Sam Chai: Generalist Growth Driver

Sam Chai: Generalist Growth Driver

The startup Sam joined was at a fork in the road. Either scale the user base exponentially and join an accelerator...or run out of funds.

Their job was to figure out how to get more people to the product’s sign-up page. ASAP.

There were almost no resources and the deadline was approaching in a matter of weeks. 

It was time to get scrappy.

After 7 hours around a whiteboard, the team had the outline of a strategy.


Step 1. Call the users and get their feedback.

Sam spent hours calling students from the current user base. After enduring countless no-answers and hang-ups they got usable insights from the go-getters who would benefit from the product (an aggregated list of scholarships that students could apply for easily). 


Step 2. Synthesize and come up with a proposal.

Sam developed a plan to reach more students. The users recommended creating an ambassador program where students could refer others and earn rewards.


Step 3: Hit the streets.

In this case, the streets were Facebook groups where students in need of scholarships could be found. Sam got the word out by joining so many Facebook groups that their account was occasionally blocked.


Step 4: Allow students to create custom referral links.

Students posted the links in their online profiles and throughout their high schools. The team offered this ambassador group support on everything from college essay feedback to college counseling.


The user base blew up from 0-100K in just 4 months.

The company was accepted to the accelerator program.

All thanks to Sam’s quick thinking and thoughtful strategy.


Allow me to introduce the star of this story, Sam Chai: Artist | Recruiter | Chief of Staff

 “Hello! I go by the name Sam and prefer they/them pronouns. Currently, I hold the position of Chief of Staff at listen.dev. Previously, I had the privilege of being an early employee at two YCombinator startups.”


During their time with this startup, Sam was responsible for one part of the customer funnel but had to be immersed in the entire journey. They now have a true knack for thinking about every single step and optimizing at each point - leading to remarkable conversion rates.


Sam offers this advice for Generalists:

Make sure you understand your bottom line metrics - whether it’s revenue, page counts, backlinks, or signups. I find a mistake that a lot of Generalists (and specialists) have is not measuring their bottom line.

If you don’t measure how effective your work is, quantitatively, it can be difficult to communicate your value to new employers, clients, or your boss. You can be a Generalist and still measure your quantitative bottom line in the many dimensions you exist in.


Join us in Breaking the Mold: Generalists Who Thrive in a Specialist's World as we explore real-life examples of generalists connecting dots, innovating, and solving problems.

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Ardith Daly: Generalist Creative Maker

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Lee Scharfstein: Creative strategy generalist