Best-in-Class Lieutenant Hiring
Map excellent adjacent companies and recruit the leaders directly below the top role
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 98%
Best-in-Class Lieutenant Hiring starts with the capability you need, not a list of people you happen to know. Define the target function and the kind of customer your company serves. Identify three or four companies that are exceptional at that function for a similar customer, including companies outside your direct competitive set. Reconstruct the relevant org charts through public profiles and trusted contacts. Instead of trying to recruit the top executive, target the lieutenant or the lieutenant's strongest deputy who has helped build the system at scale and may be ready for broader ownership. The method converts executive search into a structured talent map and widens the pool while preserving relevant operating experience.
Origin
After a founder successfully hired a third leader from Rajaram's advice, Rajaram realized he had repeatedly recommended source companies rather than individuals. He had also watched fintechs recruit layers of Square's payments, compliance, and risk teams after its IPO.
Core principles
- 01Search by demonstrated functional excellence rather than familiar competitor names
- 02Customer similarity transfers operating knowledge across industries
- 03The strongest attainable candidate is often the top leader's lieutenant
- 04An org chart turns vague networking into a systematic search
How to run it
- 1
Specify the capability
Name the function, the customer type, and the operating challenge the new leader must solve. Avoid starting with a generic title such as head of marketing.
Pro tip Describe the system they must build and the scale they must handle.
- 2
Find functional exemplars
Identify three or four companies known for excellence in that function with a similar customer. Include adjacent categories rather than restricting the search to competitors.
Pro tip Customer similarity may matter more than product similarity.
Watch out A famous company is not automatically excellent at the function you need.
- 3
Build the org maps
Use public profiles and people who know the companies to reconstruct reporting lines. Mark the top leader, direct reports, and rising deputies who owned relevant work.
Pro tip Ask contacts to correct the map rather than asking them for one candidate name.
- 4
Target the lieutenants
Approach the leaders immediately below the top executive, or their strongest deputies. Look for evidence that they built the capability rather than merely observed it.
Pro tip Offer a scope increase that makes the move a logical next step.
Watch out Do not assume a senior title proves direct ownership.
- 5
Validate and recruit
Interview for the exact operating system you need and reference-check the candidate's contribution. Frame the role around the problem and ownership, not just compensation or title.
In the wild
After Square became one of the few public fintech companies in 2015, other fintechs recruited deeply from its payments, compliance, and risk organizations. They did not limit themselves to the functional heads; they hired lieutenants and deputies who had built the systems at scale.
→ The hiring companies acquired relevant operating experience from a proven functional exemplar.
Common mistakes
Searching only direct competitors
This narrows the pool and can miss companies that serve the same customer with a much stronger version of the needed function.
Chasing only the top executive
The head may be unattainable or too removed from execution, while a lieutenant may have built the system and be ready for the larger role.
Is it for you?
Best for
Startups hiring a senior leader in sales, marketing, compliance, product, or another specialized function.
Not ideal for
Roles so novel that no adjacent company has demonstrated comparable functional excellence.
From the episode
Gokul Rajaram on designing your product development process, when and how to hire your first PM, a playbook for hiring leaders, getting ahead in you career, how to get started angel investing, more