Skillful Digest (09/23/2021)

Community Newsletter


Welcome to the third issue of the Skillful digest!

This is our bi-weekly round-up of community news, content that’s relevant to all of us and anything that can help us level up together. As always, reach out if you have any feedback or if you’d like anything featured in here. Now onto the update 👇

Insights we’re pondering 💭

Confidence is often the key missing piece to leading a successful and rewarding job search. Imposter syndrome is something that resonates with many Skillfulers, our team included!

Imposter syndrome is that nagging feeling that, despite all evidence to the contrary, you don’t deserve to be where you are. Those times where you self-select out of a competitive process because you don’t think there’s any way you could possibly come out on top. Or maybe you just never feel like you’re performing well enough.

How do you grapple with it? One thing we’ve found to be helpful is to force yourself to acknowledge that this is a normal feeling. As a schema, imposter syndrome is deceptive in that it cuts twice: almost everybody experiences it, and yet by definition if you succumb to it then you’re bound to believe that you’re the only one who does. But the sooner you appreciate that this is a natural pattern of thinking, the sooner you can escape it. That interviewer grilling you on your take-home? Odds are they felt like an idiot at some point that day. The CEO whom you’re worried doesn’t think you’re smart? You can bet they’ve thought that exact way about another CEO before.

Justin Kan wrote a recent Twitter thread that broadly touches on this dynamic and while it’s worth reading in its entirety, he has one observation that is particularly spot-on:

One takeaway here is that you can escape the cycle by embracing the fact that, especially in the tech industry, things are so new that no one knows exactly what they are doing. You’re not joining an organization because you have answers to every problem; you’re being recruited to put your head down and find them. What better way to spend your time than working in a career where your primary job is to learn?

What are some other ways you have combated imposter syndrome? We’d love to hear from you!

Skillfuler Spotlight 💡

Today we’re featuring Ali Rohde. Ali has a fascinating career path that spans congressional politics, early-stage operating and investing, all in only a few years. Ali began her career as a congressional aide, acting as a press secretary, communications director and the person you called on to help fight fires.

Ali leveraged this experience to break into tech, working as a Chief of Staff to CEOs of several top early-stage companies. You can check out Ali’s weekly newsletter where she highlights openings in startupland for roles like Chief of Staff, BizOps, Growth and more.

Events @ Skillful 📆

Speaking of Chiefs of Staff - what is a Chief of Staff and what exactly do they do? 🤔We’ll be hosting an event to help answer that, alongside our Roundtable that covers generalist roles in tech:

  • Tuesday 09/28 - Roundtable: Business Generalist Career Paths in Tech
  • For those of us who are thinking about jumping into the world of tech, or are in the process of pivoting to a new role, job titles can feel like a 🧩. Join the Skillful team & Golden Gate Recruits as we navigate through the different paths available to us;
  • The event will be open to those inside and outside of the Skillful Community, so spread the word if you can! Let's help everybody get after it, together! Sign-up here!
  • Tuesday 09/28 - Fireside Chat: What’s a CoS?!
  • Ali, Christian & Almog will be running us through their day-to-day as Chiefs of Staff, how their roles are (dis)similar and open the floor up for questions. Jump in and let’s demystify this role together - sign-up here!

Skillfuler gratitude 🤝

As we gear up to say goodbye to summer we wanted to heat things back up with a round of warm and fuzzy feelz with our new #gratitude channel.

To get things started we're asking everybody to post in the #gratitude channel and share how someone in the community has helped you and to tag them  💕 This can be anything at all… from helping you with an interview, to a keyboard shortcut that’s changed your life forever. We want to see it! The first ten to post will get a special 🎁

#community-wins 🥇

  • Skillful mentors Thiago and Eric kicked off our first ever Product Strategy Sprint this past weekend! Huge shoutout to this amazing group who have already hit the ground running - we can’t wait to see what you all come up with 🚀

  • Barkat (Core Program, August’20) and Hasan (Core Program, April’21) both recently joined the Strategy & Ops team at Placeholder, a fast-growing marketplace for warehouses. So cool to see two Skillfulers joining the same team, during the same week.
  • Thomas (Core Program, October’21), who’s been ramping up his SQL skills while waiting to start with us in October, just landed role at RenoRun as an Operations Analyst
  • Armish (Core Program, Spring’21) joined the Ops team at Sampler, a platform that helps you find your next favourite product.


Send them some love over on Slack, or if they’ve helped you in any way, post about them in the #gratitude channel 😏

Job Opportunities 💼

  • Fuzzy is hiring a Senior Data Analyst, reach out to Miguel if you’re interested
  • Clearco is hiring for RevOps Analysts focused on either supporting GTM or Product & Revenue
  • DoorDash is hiring a StratOps Manager, reach out to Julie-Anne (or one of the many others from the Skillful DD squad) if you have any questions
  • Alto Pharmacy is hiring a BizOps Associate - reach out to Sean for more details

One (fun) last thing 🐶

Mentors from our Skilful Toronto squad met up this weekend IRL! No pang of envy this time - Loren was able to join in on the fun.

Meeting up with fellow Skillfulers? First round of drinks or coffees are on us, just DM us 🍻

That’s all for this issue ✌️ If you’d like to access more news and content before the next update, you can hop on over to Slack. P.S. please give us a follow on Instagram - we’re bringing the community to your IG scroll :)

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