Airtable CRM and Automation Specialist for Two Accommodation Businesses

PROJECT OVERVIEW I operate two UK accommodation businesses and am looking for an experienced Airtable CRM and automation specialist to design and build one central business operations system. The system must cover both companies within one Airtable workspace while keeping their records, bookings, invoices and documents clearly separated by legal entity. The two businesses operate differently: 1. Company A – Corporate Accommodation and Relocation Business Company A receives corporate accommodation enquiries and passes confirmed bookings to third-party accommodation providers. The system must track corporate clients, enquiries, providers, accommodation options, bookings, client charges, provider costs, invoices, commission/margins and supporting documents. 2. Company B – Serviced Accommodation and Property Management Business Company B operates and manages serviced accommodation properties. The system must receive reservation data from platforms such as Airbnb, Booking.com and VRBO through Uplisting. It must track properties, bookings, guests, booking income, cleaning, maintenance, documents and eligible previous guests for potential future outreach. The objective is to create one easy-to-use Airtable operations hub that can also integrate with Xero, Stripe, Uplisting and a future custom-built website for Company A. The successful specialist should first review the requirements and recommend the most appropriate architecture before beginning the full build. PHASE ONE: PAID DISCOVERY AND SYSTEM DESIGN The first milestone should include: * Review of both business processes. * Video call to discuss requirements and current workflows. * Recommended Airtable database structure. * Recommendation on using one base or multiple connected bases. * Review of Airtable Team versus Business plan requirements. * Recommended integration method, such as Make, n8n or custom API development. * Review of Uplisting’s API and webhook capabilities. * Recommended Xero and Stripe integrations. * Recommendation for document storage. * Recommendation for AI-assisted administration using Airtable AI, Sintra or another suitable tool. * Consideration of future integration with a full-stack website. * Written implementation plan. * Fixed-price quotation for the complete build. The full build should only begin once the proposed architecture has been reviewed and approved. CORE CRM REQUIREMENTS A. Companies and contacts The system should store: * Corporate clients. * Client contacts. * Client finance contacts. * Accommodation providers. * Property owners. * Suppliers and contractors. * Guest records. * Contact details. * Billing details. * Payment terms. * Contracts and documents. * Communication notes. * Account owner. * Legal entity associated with each record. * Marketing preferences where applicable. B. Company A enquiries and sales pipeline The system should include an enquiry pipeline with stages such as: * New enquiry. * Requirements received. * Searching for accommodation. * Options sent. * Awaiting client decision. * Quote accepted. * Booking confirmed. * Lost. * Cancelled. Each enquiry should include: * Client and contact. * Location and acceptable travelling radius. * Check-in and check-out dates. * Number of guests. * Bedroom and bed requirements. * Parking requirements. * Wi-Fi and other requirements. * Client budget. * Accommodation options offered. * Quoted price. * Expected provider cost. * Expected commission or gross margin. * Reason lost or cancelled. * Follow-up date. * Assigned administrator or account owner. C. Company A confirmed bookings Each confirmed booking should include: * Unique booking reference. * Corporate client. * Client contact. * Accommodation provider. * Property. * Guest or workforce information. * Check-in and check-out dates. * Number of nights. * Number of guests. * Client selling price. * Provider cost. * Cleaning charges. * Additional charges. * Commission or gross margin. * Purchase order number. * Client invoice. * Provider invoice. * Payment status. * Extension history. * Cancellation terms. * Booking status. * Relevant documents. * Relevant communications. * Missing-information warnings. Booking extensions should be recorded without removing the original booking information or history. D. Company A providers and properties Provider records should include: * Legal business name. * Trading name. * Contact information. * Properties supplied. * Agreed rates. * Payment terms. * Cancellation conditions. * Provider agreement. * Insurance confirmations. * Compliance confirmations. * Document expiry dates. * Performance notes. * Previous problems or cancellations. * Total bookings placed with the provider. * Total provider costs. Property records should include: * Full address and postcode. * Property type. * Number of bedrooms. * Bed configuration. * Number of bathrooms. * Maximum