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••••••

Sierra’s first GTM hire, breaks down every step of their playbook.

Why Sierra built a design partnership program on “hard mode”

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For the founder's notepad:

"If you personally want to grow as fast as your company, you have to give away your job every couple months." – Molly Graham

“Asking ‘Why can't this be done sooner?’ methodically, reliably and habitually can have a profound impact on the speed of your organization.” – Dave Girouard

“End every meeting or conversation with the feeling and optimism you’d like to have at the start of your next conversation with the person.” – Chris Fralic

“Focus is doing things with a clear intention. It doesn’t mean you charge single-minded toward a goal. It means you pay rapt and incremental attention to how you need to turn the rudder on a project.” – Fidji Simo

“It’s essential to grow with the company — rather than having the company grow around you.” – Cristina Cordova

“You have to be impatient with shipping, but patient with your career.” – James Everingham

“‘I trust you, make the call’ might be the six most powerful words you can hear from a manager.” – Sean Twersky

“Your job as a CEO is to build fire departments, not put out fires.” – Sam Corcos

“Can you say with confidence that each report would want to be on your team again? If you aren’t sure that the answer is yes, it’s probably no — much like how if you have to ask, ‘Am I in love?’ you’re probably not.” – Julie Zhuo

“People can get addicted to yak shaving. An effective engineering generalist knows when to move on. Pay attention to whether they used their time wisely, not just the results.” – Mike Krieger

“It sounds so simple to say that bosses need to tell employees when they're screwing up. But it very rarely happens.” – Kim Scott

“You’ll know you understand the customer problem enough when you can predict 75% of what a customer tells you. Keep having these conversations until three-quarters of it is stuff you already know.” – Christina Cacioppo

“I have a rule: no company swag until the business has at least $250K of revenue or 250k users. Until then, you don’t get to “feel” the benefits of having started a company.” – Gagan Biyani

“The business model ends up becoming the business. It’s equally important as the market you’re going after and the product that you build.” – Jay Simons

“If speed is the yin, the yang is prioritization. You can’t be fast if you don’t know what’s important.” – Jaleh Rezaei

“If you treat your connections as a kind of personal ATM you use for frequent withdrawals, you’ll quickly be disappointed (and overdrawn).” – Karen Wickre

“Delighting the customer always yields better returns than countering or copying a competitor. It’s just a lot harder to do.” – Andy Rachleff

“When you’re a founder, every moment you’re not writing code or getting users, you need to be making a conscious choice: Is whatever you’re doing worth your time?” – Alexis Ohanian

“‘Why would a customer not want this?’ is often a far more interesting question than why they would.” – Rick Song

“When you leave the planning process wondering if you put too many resources behind a single bet, that’s the bet that ends up succeeding. Bold ideas need bold resourcing.” – Lenny Rachitsky and Nels Gilbreth

“Treat customer development as a one-on-one with a direct report — you just want to ask the hard questions.” – Ryan Glasgow

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