Corporate jobs

Brad and Chad celebrate the launch of their new marketing campaign, which was ready 6 months ago but had to get approved ( via Unsplash ).

Brad and Chad celebrate the launch of their new marketing campaign, which was ready 6 months ago but had to get approved (via Unsplash).

I posted a tweet this past week that took a fair amount of heat around choosing startups / riskier roles with high upside compared to ‘stable’ corporate jobs. In hindsight, it was a generalization, although that’s hard to avoid in 140 characters. Hence, I decided to put together this post to dive into it in deeper detail.

The gist of this post is that, in general, as a new graduate pursuing a career in tech and/or with an interest in entrepreneurship, you are better off working at a startup than a large corporation. Is this a ‘hot take’? Of course — but it’s something I feel strongly about, and look forward to being debated on.

Disclaimer, exceptions, externalities…

I’ve watched a ton of debates and lectures on politics, philosophy, and other topics of interest that are fairly polarized. In the Q&A, there’s always someone that comes out with an ‘edge case’ on why the argument the presenter was making is wrong. I.e. if I make the argument that an area marked ‘danger, do not enter’ should stop people from entering. Someone may retort ‘what if the person is blind and/or can’t read’. That is valid, but it’s an exception to the rule, and a minority / ‘edge case’. So in light of that, let’s dive into groups / exceptions where my argument carries less (or no) merit.

Extreme Poverty / Vulnerable Peoples

The biggest retort to my tweet, and one that I agree with (to some extent), is if you are coming from a family with very low income, and your first job needs to have a solid, stable income to help support them. Startups are probably not your best route; they don’t pay as well, the hours are / can be more volatile, and benefits (i.e. health insurance to spouse + family) may not be sufficient.

Likewise if your parents / family is in an incredible amount of debt, and you have a responsibility to help with this. Other situations of vulnerability may include: you / someone in your family is gravely ill, you are an immigrant and need a corporate job to sponsor your visa, etc. I don’t want to sound like the guy at the end of a drug infomercial, but if you think you’re in this boat, then feel free to ignore my argument.

Technical roles

I’m not a fit for engineering, data science, or other ‘technical roles, so those paths aren’t ones that I can speak to. I’ve heard arguments from both sides — startups move faster and give you more responsibility, which are universal arguments I’ll make in this post. On the other side, corporate jobs give you exposure to larger infrastructure and problems you wouldn’t see at a startup. There isn’t a true Product Manager at a 10-person startup — you’re probably 80% engineer and 20% putting out fires. However, at a company like Facebook, Google, IBM, etc. this is a great role. You’ll learn how to work with different teams and see what it takes to push out a new feature / product. So if you’re technical and want to pursue those types of careers, this post may have value to you or it may not be applicable.

Other passions / paths

I added this part as an afterthought, so I apologize for the brevity. If you want to become a doctor but have an interest in entrepreneurship, then startups probably aren’t a good fit for you. Likewise, if you love finance and want to start your own fund, startups would be a poor choice. If you want to make a stable 9-5 salary, start a family, and retire in 40 years, then startups also aren’t the greatest path.

This post is for anyone who hasn’t decided on their path yet and is choosing a corporate job because of the benefits that supposedly prepare you for entrepreneurship + maximize learning.

Why choose startups

Great, so with that out of the way, let’s dive into why startups are an amazing path for those interested in tech + entrepreneurship. The main three points I’ll argue for are (1) Hands-on experience, (2) Versatility and challenges, and (3) Learning potential.

(1) Hands-on experience

I’m a marketing / sales guy. That means my background is primarily in email marketing, content creation, marketing analytics, paid acquisition, and partnerships. When I joined Clearbit, they were 22 employees, and I was the 2nd hire on the Growth (marketing) team. There was a lot to get done, and they really couldn’t afford to silo work and set barriers because I was an intern.

So over the course of the year, I setup multiple email drip campaigns that went out to 10,000+ users, set up a dashboard to monitor the revenue and marketing/sales stats for the company, and was the main point of contact for partnerships with Zapier. This is the reality at a lot of startups — you get hands-on experience since there is an infinite amount of work to be done.

This isn’t the case at a corporation. A company like Uber has very specific roles for each function of marketing — building community (3-5 years exp), coordinating influencers (3 years exp), analyzing marketing data (5 years exp), paid acquisition (5+ years exp), and the list goes on. It’s challenging to get an entry-level role where you get hands-on experience in any of these roles; it’s more likely they’re curating you to be a manager for these types of people.

Tl;dr — it’s hard to get hands-on experience and autonomy at corporations. Instead, you get to shadow and assist people who do.

(2) Versatility and challenges

During my first college internship at Shopify Plus, the organization was 60-people and in a unique spot — they had the resources of a public company (Shopify) but the autonomy to prove out their own model, similar to a startup. This meant there was a lot of work to get done and little precedent on who should tackle it and how.

