Scrappy — the tipping point

Celine Wee
3 min readJun 11, 2023

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Spend some time in a US tech company (or on Linkedin) and you might hear the word “scrappy”, “scrappiness”. Usually, it was used in a context like:

We want “scrappy” employees who roll up their sleeves.

or

Let’s be “scrappy” in organising this event/launch/user interviews.

Curious about the word’s origin, I went to check various online dictionaries — see Cambridge, Merriam Webster, Britannica, and Reddit (for fun)!

  • More positive 👏: Determined, competitive spirit, resourceful, gritty, able to overcome/get it done.
  • Less positive 😅: Disorganized, untidy, disjointed, unsystematic, quarrelsome, belligerent, not done well.

Perhaps two sides to the same coin? Or to put another way — that a strength can equally be a weakness.

Photo by Randy Fath on Unsplash

The joy of scrappy

The joy of working in a small team to get ALOT done is immense and immeasurable.

I look back nostalgically at times when I was in a small team worked on hundreds of launch events invites via plugins, follow up emails, moved plants/chairs for events, did tear downs after and post event reviews. I have fond memories of grassroot marketing through Linkedin posts on “maximising revenue with modern payments” webinar (link), or building to scale with Google Cloud and Stripe (link) and being energised by attendee discussions and questions. All hands on deck resourcefulness drives creativity and is exhilarating.

In fact, large teams with more resources (manpower specifically) can be less effective. To quote “Mythical Man-month”, adding more manpower actually increases communication and training complexity, and is like “dousing a fire with gasoline…more fire requires more gasoline” (pg14). So with a tight-knit scrappy team, much can be accomplished.

The dangers of scrappy

However, the danger of scrappy/scrappiness is when it becomes a reason for poor planning, and never growing up.

  • All hands on deck does make sense sometimes: For example, let’s say a small team is organizing an event. Each team member manually emails 100 contacts and the emails are collated in some spreadsheet. And the same contact does the next emails and tracks each contact manually. That same spreadsheet is used for follow ups later. The team ahas a playbook with templates and images, so that more can help spread this on on social. Everyone chips in to get it done.
  • However, with growth comes the need for automation and advanced notice: When there’s a few thousand employees, ideally there’s some marketing automation system, tied to some event attendance tracking software, with a plan and cadence of invites, reminders etc. If even after growth, events (or whatever campaigns executed) are still last minute, reactive and frantic all the time (occasionally is understandable), I’d suggest that’s not “all hands on deck” scrappiness, but rather poor or no planning. Scrappiness has become an excuse, and is not a badge of honor.

Scrappy — the tipping point from joy to danger

I wrote this post with caution, as it’s not meant to dismiss scrappiness. Scrappiness in spirit is crucial, but scrappiness in execution might point towards immature and broken systems as a company scales. To bring it back to the negative definition — the tipping point is that scrappiness could have its darker side of “untidy, disjointed, and unsystematic” (as per the definitions).

I love the scrappy spirit, there is nothing like working together to solve a problem. But if every single problem requires a heroic, reactive push in a mad rush/frenzy, and has no clear goal, we’re wasting the potential of scrappiness. Wouldn’t it be wonderful if the best parts of scrappiness (resourcefulness, determination, grit) were channeled to more productive uses?

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Celine Wee
Celine Wee

Written by Celine Wee

Opinions are my own: a collection of Go To Market, Payments, Biz Ops learnings across Stripe, Coinbase, Twitter. I also write @celinewee.substack.com

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