The tools that work for a 10-person startup will frustrate a 100-person company. And the tools enterprise companies use will crush a small team with unnecessary complexity.

Right-sizing means choosing tools that fit your current size with reasonable room to grow. Not two years ahead. Not where you hope to be. Where you are.

Here’s what actually works at different stages.

The 10-Person Company

You’re small. Cash is precious. Everyone wears multiple hats. Simplicity beats sophistication.

Communication & Collaboration

Email: Google Workspace Business Starter ($6/user/month). Custom domain email, Google Drive, Meet for video calls. All you need.

Team Chat: Slack Free or Google Chat (included in Workspace). You don’t need chat history longer than 90 days.

Video Calls: Google Meet (included) or Zoom Free. Premium video features aren’t worth paying for yet.

Operations

Documents: Google Docs/Sheets. It works. Free with Workspace.

Project Management: Notion Free or Trello Free. Keep it simple. Boards and tasks. No complex workflows.

File Storage: Google Drive (15GB free per user, 30GB with Business Starter). If you need more, upgrade Workspace tier.

Sales & Marketing

CRM: HubSpot Free. No limits on contacts or users. Basic pipeline tracking. You don’t need anything more.

Email Marketing: Mailchimp Free (up to 500 contacts) or Brevo Free. Fancy automation isn’t worth paying for at this scale.

Website: Squarespace or Webflow. Don’t custom build yet.

Finance & Admin

Accounting: Xero Simple Start or QuickBooks Simple Start. The cheapest tier.

Payments: Stripe or Square. Simple setup, reasonable fees.

Expense Tracking: Manual or free tools. You don’t have enough volume to justify paid expense software.

Monthly Stack Cost

Roughly $20-40 per person per month all-in. Maybe $3,000-4,000 per year total.

What Not to Buy

• Enterprise CRM
• Complex project management
• Premium analytics
• Automation platforms
• Anything marketed to “mid-market” or “enterprise”

The 30-Person Company

You’ve got teams now. Departments with different needs. More complexity, more coordination required. But you’re still not big enough for enterprise tools.

Communication & Collaboration

Email: Google Workspace Business Standard ($12/user/month) or Microsoft 365 Business Basic ($6/user/month). You need more storage and better admin controls.

Team Chat: Slack Pro ($8.75/user/month) if you need message history and integrations. Or stick with included options if you don’t.

Video Calls: Still included tools (Meet/Teams). Zoom Pro if you need recordings or long meetings.

Operations

Documents: Google or Microsoft. Either works. Pick one and standardize.

Project Management: Asana, Monday, or ClickUp at starter tiers. You need visibility across teams now.

File Storage: Included with Workspace/M365. Might need Dropbox Business if you share heavily with external clients.

Sales & Marketing

CRM: HubSpot Starter ($20/month, up to 2 users) or Pipedrive (~$15/user/month). You need basic automation and reporting now.

Email Marketing: Mailchimp Essentials or ActiveCampaign Lite. Basic automation for nurture sequences.

Website: Same as before, or custom if marketing requires it.

Finance & Admin

Accounting: Xero Growing or QuickBooks Plus. More reporting, multi-user access.

HR: Some kind of system now. BambooHR, Gusto, or local equivalent. You have enough employees to need proper records.

Expense Management: Expensify or Dext at basic tiers.

Monthly Stack Cost

Roughly $50-80 per person per month. Maybe $20,000-30,000 per year total.

What Not to Buy

• Salesforce (unless you have very specific needs)
• Enterprise project management (Portfolio views, resource planning)
• Complex marketing automation
• ERP systems
• Anything that requires implementation consultants

The 100-Person Company

Real departments. Real processes. Need for integration between systems. Compliance requirements. You’re moving into territory where some enterprise tools make sense.

Communication & Collaboration

Email: Google Workspace Business Plus ($18/user/month) or Microsoft 365 Business Premium ($22/user/month). You need vault/archiving, better security, and admin controls.

Team Chat: Slack Business+ or Microsoft Teams (included with M365). Enterprise features like compliance, SSO, and advanced admin.

Video Calls: Dedicated platform if you do heavy video. Zoom Business or equivalent.

Operations

Documents: Google or Microsoft. If you’re this size, you’ve probably committed to one ecosystem.

Project Management: Monday/Asana/ClickUp at Business tiers. Portfolio views, workload management, integrations.

Knowledge Base: Notion, Confluence, or similar. You need institutional knowledge documented.

Sales & Marketing

CRM: HubSpot Professional, Pipedrive Professional, or Salesforce Essentials. Real automation, forecasting, and analytics.

Marketing Automation: HubSpot Marketing or similar. Lead scoring, complex nurtures, attribution.

Analytics: GA4 plus a BI tool (Looker Studio, Metabase) for custom dashboards.

Finance & Admin

Accounting/ERP: Xero Premium, NetSuite, or similar. Multi-entity, advanced reporting, integrations.

HR: Full HRIS. BambooHR, HiBob, or equivalent. Performance management, not just records.

Expense Management: Integrated with accounting. Approval workflows.

IT & Security

Identity Management: SSO solution (Okta, Google Identity). You have too many apps for individual passwords.

Device Management: MDM for laptops and phones if you issue devices.

Security: Basic security stack. Endpoint protection. Password manager.

Integration Layer

Automation: Make or Power Automate at business tiers. Real data flows between systems.

iPaaS: Maybe a proper integration platform if connections are complex.

Monthly Stack Cost

$100-150 per person per month. $120,000-180,000 per year total.

What You Might Actually Need Now

• Salesforce (if you have complex sales processes)
• NetSuite or real ERP (if operations are complex)
• Implementation help for major platforms
• Dedicated IT person or MSP

The Transition Points

Going from 10 to 30

The trigger: When free tiers start limiting you. When you need team visibility. When onboarding new people takes too long.

Key upgrades:

• CRM moves from free to paid
• Project management becomes necessary
• Need some kind of HR system

Going from 30 to 100

The trigger: When integration between systems matters. When security and compliance become real concerns. When you hire dedicated IT.

Key upgrades:

• SSO and identity management
• Proper automation between systems
• Enterprise-tier security
• Possibly ERP

The Right-Sizing Principle

At every stage, the question is: what do we actually need right now, plus room for 12 months of growth?

Not what we might need in three years. Not what companies bigger than us use. Not what the vendor wishes we’d buy.

Tools should fit your current reality. When you outgrow them, you upgrade. That’s normal and healthy. What’s not healthy is paying enterprise prices for capabilities you won’t use.

Match your tools to your size. Upgrade when you genuinely need to. Keep it simple as long as you can.