Oscar Avellaneda-Cruz

Multi-skilled professional with 10+ years of operations experience across office management, accounting support, and technology administration. I approach every role the way I would my own business — looking at the full picture of how people, processes, and tools connect, then focusing on the changes that make the biggest difference. My IT background means the systems I support stay out of the way so teams can focus on work that matters.

• Designed a bank statement categorization system across 12 spending categories, enabling leadership to verify monthly totals against QuickBooks and track spending patterns across inter-account transfers
• Built a weekly AP report scoring clients and job types by cash flow favorability — cross-referenced net payment terms against vendor timelines to protect margins and reduce late fee exposure
• Led a 250+ vendor data enrichment project: corrected 15% of records, flagged active SaaS contracts for renegotiation, and captured membership history to support business development ROI tracking
• Managed 100+ devices across workstations, tablets, conferencing, and keycard systems; maintained proactive cert renewals for 30 after-school tablets to prevent childcare operation downtime
• Built a cell phone billing verification system that caught false international roaming charges; resolved a device allocation issue outside childcare licensing requirements by building a line-assignment tracking system

• Co-managed a sequenced Windows 10→11 rollout across 25+ workstations, coordinating around AP/AR and student registration workloads while maintaining QuickBooks Desktop, Lightroom Classic, and DaVinci Resolve compatibility
• Set up Clover POS for Alaska Sales pre-launch; established baseline inventory for replenishment orders; installed 20+ security cameras for an adult home care facility ensuring resident privacy compliance (Alaska Horse Ranch)
• Developed seasonal phone-prep blueprints for after-school staff transitions, reducing device setup time by 18 hours per changeover cycle

• Monitored dual-ISP redundancy for locally hosted business applications; maintained workstation patch schedules across deployment cycles to reduce security exposure
• Partnered with IT security vendors at Alaska Sales and Camp Fire Alaska for COPPA/HIPAA staff training, access audits, and process documentation
• Managed Acumatica ERP integrations (Shopify, payment gateway, AK sales tax configurations); audited 42 legacy devices, recovered undocumented admin accounts, and eliminated unused software subscriptions
• Built a network device inventory system to verify user-device alignment and support COPPA/HIPAA compliance by ensuring only authorized staff held access to privileged information

• Built a staff-and-device directory in Notion — backed up as markdown and visualized in Obsidian — giving the Director of Operations a real-time map of people, devices, and data access across staffing changes
• Mapped document lifecycles at Alaska Sales (orders→fulfillment) and Camp Fire (incidents→debrief) to close handoff gaps and support data privacy compliance
• Simplified domain email onboarding for younger staff; conducted weekly third-party app credential audits reported to the Director of Operations with pattern-tracking tags
• Provided remote phone troubleshooting for mom-and-pop grocery clients in rural Alaska communities without broadband, guiding non-technical staff through on-site diagnostics
• Built a Claude skill that let consultants search a local copy of the O*NET job database (v29) using plain-English questions — comparing skills and knowledge requirements between roles to sharpen job sourcing, improve candidate matching, and write better-targeted paid job ads on Indeed. Results pulled up automatically in Obsidian and could be exported to PDF through a shared team Claude project.
• Process: Built a weekly check-in routine using ClickUp and a custom-built workflow in Claude to review active projects, flag stalled work, and catch early warning signs — producing a one-page Weekly Operations Report for company owners
• Outcome: Reports drove development of a cross-departmental prioritization matrix and revealed a pattern of deadline slippage tied to unresourced work — giving leadership a clearer basis for scheduling and resourcing decisions