AI Automated Outlook Follow-Ups to Boost Email Reply Rates - Contract to Hire

Project: Enterprise AI-Powered Automated Email Follow-Up System (Outlook / Microsoft 365) About Us We are a large enterprise organization building an internal AI-driven automation platform (“KI-Platform”) used across multiple business units. We are looking for a high-quality, reliable, long-term automation partner to design and implement an AI-based email follow-up solution that can scale across many users and teams. This project is intended as the first phase of a broader automation roadmap, and strong performance may lead to long-term collaboration, additional phases, and ongoing ownership. Business Problem Sales representatives typically send initial outreach emails but often fail to follow up when no response is received. This leads to: Lost revenue opportunities Low email reply rates High manual workload Inconsistent follow-up timing and quality Despite best intentions, follow-ups are frequently forgotten or delayed, especially when sales reps manage many parallel conversations. Project Goal Design and implement a system that automatically generates and sends context-aware, personalized follow-up emails using AI, based strictly on existing email conversations. The solution should: Increase reply rates Improve consistency and professionalism of follow-ups Reduce manual effort for sales teams Be scalable, secure, and enterprise-ready Success Metrics (Internal KPIs) The solution will be evaluated based on: Increase in email reply rate (%) vs. baseline Time to first reply Number of follow-ups sent per opportunity Conversion rate (optional, later phase) Salesperson adoption rate Core Scope of Work (Phase 1 – In Scope) 1. Email Account Integration Secure connection to user email accounts (Outlook / Microsoft 365; similar providers acceptable if architecture allows) Minimal user-side setup (e.g., enter email address + confirm via link) OAuth-based consent where required Configurable minimum permissions (read-only where possible) Ability to restrict access to selected folders only (Inbox, Sent, Sales folder, etc.) 2. Follow-Up Eligibility Detection The system must automatically identify email threads eligible for follow-up using logic such as: Initial email was sent by the user No reply received from recipient Auto-replies and out-of-office messages must be excluded Last activity older than a configurable threshold Configurable maximum number of follow-ups per thread to avoid spam risk 3. AI-Generated Follow-Up Emails Generate follow-up emails using AI based only on existing conversation context No hallucination or invention of facts Respect user-defined tone, style, and brand guidelines Output must be professional, concise, and sales-appropriate 4. Scheduling & Trigger Rules User-defined follow-up timing rules, e.g.: First follow-up after 1 day Second follow-up after 1 week Additional follow-ups after X days Must respect: Business hours User timezone Support pausing or disabling follow-ups per user or per account 5. Scalability & Architecture Support many users in parallel Stateless execution per user Queue-based processing No cross-user data leakage Ability to handle burst workloads (e.g., Monday mornings) Reliable retry mechanisms for API or network failures 6. UI & Platform Integration The feature must be accessible via our internal KI-Platform: Enable/disable follow-up agent per user Configure timing rules Configure tone & brand guidelines Preview AI-generated follow-ups before sending View sent follow-up history Exposed via API UI embedded in or integrated with KI-Platform Authentication aligned with KI-Platform users 7. Monitoring, Logging & Analytics System must track and log: Follow-up generated Follow-up sent Reply received AI errors or failures Logs per user and per email thread Exportable data (e.g., for Splunk dashboards) 8. Compliance & Security Full GDPR compliance Clear data isolation between users Secure handling of credentials and tokens Out of Scope (Phase 1) CRM integration or opportunity management Phone or LinkedIn follow-ups Fully autonomous deal closing Advanced analytics or forecasting (later phases possible) Optional / Nice-to-Have Scope Human-in-the-Loop Control Users can choose how follow-ups are handled: Auto-send mode Draft-only mode (approval required) Requirements: Mode configurable per account Drafts appear in Outlook or KI-Platform UI User can edit drafts before sending Multi-Language Support Ability to generate follow-ups in multiple languages Risks & Expectations RiskImpact Mitigation AI hallucination Loss of trust Strict prompts, context-only generation Brand or tone mismatch Brand risk User-defined guidelines + preview Outlook API limits Missed follow-ups Queuing & throttling User resistance Low adoption Draft-only mode initially Ideal Partner Profile We are looking for a partner with: Strong experience with Outlook / Microsoft 365 APIs Proven AI/NLP experience (context-aware generation) Experience building scalable, multi-tenant SaaS systems Familiarity with enterprise security & GDPR requirements Ability to think architecturally, not just implement features Partnership Mindset This is not a one-off project. We are explicitly looking for a long-term automation partner who can: Own the solution technically Evolve it across phases Support enterprise-scale rollout Collaborate closely with internal stakeholders If you are interested, please include: Relevant experience Similar projects or architectures you have built Your preferred engagement model (freelancer vs. agency) Initial technical thoughts or assumptions Apply tot his job