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What to Expect When You Join a Startup

We are in the age of the startup. Everywhere you look, there is another small business, Series A or Seed company sprouting from the ground, offering new and exciting perspectives on products and services deemed traditional or outdated.  

And what is a startup, exactly? Some elaborate billionaire brainchild destined to soar to the moon, or a scrappy shop built out of a garage that no one’s ever heard of? It certainly spans the range, but broken down on a technical level, the core components of a startup include: 

  • Early stages of development and business case 
  • Self-funding and/or seeking venture capital from individuals and banking institutions 
  • 1-3 founding members 
  • Fewer than 50 employees 
  • A large focus on growth 
  • A unique solution for a niche market 

But despite all the buzz about these small businesses over the last couple of years, there are certain asterisks that hopeful job applicants should be aware of. Simply put, startups are not for everyone. Like every other product or service comparison, you need to do research to figure out whether the workload, company structure and overall culture are right for you. If there is a specific startup you are particularly interested in, we recommend you check out their career page, their job postings, socials and anything else that might tell you about their employer brand. 

We can’t help you decide between buying an iPhone or an Android, or whether pineapple should or shouldn’t be a topping on your next staff party pizza, but we do know a thing or two about startups and corporations. So, here is a comprehensive list of reasons why you might love or hate working at a startup: 

The pros: 

1. Infinite learning opportunities.

At a startup, you are guaranteed to learn something that you didn’t know before. Some of that learning will be fast, some of it turbulent and uncomfortable, but you will emerge on the other end of your startup career with skills that will make you invaluable anywhere else.  

Something that large, established institutions struggle with is allowing their employees to try and fail at things. With corporations, you are entering the production of an epic novel halfway through and building on the existing story – the plot firmly set up. In a startup, you are instead helping to write the early drafts of the story and developing the protagonist; you may go back to the drawing board a few times, but when you are getting something wrong, you are also figuring out how to do it better. 

2. Flexible schedules.

Even before Covid-19 shook the global workforce, many startups had experimented with (if not fully implemented) work-from-home structures, hybrid working models, and schedules that accommodates the employee so long as they performed well and got things done on time.  

Due to their size, startups can inherently foster a tighter team where everyone is seen, and everyone matters. If you have children, or a long commute, a sick grandparent, a maniacal, destructive dog home alone in your delicately furnished apartment, have no fear. Many startups are going to listen and respond to your needs because they value you a lot more than a corporation that employs tens of thousands. 

3. Unique perks.

Where larger businesses tend to win over candidates with massive salaries and blowout health benefits packages, startups and scaleups usually have less access to capital and need to get a little more creative. One of the ways in which they do this is by supplying cool and unique perks that both serve to reward candidates and define the company’s character. Some examples include: 

  • Catered lunch and snacks 
  • A “bring your pet to work” day 
  • Having a relaxed dress code 
  • Supplying the latest industry tools and gadgets 
  • Company-branded merchandise 
  • Team retreats 
  • A work-from-home stipend 
  • Unlimited vacation time 

The bottom line is while they try their best to be engaged, corporations are massive and have a lot on their plate. At a startup, you’ll always feel like you are an integral part of the team’s success and growth. 

4. Little-to-no micromanagement.

I’m sure at one point or another, we’ve all had a boss that constantly breathes down everyone’s necks at work –whether literally, at the office, or metaphorically through hourly calls, email check-ins, and online activity tracking.  

You see fewer of those types of leaders when you’re working in a startup. Why? Because in the office you can have a candid conversation with the CEO about work without having to book a meeting, days in advance. You can have your entire company updated in a single Zoom call. 

Since medium and large businesses have so much at stake financially, any slope in productivity could snowball into huge consequences down the road if managers don’t stay on top of them. The unfortunate biproduct of over-preparedness is a series of silos and a lack of trust from the top down. Every employee becomes specialized and pigeon-holed into their specific task so that there are no mistakes made. 

5. High-speed innovation.

There are endless opportunities for even the most junior employees to make their mark with bold new ideas. Most decent startup bosses are more than happy to foot the bill for new software and tools to keep your team ahead of the curve and will even help you get certifications to upskill. If you want to work on something from the ground up and build it quickly, then a startup is a great place for you. 

Conversely, if someone in a multi-national company that serves millions of customers wants to introduce a new service or product, it’ll take some good industrial binoculars to see the end of that red tape. Bureaucracy keeps things organized and a consistent company direction. But the drawback to that structure is that things are sometimes unbearably slow to market. This is why you often hear about corporate giants swallowing up startups – it’s just easier for them to own a product than to make one of their own. 

