As Canada’s tech ecosystem scales, an oft-cited ingredient needed to take it to the next level is more senior talent.
The problem is, beyond the traditional path of finding and working with mentors, there aren’t many resources available for time-strapped founders to embed healthy processes derived from senior talent within their organizations.
Johnathan and Melissa Nightingale — co-editors of The Co-Pour management series, which is syndicated on BetaKit — want to do their part to address this experience gap in Toronto’s tech community through Raw Signal Group. With Johnathan’s experience former CPO at Hubba and VP at Mozilla, and Melissa’s past work as former head of creators at Wattpad, both have had their share of good and bad experiences as managers — and they want to pass the knowledge on.
“Seeing people make the same mistakes was hard to watch. The more we learned about it, the more we realized there weren’t a lot of people teaching management and leadership the way we understood it,” Johnathan said.
From tackling the basic questions of hiring, to addressing more complicated issues like building companies with a conscience, BetaKit spoke with the Nightingales about their mission to transform Toronto tech for the better.
Why did you launch Raw Signal Group?
Johnathan: Both of us had to learn management the hard way, and both of us have been working in tech for over 20 years — certainly, the latter half has been teaching other people to manage.
We’re both in Toronto for the long haul, and we go to events like BetaKit150 where we find out how to build a thriving world class tech ecosystem. And we felt we had a bigger job to do than we could working at an individual company and working with our peers. And if we really want to be world class, we have to step up management and leadership stuff, because it’s a place where we’ve got work to do.
Melissa: The most common complaint from Toronto investors, founders, and CEOs is that they have a hard time sourcing senior talent. And with me, it happens in hallways and private conversations, and with Johnathan, people would be like ‘we need 10 more of you.’
I was not like this in my 20s. I didn’t know the things I know now when I was 25. And at some point, I had to learn them. And the idea that it’s stuff you’re born with or not is core to our approach. We don’t think it’s stuff you have to be born with. You can learn on the go.
When it comes to helping startups, what is your approach?
M: One of the things we did as we were getting ready to launch, we sat down and said, ‘what is everything you wish you knew when you were starting out as a boss?’
And we pulled out themes and said, there’s a bunch there: how you talk to employees, how you hire, how you fire, how you do performance management. How you have awkward conversations to help people get the best work done on a daily basis.
Are there any consistent problems that you see with scaling companies, or certain areas where you can lend particular expertise?
J: There’s a lot, but I will touch on three. Teams do a terrible job, by and large, of building diversity into the process. I want to be clear, we are not selling ourselves as diversity consultants. There are great people doing that work in Toronto. But talking to leaders about why they should care about it — sometimes you really need to start with fundamentals.
If no one on your board is pressuring you to build a decent company, you skip that stuff.
Second one we found is that the actual fundamentals of management, things like how to think about compensation, how to think about when to fire employees when it doesn’t work out. That’s 101 level stuff, but you have to learn it somewhere and very few people learn it in school. So that whole category of basic skill development matters a lot.
If I was going to give you a third, I see organizations, as they grow and get past 20 to 30 people, really fall down on how to design organizations. How to think about who goes where, how ownership is divided, how to hold people accountable. What that management structure looks like. A lot of startups want to play fast and loose and it bites them because as soon as they scale it blows up in their faces.
In your manifesto, you mention that the ‘growth at all costs bubble is going to burst’ — why do you think that?
M: It’s an interesting time to be in tech. Maybe I’m lucky enough to work in an industry where I felt that way for the past 17 years — but the last couple of months have been a really interesting time to be in tech, and thinking about the relationship between scale and the business you want to build.
If you’re not paying attention to Uber, and you think what happened to Uber can’t happen to your company…it should be a wake up call that that bad behaviour people turn a blind eye to — we need to invest in robust structures for people who work in tech so we don’t burn them out.
Back to your point to Uber, would you say that the reason why this blows up in people’s faces is because it becomes a PR issue? Or does it go deeper than that?
M: It’s not a PR problem that your female engineers feel like they’re having a horrible experience. It’s not a PR problem that your senior staff is collecting [medical] records from victims. That’s not a PR problem, that’s a culture and values problem. That someone decided to write an article that was uncomfortable, that put the spotlight on you and your organization, is not a PR problem. The problem first and foremost is in the approach, is in the values of organization, and in the tone that comes from the top down.
There’s a huge opportunity in the fact that many of the entrenched norms that get the Valley in trouble are not present in Toronto. We haven’t set those molds in place as deeply.
J: We talk to a bunch of founders, and the pressure they feel from boards is really around moving numbers, and when that’s the thing you feel pressed on you, you try to do it. And if no one on your board is pressuring you to build a decent company or take care of your people, you skip that stuff or it comes from your own sense of what’s right and what company you want to build and your own skills… so it’s fine to say, ‘companies will be more ethical when investors push them to be more ethical,’ but that’s bogus because a company should be ethical because that’s the leader you want to be.
The good news is, you can do that, and build a world-class company. Think how world class Uber would be if they weren’t constantly fighting fires and firing people.
Are you optimistic about your potential to make an impact?
M: I am incredibly optimistic. I moved to Toronto after 13 years of living and working in tech in Silicon Valley.
One of the things that everyone lined up to tell me when I moved here is that Toronto is a young ecosystem, it’s a more intimate ecosystem, people really do know each other and it’s a tight-knit community.
For us starting out, there’s a huge opportunity in the fact that many of the entrenched norms that get the Valley in trouble are not present in Toronto. We’re newer, we’re younger, we haven’t set those molds in place as deeply. There’s plenty of opportunity for us to identify who we want to be as a community.
J: One thing I’ve started mentioning is a point Vitaly [Golomb, at BetaKit 150] made in his keynote, when he was talking about things that set the Valley apart, is that there are 50,000 director level or above executives [in the Valley] that have experience, and that allows you to create a new startup tomorrow and know you have talent pool to draw on.
He’s right on. That management is big differentiator there and it’s a thing we can build. That drove us to start this thing — both of us have done that work, both of us have taken individual contributors that we were managing, helped them grow into managers, helped them grow into directors and VPs.
It doesn’t matter if it’s 50,000 people — if there’s a pool of people who know what it is to manage a large organization or systems for how to think about it, that unlocks so much. The bigger you get, the more you have to deal with scale, the more the problem set changes. It doesn’t mean Canadians are genetically incapable of doing it. We just need to learn.
This interview has been edited and condensed for clarity.