occupancy. * Parking. * Wi-Fi. * Facilities and amenities. * Photographs. * Property brochures. * Provider rates. * Availability notes. * Compliance confirmations. * Provider contact. * Previous bookings. E. Company B properties and bookings The Company B section should include: * Properties. * Platform listings. * Uplisting property reference. * Airbnb booking reference. * Booking.com booking reference. * VRBO booking reference. * Direct booking reference. * Guest name. * Permitted guest contact details. * Check-in and check-out dates. * Number of nights. * Number of guests. * Booking value. * Platform charges and fees. * Payment status. * Payout status. * Cleaning requirements. * Maintenance tasks. * Guest communication notes. * Problems and incidents. * Damage records. * Complaints. * Reviews. * Repeat-guest status. * Marketing permission. * Email marketing permission. * SMS or WhatsApp marketing permission. * Opt-out status. * Date and source of marketing permission. Uplisting should remain the main source of truth for live property availability and platform reservations. F. Invoices and financial tracking The CRM should display: * Client invoices. * Provider invoices. * Supplier invoices. * Invoice number. * Xero invoice ID. * Invoice date. * Invoice due date. * Net value. * VAT value. * Gross value. * Draft status. * Sent status. * Part-paid status. * Paid status. * Overdue status. * Credited status. * Stripe payment reference. * Provider costs. * Expected margin. * Actual margin. * Missing-invoice warnings. * Legal entity responsible for the invoice. * Linked client, provider, booking and property. Xero must remain the official accounting source of truth. The CRM should track or retrieve the relevant financial information without creating an uncontrolled duplicate accounting system. All financial automations should use approval stages. The system must not automatically send invoices, issue refunds, make payments, change bank details or decide VAT treatment without authorised approval. G. Legal entity and tax controls Every relevant record should have a compulsory legal-entity field: * Company A. * Company B. The system should prevent or warn against issuing an invoice under the wrong company. Once an invoice has been approved or issued, the legal-entity field should be locked or protected against unauthorised changes. Relevant Company A records should also be capable of storing accountant-approved classifications such as: * Acting as agent. * Acting as principal. * Commission-only transaction. * Potential TOMS treatment. * Other VAT treatment. * VAT treatment approved by. * Date approved. * Supporting contract or evidence. * Historical correction required. The system should record these classifications but should not allow AI to make the final accounting or tax decision. H. Document management The system should include a searchable documents register for: * Client invoices. * Provider invoices. * Supplier invoices. * Quotations. * Receipts. * Client contracts. * Provider agreements. * Insurance documents. * Property documents. * Complaints. * Incident records. * Policies and procedures. * Compliance documents. * Purchase orders. * Booking confirmations. * Credit notes. * Maintenance invoices. * Other business documents. Documents should be linked to the correct: * Legal entity. * Client. * Provider. * Guest. * Property. * Booking. * Invoice. * Supplier. * Incident or complaint. Documents should be searchable by: * Company. * Client. * Provider. * Property. * Booking reference. * Invoice number. * Document type. * Issue date. * Expiry date. * Status. The specialist should advise whether documents should be stored directly in Airtable or in secure external storage with links recorded in Airtable. USER INTERFACES REQUIRED The system should have simple interfaces so normal users do not need to work directly in the underlying Airtable tables. 1. Group Dashboard The Group Dashboard should show: * Overview of both companies. * Active enquiries. * Active bookings. * Upcoming arrivals. * Upcoming departures. * Revenue. * Provider and supplier costs. * Commission and gross margin. * Outstanding invoices. * Missing documents. * Overdue tasks. * Recent incidents. * Records requiring approval. 2. Company A Dashboard The Company A Dashboard should show: * Corporate clients. * Enquiry pipeline. * Accommodation searches. * Options sent. * Passed-on bookings. * Providers. * Properties. * Client charges. * Provider costs. * Commission and margin. * Missing client invoices. * Missing provider invoices. * Outstanding payments. * Upcoming booking extensions. * Records requiring review. 3. Company B Dashboard The Company B Dashboard should show: * Properties. * Upcoming reservations. * Arrivals and departures. * Guests. * Cleaning tasks. * Maintenance tasks. * Booking income. * Platform payouts. * Problems and complaints. * Damage records. * Previous eligible guests. * Guest marketing permissions. * Repeat-booking opportunities. 