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

1. Prioritize Serendipity & Curiosity

Actively seek out what others are working on within your company and build relationships, as non-linear opportunities often arise from curiosity and serendipitous encounters. Always do your core job well, but remain open to exploring other projects.

2. Pay It Forward Generously

Help smart people, chat with them, and offer support without expecting immediate returns. Building a reservoir of goodwill through paying it forward will lead to unexpected positive outcomes and opportunities in the future.

3. Join a Market Leader

When choosing a company, prioritize joining a potential number one player in its segment, even if it means a slightly lower title. Working at a market leader provides invaluable experience, brand halo, and access to top talent.

4. Seek Mission-Driven Founders

Look for founders who genuinely live and breathe their company’s mission, rather than being solely motivated by money. Authentic, mission-driven founders are more likely to build large, impactful companies.

5. Be an Authentic Founder

Founders must be authentic to themselves and build a company culture that is synonymous with their image. Trying to build a company inauthentically to who you are as a founder will not work.

6. Focus on Customer Problem Solving

Seek roles or companies where you get energy from the specific problems you’re solving and the customer segment you’re serving (e.g., small businesses, long-tail users). This passion for the problem, rather than just the product, drives engagement and impact.

7. Join Mid-Stage Companies

New entrants to the workforce should generally join mid-stage companies (300-500 people) that have achieved product-market-channel fit. These environments offer mentorship and opportunities to build deep skills, unlike very early-stage startups.

8. Avoid Early-Stage Startups (Currently)

Unless you know the founders extremely well, be cautious about joining very early-stage companies, especially in a brutal market. Companies can deflate or die quickly, so thoroughly understand their financials before committing.

9. Build a Remarkable Product

Ensure your product is significantly better than competitors in key dimensions, making it compelling enough for people to talk about it organically. Aim for 40-50% of new customers to come from organic channels to avoid over-reliance on paid acquisition.

10. Founders: Dedicate Time to Hiring

As a founder of a young company, commit two hours daily to hiring: one hour for outreach (LinkedIn, tools) and one hour for meeting one to two candidates. Establish a clear hiring process upfront to ensure effective and strategic recruitment.

11. Hire Leaders from “Lieutenants”

To hire strong leaders, identify best-in-class companies for the desired function in a similar space (not competitors). Then, target and recruit the ’lieutenants’ or even ’lieutenants of lieutenants’ who report to the top leaders at those companies.

12. Delay Senior Titles

Avoid granting ‘Director’ and ‘VP’ titles too early in a company’s lifecycle, as these can cause contention and limit future organizational flexibility. Instead, use descriptive titles like ‘Lead’ or ‘Head of’ to focus on scope and impact.

13. Empower Product Development Teams

Founders should present problems, not just tactics, to their product development teams (engineers, designers, PMs). Trust and empower these teams to brainstorm solutions, prioritize opportunities, and take ownership of solving customer problems.

14. Hire PM When Engineers Need Support

Consider hiring a Product Manager when your engineering team reaches 8-10 people and the founder lacks the bandwidth to effectively guide them. A PM ensures the most expensive resource (engineers) is well-leveraged and solving the right problems.

15. Hire First PM Internally

The first Product Manager should ideally be an existing analyst, engineer, or designer within the company. This internal transition fosters trust with founders and the engineering team, ensuring cultural assimilation and effective collaboration.

16. Coach PMs on Customer Focus

When coaching new PMs, especially those transitioning from engineering or design, push them to focus on customers and understanding their problems. This helps them shed their previous persona and embrace a customer-centric PM mindset.

17. Monitor PM Effectiveness

Regularly check in with engineers and designers to assess if the Product Manager is adding value and not overstepping into the ‘how’ of building products. A PM’s value is measured by their impact on customer behavior, not just features shipped.

18. Delay PM Hire If Team Empowered

If your product development team is already empowered, takes ownership, and can independently identify, prioritize, and execute solutions to problems, you may not need a PM yet. Only hire a PM to solve a clear problem or gap in team functionality.

19. PMs Report to Functional Leader

Once a company has three to four Product Managers, they should report to a dedicated functional product leader. This structure provides mentorship, coaching, and helps build a consistent product culture and discipline across the team.

20. Adopt Simple Product Planning

For very early-stage companies, maintain a weekly product plan, adapting week-to-week to find product-market fit. As the company grows (e.g., Series A), transition to quarterly goals that then inform weekly tasks.

21. Develop Product Strategy Doc

As a company grows beyond 20-25 people and hires its first PM, begin to clearly articulate a separate product strategy document. This document makes explicit choices about customer segments and guides product development, emerging from the broader company strategy.

22. Maintain Daily Team Stand-ups

Ensure atomic product development teams (engineers, PM, designer, analyst) meet daily for stand-ups and review tasks weekly. This consistent cadence is crucial for effective collaboration and progress, regardless of company size.

23. Use Simple Product Tools

Keep product management tools simple, such as a basic spreadsheet, especially in early stages. Overly complex tools can hinder adoption and efficiency for engineering and product teams, leading to confusion.

24. Angel Invest in Founders, Not Markets

Prioritize investing in founders you know and respect, rather than solely focusing on market trends. Great founders can pivot or create new markets, and maintaining relationships ensures optionality for future investments.

25. Avoid Sins of Omission in Investing

Be less selective with early-stage investments in founders you trust, even if the market seems uncertain. The potential loss of a relationship or future opportunities with a founder outweighs the financial risk of a small check.

26. Look for Authentic Founder Motivation

When considering an investment, deeply understand why founders are starting their company. Invest in those driven by solving a problem they’ve personally experienced or observed, not just chasing trends or reading about them in TechCrunch.

27. Assess Founder’s Hiring Ability

Look for founders who can demonstrate an ability to attract and line up amazing talent, even before securing funding. The capacity to build a strong team is a key indicator of a company’s potential for success.

28. Prefer Two-Person Founding Teams

Favor investing in companies with at least two co-founders, ideally with complementary skills (e.g., builder and seller). Solo founders are generally riskier due to the breadth of skills and workload required to start a company.

29. Time Box Side Activities

To manage multiple commitments like a full-time job and angel investing, strictly time box your side activities. Aim to spend no more than two to three hours per day, including weekends, on non-core work to maintain sustainability.

30. Build Your Personal Brand Online

Actively share non-obvious insights and expertise through writing (articles, tweets) to build your personal brand. Your online presence should reflect your unique value and differentiation, transcending your current company identity.

31. Define Your Angel Value-Add

Before seeking deal flow, clearly articulate your unique differentiation and what value you bring to companies as an angel investor. The best companies are oversubscribed, so they will only take money from investors who can offer more than just capital.

32. Cultivate Angel Deal Flow

To get investment opportunities, build your brand online, inform other angel investors of your interest, and connect with VCs who often allocate spots for angels. This proactive approach helps you access promising companies.

33. Ask About Proudest Achievement

In interviews, ask candidates about their proudest career accomplishment. This question reveals how they measure impact, what they value, and their approach to teamwork versus individual contribution.