How to pick the right startup to join?

How to pick the right startup to join?

You want to change your career and the big corporate job is just not what you want to do anymore. Well, let me first discourage you a bit from joining a startup in the first place.


A) You will have to work really hard

B) Your current company benefits are probably better

C) Most startups fail


I could go on. There are a lot of reasons not to join a startup but if you’re still reading you came to the right post.


When I was at Accenture and later at Salesforce I always had an urge to do more than what was prescribed in my role. There was always an inherent entrepreneurial spirit in me and finally, after 5 years in big companies, I felt it was time to join a startup.

As you want to evolve in your career and grow there are a few things to consider and look for when you join a startup.

Not every startup is created equal and you can definitely make mistakes joining the wrong startup. 


The 5 things to identify the right startup for you 


These are my 5 things and I would say they apply to everyone considering joining a startup. There will inevitably be more factors but these are a good starting point. 


1. Founders & Exec Team

The founders and executive team are crucial. Check each one of them out on LinkedIn and see how long they’ve known each other. You want them to be pros at what they’re doing. They need a track record of success. Ask yourself:

  • Are they a tightly-knit team that trusts each other?

  • Have they been successful in the past?

  • What are the values and the culture they’re building?


Don’t underestimate the values. The company’s values matter a lot in how they will navigate good and bad times. There will be both, trust me. In my interview I asked everyone very directly, how are you living the values in your company? Which is the top value? What value do you think exemplifies the CEO the most?

Check: LinkedIn, find videos, tweets,… to get a taste.


2. VC Backing

Startups most of the time will need some kind of funding to the started. They will get this from so-called Venture Capitalists (VCs). A great VC will bring great board members to the company that can help and ensure success.

Some of the top tier 1 VC firms are Sequoia Capital, Benchmark, and Andreessen Horowitz. You can always visit Crunchbase or PitchBook data to see who has invested in the startup you think of joining. If it’s a list of no-names, then think twice. If you see a Tier 1 VC firm, that is generally a good sign.

Check out VC firms on CB Insights.


Once you know who the VC is, check out how much the startup has raised. Ideally, they will have enough cash in the bank for another 12 or so months when you join. Typically, a startup is funded by VC for 18-24 months and then the expectation is to get more funding. 


If your startup hasn’t raised money in 24+ months, then ask them, how are things financially? How are they making money? These are questions you should not be scared to ask.


Here’s an example of Gong, a B2B SaaS startup with great investors and a big recent round. This will mean they are in growth-mode, have a lot of capital ready and probably an amazing team of board members that can advise the company on their scaling journey.

Gong Crunchbase
Gong Crunchbase Source:



3. Product-Market-Fit

Most likely you want to pick a company that knows what they’re doing. If you’re in a stable job now then you want a startup that works. In a nutshell that means it has to pay customers. The startup will only have to pay customers if it’s solving a real problem and that’s what people call Product-Market-Fit. 

In your prospective startup, check who are current customers, can you find testimonials? If yes that’s great. Read up on reviews on portals like G2

That will give you an idea if it’s just a college drop-out’s pipe dream or something that could become a company of consequence.

Sometimes a good sign is competitors. If there are competitors, then you know there’s a market to be won.

Here’s an excerpt from G2 and customer reviews. A great resource to identify what is happening in that market and what horse you want to bet your career on.

G2 Grid Comparison Project Management Source:



4. Trajectory

This is a hard one. What are good indicators if the company is growing? There are a few things that you can find out while doing your research but then always use the interview as an opportunity to find out how much growth there is. Are they signing more deals, increasing revenue, hiring people?

A few things you can look at:

  • How many employees do they have and what functions?

  • What do Glassdoor reviews say?

  • Are they hiring many people currently on their careers page?


For example, on Glassdoor, you will get a great idea of the culture, how the company is doing and what people are saying about the prospects of the business.

The example here is by Seismic. 


Glassdoor Seismic
Glassdoor Seismic Source:


5. Personal Opportunity

Lastly, the key question is, what does this mean for you personally? Let think back to the start of this post. You want to escape the 9-5 grind and do something more exciting.

Ask yourself, what is it that you are expecting to do in the startup and are you sharing this with them? Of course, you will fill a box on the org chart but if you talk to the hiring manager he or she should know what you want to truly achieve in that company. Do you want to become the foremost expert in a field? Do you want to build a new office in a new location? Do you want to become a leader?

Always ask yourself:

  • Will you get a position that fits your personal ambitions?

  • What is the role you will have in the company?

  • How are they developing, coaching, leading people?

One more time, I suggest you read up on Glassdoor what it says about the company and ask in the interview. Ask the hard questions, how do you ensure a great culture of learning and development? Many startups don’t think about this early and well enough. These will struggle to attract and retain great talent in the future. You want to bet on the right opportunity for your personal career. 


My final words

That’s it. These are the five things I looked for when joining Clari. You might have more factors than those. I would suggest researching these as a bare minimum and then in the interview ASK all the hard questions.

You should interview a startup just as much as they interview YOU.

What have I missed and what are you looking for? Join the conversation on LinkedIn.



Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.