It seems that working for a startup is now a “hip” and “cool” trend when it comes to considering a new job.  I might just be noticing it since I am working at a startup and people get very interested when I mention it, but interest in startup jobs is definitely growing. Just check out the chart below if you don’t believe me.

A graph showing the increasing trend in Google searches for the term "startup jobs"

Number of searches for “startup jobs” – Jan. 2006 – Nov. 2014 (partial) (Source: Google Trends)

Sure, working at a startup sounds cool. You’ve heard about the perks: kegs every Friday; foosball tables in the office; unlimited vacation days — benefits you likely wouldn’t get at a normal 9-to-5 corporate job. Even though working at a startup is fun and exciting, it’s not always a party. You bust your ass every day (even weekends), and if you blow it, you could bring the whole company down with you.

That said, I firmly believe that working at a startup has changed my life and I’m loving the fast pace of everything. Every day there is something new to tackle. I started full-time here as Digsy’s first employee about 14 months ago and thought it would be beneficial to share my experience. Additionally, I asked seven other people who are also currently employed at startups to share their experiences working at a startup. So, let’s dig in:

1. You are directly tied to the success or failure of the company

Bailey Nelson at EveryMove We are creating something together, and it’s up to us whether we make it big or we fizzle out. There’s something very unique about that feeling.

Bailey Nelson – Marketing Manager – EveryMove

In a startup, often everyone’s opinion and expertise is considered in decision making.

Brent Chow – Co-Founder and CEO – Bolt

One of the first things I noticed when I started working at Digsy was how much of an impact I had. Digsy has 4 employees: the three co-founders and me. Before Digsy, I had previously worked a corporate job at Chase bank, and my experience at Digsy has been a complete 180° from my previous position. I’m not just another drone in the hive.

I am always included on big meetings about the future of the business, something usually reserved for high level executives at a corporation. No matter how mundane of a task I complete, the team is always there to let me know that I’ve done a great job. Being able to see how my efforts have a direct result on our success is very rewarding.

2. Being in a startup gets you direct access to talented people that can mentor you and help advance your career path

Reilly Starr at My mentors have changed from those in more senior positions to my peers that are startup veterans.

Reilly Starr -Director of Public Relations –

I get a lot of 1:1 mentorship and access to leadership.  I am able to have input on the direction of a product and the growth of the company.

Betsy Rogers – Account Executive – InternMatch

Having access to those that can help mentor me has been one of the greatest benefits of working at a startup. I share a desk with our Chief Executive Officer and our Chief Product Officer, I can’t think of any other job where a full-time employee would be sharing a desk with the officers of a company.

Being able to have access to leadership not only allows me to have a direct impact on the success of our business, but it has also helped me grow personally and professionally. I might still be at a point in my life where I am deciding what my career path will be, but being able to work so closely with the co-founders has already helped guide my career path.

3. You must be able to adapt quickly

Dan at The Black Tux [Working for a startup] requires a lot of initiative, more so than other jobs I’ve held, and the ability to be ready for the unexpected at anytime. Things can obviously change quickly in an environment like this. What you are doing one day may be completely irrelevant the next, because something of greater importance has come up. The ability to be flexible and kinda fill in where needed is more important.

Dan Wenhold – Director of Customer Experience – The Black Tux

I think the biggest thing I’ve noticed about is how important it is to be able to “roll with the punches” – the entire focus of the company might shift, and you just need to embrace it, trust it, and shift your plans to match.

Bailey Nelson – Marketing Manager – EveryMove

For those who need stability and a consistent work life, the startup life could be a challenge . One must prepare to turn on a dime and adapt to new circumstances to thrive in a startup system.

Josh Weinstock – Head of Public Relations – Moviepilot

I’ll just say this: if you can’t adapt quickly you shouldn’t be working at a startup. Period. If you read our last post, you know that we built two iterations of our product and they both failed. Each time we failed we all had to adapt quickly. It was our team’s ability to adapt quickly that saved us each time we failed.

With my previous corporate jobs, I rarely had to adapt. I would do the same thing every damn day — and I couldn’t question it. In our startup, I might work the same task for a day or a month, but I know just around the corner something new for me to work on is coming. Some tasks that I spent three months working on in the past are completely irrelevant now. You must be able to adapt if you want to thrive in a startup.

4. You have more flexibility to be creative and spread your wings

Hosh Spenta at Connectifier A startup is all about new ideas and having the ability to think outside the box. Filled with the excitement of an ambiguous but optimistic future, a startup is where most of tomorrow lies. Being able to come up with new ideas, challenging an existing working idea and making it better and being able to think outside the box are a few things that are expected of anyone working at a startup!

Hosh Spenta – Account Management, Sales, and Business Development – ConnectIfier

The startup culture is a dream come true for me. Free-flowing ideas, constant iteration but always with big picture goals in mind […] To make a startup work, you need phenomenal people who work their chance to shine through in the startup environment, where they’re often stifled in a more corporate setting.

Josh Weinstock – Head of Public Relations – Moviepilot

In my past corporate jobs, I remember saying to management “Hey, we should try doing this”. The response was always “let me ask upper management”, and I would never hear about it again.

However, at Digsy, I was shocked the first time I suggested some creative, out-there idea and it  was received with “Sure, let’s A/B test it”. We are constantly testing new things — sometimes things that sound pretty weird. Creativity is key in a startup.

