BUSINESS OPERATIONS & STRATEGIC EXECUTION
I turn complex, high-stakes requirements into executable systems.
I build and manage the financial, operational, and organizational infrastructure that allows growing companies to scale cleanly. My work sits at the intersection of multi-entity financial management, project controls, compliance, systems engineering, and strategic business development.
PROJECT CONTROLS
$20M Workforce Housing Development
BUSINESS DEVELOPMENT
55+ Proposals / $45M+ Construction Value
OPERATIONAL MARGIN
27.8% Net Profit Margin (~$764K Profit)
Four Pillars of Operating Practice
01 — Financial Operations & Capital
Forensic financial reconciliation, cash flow controls, AP/AR systems, and multi-entity accounting. Managing state housing grant compliance and capital disbursement audits.
02 — Strategic Business Development
Directing proposal architecture, compliance matrix auditing, subconsultant integration, and shortlist pitch deck strategy for 55+ municipal and commercial pursuits.
03 — High-Pressure Pursuit Execution
Rapid-turnaround project management, executive review synchronization, production logistics, and strict deadline execution under zero-defect municipal guidelines.
04 — Systems & Technical Problem Solving
Root-cause diagnosis of complex software/hardware failures, environment stabilization on non-standard architectures, asset recovery, and operational continuity.
Case Studies & Operational Outcomes
Detailed evidence of problem-solving across finance, pursuits, project controls, and technology systems.
01 — FINANCIAL OPERATIONS & CAPITAL
$1.56M MaineHousing AHOP Reimbursement & Audit Mitigation
Situation & Challenge: Executing a final $1.56M Affordable Housing Outreach Program (AHOP) reimbursement request for a workforce housing development. The submission required 100% verified proof of paid costs, proof of a $300K partner cash equity contribution, and strict exclusion of non-reimbursable soft costs across fragmented legacy ledgers.
Execution: Conducted a forensic audit of AP accounts and banking records to isolate strictly eligible costs. Proactively identified and excluded over $87K in non-reimbursable pre-development/closing invoices to eliminate state agency audit risk. Controlled the financial narrative around CPA tax roll-forwards to clearly validate the $300K gross equity contribution without underwriting friction.
Outcome: Secured access to the full $1,562,810 in critical project capital with zero state agency audit requests or underwriting revisions.
02 — STRATEGIC BUSINESS DEVELOPMENT
$750K City of Augusta Public Works Campus Contract
Situation & Challenge: Bidding on a high-priority municipal A&E proposal capped at a $750K budget ceiling. The RFP mandated a rigid 14-section compliance checklist, a strict portrait-format layout, and a 20-page narrative cap—requiring a complete overhaul of the firm’s standard horizontal proposal framework.
Execution: Redesigned proposal architecture from the ground up to fit vertical municipal standards. Audited multi-disciplinary engineering inputs (VHB, Salas O’Brien), enforced strict page-cap compliance, managed complex physical/USB delivery, and built the shortlist presentation deck linking architectural design to Augusta’s Comprehensive Plan.
Outcome: Won the contract award at the $750K maximum value ($189K immediate Phase 1 authorization) and established a repeatable vertical proposal asset for future municipal bids.
03 — HIGH-PRESSURE PURSUIT EXECUTION
72-Hour Turnaround: Town of Fairfield Municipal Complex
Situation & Challenge: Delivering a multi-part municipal proposal requiring 16 bound physical volumes (1,100+ total pages) under a 72-hour holiday weekend deadline with zero external print vendor availability.
Execution: Built the entire 75+ page master document, led iterative scope/fee review sessions with the Principal Architect, conducted line-by-line compliance audits, and managed 100% in-house printing, precision cutting, and binding.
Outcome: Awarded $89,538 Phase 1 contract and secured primary positioning for the follow-on multi-million-dollar construction phase.
04 — Operational & Systems Problem Solving
QuickBooks Deployment on Unsupported ARM64 Hardware
Problem: QuickBooks Desktop failed to launch on a Snapdragon ARM64 Surface Pro due to x86 emulation layer blocks, service timeouts, and Memory Integrity security conflicts.
Action: Reconfigured system registry parameters, adjusted service timing to Automatic (Delayed Start), manually bridged Visual C++ x86 libraries, and stabilized background database services.
Result: Restored financial system access without hardware replacement or cloud migration costs.
Workstation Hardware Failure Isolation & Asset Protection
Problem: Recurring system crashes during disk-intensive tasks threatened a core graphics workstation, initially appearing as an SSD failure.
Action: Conducted Event Viewer log analysis, component elimination testing with fresh OS installs, and isolated the fault to a defective motherboard M.2 controller slot before securing vendor RMA.
Result: Secured full manufacturer warranty replacement while retaining and protecting a $230 SSD asset.
Interested in Operational Support or Leadership?
Whether discussing business operations roles, strategic consulting, or project controls, feel free to reach out directly.
Dylan Lepore 