4. Finance and Documents Dashboard The Finance and Documents Dashboard should show: * Client invoices. * Provider invoices. * Supplier invoices. * Payment status. * Overdue invoices. * Missing paperwork. * Document expiry dates. * Invoices requiring approval. * Unmatched Stripe payments. * Xero synchronisation status. * Margin discrepancies. 5. Administrator Dashboard The Administrator Dashboard should show: * New enquiries requiring review. * New bookings requiring review. * Documents requiring upload or classification. * Missing booking information. * Overdue tasks. * Records requiring approval. * Duplicate warnings. * Integration errors. * Missing invoices. * Provider compliance documents approaching expiry. INTEGRATIONS REQUIRED 1. Uplisting Uplisting offers API and webhook access. The system should automatically receive appropriate Company B reservation information, including: * New reservations. * Reservation updates. * Date changes. * Cancellations. * Guest details where permitted. * Check-in and check-out dates. * Property references. * Platform booking references. * Booking values. * Reservation statuses. * Other relevant booking information available through the API. The integration must: * Prevent duplicate reservations. * Match guests and properties correctly. * Record the original Uplisting booking reference. * Maintain an integration activity log. * Flag failed integrations. * Maintain Uplisting as the main booking and availability system. * Avoid making uncontrolled changes to live availability. 2. Xero Desired workflows include: * Creating a draft Xero invoice from an approved CRM record. * Selecting the correct legal entity or Xero organisation. * Returning the Xero invoice number to Airtable. * Returning the invoice status to Airtable. * Updating Airtable when an invoice is paid. * Updating Airtable when an invoice is credited. * Linking or attaching invoice PDFs. * Highlighting overdue invoices. * Highlighting missing invoices. * Matching invoices to clients and bookings. * Recording integration errors. 3. Stripe Desired workflows include: * Matching Stripe payments to clients. * Matching Stripe payments to bookings. * Matching Stripe payments to invoices. * Updating payment status. * Recording Stripe payment references. * Highlighting unmatched payments. * Highlighting failed payments. * Highlighting refunds and disputes. * Ensuring payments are linked to the correct legal entity. 4. Email and documents The specialist should advise on connecting Gmail or Outlook for: * Recording important correspondence. * Drafting follow-up messages. * Receiving invoice attachments. * Receiving booking attachments. * Creating draft records from incoming enquiries. * Linking emails to clients, providers or bookings. * Identifying emails requiring action. AI AND ADMIN ASSISTANT REQUIREMENTS I would like an AI-assisted administrator to be able to perform controlled tasks such as: * Find a client, guest, provider, property, booking or invoice. * Upload and classify documents. * Extract invoice details from PDFs and images. * Create draft records from incoming emails. * Identify missing information. * Summarise outstanding invoices. * Produce daily or weekly booking reports. * Draft client emails. * Draft provider emails. * Identify bookings with missing provider invoices. * Highlight unusual or low-margin bookings. * Identify duplicate documents or records. * Summarise upcoming arrivals and departures. * Produce a list of overdue tasks. * Retrieve specific documents when requested. Please advise whether Airtable AI, Sintra, another AI platform or a combination is most appropriate. AI access must be permission-controlled. Initially, AI should not be allowed to: * Send invoices without approval. * Make payments. * Issue refunds. * Change bank details. * Delete financial records. * Approve tax classifications. * Make final VAT decisions. * Send bulk marketing communications without approval. FUTURE FULL-STACK WEBSITE REQUIREMENTS A future custom website for Company A may include: * Corporate accommodation enquiry forms. * Secure client accounts. * Client booking requirements. * Accommodation options. * Quote acceptance. * Booking status. * Booking extension requests. * Purchase-order uploads. * Invoice access. * Document access. * Provider registration. * Provider property submissions. * Provider document uploads. * Internal administration features. The Airtable system must therefore be API-ready and structured using permanent identifiers for: * Clients. * Contacts. * Providers. * Properties. * Enquiries. * Bookings. * Invoices. * Documents. The build should not expose Airtable credentials or API tokens to website users. The specialist should document how a future website developer can securely read information from and write information to the system through a suitable server-side integration. The architecture should also allow Airtable