One-Page Cheat Sheet
More than a checklist. A look at how IT evolves as your business grows.
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From IT Maintenance to IT Leadership
A Better Way to Build an IT Foundation That Scales
Capability
Base Recommendation
Upgrade Triggers
Identity & Access
Use IdP (Okta) as control plane with MFA everywhere; extend SSO to critical apps; adopt PAM (Keeper) when needed; capture audit evidence (access reviews, deprovisioning).
If: Headcount >200, multi-office, or enterprise deals → Then: Expand SSO coverage, enforce conditional access, and automate access reviews.
Device Management
Deploy zero/near zero-touch provisioning with MDM; enforce encryption, patching, and lock/wipe; maintain a 5-10% spare pool.
If: Devices >200, formal audit, contractor-heavy → Then: Proactive hardware refresh (3 years), compliance reporting.
Security
Enforce MFA, deploy EDR on all devices, maintain immutable backups, enable basic email security (SPF/DKIM/DMARC), and provide secure remote access (ZTNA or VPN).
If: SOC 2 required, enterprise deals, or incident occurs → Then: Add SIEM, vulnerability scans, and a formal incident response program.
Networking
ISP with LTE/5G failover; cloud-managed firewall+ network stack; simple 3 network segmentation; secure remote access via VPN or simple ZTNA.
If: Multi-site, high-density workspace, or uptime challenges → Then: Add redundant ISPs, enterprise NGFW, and expanded segmentation.
Data & SaaS Governance
Track SaaS via IdP (Okta); run access reviews; default sharing to private; enforce retention policies; enable audit logging; assign ownership.
If: SaaS apps >50 or license waste >15% → Then: Deploy SaaS mgmt platform and formalize governance reviews.
Workforce Enablement
Hire MSP or implement basic ticketing system; publish a knowledge base; script top 3-5repetitive tasks; create lightweight run books.
If: Tickets exceed SLA or headcount >200 → Then: Formalize SLAs, expand automation, and add reporting/escalation
Policies & Documentation
Prioritize incident run books, system configs, on/off boarding checklists, and incident response plan; capture evidence artifacts.
If: Pursuing SOC 2, ISO 27001, or enterprise contracts → Then: Expand policy set and integrate with compliance automation.
Compliance
Prep for SOC 2 or SOX with documented policies, evidence collection, and annual risk assessment; manage artifacts manually at first.
If: Enterprise/regulated deals require proof → Then: Use compliance automation (Vanta/Drata) and centralize evidence collection.
Budgeting
Track IT spend; allocate SaaS by department; expect 15–20% waste buffer from SaaS sprawl and shadow IT.
If: Annual IT spend >$1M or waste exceeds buffer→ Then: Formalize forecasting, vendor negotiations, and procurement review.
Employee Experience
Use checklists for onboarding; survey annually; position IT as partner by reducing friction and publishing IT roadmap.
If: Headcount >200 or employee churn rises → Then: Automate onboarding, survey quarterly, and add self-service IT resources.
IT/Business Alignment
IT lead participates in exec meetings; ensure IT is represented in strategic discussions.
If: Headcount >200 or recurring IT issues affect business → Then: Establish CIO/CISO role, strategic roadmap, and board reporting.
From IT Maintenance to IT Leadership
A Better Way to Build an IT Foundation That Scales
Capability
Base Recommendation & Upgrade Triggers
Identity & Access
Base: Use IdP (Okta) as control plane with MFA everywhere; extend SSO to critical apps; adopt PAM (Keeper) when needed; capture audit evidence (access reviews, deprovisioning).
Upgrade If: Headcount >200, multi-office, or enterprise deals → Then: Expand SSO coverage, enforce conditional access, and automate access reviews.
Upgrade If: Headcount >200, multi-office, or enterprise deals → Then: Expand SSO coverage, enforce conditional access, and automate access reviews.
Device Management
Base: Deploy zero/near zero-touch provisioning with MDM; enforce encryption, patching, and lock/wipe; maintain a 5-10% spare pool.
