How Should You Structure Your Team?

The Startup Help Desk

In this episode we talk about team structures. As soon as you have employees, you need to decide how to organize them. What are the best organization structures? What are the trade offs? We are here to help! In this episode we answer questions including:

• How many people should you have reporting to you?
• When should you hire leaders like a VP of Sales?
• Do you need product managers?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!
Your hosts:

• Sean Byrnes: General Partner, Near Horizon www.nearhorizon.vc
• Ash Rust: Managing Partner, Sterling Road www.sterlingroad.com
• Nic Meliones: CEO, Navi www.heynavi.com

Reminder: this is not legal advice or investment advice.

Q1: How many people should you have reporting to you?

As a startup CEO, you have to delegate management to avoid becoming a bottleneck. The absolute maximum number of people that should report to you at the early stage is 10. A good rule of thumb is to consider how many one-on-one meetings you can realistically handle every two weeks.

Your first hires should be leaders who can build and own major functions of the company, such as product, engineering, or sales/marketing. These leaders provide leverage, freeing you up to focus on other critical areas of the business. Managing too many people or managing people who are not leaders of their own functions can prevent you from executing on your core responsibilities. Remember, you want to hire exceptional people to do important work in areas you can't or don't want to do alone.

Q2: When should you hire leaders like a VP of Sales?

Hire a leader before your time becomes a bottleneck, but be careful to hire the right person at the right time. A "VP of Sales" is typically a scaler, not a builder. They will likely burn out or fail if your company's sales playbook isn't already baked.

Founders should own the sales process until it's proven and repeatable. Bring in a VP of Sales when you have a clear Ideal Customer Profile (ICP), have closed multiple deals beyond the initial founder hustle, and can hand them a clear playbook instead of a puzzle to solve.

For a sales team of 5-10 people, a Director of Sales with 3+ years of experience is often sufficient. For a team of 10+, you'll likely want a VP with 5+ years of experience. Find someone who can run the sales team better than you can, allowing you to focus on other aspects of the business.

Q3: Do you need product managers?

There is a lot of debate on this! Don't hire a product manager too early. The CEO is the de facto Product Manager (PM) until you achieve product-market fit (PMF). The learning loop is too critical to delegate at this stage.

You know it's time to hire a PM when:

• Customers love your product and keep using it.
• You're seeing organic growth or referrals.
• Engineers are spending too much time in product discussions instead of building.

A PM's role is to be the voice of the customer and ensure engineering time is used effectively. The need for an early PM can also depend on your product. For example, a consumer product may need a PM earlier than a developer-focused tool.