Software Selection Consultant – Trailer Leasing Fleet Management

Overview We are building a commercial trailer leasing business and are preparing to launch a fleet of approximately 100 trailers. Before we go live, we need to select the right software platform to manage our operations. We are looking for an experienced consultant who has run structured software selection processes for equipment-intensive businesses — fleet, transportation, construction, industrial, or similar. You do not need prior experience with trailer leasing software specifically; what matters is that you know how to evaluate, score, and recommend enterprise software in categories like this. What We Need We want a consultant to run a structured software selection process and deliver two things: 1. **Vendor Shortlist** — A ranked list of 10 software platforms suited to a trailer leasing operation at our scale (~100 units), with clear pros and cons for each. We have already identified vendors to include in scope (list provided at project start), but we are very interested in finding others that might be a fit. 2. **Final Recommendation Report** — A clear written recommendation identifying the 2–3 platforms worth advancing into a deeper review process (demos, detailed pricing, reference checks), with a structured rationale for why those made the cut and why others were eliminated. Our Requirements -Multiple agreement types — short-term rentals, long-term leases, and lease-to-own contracts, all within the same platform -Per-trailer asset tracking and per-unit P&L reporting -Maintenance scheduling and cost tracking -Automated billing and invoicing -REST API layer for integration with our other business tools (CRM, accounting, etc.) -Online inventory and customer booking — customers must be able to view available trailers and initiate agreements online -GPS / telematics integration — real-time location tracking for the fleet -Insurance tracking — ability to track insurance certificates, expiration dates, and coverage per asset or customer -Accounting integration and/or Built-In Accounting Functionality -Scalability beyond 100 units -Customer self-service portal Ideal Candidate - Has led or supported software selection projects for equipment-heavy businesses — fleet management, transportation, construction, industrial equipment, or similar categories - Knows how to build a requirements matrix, run structured vendor evaluations, and facilitate or review demos - Can verify API capabilities directly with vendors, not just from marketing materials - Delivers clear, opinionated written recommendations — not just feature comparison tables - No prior experience with trailer leasing software vendors required; a strong selection methodology matters more Deliverables & Timeline - Vendor shortlist with analysis: within 2 weeks of project start - Final recommendation report: within 2 weeks of project start Both deliverables should be in written document format (Word or PDF).