Hiring

One of the clearest markers of a future generational company is ambition that borders on ludicrous, where the founder's goals sound crazy to most people.

The quality of the founders matters above all other variables when evaluating whether to join a startup early.

None of the serial early employees at iconic companies found their jobs through applications or recruiters; their paths were serendipitous and driven by personal connections.

The best way to manage scaling is to give away your Legos -- resist the instinct to grab back responsibilities from new hires and instead find a bigger, better tower to build.

Who you work with matters more than almost anything else about the job, and choosing a job based on colleagues is the single most cited career choice for avoiding burnout.

Analytical thinking interviews should follow a five-step linear flow: assumptions and game plan, product rationale, metric framework, goal-setting, and tradeoff evaluation.

Top candidates in tradeoff evaluation specify what would need to be true for them to change their mind, because it solidifies how they think about the fundamental factors that influence their thinking.

Outlining your game plan at the start of an analytical thinking interview is like sitting down to play a game with someone who knows the rules — it signals to interviewers that you will generate the signals they need.

Gathering intelligence about organizational power dynamics, decision-maker psychology, and strategic pain points creates more negotiation leverage than showcasing credentials or experience.

Product sense and analytical thinking interviews originally popularized by Facebook and Google have now been widely adopted across the tech industry, including at Stripe, OpenAI, Block, and even earlier-stage companies.

The best team members are those who opt in rather than being assigned, and if you need to sell someone really hard to join your project, they are probably not the right fit.

Stripe PMs do not rank highly on traditional career metrics because they get hired as star PMs at rocketship companies like OpenAI, Anthropic, and Mercury rather than starting companies or climbing the ladder.

Solo founders are at a growing disadvantage at YC, with the proportion accepted declining to around 10% in the latest batches despite YC officially saying it is not a deal-breaker.

The rise of the IC career path is reinforced by recent layoffs disproportionately affecting middle managers, flattening organizations.

Remote PM jobs have declined approximately 35% from their peak, dropping from over 35% of open roles to 22.5%.

Over one in five open PM roles is in the San Francisco Bay Area, with the share growing 25% year over year from 15.4% to over 20%.

The three most common hard skills hiring managers look for from PMs are SQL, Jira, and experience with LLMs, with LLMs being the fastest-growing requirement.

Machine-learning engineers and data engineers are the fastest-growing tech roles, growing 79% and 55% year over year respectively.

Diversity and scrum master roles are the fastest-shrinking in tech, with only 70 open diversity roles and 74 scrum master roles (none at FAANG).

AI companies are hiring almost exclusively engineers and data scientists; there are only 456 open AI PM roles out of 16,935 total AI company openings.

Growth roles are the fastest-growing product-adjacent roles in the U.S., growing much faster than sales and marketing roles, potentially signaling an increasing focus on product-led growth.

Product management roles are not shrinking despite layoff fears; there are about 450,000 active PMs in the U.S. with 2,500 to 4,500 being hired each month, holding steady after a 2022 hiring acceleration.

User research is the second-fastest-growing role after going through massive layoffs, as companies realized they went too far in cutting UXR teams.

Scrum master is the only product-adjacent role that is actively shrinking, with more people being let go than hired each month.

Product owner roles are the third-fastest-growing role with around 65,000 active roles, likely partly explained by former scrum masters transitioning to this title.

The most revealing interview questions explore times when things did not go as planned, because you learn the most about how a person operates, thinks, and collaborates from their failures.

Asking candidates a contrarian-opinion question breaks the interview performance mindset and reveals authenticity, which is critical because prepared candidates often tell you only what they think you want to hear.

People are rarely accurate about what critiques others have of them but are usually accurate about their own strengths, making the reference-triangulation question particularly revealing.

Work trials provide significantly more signal on candidates than traditional interviews because it is frequently surprising how someone performs relative to what was expected from interviews alone.

Conventional interviews can be performed without real productivity, and some people who are amazing interviewees turn out to be poor employees, which is why working alongside someone in the trenches is the only reliable signal.

Convincing candidates to do work trials is much easier than most recruiters expect; paying candidates and framing it as a two-way evaluation makes it feel reasonable and even attractive.

The typical B2B company waited two to three years to hire their first product manager, usually at 10-15 engineers and 15-25 total employees.

