The Commons Digest (12/02/2021)

The COmmons Insider Newsletter

Welcome to the eighth issue of The Commons digest!

This is our bi-weekly round-up of community news, relevant content 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 👇

One (community) announcement

We have a new look 🎉

The Commons team has worked *very* hard to launch our new website. We wanted to better convey what we’re all about: our Sprints, community (that’s you) and amazing mentors.

Check it out here and let us know what you think!

Insight we’re pondering 💭

One recurring theme in our community is how daunting career changes can be. That’s why we recently spoke with three startup leaders (one of whom is Chong, whom you’ll meet later in this issue) about their evolving relationship with risk.

Each of them acknowledged that career moves are scary propositions. But interestingly, they’ve taken progressively riskier bets over the course of their careers. All three of them, for example, started their careers in strategy consulting or finance before joining Uber as BizOps managers. Now one of them is co-founder of a leading startup and two are Ops leaders at early-stage VC-backed businesses.

So what changed? In a word, asymmetry.

Most risky career moves, at least for the types of entrepreneurial or operating roles we often see at Skillful, are really just asymmetric bets. In other words, the potential upside of these decisions might outweigh any potential downside.

That newly-funded startup an old mentor wants to recruit you for? It just might become a category leader. Think about what that might do for your career! And if, in the worst case, it fails? You have a whole set of skills and experiences to fall back on, plus some new ones you almost certainly will have picked up in that role. Near-limitless upside and capped downside. Obviously this does not mean you should be reckless. In fact, you might actually turn down a lot of opportunities when you put them through this framework. And there are all sorts of other factors you should consider when evaluating a move!

We’ll be diving deeper into this topic in our upcoming podcasts, but in the meantime if you’re thinking through a change and whether it’s right for you, reach out! We’re always happy to be a sounding board :)

Member Spotlight 💡

Today we’re featuring Chong Zhai. Chong is a Skillful alum and the Head of Operations at WISK, a restaurant technology platform startup.

Chong is a great person for people in our community to learn from because he’s really seen it all. After business school, Chong worked in product strategy at BlackRock and TD before joining the Marketplace Ops team at Uber after completing the Core Sprint at Skillful. Now he’s Head of Operations at a fast-growing startup. Chong is incredibly generous with his time, intellectually curious and has a profound thought process when it comes to professional development. He loves to share his experience, so we posted a profile on him which you can check out here. You should especially read it if you aspire to lead an early-stage company one day.

Get early access to 2022 Sprints!

It's only December 2nd but we're already excited for the new year, particularly because we’re launching two amazing Sprints in January 🚀

Applications open to the public early next week but we're giving you priority access today. Given the limited size of each Sprint, we recommend securing your seat asap. Both Sprints kick off the week of January 24th and will run for 5 weeks.

🎯 Product Strategy with Eric Liou and Thiago Silva

This one's for you if:

  1. You are exploring a career in Product or see Product on your career roadmap, now or in the future
  2. You’re a business generalist who wants to add product strategy to your toolkit
  3. You currently work closely with or adjacent to the Product team

📈 Finance with Sean Newman and Callum Travaglini

This Sprint is for you if:

  1. You currently work in a traditional finance role and want to explore a pivot into the tech industry (for example: corporate finance, corp dev, FP&A, accounting, investment banking)
  2. You work in a business generalist role in tech and want to build your finance skill-set to understand the financial impacts of strategic decisions

Join Waitlist - Product Strategy

Join Waitlist - Strategic Finance

Events @ The Commons🗓

  • Wednesday December 1st: Yesterday we welcomed Gary Yang for a fireside chat. Gary is the Head of Product & Operations at Placeholder, a marketplace that helps fast-growing companies find warehouse space. Gary spoke about breaking into tech from consulting, switching from BizOps to Product, becoming an executive and everything in between. Community members can DM us for a copy of the recording 🎥
  • Next week we’re hosting two (!) IRL meetups for Skillfulers and friends of the community. Join us for networking, drinks and amazing conversation. This is a great chance to mingle with other Skillful community members. And, if you’re an extended member of the Skillful family, we guarantee that you’ll meet some interesting people.
  • 🍁 Toronto on December 8th at 6:30pm. We’ll also have a photographer there to snap your next LinkedIn profile picture 📸 RSVP HERE.
  • 🍎 New York City on December 10th at 6:30pm. We’re hosting this with Skillfulers Andrew Yeung and Eric Liou, as well as our friends over at Free Agency. RSVP HERE.

#community-wins 🥇

We celebrated some hiring announcements and promotions!

  • Saumil Shah (mentor) is now Growth Strategy & Analytics Lead at SafeGraph, where he was previously part of the BizOps org 📈
  • Angelina Lu (mentor) recently joined Wealthsimple as a Product Manager 🏦
  • James Prince was promoted to Manager Strategic Partnerships, Team Lead at Vidyard 📹
  • BK Babatunde just joined Jobber as Senior Data Analyst, Fintech 👷 BK will be working with Skillful mentor Sandeep Kittur, who had this to say:

We're trying something new!

Every alternate week (i.e. when we don’t circulate the Digest), we’ll send a collection of community posts to our internal job board.Keep an eye out for it 👀

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 directly to your feed :)

See anything your friend might find interesting? Feel free to forward this issue! This community grows stronger and more valuable to everyone in it the more smart people - i.e. folks like you - learn about Skillful. Sign-up to receive all things Skillful right here.

Interested in more?
The Commons Digest (02/10/2022)
The COmmons Insider Newsletter
The Commons Digest (02/10/2022)
Everything going on in the community including a member spotlight on Gurmee Sodhi, BizOps at Uber.
The Commons Digest (02/25/2022)
The COmmons Insider Newsletter
The Commons Digest (02/25/2022)
Everything going on in the community including a member spotlight on mentor, Max Nimaroff, GM at Uber.
The Commons  Digest (11/18/2021)
The COmmons Insider Newsletter
The Commons Digest (11/18/2021)
Just. Get. Started. That’s one of our biggest takeaways from Christian Keil’s excellent profile of Packy McCormick from a few weeks ago. Packy is of course the author and creator of Not Boring, a business strategy and trends newsletter that has evolved into a community, investing syndicate, job board and VC fund.
Skillful is now The Commons.
We’re more than just skills training. We're the place where high achievers come to fulfill their career potential. We combine education, mentorship and community to empower the next generation of ambitious professionals to achieve their career goals.
The time to build the education institution of the future is now. And we're doing it.

Careers are catalyzed through skills-training, mentorship and a supportive network. At The Commons, we're delivering those critical career elements together through learning experiences that are social, mentorship-based and community-first.

Join to learn and stay for the community.