Over the course of the summer, I had a variety of responsibilities. At one point, we had a ‘concierge’ service where I’d take incoming calls from the Shopify Plus website — very representative of an intern role. On the other end, I had the freedom to send multiple sequences of outbound email to potential Plus customers, conduct a discovery call, and, if it got to that point (which it didn’t), negotiate the contract and close a deal.

In my 2nd summer at Shopify Plus, the organization had grown to ~ 300 people. I was on the revenue operations team, had great direction & mentorship, and learned a ton. However, there was the added bureaucracy and red tape of a bigger company. Certain projects were high-priority and out of my scope, others I had the freedom to tackle but had to jump through hoops to get approval for moving it forward.

Large corporations can’t afford to (and honestly don’t need to) take chances on new grads to get work done. Instead, they have training programs like these — two years of rotating between different departments so you can learn how the organization functions and how to navigate it. This is an incredibly powerful role, but keep in mind that they have this program for a specific purpose.

More specifically, there are things they’re expecting you to do, and things they aren’t. They know how to challenge you, and what you’re capable of doing. You’re most likely the 95th+ person to go through this program, so there shouldn’t be any surprises. I have friends in some of these roles where it’s frowned upon to work beyond a certain amount.

Startups don’t have this — in (most) of the roles I’ve taken, I was doing things I’ve never done before or didn’t know how to. I was challenged beyond my means (which helped me to learn faster), and my role was never silo’d into one thing or another. Early on in your career, I think that’s exactly what you need to grow.

Tl;dr — corporate roles are well-defined, in terms of responsibilities and challenges. Startup roles aren’t, and that helps you grow faster.

(3) Learning potential

I’ll never forget an interview I had with a sales manager at Shopify Plus in late 2016. I was ecstatic about sales, and made my entire ‘pitch’ about my passion for it, what I wanted to learn, and what I could do. His response made me think I didn’t get the job:

You can learn sales anywhere. The most you’ll take from this internship is seeing what happens when a company is growing this quickly. It’s a rare opportunity.

He was right — the sales team was ~ 10 people, and we were very much still figuring out what worked and what didn’t. Witnessing those conversations, how people sold a new product, and what experiments worked (or didn’t) was infinitely valuable.

That’s the benefit of a startup. Things move so quickly, that your role (and the company) 3 months ago is very different from what it is today. These learnings helped me understand what it took to build a business. What it meant to hire for sales, find new channels for leads, retain customers once you’ve signed them. Essential learnings, in my opinion, to being a good entrepreneur.

Corporations don’t give you this opportunity. The business has been around for decades (if not more), meaning that while it has changed, it does so slowly and not in ways a new grad can observe. I.e. the conversations on what direction Facebook is taking certain products will not be visible to someone who is in charge of shadowing the person that grows the use of Facebook Marketplace in Canada.

Tl;dr — corporations move slowly and are siloed, so learning how the business grows is stifled. Startups change quickly, so learning what it takes to go from $1M to $5M, or $5M to $10M is drastically different.


I’d assume (and hope) I ruffled some feathers with this post. So to clarify, I see a ton of merit to corporate jobs, and I don’t think anyone is making an objectively ‘bad’ decision by pursuing one. You get a good salary, clear opportunities for progression, and far more resources for mentorship. I have friends in these roles — whether it’s consulting, banking, product or product marketing — and I think those are phenomenal opportunities.

You learn how to be a manager, how to work with different stakeholders, and how to solve problems. These are universally applicable skills, but I don’t believe they are (as) useful as an entrepreneurship. You need to know how to sell to start a business. To generate leads and grow your presence as a marketer. To retain the first customers (and revenue) your business has ever seen. This all happens with limited resources and no direction. Working in startups prepares you for this a lot more than working at a corporation ever will.

I omitted a few points for startups that didn’t fit neatly into the categories above. Throughout your time, you’ll develop a huge network of people (marketers, salespeople, developers, etc.) that you may eventually want to start something with, or hire them. You’ll also meet mentors who have done it before and venture capitalists who can fund your idea. There is overlap here, as I’m sure you’ll meet this types of people while working at a corporation like Facebook or Google. Unlikely you’ll meet them at a CPG company or a big bank.

Lastly, I want to stress the absolute nonsense of prioritizing salary / prestige if you’re not in the ‘exception’ boats I mentioned above. I’m 22, what am I really going to do differently if I’m making $100k instead of $70k? Factoring in taxes and other factors, not much. I’d also be very hesitant to start a company with anyone who doesn’t have execution experience, regardless of whatever brand name they have on their resume. Management skills, in my opinion, are far less important when you don’t have product-market fit or consistent revenue.