More than half of top B2B companies hired their first PM before finding product-market fit, counter to conventional advice.

Most first PMs were IC-level or senior PMs, and nearly a quarter were engineers transitioning into the PM role, rather than directors or VPs.

Many first PMs come from internal transfers rather than external hires, because trust and existing product knowledge make them more effective.

Over two-thirds of top B2B companies hired an engineer as employee number one, and 100% hired at least one engineer among their first three hires.

Every B2B founder should start with founder-led sales and wait until $300-500K ARR before hiring their first full-time salesperson.

Your first sales hire should be a 'hungry senior AE' who can break new ground rather than someone who excels only at repeatable processes from later-stage companies.

Cold outreach through LinkedIn and GitHub is the second most common channel for finding early startup employees, and is accessible to any founder regardless of network size.

Linear uses paid work trials of 1-5 days as the final hiring step, where candidates join the team and work on a real project, which gives both sides a much better signal than traditional interviews.

Growth teams should not be hired before product-market fit is validated; growth is about increasing distribution of core product value, and if PMF does not exist, there is nothing to grow.

A growth leader should not be your first growth hire; instead hire a builder-profile IC focused on a specific growth lever like acquisition or activation, because even experienced leaders take 6-12 months to understand the local problem.

Snowflake hires 'drivers' instead of 'passengers' and starts almost every product interview with a candidate presentation on any topic they choose to assess communication, passion, and product sense.

For interview prep, pick 3-5 recent major projects and recall every detail about them rather than writing answers to hundreds of behavioral questions, because deep recall of a few projects prevents brain overload and blackouts.

Use STAR++ for behavioral questions: after stating Situation, Tasks, Actions, and Results, add what you learned and how you evolved your approach in a future situation to demonstrate growth mindset.

Interviews are often won or lost by the questions you ask the interviewer at the end; formulating high-signal questions that show you have done your research gets interviewers thinking and makes you stand out.

Hiring the literal world's number one person in each critical discipline creates cascading advantages because top people have disproportionately more access to knowledge, opportunity, and other top talent.

Notion has fewer than 15 PMs out of 550 people and waited until they had 50-60 engineers before hiring their first product manager.

Ramp reached $100 million ARR with fewer than five PMs and fewer than 50 engineers, demonstrating that extreme efficiency is possible by restricting headcount.

Hiring people with high slope (learning ability) over high intercept (current domain expertise) is critical at fast-growing companies because scope will be much bigger in six months.

Headcount is a cost center, not a sign of progress, and the only metric that merits congratulations is product traction and product-market fit.

PM interview preparation has three parts: research the product and company, practice with real people through mock interviews, and study frameworks and core PM skills.

Preparing for PM interviews gives candidates a big leg up even with just a few hours of effort, despite interviewers believing they can see through preparation to a candidate's true PM nature.

You need to talk to an average of 23 PM candidates to hire one great one, with only 13% of inbound applicants making it to the first screen.

The six core IC PM skills to interview for are communication, collaboration, execution, strategy, impact, and product sense.

The project portion of PM interviews is the most informative component because it is the only time you see a candidate tackle a chunky new problem, watch them in action, and discuss their approach.

Companies should treat closing a candidate almost exactly the same as closing an investor, because candidates are investing something even more valuable than capital: their time.

Founding teams should create the first growth model themselves rather than outsourcing it to a Head of Growth hire, because only they understand the DNA of the product and market deeply enough.

The first growth hire should be a Builder generalist who proves the growth model's validity, not an Innovator who thinks big or an Optimizer who squeezes marginal gains.

Nearly one in seven US companies now provide extended leave to employees, and sabbatical programs have become prevalent in the employee benefits arms race for top talent.

The most important factor in early-stage hiring success is the effectiveness of the company's mission or vision in compelling top candidates.

Hiring compounds: great early hires create a snowball effect where the quality of the existing team organically attracts more exceptional people.

Communication, execution, and product sense are the three most frequently valued PM skills, while design/UX, empathy, and raw intelligence are least frequently valued.

When seeking a growth role, focus on demonstrating foundational tools like data analysis, user psychology, and experiment-driven methodology rather than listing tactical ideas.