Book Your 48-Hour Roadmap

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Mid & Full IT Maturity Assessment

Get a Clear 24-Month Roadmap in Just 48 Hours.

Stop wondering if your technology is helping or hindering your growth. Our Rapid IT Maturity Assessment is a high-impact diagnostic designed to give Grand Cayman SMBs total clarity.

  • Identify Hidden Risks: We pinpoint cybersecurity gaps and operational vulnerabilities before they become expensive problems.

  • Audit Your Tech Spend: We review your existing vendor contracts to ensure you are getting maximum value for every dollar spent.

  • Build Your Roadmap: You receive a practical, jargon-free plan that aligns your IT investments with your 2026-2027 business goals.

💼 Flexible Pricing for Cayman Businesses
Fractional IT Leadership That Fits Your Size, Needs, and Budget.

Why Flexible Pricing Matters

At ILS IT Advisory Services, I know from Experience that no two businesses are alike. That’s why I offer flexible pricing options designed for small and medium-sized businesses in the Cayman Islands — whether you need a few hours of expert guidance or a dedicated IT leader on retainer.

  • Option A: The Strategic Pulse Check (Quick Risk Scan)

    Price: CI $350

    • The Grabber: A high-velocity, 48-hour review designed to identify immediate vulnerabilities before they become liabilities.

    • Executive Deliverables:

      • Rapid Diagnostic Scorecard: A high-level evaluation of your current backups, security fundamentals, and critical compliance gaps.

      • 1-Page Executive Risk Summary: A clean briefing featuring your Top 3 priority risks and immediate "quick wins" for remediation.

      • Strategic Next Step: A clear recommendation for long-term stability.

    • The Advantage: Includes an optional credit toward a Full Rapid IT Maturity Assessment.

    Pillar 1: The Governance Foundation (Policy Starter Kit)

    Price: CI $250

    • The Grabber: Most security breaches are the result of human error, not technical failure. These Enterprise-Grade Policy Frameworks—refined over three decades—establish the clear rules of engagement required to protect your staff, data, and reputation.

    • Executive Deliverables:

      • Core Policy Pack: Professional frameworks for Acceptable Use (AUP), Password Security, Data Backups, and Vendor Management.

      • Implementation Guide: A step-by-step rollout checklist to ensure company-wide adoption and enforcement.

      • Institutional Knowledge Blueprint: Documented standards that ensure your operational "rules of the road" are clear to all staff members.

    Pillar 2: The Oversight Framework (Vendor Scorecard Pack)

    Price: CI $350

    • The Grabber: You aren’t just paying for a scorecard; you are hiring a 31-year veteran to audit your providers for "Vendor Drift". I identify the risky clauses and service gaps that technical vendors often overlook.

    • Executive Deliverables:

      • Standardized Vendor Scorecards: Independent audits for up to five key partners to measure performance against Service Level Agreements (SLAs).

      • Vendor Prioritization Matrix: A visual risk assessment showing which partners are critical to your daily operations.

      • Governance Action Summary: Targeted remediation suggestions to improve vendor accountability and protect your IT budget.

    Pillar 3: The Resilience Blueprint (Business Continuity Mini-Plan)

    Price: CI $500

    • The Grabber: In the Cayman business environment, resilience isn’t a technical feature—it’s a leadership mandate. This high-impact "Mini-Plan" distills enterprise-level disaster recovery into a concise, 72-hour execution guide.

    • Executive Deliverables:

      • 72-Hour Recovery Runbook: A prioritized, step-by-step timeline for responding to critical outages or disasters.

      • Critical System Priority Table: Clearly defined recovery time (RTO) and recovery point (RPO) targets for your most essential functions.

      • Leadership Execution Checklist: A task list with assigned roles to ensure your people know exactly how to respond when the stakes are highest.

  • Strategic clarity and a 24-month roadmap for every stage of growth.

    Tier 1 — Business Foundation (1–10 employees)

    Investment: CI $750 Perfect for micro-businesses and professional offices needing a stable, secure starting point.

    • Holistic Maturity Score: A 5-domain evaluation of your current technical health.

    • Operational Heatmap: Immediate visual identification of your most critical gaps.

    • The 90-Day Quick Win Plan: Actionable steps to stabilize your environment right away.

    • 12-Month Roadmap: A practical plan to align your technology with your business goals.

    • Strategic Light Review: High-level oversight of your primary vendors and compliance notes.

    • Executive Results Call: A 30-minute session to review findings and prioritize next steps.

    Tier 2 — Strategic Growth (11–35 employees)

    Investment: CI $1,500 Ideal for growing teams navigating increased operational risk and vendor complexity.

    Includes everything in Tier 1, plus:

    • Institutional Vendor Oversight: Deep-dive analysis of vendor performance and accountability.

    • Regulatory Compliance Overlay: Specific focus on AML, Data Protection, and Business Continuity (BC).

