Digital Transformation Symptoms

The 20-Employee Pivot: Using Technology to Empower Your First Middle Managers

Growing a business is like a unicyclist maintaining balance—it requires constant motion. With fewer than ten employees, your structure was likely informal and personal. As you pivot past 20 employees, operations become more complex.

At this stage, you can’t attend every meeting or oversee every transaction. Introducing middle management to lead specialized departments often creates “growing pains.” If not managed carefully, growth can dilute the branding and value that initially led to your success.

To navigate this tricky phase, bridge the gap between your close-knit past and your new needs. Use technology to help your new managers. This will maintain company culture and service quality.

The Visibility Gap: From Informal to Structured

When your team is small, communication happens naturally. But as you grow, information silos begin to form. Your new managers need more than just “gut feelings” to lead; they need data.

A Customer Relationship Management (CRM) platform provides your managers with a unified view of customer interactions, streamlining updates and highlighting issues before they affect the customer experience.

Replacing the “Founder’s Intuition” with Process

One of the hardest parts of delegating is trusting that your team will handle responsibilities with the same care you do. With 20+ employees, you must replace informal chats with structured processes.

• Communication Tools: Platforms like Slack or Microsoft Teams prevent communication breakdowns by organizing conversations by department or project.

• HR and Onboarding: When managers handle hiring, tools like Gusto, BambooHR, or Rippling help. They make onboarding consistent and help keep your company's values strong from day one.

• Marketing Automation: Tools like Mailchimp, Constant Contact, or ActiveCampaign allow managers to nurture leads and maintain a unified brand voice across all channels, even when you aren’t personally hitting “send”.

Empowering Managers through Digital Adoption

Technology is only useful when your team actually uses it. Often, businesses buy expensive software, but staff use workarounds, such as spreadsheets. This low usage hides costs and slows growth.

Empower managers by conducting Software Engagement Check-Ups to ensure effective tool use. This helps identify training needs, boost productivity and morale, and streamline processes.

Prioritizing Growth with the RICE Technique

Your first managers may be overwhelmed by the number of improvement ideas. I help leadership teams use the RICE technique (Reach, Impact, Confidence, and Effort) to objectively prioritize which opportunities to pursue first.

• Reach: How many customers will benefit?

• Impact: How much will they benefit?

• Confidence: How sure are we about these numbers?

• Effort: How much work will it take?

This systematic approach ensures your managers are focusing on the most cost-effective improvements that drive customer retention and profitability.

The Bottom Line

Turning into a managed organization should not feel like losing control. Instead, it should feel like building a strong base for more growth. By using the right technology, you make it easy for managers to give great service. This lets you focus on the bigger picture.

If your digital ecosystem feels fragmented as you scale, let's talk. Schedule a call to learn how technology can simplify growth for you and your management team.