CollegeVine HQ is where our team of 50 or so are revolutionizing an entire industry with AI. We used to be based in Cambridge, MA but have since gone fully remote.

If you want to learn more about CollegeVine, I’d recommend checking out our website.

If you want to learn more about me at CollegeVine, my LinkedIn is a good place to start. My bio links to a piece of writing that was originally intended as a scaling tool, but which turned out to be better as an advertisement for our organization to potential candidates: Working with Mohan.

Organization Building

So much can go wrong between the 25 to 100-employee ramp that I consider it make-or-break for a promising startup. Sure, if the market pull is strong enough, you’ll “succeed” whether you were intentional about it or not, but man—just the amount of unnecessary suffering when it’s done poorly!

I build antifragile organizations using a three-part formula. Antifragile means the organization gets better with more stress put on it, so a mechanical mental model won’t cut it—you need to think ecologically.

1. Design the system: I build a “work OS” from first principles so that the form of the company completely matches its function
2. Know the team: I observe and learn the individuals in the company better than they know themselves and activate people in 1:1 settings
3. Guide the evolution: I prefer tooling over process for earlier stage companies, which naturally selects for a higher talent density

Sometimes I summarize this as simply: purpose, people, process.

Advising

Before I was COO at CollegeVine, I was CTO for 6 years. I coach both COOs and CTOs and advise CEOs.

For early stage CEOs and scaling COOs, I teach a simple model of “business, product, engineering” to help you identify where the bottleneck is in your company. However, don’t let the simplicity fool you—each of these expands into a large set of mental models and lenses that you can apply to your business.

Sometimes founders think it’s a magic trick when I ask them three simple diagnostic questions about their business and then proceed to list out all the problems they have in the business in roughly priority order. It’s not a magic trick: it’s actually just a traversal of a lattice of mental models about early stage and scaling startups.

For CTOs, I’ve worked with engineering leaders at startups that are in an earlier stage than CollegeVine and have found great joy in helping them transform their engineering teams by teaching important concepts and principles that I’ve learned over the years.

I didn’t realize it at the time, but the intuition for why I’ve captured and distilled the right framework and principles is that CollegeVine essentially allowed me to do the closest thing possible to a controlled experiment on culture: we built the business one way through 2019, decided we didn’t like that business model, pivoted and downsized, I did a bunch of thinking about engineering’s role in all that, and did it all over again with another business model and culture with the same core group of people.

So the people didn’t change, but the results were drastically different this time around. That’s probably as close to an A/B test on culture as you’ll get in this line of work.

But don’t take it from me. Here’s what a grateful advisee had to say:

“Just wanted to say thanks again for all the advice man. We’ve talked to many CTOs at various stages but you are the one who [our lead engineer] and [engineering manager] consistently want to hear more from.” — a founder/CTO

Due to these positive experiences, I’ve vowed to always take a call from any budding engineering leader who wants help. Think of it as my way to pay it forward for all the good mentorship I’ve gotten over the years.

2015

I co-founded Canopy Education Inc. (dba CollegeVine) in 2015 with my cofounders Zack, Johan, and Vinay with a mission to bring lifelong guidance to the next generation.

As our story is not fully written yet, I feel like there’s no point waxing poetic about the nature of the rollercoaster ride, though there’s no doubt we’ve had a colorful decade thus far.

We’ll tell the full story someday when the time is right, but for now, we’re focused on what the present brings and what the future holds.