Grow as the vineyard grows, plants, exponential impact… I just really liked this photo!

I’ve seen lots of articles (and written some of my own — here and here) on ‘choosing a career’. The act of distilling your passions, understanding what you’re good at, and trying different roles until you find something that’s a fit. This isn’t one of those posts.

Instead, I’m going to write on career growth — what happens when you know you’re in the right career path, but you struggle with how to grow, and what roles / jobs will optimize for growth. Quick recap:

5 years ago I started in sales, then moved to growth (marketing), and finally ran my own business (a marketing agency)
I learned along the way what I liked / disliked about each role, and further refined what I’m looking for in the ‘ideal role’ — along with what I still want to learn
There are some personal skill sets I want to learn, and some company criteria that any employer will need to pass for me to take the role
Nothing is perfect: I’ll make the most logical decision I can based on information available to me, and hope it pans out!

Shifting motivations

For context, I’ll give some background on my path and where I’m at now. I started at Exposoft Solutions, a small event management software company, back in 2015 as a sales rep. It was my first real job, and also my first exposure to tech. I loved sales; it rewarded hard work where ‘the sky’s the limit’ on how much you could earn based on closing deals. It led me to joining Shopify Plus a year later in sales, which is where things took off.

What I liked about sales: High earning potential, ‘hustler’ mentality, leveraged my people skills.

What it was missing: Lack of ‘hard’ skills; prospecting, conducting discovery calls, and closing took effort but it didn’t leverage hard skills like coding or financial analysis.

This led to an interest in marketing — I knew how to convince someone who was interested that our product was a good fit, but how did they become interested in the first place? I went down a rabbit hole on tech marketing, reading HubSpot’s blog, Neil Patel’s blog, and more. I took on some contract roles at Turnstyle Solutions (Yelp WiFi) and #paid doing email marketing, content marketing, and even some SEO work. Eventually, while I was working at Shopify, a role at Clearbit came up in ‘Growth’. Fast forward a couple of weeks (August 2017), I got a job on their 22-person team and moved out to San Francisco to join them. Fast forward another year, and I was faced with the following dilemma:

What I liked about growth: Becoming ‘good’ at certain channels (paid ads, email, etc.), ability to grow any business, direct impact to organization’s bottom line.

What I disliked about growth: Specifically, working for someone in an Individual Contributor (IC) role… I wasn’t involved in leadership discussions (company vision), I was tied to a pay check, and I didn’t have a lot of agency (based on boss’ directions).

I moved back to Toronto, toyed with a few startups ideas + did an accelerator, but finally settled on running an agency (Feb 2019), which eventually morphed into Divisional. We do growth for early-stage startups. I manage a team of contractors of around 5-7 people and work remotely from Toronto. Sounds great, right? Well, fast forward 1.5 years and here’s where I’m at:

What I like about running an agency: Flexible hours, pays very well + high earning potential, exposed to different startups and growth problems.

What I dislike about running an agency: Limited mentorship / learning (all my employees are contractors), less challenging work, not building something ‘bigger’.

Talk about an exciting 5 years, am I right? So let’s see where that leaves me…

Taking Stock

I know that I don’t like solely being an individual contributor (do work that someone tells you to), but simply ‘being an entrepreneur’ didn’t cut it for me. Services businesses are great — by leveraging contractors and working with clients, I can make 2-3x what I would as a full-time employee. However, and I know this is cliche, it’s not just about the money.

I’m still early on in my career. Making money is great if I’m learning, and specifically, learning what I want to learn. Building a services business is NOT easy — hire contractors, build workflows, find ways to scale your sales, etc. I have an incredible amount of respect for people who are doing it. But those aren’t skill sets I want to build (right now). Instead, I’d rather focus on:

Managing people: How do I recruit and retain good talent? How do I convince them of my mission and help them grow? You don’t get this with contractors, since they’re hired for a specific purpose + with clear outcomes. Even as an agency, I’m not accountable to anything my clients do aside from the work I’m contracted for.
Cross-functional skills: I want to build a software company one day. This means understanding product and engineering, customer success, sales, marketing, and everything else. It also means understanding how other people think, including those roles but also people with different backgrounds (i.e. MBA vs 5 years in startups). Simply working as a ‘growth marketer’ doesn’t build these muscles, it just makes me really good at growth. And while I can build a full career around that, it’s not what I want to do.

Great! So I’ve narrowed down some key focus areas for what I want to learn. Now, how does this factor into finding a job?

Find great companies

Unfortunately, being 2+ months into my search, not that easily. Why?

Problem Space: I could get the two items above at a lot of companies. But which ones do I really want to work for? One criteria here is ‘problem space’ — is the problem this company is addressing, and their solution/way they think about it, really amazing? To give an example, I’ll help a tech company that automates SMS for Shopify stores all day as an agency. There’s no way I’d join them as a full-time employee.
1. Possible areas: Education & retraining, workforce management, community building / happiness
Team: I love working with smart people. Don’t get me wrong, I work with a lot of smart people now — but not the same way like when I was at Clearbit, Shopify, or other companies. It’s more of an agency-client relationship than a colleague relationship. Why does this matter? Well, working with very smart people means I’ll get exposed to how they think, learn from them, and share my knowledge. This is a BIG part of career growth.
1. Possible proxies: Serial entrepreneurs, operators who have built other businesses, people with extensive background in a specific area (i.e. the vertical of the company)
2. Sad reality: None of these are perfect. I recently worked with a crypto founder (made tens of millions of dollars) who was easily the worst person I’ve ever worked with in my life. Success != good to work with.
Compensation: I recognize that running your own business (agency) compensates me more than a lot of full-time jobs would. I know that this is a trade-off I’ll have to make — greater learning for a pay cut. However, I don’t think this is a binary; I’m not sacrificing my lifestyle and worth just for learning. There should be a balance here where the company compensates me fairly, but I’m also incentivized to perform.
1. How this manifests: Evaluating my monthly burn rate, going rate for people with similar skill sets (read: NOT education, years of experience, or other poor proxies).
Culture: This is a VERY tricky subject that I could write a full post on by itself. Culture for me means a team that cares about what they do and is empathetic to other members of the team. I don’t want to work for a company that ‘grinds’ from 7am to 12am simply because. Performance should be evaluated based on merit — pick a number, outcome, etc. and own it.

Buckle up.

I’d like to think I’m a very logical person — I want to make the smartest decisions I can, by maximizing the due diligence I do and the amount of thought I put in. However, nobody is perfect. I’ve mentioned before (this post) that the best I can do is optimize based on the information that I have available to me. The rest will figure itself out in the future.

I want to find a company that I can work at for 2+ years, help them build something great, and develop as a professional along the way. There are perfect scenarios here. There’s also a scenario where I join, notice flags within the first 3-4 months, and quit before the half-year mark. Nobody wants this, especially me. But here’s what I do know: I have a great skill set and will put my heart and soul into any role I’m taking on. Where that leads me, who knows?