to remain the internal CRM if a dedicated website database is introduced later. SECURITY AND DATA PROTECTION The system will contain business and personal information. The build must include: * Appropriate user permissions. * Restricted access to financial data. * Restricted access to guest information. * Separate interfaces for different user roles. * Marketing permission records. * Consent source and date. * Opt-out records. * Do-not-contact or suppression status. * Audit history where available. * Secure handling of API credentials. * Backup and recovery recommendations. * Data-retention recommendations. * No storage of payment-card details. * GDPR-conscious handling of guest and client information. * Appropriate controls for document access. * Ability to remove or restrict access when staff or contractors leave. DELIVERABLES The completed project should include: * Approved database and architecture design. * Fully configured Airtable workspace. * All required tables. * Correct table relationships. * Required fields and validations. * User-friendly interfaces. * Management dashboards. * Administrator dashboard. * Forms. * Approval workflows. * Uplisting integration. * Xero integration. * Stripe integration. * Email integration recommendations or implementation. * Document-management workflow. * AI-assisted administration workflow. * Duplicate-prevention controls. * Error handling. * Integration activity logs. * Testing with sample enquiries. * Testing with sample bookings. * Testing with sample client invoices. * Testing with sample provider invoices. * User-permission configuration. * Written system documentation. * Data dictionary explaining tables and fields. * Automation documentation. * Integration documentation. * Administrator operating guide. * Recorded training session. * Full ownership and transfer of all accounts, automations, scripts and credentials. * Agreed post-launch support period. SPECIALIST EXPERIENCE REQUIRED Please apply only if you have demonstrable experience with several of the following: * Airtable relational database design. * Airtable Interface Designer. * Airtable automations. * Make. * n8n. * Comparable workflow automation platforms. * REST APIs. * Webhooks. * Xero integrations. * Stripe integrations. * Property-management systems. * Booking systems. * Uplisting or comparable channel managers. * Document extraction and OCR. * AI agent integrations. * GDPR-conscious system design. * Role-based access. * Website and API architecture. APPLICATION QUESTIONS Please answer all of the following: 1. Please provide examples of similar Airtable CRM or operations systems you have built. 2. Have you integrated Airtable with Xero, Stripe or a property-management/channel-management platform? Please explain what you built. 3. Have you worked with Uplisting’s API or webhooks? If not, what comparable booking platform have you integrated? 4. Would you recommend one Airtable base or multiple connected bases for these two companies, and why? 5. Would you recommend Make, n8n or custom code for this project, and why? 6. How would you prevent duplicate bookings, invoices, contacts and documents? 7. How would you keep Company A and Company B legally and financially separated while providing one management dashboard? 8. How would you ensure invoices and payments are linked to the correct legal entity? 9. How would you design the system for integration with a future full-stack website? 10. What would you recommend for AI-assisted document uploads, data extraction and administrative queries? 11. How would you manage user permissions and protect guest and financial information? 12. What security, backup and error-recovery arrangements would you include? 13. Please provide your proposed approach, estimated timescale and indicative cost for: * Paid discovery and architecture. * Core Airtable CRM build. * Company A workflows. * Company B workflows. * Uplisting integration. * Xero and Stripe integrations. * Document-management workflow. * AI administration. * Testing, documentation and training. 14. Please confirm that all Airtable bases, automations, integration accounts, scripts, documentation and credentials will be owned and controlled by the client upon completion. PROJECT ARRANGEMENT I prefer a staged fixed-price project with clear milestones: * Milestone 1: Discovery and technical specification. * Milestone 2: Core Airtable database and interfaces. * Milestone 3: Company A workflows. * Milestone 4: Company B workflows and Uplisting integration. * Milestone 5: Xero, Stripe, document and AI workflows. * Milestone 6: Testing, training, documentation and handover. Please do not submit a generic proposal. Applications should specifically explain how you would approach a two-company accommodation system involving corporate relocation bookings, managed accommodation bookings, guest records, invoices, documents, AI-assisted administration and future website integration.