Upgrade If: Devices >200, formal audit, contractor-heavy → Then: Proactive hardware refresh (3 years), compliance reporting.
Upgrade If: Devices >200, formal audit, contractor-heavy → Then: Proactive hardware refresh (3 years), compliance reporting.
Security
Base: Enforce MFA, deploy EDR on all devices, maintain immutable backups, enable basic email security (SPF/DKIM/DMARC), and provide secure remote access (ZTNA or VPN).
Upgrade If: SOC 2 required, enterprise deals, or incident occurs → Then: Add SIEM, vulnerability scans, and a formal incident response program.
Upgrade If: SOC 2 required, enterprise deals, or incident occurs → Then: Add SIEM, vulnerability scans, and a formal incident response program.
Networking
Base: ISP with LTE/5G failover; cloud-managed firewall+ network stack; simple 3 network segmentation; secure remote access via VPN or simple ZTNA.
Upgrade If: Multi-site, high-density workspace, or uptime challenges → Then: Add redundant ISPs, enterprise NGFW, and expanded segmentation.
Upgrade If: Multi-site, high-density workspace, or uptime challenges → Then: Add redundant ISPs, enterprise NGFW, and expanded segmentation.
Data & SaaS Governance
Base: Track SaaS via IdP (Okta); run access reviews; default sharing to private; enforce retention policies; enable audit logging; assign ownership.
Upgrade If: SaaS apps >50 or license waste >15% → Then: Deploy SaaS mgmt platform and formalize governance reviews.
Upgrade If: SaaS apps >50 or license waste >15% → Then: Deploy SaaS mgmt platform and formalize governance reviews.
Workforce Enablement
Base: Hire MSP or implement basic ticketing system; publish a knowledge base; script top 3-5repetitive tasks; create lightweight run books.
Upgrade If: Tickets exceed SLA or headcount >200 → Then: Formalize SLAs, expand automation, and add reporting/escalation
Upgrade If: Tickets exceed SLA or headcount >200 → Then: Formalize SLAs, expand automation, and add reporting/escalation
Policies & Documentation
Base: Prioritize incident run books, system configs, on/off boarding checklists, and incident response plan; capture evidence artifacts.
Upgrade If: Pursuing SOC 2, ISO 27001, or enterprise contracts → Then: Expand policy set and integrate with compliance automation.
Upgrade If: Pursuing SOC 2, ISO 27001, or enterprise contracts → Then: Expand policy set and integrate with compliance automation.
Compliance
Base: Prep for SOC 2 or SOX with documented policies, evidence collection, and annual risk assessment; manage artifacts manually at first.
Upgrade If: Enterprise/regulated deals require proof → Then: Use compliance automation (Vanta/Drata) and centralize evidence collection.
Upgrade If: Enterprise/regulated deals require proof → Then: Use compliance automation (Vanta/Drata) and centralize evidence collection.
Budgeting
Base: Track IT spend; allocate SaaS by department; expect 15–20% waste buffer from SaaS sprawl and shadow IT.
Upgrade If: Annual IT spend >$1M or waste exceeds buffer→ Then: Formalize forecasting, vendor negotiations, and procurement review.
Upgrade If: Annual IT spend >$1M or waste exceeds buffer→ Then: Formalize forecasting, vendor negotiations, and procurement review.
Employee Experience
Base: Use checklists for onboarding; survey annually; position IT as partner by reducing friction and publishing IT roadmap.
Upgrade If: Headcount >200 or employee churn rises → Then: Automate onboarding, survey quarterly, and add self-service IT resources.
Upgrade If: Headcount >200 or employee churn rises → Then: Automate onboarding, survey quarterly, and add self-service IT resources.
IT/Business Alignment
Base: IT lead participates in exec meetings; ensure IT is represented in strategic discussions.
Upgrade If: Headcount >200 or recurring IT issues affect business → Then: Establish CIO/CISO role, strategic roadmap, and board reporting.
Upgrade If: Headcount >200 or recurring IT issues affect business → Then: Establish CIO/CISO role, strategic roadmap, and board reporting.
We Manage Your IT So You Can Manage Your Business
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