    • Risk & Vulnerability Scoring: A deeper look at your security posture and data protection.

    • Strategic Budget Recommendations: Helping you plan your tech spend with 100% predictability.

    • 60-Minute Executive Session: A detailed review of your roadmap and risk profile.

    Tier 3 — Institutional Rigor (36–75 employees)

    Investment: CI $2,500 For established firms requiring enterprise-grade oversight and total regulatory alignment.

    Includes everything in Tier 2, plus:

    • C-Suite Policy Gap Analysis: Ensuring your internal processes match institutional standards.

    • Full Vendor Contract Mediation: Reviewing key agreements to protect your budget and ensure service levels.

    • Institutional Documentation Review: Ensuring your tech estate is fully documented and audit-ready.

    • Compliance Alignment Summary: A dedicated report for leadership and board-level review.

    • 90-Minute Strategic Workshop: A comprehensive session to finalize your long-term IT roadmap.

  • Enterprise-grade oversight for Grand Cayman SMBs—without the full-time executive overhead.

    Starter Tier — Strategic Foundation

    Investment: KYD 1,800 per monthIdeal for small teams (10–30 staff) beginning their journey toward professional IT management.

    • Monthly Strategic Review: A dedicated session to ensure your tech is aligned with your business goals.

    • Active Vendor Oversight: I manage your IT partners so you don’t have to.

    • Continuous IT Health Check: Regular monitoring of your system's stability and security posture.

    • Quarterly Roadmap Updates: Keeping your 12–24 month plan current and actionable.

    • Leadership Guidance: Expert advisory on one high-priority technology item each month.

    • Commitment: 8 hours per month (Flexible scheduling).

    Growth Tier — Operational Excellence

    Investment: KYD 3,000 per monthFor scaling businesses (20–60 staff) requiring deeper compliance and project oversight.

    Includes everything in Starter, plus:

    • Strategic Project Oversight: Expert leadership for your small-scale IT shifts and implementations.

    • Policy & Compliance Management: Regular updates to ensure you meet local and industry regulations.

    • Comprehensive Monthly Reporting: Data-driven insights into your IT performance and spend.

    • Staff Awareness Sessions: Building a security-first culture within your team.

    • Prioritized Remediation Plan: A clear path to fixing identified vulnerabilities.

    • Commitment: 16 hours per month (Flexible scheduling).

    Pro Tier — Institutional Leadership

    Typical Investment: KYD 4,000 per monthFor medium-sized firms (50–100 staff) needing consistent, high-touch executive IT leadership.

    What I deliver:

    • Full Fractional IT Leadership: I serve as your dedicated IT Director at the boardroom table.

    • Roadmap Delivery & Execution: I don't just plan the roadmap; I oversee its successful implementation.

    • Elite Vendor & Contract Mediation: Protecting your budget through rigorous performance and contract management.

    • SLA & Performance Reporting: Ensuring your technical partners are meeting their contractual obligations.

    • Incident Oversight & Coordination: Senior-level leadership during critical technical challenges.

    • BC/DR Governance: Comprehensive Business Continuity and Disaster Recovery readiness reviews.

    • Commitment: 20 hours per month (Flexible scheduling).

    Every Strategic Retainer Includes:

    • Free Initial Onboarding Session: To align our processes from day one.

    • Quarterly Strategy Deep-Dive: Ensuring long-term alignment with your business vision.

    • Vendor Alignment Check: Verifying that your tech stack is still the best fit for your scale.

    • Executive-Level Reporting: Jargon-free summaries for owners and boards.

  • On-demand executive insight for critical technology decisions.

    Best For:

    Businesses needing quick, expert guidance on a specific IT decision, vendor quote, risk, or project.

    What You Get:

    • Decision support

    • Vendor/quote review

    • Cybersecurity or compliance guidance

    • Project or roadmap clarification

    Investment:

    • KYD 150 per hour

    • 10% discount for prepaid block hours

    CTA: Book an advisory session

    Important

    This is advisory only — not technical support

Our Methodology: The ILS Strategic Framework

At ILS IT Advisory Services, we don't follow generic academic courses or "one-size-fits-all" software checklists. Our assessments are built on The ILS Strategic Framework—a proprietary methodology forged through 31 years of enterprise-grade leadership within the Cayman Islands’ unique business landscape.

Why Our Framework Outperforms Standard Certifications:

  • Evidence-Based Maturity: Instead of theoretical "maturity levels," we use a 3-Decade Pattern Recognition model to identify exactly where your IT is a liability and how to bridge the gap to high-performance stability.

  • Cayman-Specific Resilience: Our disaster recovery and continuity standards aren't just based on global manuals; they are built on real-world experience managing critical infrastructure through local hurricanes, power outages, and supply chain shifts.