The challenges:

1. A different approach to salary and benefits

Let’s not sugar-coat this. Something candidates need to understand is that while some startups are in decent financial shape, some are in pre-funding or pre-revenue positions when they are looking to hire. This means that you are likely looking at a less boastful compensation package than the firm’s behemoth neighbors.  

In this regard, big tech blows little tech out of the park. Therefore, you’ll see many job postings that decline to advertise the salary range before you are well into the recruitment process. The hope is that if they can win you over with a great product, mission and vision for the future, you may choose to forego the razzle-dazzle of a bountiful pay day.  

Though, also important to note – just because you start at a lower salary than you might in a larger corporation, startups are looking to scale and scale quickly which often results in a lot of opportunity to grow personally and end up with that dream salary in your dream role in a company you help build. 

2. Not a traditional 9-5.

While scheduling flexibility can be tuned to your favor, work-life balance while you are on the job is another thing entirely. It may prove to be extremely difficult to get away from your computer within the cozy 8-hour cutouts that corporations often guarantee you. Part of this is because startups are still trying to prove their concept to existing and potential buyers so they can build a stronger reputation and grow.  

You might find yourself handling important clients calls outside of your regular work hours, especially if there aren’t many members of your department. Until the company grows, and you are working within a larger team or managing a team of your own, you’ll likely be a go-to person for a lot of things, especially if you’re talented. You may not vacation without your work phone, but you will find purpose in your role. Although not for everyone, having an important role that is critical for the functioning and growth of a scaleup is rewarding for the right people. 

3. Loose structure.

For people who crave structure, order and a clear direction in their work lives, the most challenging  thing about startups is their lack of hierarchy, organization, in some cases, priorities. Many small businesses will hit the ground running with an amazing idea before they take the time to properly set up their infrastructure. This affects everything from pay equity, interview effectiveness, quality of hires, timelines on deliverables, legal affairs and overall execution. 

So when you are perusing company career pages and online job boards, here are some common red flag phrases that will give you some insight into the current company culture: 

“We’re a family here!”  

  • This would suggest the work environment is relaxed but very much an all-hands-on-deck kind of environment. You may find yourself doing things that weren’t outlined in your job description. “Our business has a flat organizational structure” 
  • This could suggest a few things; first the company might not have enough people yet to have a hierarchal structure in place. Second it could suggest that there isn’t clear direction on who handles what yet. “We always put the client first” 
  • This can be an indicator that the company’s work flow is built around the needs of customers because they are still heavily in a growth phase. In this scenario, the focus might not be on building a company culture, rather building the company. Keep in mind, this also means there is plenty of opportunity for you to put your fingerprint on that culture and help shape the direction of the company itself.  

4. Ambiguous mission and values:

While the product or service may be outstanding, there might not be much of an employer brand or strong company direction. It is new, it is fast-growing, and it is unique, and therefore it is likely that you are going to be one of the bricklayers of the company’s cultural foundation. It might be messy, and you should be prepared to see the company pivoting on hairpin turns until it truly finds its stride.  

But missions and values go beyond sales and stakeholder demands. You’ll often find early-stage startups are exceptionally good at defining what they do, but don’t talk much about who they are. You need the drive and the patience to stick around with a startup until it figures that out, but when they do, they’ll be appreciative of that fact and show you they are lucky to have you. 

5. Few training frameworks.

One of the pros to working at a startup or scaleup is the opportunity to get yourself online certifications so that you can take full advantage of the programs the job requires. But you also have to apply what you know and what you’re learning to your job in real time, and there often aren’t enough employees in the organization who have the time to train you. So, you learned how to drive well with an automatic, but the company is giving you a standard, and your only recourse is to get in, fumble around with the clutch and hope you don’t stall on the highway.  

OK, I admit that that was a bit dramatic. But being self-motivated with the drive to own your work and the autonomy to solve your own challenges will serve you well in a startup. 

There will be a good amount of time in the beginning when a colleague will walk you through things and probe you for questions, but if you’re looking for formalized, full-week programs with exercises, you may be out of luck.  

Finding balance 

Are you a fast-learner looking to embark on something new and exciting, but willing to sacrifice a pay cut for a company that feels like it was made for you? Or are you more interested in big paychecks, plump benefits, and a pension alongside rigid schedules, limited learning, a lurking boss and underwhelming team culture? 

The truth is startups and corporations stand for two polar extremes in the world of work and there is something in between for everyone. Take stock of these pros and cons and give some real thought to what you want your next career-move to be.  

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