I imagine us as mini MacGyvers — piecing different things together, to get our business to take off. You’re constantly looking for ways to make things better, and it’s a breath of fresh air.

5. Being a self-starter is a necessity, not just a bullet point on a job description

Josh Weinstock at Moviepilot The startup culture breeds critical thinking and independence , a need for even the newer staff to be creative and bold

Josh Weinstock – Head of Public Relations – Moviepilot

This role has required me to take much more initiative – like many new hires, I took on a newly created role. You aren’t taking over for anyone and there isn’t a set objective or plan in place – you have to take on the responsibility of finding out where best to spend your working time and how you can make a big impact, fast.

Bailey Nelson – Marketing Manager – EveryMove

I would say you definitely have to have a strong sense and ability to be a self-starter here, versus working in a more structured environment where there may be more organized teams and deadlines you have to meet in projects. A lot of the work over the first four or five quarters here has largely been recognizing opportunity, stepping in,and filling that opportunity to the best of your ability. It requires a lot of initiative, but much more so than other jobs I’ve held.

Dan Wenhold – Director of Customer Experience – The Black Tux

The need to be a self-starter was one of the most immediately apparent things I noticed when I started working at Digsy. I took a position that didn’t exist until I was hired. I didn’t have any training program on how to do my job.

Every now and then I’ll just focus on a task or improving something, even though I haven’t been asked to do it. It’s important that you spend your time wisely, but you don’t have set tasks every single day. You need to recognize when there is a need for something without being told — and fill that need.

6. Be prepared to wear multiple hats and be a jack of all trades

Brent Chow at Bolt I can say that startups move a lot faster than non-startups. Everything is moving faster and the responsibilities are much broader. Just because you title may be XYZ doesn’t mean that’s what you’re going to be doing most of the time. If something needs to get done and you’re on a small team you have to figure out a way to get it done

Brent Chow – Co-founder and CEO – Bolt

At InternMatch, all team members are expected to contribute to improving our product to make it awesome for our students and employers – finding bugs, new capabilities and features, improving current features.  Its not unusual to find teams working cross functionally on projects to make improvements.

Betsy Rogers – Account Executive – Internmatch

When asked what I do at Digsy, I usually struggle to come up with an answer. Of course, I start by telling them that I am the Director of Customer Success — but that’s just a title. I do tons of things other than customer service: marketing, bug testing, conversion rate optimization, etc…

Pie chart of Kyle's tasks

Distribution of Kyle’s responsibilities

As you can see, I wear multiple hats and so does everyone else on our team. It comes with the territory when working at a startup. This goes hand-in-hand with being able to adapt quickly — but it also means I’m learning a ton of different skills simultaneously. Aside from customer service, I had never done anything remotely close to any of the  other tasks I help out with here. Being able to wear multiple hats and learn quickly is a must at any startup, especially one with a small team.

7. Your team is everything

Betsy Rogers at InternMatch At times progress can seem uncertain and you have to make sure you are working with a team you believe in and can see the bigger picture.

Betsy Rogers – Account Executive – InternMatch

There’s also a greater weight placed on chemistry. In such a tight and energized work space, working well together is a must. We look for compatible people who enjoy each other’s company and bounce ideas well.

Josh Weinstock – Head of Public Relations – Moviepilot

Everyone is very focused and centered upon a single goal. Everyone has very much bought into the companies long term vision and success and is working very hard towards that.

Dan Wenhold – Director of Customer Experience – The Black Tux

I firmly believe that a team is one of the most important attributes to look for in a startup. Here at Digsy, everyone enjoys being with each other and we all believe in Digsy’s success. In turn,  we all work towards that success.

A corporate job is different: someone might be working just to get experience, while someone else might just be working to make money. In a corporate position, I know that not everyone is so deeply in love with their job that they strive to make sure the company is a success. In a startup, you must believe in your team to be successful.

Don’t just rush out to get a startup job

At this point you might be telling yourself “Well, I fit all of these skill sets and expectations, so I should work at a startup!” Keep in mind that while a startup sounds great — and for the most part it is —there is uncertainty and some other cons in working at a startup.

  • Job security is the biggest issue, especially for newer startups. You never know if the startup will be around in one year.
  • The hours are irregular. Don’t expect to work 9 to 5. Expect to work nights and weekends.
  • There’s less structure. You need to be able to carve your own path and make decisions on your own. If you thrive in a rigid, structured environment, startups may not be for you.

That said, having a startup job is a very rewarding experience. I learn something new every day and have gained a heap of experience. If you feel you would excel in a startup, then give it a shot — just make sure you do your research and believe in the startups you apply for.

Agree or disagree, let me know in the comments below. If you have any similar experiences I’d love to hear them.

Written by Kyle Pinzon

Kyle is the Director of Customer Success at Digsy and also dabbles in Marketing at Digsy. Kyle started at Digsy in June of 2012, as a part-time contractor. Kyle became Digsy's first full-time employee in August of 2013. While new to the startup environment, Kyle is loving every minute of it and excelling. Kyle resides in Placentia, CA. He enjoys NASCAR and rooting for the Anaheim Ducks, Anaheim Angels, and the San Diego Chargers. Lover of all things tech-related. Science nerd.