What Should a Technology Roadmap Look Like for a 20-Person Company?
If you're running a 20-person business, you're in a unique position. You're past the scrappy startup phase where you could get by on cloud storage and a couple of apps, but you're not yet large enough to have a dedicated IT department. This is exactly where a solid technology roadmap for small business becomes critical—not as a 100-page strategic document, but as a practical, living guide that helps you make intentional technology decisions instead of reactive ones.
We've worked with hundreds of companies at this exact stage, and we've seen the pattern: businesses without a tech roadmap end up with fragmented systems, repeated spending on overlapping tools, frustrated teams using outdated software, and security vulnerabilities they didn't know existed. A 20-person company with no direction on technology often runs like it's still operating on a shoestring budget, even as revenue has grown significantly.
The good news? A meaningful IT strategy small business doesn't require hiring a CTO or spending six months in planning meetings. It requires clarity on three things: where you are now, where you need to be, and the logical steps to get there.
The Core Components of a Small Business IT Roadmap
A practical technology roadmap for a 20-person company should contain five key elements. These aren't chapters in a binder—they're conversations and decisions that fit on a one-page document that you actually reference monthly.
Assessment of Current State is where you start. Document what systems you're currently using: email, accounting software, CRM, project management tools, security measures, backup systems, and any industry-specific software. Write down what's working well and where people are complaining or workarounds are being created. This inventory exercise alone often reveals surprising gaps—like the fact that three different departments are managing customer data in three different ways.
Security & Compliance Baseline deserves its own line item. If you have any customer data, financial records, or personal information in your systems, you have compliance obligations. Whether it's HIPAA, PCI-DSS, or just basic data protection, ignoring this creates liability. Your roadmap should address: data backups, password management, access controls, and employee security training. For a 20-person company, this isn't complicated—it's a checklist of non-negotiables.
Technology Infrastructure covers the bones of your operation: your network, WiFi quality, computers and devices, and internet connectivity. Many 20-person companies inherit infrastructure from when they had five people, and it's showing stress. A roadmap should clarify: Do you have professional WiFi or are you sharing a consumer router? Are computers being updated? Is your internet fast enough for video calls and cloud software? These foundational elements affect everything else.
Application Strategy means deciding which tools your team actually needs and when to implement them. This is where most companies go wrong—they buy software reactively, based on one person's request or whatever's being advertised. A roadmap approach says: "For sales, we need a CRM with integrations to our email and accounting. We'll evaluate options Q2 and migrate in Q3." That timeline and intention makes all the difference.
People and Process Alignment acknowledges that technology only works if people actually use it correctly. Your roadmap should outline: which teams need training, who owns password management, how decisions about new tools get made, and who troubleshoots basic issues before calling an outside vendor. A 20-person company often has someone informally doing IT—your roadmap should formalize that role (even if it's part-time).
Creating Your Roadmap: The Practical Process
You don't need a consultant to write this—you need to involve your team. The best IT planning for SMB comes from people who actually use the tools daily.
Start by scheduling a two-hour working session with three to five key people: your operations manager, your finance person, a frontline team member, and yourself. Go through the components above. Ask: "What's slowing us down? What security concerns keep you up at night? What tool are we paying for that nobody uses?" Write down everything without judgment.
Next, categorize these into three time horizons:
Q1/Q2 (Immediate—3-6 months): These are fixes that affect day-to-day operations or security gaps you can't live with. Examples: setting up a password manager (everyone should have one), implementing consistent backups, auditing who has access to what systems, upgrading computers that are more than five years old, or stabilizing your WiFi network.
Q3/Q4 (Medium-term—6-12 months): These are meaningful upgrades that require some planning but don't need to happen tomorrow. Examples: implementing a CRM, moving from email-based document storage to a shared file system, bringing in a new accounting tool that integrates with payroll, or implementing multi-factor authentication across all critical systems.
Year 2+ (Strategic): These are transformation projects that align with business growth. Examples: building out API integrations between your systems, implementing advanced analytics to understand customer behavior, or preparing for expansion into new markets or locations.
The key to this prioritization: a roadmap isn't a promise carved in stone. It's a framework that keeps you focused while leaving room for the urgent things that always come up.
Questions Every 20-Person Company Should Ask
Use these questions to test whether your roadmap is realistic and aligned with your business:
Can we afford it? Technology doesn't have to be expensive, but you should budget for it—roughly 5-8% of revenue for a growing company is typical. Your roadmap should identify which initiatives require capital investment and which are operational expenses.
Do we have the bandwidth to implement it? A big technology change takes more than just money. It takes time for training, testing, and the inevitable troubleshooting. If you're in growth mode, a roadmap that requires your founder to spend three months configuring software is unrealistic. It might make sense to bring in fractional help for larger implementations.
Is this solving a real problem? Every line item on your roadmap should connect to something that hurts—lost time, security risk, customer complaints, or wasted money. "We should implement this because it's best practice" isn't a good enough reason. "We should implement this because customer data isn't being protected" is.
Who owns the rollout? For each initiative, identify a person—not a committee, a person—responsible for seeing it through. That person doesn't have to be a tech expert, but they need to be accountable.
The Role of Outside Help
Many 20-person companies try to do all of this alone and end up without any roadmap at all because it feels like too much. That's where fractional CTO services come in. We work with businesses your size to assess your current technology stack, identify gaps, and create a realistic roadmap that you can execute without needing to hire a full-time technology leader.
A good fractional CTO for small business doesn't just hand you a document. They help you think through implementation, advise on tool selection, and often manage the actual vendor relationships and technical setups. For 10-15 hours per month, you get strategic technology guidance and someone who keeps your roadmap moving forward.
Moving Forward
A technology roadmap for a 20-person company should be practical, not perfect. It should fit on a single page. It should be reviewed quarterly and updated when priorities shift. It should connect each technology decision to a business outcome.
The companies we work with that have clear technology roadmaps experience less downtime, make better tool decisions, spend less money on duplicative or underused software, and have teams that feel supported by the technology they work with. That's not magic—that's the result of intentional planning.
Ready to Build Your Technology Roadmap?
If you're a 20-person company tired of making reactive technology decisions, we'd like to help. We work with businesses just like yours to assess where you are, clarify where you need to be, and create a realistic roadmap to get there—without requiring you to hire a full-time CTO.
We'll spend 30 minutes understanding your current technology situation, identifying your biggest pain points, and discussing what a realistic roadmap looks like for your business. No sales pitch—just honest advice from people with 15+ years of experience helping businesses like yours.
Call us: (804) 510-9224 | Email: info@sandbarsys.com