  • The Strategic Bridge™: We apply the same rigorous governance and vendor accountability standards used by multi-million dollar enterprises, scaled down to fit the specific needs and budgets of Cayman SMBs.

  • Regulatory Pragmatism: Our methodology ensures your IT environment aligns with the Cayman Islands Data Protection Act (DPA) and local industry standards through practical, enforceable policies rather than dense legal jargon.

"In the boardroom, certificates don't protect your data—experience does. We don't just assess your IT; we audit it through the lens of a veteran who has seen every technical shift in the Cayman market since 1994."

What It Is: Your Strategic Framework

An IT Maturity Model is more than a technical checklist; it is a sophisticated framework designed to evaluate the synergy between your people, processes, and technology. I leverage my experience leading IT for one of the island’s largest enterprise groups to measure how effectively your current setup delivers predictable, value-driven outcomes. This assessment scores your current capabilities and identifies the critical gaps—giving you the same high-level clarity used by enterprise-grade organizations.

Why It Matters: Clarity and Accountability

This assessment transforms your technology from a source of frustration into a primary growth engine by aligning your IT investments directly with your business strategy. We bridge the "Strategic Gap" by revealing hidden process weaknesses and automation opportunities that reduce both operational risk and unnecessary costs. You receive a practical 12-24 month roadmap with measurable milestones, ensuring your technology remains predictable, secure, and fully accountable to your bottom line.

  • Free IT Maturity Mini‑Assessment

    A 3‑minute snapshot of your IT environment — built for Cayman small businesses.

  • Why This Matters

    • Clarity — Understand where you stand today

    • Confidence — Know your biggest risks

    • Direction — Get simple next steps

  • HOW IT WORKS

    1. Answer 6 simple questions

    2. Get your maturity score

    3. Receive tailored recommendations

    4. Optional: Book a Snapshot Review

  • WHAT YOU’LL RECEIVE

    • Maturity category

    • Risk summary

    • Recommended actions

    • Roadmap template

    • Option to book a review call

  • WHO THIS IS FOR

    Cayman SMBs with 5–75 employees who want clarity around:

    Security • Vendors • Compliance • Costs • Stability

  • CTA BLOCK

    Start Your Free Mini‑Assessment

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Let’s Build Your Strategic Roadmap Together

I’m Tony Pacheco, and I help Grand Cayman businesses access the senior-level leadership of a seasoned IT Manager—without the prohibitive cost of a full-time executive hire. With 31 years of experience leading IT operations for one of the island's largest groups, I provide the strategic bridge between your business goals and your technology execution.

Whether you are a growing firm needing a high-impact Rapid IT Maturity Assessment or an established business seeking ongoing Fractional IT Leadership, we provide a structured, enterprise-grade partnership tailored to your specific scale. I work seamlessly with your existing leadership teams and vendors to ensure your technology remains a growth engine, not a bottleneck.

Book Your 15-Minute Strategic Consultation

How I Help

Fractional IT Manager (Monthly Retainer)

C-Suite Strategic Oversight Without the $150k Executive Salary.

Most local firms need senior leadership but cannot justify the high cost of a full-time IT Director. As your Fractional IT Manager, I sit at your leadership table to provide the strategic oversight you’ve been missing.

  • Vendor Accountability: I manage your local and overseas vendors, ensuring they stay on schedule and on budget.

  • Compliance & Governance: We ensure your business is audit-ready and compliant with industry regulations—crucial for firms in the SEC and regulated sectors.

  • Predictable Leadership: Get enterprise-grade IT management on a flexible schedule that fits your business's scale.

Hourly Support & Advisory

Expert Advice When You Need It—Zero Long-Term Commitment.

Sometimes you just need an expert second opinion or help navigating a specific technical hurdle. We offer flexible hourly advisory services to help you make informed decisions with confidence.

  • Project Leadership: I provide oversight for major technology shifts or office moves to ensure nothing falls through the cracks.

  • Contract Mediation: Use my 30+ years of local experience to help you renegotiate IT contracts or select new vendors.

  • On-Demand Strategy: Get high-level consulting for specific business challenges without the need for a monthly contract.

IT Starter & Essential Kits

Stabilize Your Environment and Protect Your Growing Business.

If you’re not ready for a full retainer but need to move beyond "basic support," our IT Kits provide the fundamental structure needed to stabilize your operations.

  • IT Starter Kit: Ideal for smaller teams needing a foundational security framework and professional oversight.

  • IT Essential Kit: A robust package for growing firms that need deeper compliance readiness and helpdesk performance improvements.

  • Security First: Both kits focus on protecting your data and ensuring your team stays productive without technical bottlenecks.

    Book My Assessment

Not sure where to start? Most Grand Cayman SMBs begin with the Rapid IT Maturity Assessment. It’s the quickest way to get a professional "health check" on your technology without a long-term commitment.

Book My Assessment