008). What channels will actually be available when Danny onboards the first customer? If it is web chat only (no WhatsApp, no voice), we need to set expectations and adjust the onboarding flow accordingly.
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Onboarding pricing — is it included or charged? The packaging matrix shows “dedicated onboarding session” for Professional and “dedicated account manager” for Enterprise. Is onboarding free for Starter, or do we charge a one-time setup fee? For early adopters, recommendation: include it free and use it as a selling point.
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How do we handle the gap between the demo and actual onboarding? The lead tiers playbook targets 7 days from first contact to go-live for hot leads. Is that realistic given the current state of deployment? Danny needs to know exactly what he can promise.
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What does the “early adopter” experience look like? The first 3—5 customers will be onboarded while the product is still being polished. Do they know they are early adopters? Do they get a special rate? Are they expected to provide feedback? How transparent are we about the product’s maturity?
Appendix: Research Sources
This matrix was informed by the following external research on B2B SaaS onboarding best practices:
- SaaS Customer Onboarding Guide: Best Practices & Templates (Dock)
- B2B SaaS Onboarding — The Complete Product Manager’s Guide (ProductFruits)
- Customer Onboarding Best Practices for CS Leaders in 2025 (OnRamp)
- SMB vs Mid-Market vs Enterprise Customer Onboarding: What’s the Difference? (Simplemnt)
- Customer Onboarding: Effective Segmentation Strategies (BeaconGTM)
- Time to Value: The Metric You Can’t Afford to Ignore (Product School)
- 12 Essential SaaS Onboarding Metrics to Track (Exec)
- How to Identify Churn Risk Factors in SaaS (Userpilot)
- How to Build Scalable Customer Onboarding That Feels High-Touch (ChurnZero)
- Property Management Onboarding Checklist (ContentSnare)
This matrix is a proposal for discussion in Session 3. It is designed to give Danny a concrete, step-by-step playbook he can start using with the first customers — while flagging the open questions and resources needed to make it repeatable at scale.