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Resources for SMB Technology Leaders

Practical guides, checklists and sample reports for owners and leaders of small and mid-sized businesses. Use them on your own, or bring them to a free IT Strategy Session.

5-minute self-check

Who owns your technology function?

Answer 20 quick statements and see which technology decisions have a clear owner and which fall between the cracks. No email needed to see your score.

Browse the library

Guides, checklists and sample reports

The SMB Guide to Choosing a Managed Technology Provider cover

Guide · Strategy & leadership

The SMB Guide to Choosing a Managed Technology Provider

How to find a technology partner who owns the plan, works well with the providers you already have, and keeps technology tied to your business goals.

18-page PDF · short form

Who Owns Your Technology Function? cover

Worksheet · Strategy & leadership

Who Owns Your Technology Function?

20 statements that show which technology decisions have a clear owner and which fall between the cracks. Prefer it online? Take the self-check.

5-page PDF · instant download

Is Fractional Technology Leadership Right for You? cover

Guide · Strategy & leadership

Is Fractional Technology Leadership Right for You?

What a Fractional CIO and a Fractional CISO actually do, how to tell which one you need, and how to get value from the first 90 days.

7-page PDF · short form

The SMB Technology Planning Guide cover

Guide · Strategy & leadership

The SMB Technology Planning Guide

How to build a technology plan your leadership team can actually use, review and keep current.

7-page PDF · short form

Building a Security Program Without a Full-Time CISO cover

Guide · Security & compliance

Building a Security Program Without a Full-Time CISO

How to give cybersecurity a clear owner, a plan and a regular check that it’s working, without a full-time hire.

7-page PDF · short form

SMB IT Planning Checklist cover

Checklist · Strategy & leadership

SMB IT Planning Checklist

A year-ahead planning checklist that ties your technology decisions to your business plan, with budget categories and a one-page roadmap.

7-page PDF · instant download

IT Vendor Evaluation Checklist cover

Checklist · Strategy & leadership

IT Vendor Evaluation Checklist

42 questions to ask before you sign with any technology vendor, a side-by-side scoring sheet and the red flags to watch for.

5-page PDF · instant download

Business Expansion IT Checklist cover

Checklist · Strategy & leadership

Business Expansion IT Checklist

What to line up before you open a new location, take on an acquisition or hire fast, from circuit lead times to the first 30 days.

6-page PDF · instant download

Know Where You Stand: A CMMC Guide for Small Defense Contractors cover

Guide · Security & compliance

Know Where You Stand: A CMMC Guide for Small Defense Contractors

What still applies to your contracts, how your SPRS score works, and how to get to an affirmation you can sign with confidence.

7-page PDF · short form

CMMC Preparation: What to Gather Before You Start cover

Checklist · Security & compliance

CMMC Preparation: What to Gather Before You Start

For small defense contractors: the documents, facts and people to pull together so you know where you stand.

7-page PDF · instant download

Business Continuity Checklist for SMBs cover

Checklist · Security & compliance

Business Continuity Checklist for SMBs

What to have in place so a disruption becomes a bad day, not a business-ending week. Includes a critical process worksheet.

7-page PDF · instant download

Sample Cybersecurity Assessment Report cover

Sample report · Security & compliance

Sample Cybersecurity Assessment Report

What a clear, prioritized cybersecurity assessment report looks like, shown for a fictional 60-person professional services firm.

8-page PDF · short form

Cloud Migration Planning Checklist cover

Checklist · Cloud & infrastructure

Cloud Migration Planning Checklist

A phase-by-phase checklist for planning a move to the cloud, from the first business case to the months after go-live.

6-page PDF · instant download

Sample IT Infrastructure Assessment Report cover

Sample report · Cloud & infrastructure

Sample IT Infrastructure Assessment Report

What an infrastructure assessment report looks like, shown for a fictional 45-person manufacturer, with findings and a 12-month roadmap.

8-page PDF · short form

SMB Workflows Worth Automating with AI cover

Guide · AI & automation

SMB Workflows Worth Automating with AI

Eight everyday workflows where automation and AI pay off, what to have in place first, and a worksheet for picking your first one.

8-page PDF · short form

The AI-Powered Business Playbook cover

Guide · AI & automation

The AI-Powered Business Playbook

Where AI fits in a small or mid-sized business, a starter acceptable-use policy outline, a 90-day rollout plan and how to measure value.

8-page PDF · short form

monday.com for SMBs: Smart Setup Checklist cover

Checklist · AI & automation

monday.com for SMBs: Smart Setup Checklist

What to decide and check when you set up or clean up monday.com, so your team actually uses it and the data stays useful.

6-page PDF · instant download

MVP Scoping Guide for Founders cover

Guide · Software

MVP Scoping Guide for Founders

How to decide what your first version must do, what can wait, and how to brief a development partner.

9-page PDF · short form

Close the loop on your technology.

Not sure which one you need? Tell us what you’re working on and we’ll point you to the right starting place. Every engagement starts with a conversation about your goals and your current technology.