Hire the Lieutenant

"You don't hire the person, the head of marketing at these companies. You hire the person who's reporting to them, the lieutenant. And actually, Adam Zamos, who was the head of people at Square chimed in to say, 'At Square, early days we used to go hire the up and coming lieutenants of the lieutenants.'" - Gokul Rajaram

What It Is

Hire the Lieutenant is a recruiting playbook for finding exceptional talent: instead of targeting the heads of functions at best-in-class companies, target the rising stars one or two levels below them. These lieutenants have learned from the best, are hungry to prove themselves, and are more likely to join your company.

Gokul developed this insight after watching Square get systematically raided by fintechs after going public in 2015. The smartest recruiters didn't chase Square's department heads - they targeted the promising managers and senior ICs who had absorbed Square's operational excellence but were ready for their next challenge.

How It Works

The approach has three key steps:

Step 1: Identify Best-in-Class Companies

For the function you're hiring, identify 3-4 companies that are excellent at that specific capability serving similar customers (not necessarily competitors):

• Hiring head of marketing? Which consumer companies excel at marketing?
• Need a compliance lead? Which fintechs have navigated complex regulatory environments?
• Building sales team? Which companies sell to your customer segment exceptionally well?

Step 2: Build the Org Chart

Use LinkedIn and your network to map out the organizational structure:

• Who are the leaders of these functions?
• Who reports directly to them (lieutenants)?
• Who are the lieutenants of the lieutenants (rising stars)?

Step 3: Target the Right Level

Don't target: The head/VP of the function (expensive, less likely to move, may have skills outdated by seniority)

Do target: People 1-2 levels below who:

• Have absorbed best practices from top leadership
• Are hungry to take on more responsibility
• Are more accessible and affordable
• Will bring proven playbooks they've executed

How to Apply It

1. Map your hiring needs to company strengths - Which companies are genuinely excellent (not just well-known) at the specific function you need?

2. Look beyond competitors - Don't limit yourself to your industry. Look at any company serving similar customer types (consumers, SMBs, enterprise, etc.)

3. Invest in LinkedIn research - Spend time mapping org structures, not just finding candidates

4. Leverage your network for org context - Ask friends at target companies to help you understand who's really good and who might be looking

5. Focus on career trajectory - Lieutenants are often stuck behind strong leaders and hungry to run their own show

6. Offer meaningful scope increases - They're trading brand prestige for growth opportunity

When to Use It

• Hiring any leadership role (head of, director, VP)
• Building out a new function from scratch
• Competing for talent against larger, better-funded companies
• Looking for people who can bring proven playbooks
• Hiring for specialized skills (compliance, risk, growth, etc.)

Why It Works

The lieutenants at best-in-class companies have several advantages:

1. Battle-tested: They've operated in high-performing environments
2. Current skills: They're executing playbooks right now, not from memory
3. Teachable moments: They've learned from both successes and failures at scale
4. Motivated: They want to prove they can lead, not just follow
5. Accessible: They're not getting constantly recruited like their bosses

Source

• Guest: Gokul Rajaram
• Episode: "Picking where to work, hiring, investing, and product development"
• Key Discussion: (00:35:49) - How to hire leaders for any function
• YouTube: Watch on YouTube

Related Frameworks

• Best-in-Class Targeting - Identifying top-performing companies by function