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
Gokul Rajaram, DoorDash product/business leader and board member at Coinbase/Pinterest, shares insights on career growth, selecting companies, product development, hiring leaders, and angel investing. He emphasizes authenticity, organic growth, and the power of serendipity.
Deep Dive Analysis
16 Topic Outline
Gokul's Serendipitous Path into Tech and Product
Key Considerations When Choosing a Company or Role
Why Joining a Market Leader and Mid-Stage Companies is Beneficial
Lessons from Successful Companies: Diverse Paths and Remarkable Products
Setting Up Product Development Processes in Early-Stage Startups
Avoiding Common Product Development Pitfalls
Strategic Timing and Approach for Hiring Your First Product Manager
Evaluating Product Manager Performance and When to Delay Hiring
Structuring Product Teams and Hiring Senior Leaders
Best Practices for Founder Time Allocation in Hiring
The Impact and Management of Titles in Startups
Gokul's Founder-Centric Philosophy for Angel Investing
Essential Qualities and Traits Gokul Looks for in Founders
Sustainable Strategies for Part-Time Angel Investing
Building Deal Flow and Personal Brand as an Angel Investor
Lightning Round: Quick Insights and Recommendations
6 Key Concepts
Serendipity in Career Growth
Many career opportunities don't come linearly through promotions but arise from being curious, building relationships, and being open to unexpected connections and opportunities. It involves actively exploring what others are working on and helping people without immediate expectation of return.
Founder Authenticity
Successful founders genuinely live and breathe their company's mission, driven by a desire to solve a problem and win, rather than primarily by financial gain. This authenticity helps build a strong company culture and mission-driven team.
Product Remarkability
A product's inherent quality that makes it significantly better than alternatives along key dimensions, compelling users to talk about it and share it organically. This word-of-mouth growth is crucial, especially for consumer companies, reducing over-reliance on paid customer acquisition.
Feature Factory
A common pitfall in product development where teams focus on shipping a continuous stream of features without truly understanding or measuring their impact on customer behavior or problem-solving. This often stems from founders being too tactical and disempowering their teams.
Founder-Centric Investing
An investment philosophy that prioritizes the quality, motivation, and adaptability of the founder(s) over the specific market or idea. It emphasizes supporting individuals who are deeply immersed in a problem, authentic in their mission, and capable of pivoting or creating new markets.
Sins of Omission (in Investing)
The regret or missed opportunity that comes from *not* investing in a founder or company, especially when you know and respect the individual, even if the initial market or idea seems less promising. This is contrasted with 'sins of commission' (losing money on an investment), which is often seen as less detrimental to long-term relationships and future opportunities.
11 Questions Answered
Serendipity can lead to unexpected and significant career opportunities by being curious about what others are working on, building relationships, and helping people, rather than solely focusing on linear promotions.
Focus on the type of problems you get energy from solving and the customer segment you enjoy serving, rather than just the specific product. Also, look for founders who are authentically driven by the mission, not just money.
Working at a leader in any space provides access to higher quality talent, a stronger brand halo, and network effects that accrue to your personal and professional growth.
New entrants should generally join mid-stage companies (around 300-500 people) that have achieved product-market-channel fit, as these offer mentorship and opportunities to build deep skills, unlike very early-stage startups where roles can be less defined.
A major pitfall is founders becoming too tactical and disempowering their teams, leading to a 'feature factory' culture where features are shipped without truly solving problems or measuring customer behavior change.
A startup should consider hiring its first PM when it has around 8-10 engineers, especially if the founder lacks the bandwidth to effectively manage the product development process, ensure engineers are solving the right problems, and prioritize work.
Identify best-in-class companies for the specific function you are hiring for (beyond direct competitors) and then recruit their lieutenants or even the lieutenants of their lieutenants, who have experience operating at scale within a high-performing environment.
Founders of young companies should aim to spend about two hours a day on hiring: one hour for outreach and process refinement, and one hour for meeting with one or two candidates.
Startups should delay granting titles, especially 'Director' and 'VP' levels, for as long as possible. This encourages a culture where people prioritize scope and impact over titles, and avoids issues when needing to upgrade roles as the company scales.
He prioritizes founder authenticity, looking for individuals who are deeply immersed in and passionate about solving a problem they've personally experienced or observed, rather than just chasing trends. He also prefers two-person founding teams with complementary skills.
Build a personal brand by sharing non-obvious insights online, network with other angel investors, and connect with venture capitalists who often have angel allocations in their rounds. It's crucial to define your unique value proposition to founders.
33 Actionable Insights
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.
6 Key Quotes
It's very important to do your core job really well at any company, but it's equally important to have curiosity and be open to serendipity.
Gokul Rajaram
I would much rather be the number two or number three person, if you think of it that way, at the leader in a space than the top person.
Gokul Rajaram
If a feature is shipped, but it doesn't change customer behavior at all, is it really a feature or no? It's like a tree falling in a forest.
Gokul Rajaram
A bad PM can really screw up your, like can screw up the work of 10 engineers, right? So it's much more important to hire a good PM than it is to hire a good engineer.
Gokul Rajaram
The biggest mistakes I made early on were after a few checks, I said, oh, I'm going to be much more selective. I'm not just going to write checks with all my friends. I'm going to look to see what the market they are in. So I basically just started making these assumptions. Oh, well, you know, I should not invest in this company. In terms of almost all of them were sins of omission.
Gokul Rajaram
My rule of thumb is when they do a search for you on Google, if your LinkedIn profile is the first thing that comes up, you've probably done something wrong.
Gokul Rajaram
4 Protocols
Product Development Process (Early Stage)
Gokul Rajaram- Maintain a weekly plan for tasks.
- Use a simple spreadsheet for tracking tasks and assignees.
- Founders update the spreadsheet and communicate tasks.
- Team meets daily for stand-ups.
- Atomic product development team (engineers, product, designer, analyst) reviews tasks weekly.
- Focus on achieving product-market fit through rapid iteration.
Product Development Process (Mid-Stage)
Gokul Rajaram- Establish quarterly goals that guide planning.
- Develop a separate, clearly articulated product strategy document based on company strategy.
- Product strategy makes explicit choices about customer segments.
- Iterations and sprints emanate from the quarterly goals.
- Atomic product development team (engineers, product, designer, analyst) meets daily and reviews tasks weekly.
Hiring Senior Leaders
Gokul Rajaram- Identify best-in-class companies for the specific function you are hiring for (e.g., marketing, sales, engineering).
- Look beyond direct competitors to companies serving similar customer types (SMBs, enterprises, consumers).
- Do not target the head of that function at the identified companies.
- Instead, target their lieutenants (the people reporting to them) or even the lieutenants of the lieutenants.
- Construct an organizational chart using LinkedIn and network contacts to identify these individuals.
- Reach out to these identified candidates.
Building an Online Brand for Angel Investing
Gokul Rajaram- Share non-obvious insights related to your expertise (e.g., product development, payments, crypto).
- Utilize social media channels and writing platforms (e.g., articles, tweets) to publish your content.
- Aim for search results where your written content or mentions appear before just your LinkedIn profile.
- Continuously evolve and increase the scope of your insights as your experience grows.
- Take ownership of your online identity beyond your current company affiliation.