By name: leadership-recruitment-lieutenant-strategy description: A methodology for identifying and recruiting top-tier functional leaders (Product, Sales, Legal, etc.) by targeting high-performing "lieutenants of lieutenants" at best-in-class companies. Use this when you need an expert leader but want to avoid the friction and potential mismatch of hiring a sitting VP from a giant corporation.
This strategy focuses on "raiding" the lieutenants of best-in-class organizations to find battle-tested talent that is ready for a "step up" in scope without the baggage of inflated titles.
The Lieutenant Search Process
1. Identify Reference Companies
Do not look at your direct competitors. Instead, identify companies that are "best-in-class" at the specific function you are hiring for and serve a similar customer profile.
- Match Customer Types: If you serve SMBs, look at companies like Square or DoorDash. If you serve Enterprise, look at Salesforce or Workday.
- Functional Excellence: Identify who is currently winning in the specific domain (e.g., Square for Compliance/Risk, Airbnb for Design, Facebook for Growth).
2. Map the Org Chart
Use LinkedIn and your network to reconstruct the organizational structure of the reference company.
- Identify the "Head of": Find the person currently leading the department at the reference company.
- Identify the Lieutenants: Look for the people reporting directly to that head.
- Target the "Lieutenant of the Lieutenant": These individuals are often the ones doing the deepest tactical work while managing significant teams. They are frequently ready for a "Head of" role at a smaller company but are blocked by the hierarchy at their current firm.
3. Implement the 2-Hour Daily Hiring Habit
Founders must dedicate significant, consistent time to this outreach to build "deal flow" for talent.
- Hour 1 (Outreach): Perform manual LinkedIn searches and personalized reach-outs. Do this during low-energy periods of the day, as it is "busy work" that requires consistency over creativity.
- Hour 2 (Interviews): Dedicate this hour to two 30-minute introductory calls.
- Goal: By meeting two people daily, you will vet 40-60 high-potential candidates per month.
4. Vet for Impact and Problem Solving
Use specific questions to determine if the candidate is a "problem solver" or a "feature factory" worker.
- The "Pride" Question: "Tell me about the career accomplishment you are most proud of."
- Listen for: Do they describe the impact on customer behavior/metrics, or just the fact that they shipped a feature?
- Listen for: Do they emphasize their personal contribution versus the team's contribution?
- Empowerment Check: Ask how they solved a specific problem. Look for candidates who understand the "why" behind a project, not just the "how."
5. Standardize Minimalist Titles
To maintain flexibility for future "upgrades" as the company grows, avoid granting VP or Director titles too early.
- Use the "Lead" or "Head of" Suffix: Instead of "VP of Product," use "Product Lead" or "Head of Product."
- The Scope Rule: Titles like "Director" often lead to internal contention and focus on hierarchy rather than impact. Keeping titles vague (e.g., "Square Lead") keeps the focus on the work.
Examples
Example 1: Hiring a Head of Marketing for a Consumer App
- Context: A Series B startup building a consumer subscription app needs a marketing leader.
- Reference Company: Instead of looking at direct competitors, they look at Duolingo or Spotify (best-in-class consumer growth).
- Target: They identify the "Director of Performance Marketing" who reports to the VP at Duolingo.
- Offer: They offer the title "Growth Lead" with the promise of building the entire marketing function from scratch.
Example 2: Hiring a Lead Lawyer for a 25-Person Fintech
- Context: A small fintech is in a legal-heavy space and needs a dedicated lawyer.
- Reference Company: They look at Square or Stripe (best-in-class fintech compliance).
- Target: They find a Senior Counsel who has been at Square for 4 years and knows the regulatory landscape deeply.
- Offer: They offer the title "Head of Legal" rather than "General Counsel" to leave room to hire a more senior GC when the company reaches 250 people.
Common Pitfalls
- Hiring Sitting VPs: Hiring someone who is already a VP at a giant company often fails because they are used to having massive support structures and may no longer be "builders."
- Granting the "General Counsel" or "VP" Title Too Early: If you give a VP title at 25 people, you cannot easily hire someone more senior above them later. You will likely have to fire the original hire to "upgrade" the role.
- Outsourcing Outreach: Founders often try to have an assistant or recruiter do the LinkedIn reach-outs. Gokul argues the founder's personal touch in the initial message is what converts "passive" lieutenants at great companies.
- Ignoring the First PM Internal Transfer: For the very first PM hire (usually around 8-10 engineers), the best candidate is often an internal engineer or analyst who already has the trust of the team, rather than an external "professional" PM.