012. @jenistyping’s Rules for Startup Scaling, Part 1

Pithy Principles from your People Princi-pal ??

(Look out for future editions specifically focused on hiring and management!)

• ?Product is what you build. Growth is how you turn it into money. Org is what grows Product and Growth.?
• Most startups take too long to take Org work seriously. Before they feel enough pain and realize they’re throttling their own growth, most startups waste precious time trying to avoid it or outsource it.?

• “Work” is in the midst of a monumental shift – from a transaction, with power concentrated in one party (corporations), to a relationship, where power is multifaceted.

• Being a startup founder is personal growth on extreme hard mode.?

• Planning is seriously underrated in startups.?

• After Product-Market Fit, the founder must let go of IC work and shift focus to being an Organizational leader.

• At that stage, being a founder means being the Communicator-in-Chief. Expect to be repeating yourself over and over and over and over and–

• As a founder, your job's biggest Organizational priorities are the following: 0-50: Hire the best people possible. 50-150+: Build the foundation for an extremely strong Ops/People team and executive teams.- At 50-150+: The People team’s biggest priorities are 1) Scaling great hiring 2) Building the foundation for an extremely strong middle-management layer.?

• Pedigree for executives is a poor predictor of success. Assume incompetence until proven otherwise.?

• Executives are inherently world-class at presenting themselves in a positive light. Be appropriately suspicious. Same with executive recruiters, whose incentives are not aligned with yours.

• Denying politics exists at your startup means you’re the one getting f*cked.?

• Something that no scrappy startup full of young, idealistic builders is ever prepared for: Traction brings in a horde of new employees with very different motivations. The original culture will be hijacked and brutal internal politics will ensue – unless you keep your eye on the ball and effectively scale hiring, culture, and people operations.?

• Never work with narcissists/sociopaths/abusers. It doesn’t matter how rich and powerful they are, or whatthe benefits they dangle in front of you. The cost on your soul and the mindf*ck is never worth it.

• Unlike Product or Growth, there are no commonly agreed upon-indicators or benchmarks for scaling People/Ops work. Under-invest in this at your own peril.(Other standards include: X number of leads means hiring Y sales reps and Z trickle-down effects, or PMs or designers can support X engineering teams, etc.)???

• >90% of management/culture scaling problems can be seen from a mile away, and it’s absolutely bonkers that every startup is left largely on their own to strugglebus their way through it. (It is downright irresponsible and there is little accountability, e.g. for investors)?

• Org/People work is hard for many reasons. Here’s just some of them:?- The efforts and effects of People work are difficult to quantify.- The collaborative nature of People work means it’s difficult to isolate causes.- Good people work takes time.?

• People problems cannot be solved by software.?- HR tech is mostly a distraction, and a terrible startup category in general . Finding the rare gems in the noise requires evaluating Efficiency Problems vs Judgment Problems. )

• Why People & Culture work matters: When employees feel genuinely cared for by leaders and the org, they can finally stop worrying about what's best for themselves, and start doing what's best for the team.

• You can’t solve employee / culture problems by complaining about it. Acknowledge it’s a problem, but also that YOU, as the leader, have the power. If you want things to be different, YOU have to take the first step, and employees will respond in kind.?

• Title inflation is killing our industry.- I can speak especially to my domain – A lot of these Heads of People and Heads of Recruiting have no business being called that . They are too junior, but claim senior titles due to the chaotic market, lack of standards, and lack of serious peer competition. There simply aren’t enough qualified People pros to go around. The solution is to create more.

• Most startup Heads of People do not have a recruiting background and cannot be truly strategic about it. Because of that, HR and Recruiting are separate jobs, and expecting one person to do both – unless you’ve truly found a unicorn – will lead to disappointment.?

• Diversity is the result of great hiring/org practices that allows companies to hire and retain the best talent. Trying to increase diversity numbers without a hard look at internal processes is a waste of everyone’s time.

• Underrepresented people in your company are like canaries in the coalmine – they provide you clues to what needs the most attention in growing a healthy, functional organization.

• Most people who claim to be culture experts may have been at companies with great culture, but were not in leadership roles or early enough to understand how that great culture was built.?

• There are 2 types of tech company cultures:?- Type 1: "results-oriented" leaders → aggression is coded into the culture, conflict runs rampant (e.g. Uber, Amazon)?- Type 2: "nice" leaders who avoid healthy conflict → culture of false consensus/passive-aggression (everyone else)- Both lack emotional intelligence.

• For startups, building a culture that makes employees feel like they belong is critical. Not for the sake of the warm and fuzzies, but in recognizing that every person there is taking a career risk. Lack of belonging creates an undercurrent of anxiety that gets in the way of productivity.

• High achievers on a burnout spiral will take minimum 6 months to even realize and admit it (i.e. slow-boiling frog).??

• Work can be a vehicle for extraordinary growth. A high-pressure job can be brutal, but it can also allow people to realize what they're really made of and that's beautiful.?

• Startups are supposed to be fun. To the right kind of person, you can’t imagine doing anything else.?

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Jennifer Kim is the CEO/Founder of Workflow , an education and consulting company that trains the next generation of startup leaders on all things Recruiting, People Ops, and DEI. Through its flagship program, the HireEd Accelerator, Jen and her team have taught hundreds of startup leaders to make hiring a competitive advantage. Previously, Jen was Head of People at Lever and was Advisor to dozens of top startups. She is also a Venture Partner at Symphonic Capital, and is known for her hot takes on tech industry and culture as @jenistyping.