Hiring a technical leader

One of the most challenging things for startups is hiring a really great technical leader. 

Early-stage tech companies that don’t have a technical founder are often pressured by investors to land this crucial hire.  Investors know that hiring this individual is like finding and capturing a proverbial unicorn; they’ve seen this play out across numerous companies.

A great tech leader will guide the team in terms of architecture, operations, engineering practices, employee growth, retention, etc.  All these things allow for the product and company to grow and scale.  This person is generally well-respected within the engineering community, this, in turn, attracts top talent to the company. 

They are rare because there are several forces at play. In years past, technical leaders at startups typically spent a few years in software development or middle-management at large tech companies and decided to seek out the startup life.  The last few years have been really good to large tech.  Their middle-management and senior engineering talent have been rewarded handsomely, usually not enough to retire, but enough that they’ve grown complacent.

Someone who’s spent considerable time at Amazon, Google, Netflix, Facebook, etc have likely gotten used to their internal tools, the support infrastructure, their peculiar ways of doing things and that work-life balance.  When one finds themselves outside that ecosystem, they can suddenly feel lost at sea.  Some may even feel entitled and not willing to do things they feel are beneath them.  What they don’t realize is how good they had it, many of the problems were already solved for them years ago at these companies.  They are cogs in a machine.  They are just expected to operate.  Life is very different at startups. 

Startups the past few years have also been doing quite well.  Some are startups only in name (Uber, AirBnB, etc).  These people aren’t likely going to leave a rocket ship or don’t really want to rough it out again, they’re waiting for their payday.  The rate of new startups being created has actually slowed down in past years, of course, many have failed.  Developers and engineering leaders find it a lot less risky (and lucrative enough) to join an established company. There are many engineering leaders that have failed, the really great ones that can execute and build engineering teams are an elite few.  This makes for a very tight talent pool for experienced senior technical leadership.  

Many teams make the mistake of not hiring this individual and they make lots of engineering mistakes, eventually, they fail to execute.  You can’t expect a developer with 2-3 years experience to fill this role, without years of making mistakes and mentoring.  Technology is a very expensive place to make mistakes.  Many startups have mountains of technical debt, monolithic codebases and no rational plan or experience for managing it.  Investors push founders to hire someone with pedigree (i.e. has a big name on their resume) because it’ll make other investors at ease that they have someone experienced at the helm, but often this person is not the right person for the all the aforementioned reasons. 

Finding this talent is hard. When they do, startups should be prepared to pay for it in cash and equity.  If you’re early stage and cash-strapped, perhaps tie create a year-end bonus correlated to company metrics.

In any case, good luck!

Amazon HQ2

The Toronto tech scene is hot.  Last year, more tech jobs were created in Toronto than San Francisco, Seattle, and NYC combined.  By making Amazon’s HQ2 shortlist, Amazon essentially vetted Toronto as a great tech hub.  Amazon saved all these companies thousands of hours of research, cities put pitch decks together for all to see, and now tech companies are moving in fast.

In the past few months, Bay Area startup heavyweights and big tech-behemoths have announced they’ll be recruiting large engineering teams in Toronto. Uber announced they’re investing $200M to build an engineering hub in Toronto.  Microsoft announced they’re moving their Canadian HQ to Toronto. If Toronto becomes the site for HQ2, we should rename Toronto to Seattle2.  Amazon already has over 700 tech employees in Toronto working on Alexa, Supply Chain, and Fulfillment systems.  Their footprint here is already sizeable.  The Bay Area heavyweights are all talking about building 200+ person engineering teams in Toronto.  

This will have both positive and negative effects for sure.  It’s going to drive up the cost of talent, poaching talent away from promising startups to join more established companies.  I honestly believe that life as a software developer is vastly different at Amazon vs a startup.  But companies like Amazon and the more established startups serve an important part of this ecosystem, they are finishing schools for new grad talent.  I’m convinced after they’ve worked a few years in a big-tech company, they’ll itch to join a startup and have more impact.  

In the short term, the biggest losers will be early-stage startups that are trying to find product-market fit and have limited funding because the loss of talent will be felt most acutely. Time will tell, but I believe these developments are good for Toronto, but there will be growing pains.