Want To Join A Startup? Ask These 5 Types Of Questions: A Founder’s Perspective by Forbes – Entrepreneurs

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By Rachel ten Brink

Rachel ten Brink is an entrepreneur and growth advisor. She is a co-founder and the former CMO of Scentbird.


Rachel ten Brink, Co-founder and former CMO of Scentbird.

Credit: Aurelie Graillot

Joining a startup has an undeniably magnetic appeal. While it can be exciting, and even life-changing, it’s not all fun and ping-pong. I spent the last five years in a fantastic ride as a Co-Founder and CMO of Scentbird, and also have the perspective of 15 years in corporate (L’Oreal, Estee Lauder, Gillette). As in many things in life, I didn’t know all the answers, but I did find asking the right questions helped greatly. Whether right out of school or well into your career, these are five types of questions you should ask before joining a startup:

“Have some savings in the bank and keep your expenses down and flexible.”

Credit: Pxhere

1) How do your financial needs and expectations align with a startup?

Understand your motivations for joining a startup. Know that it’s almost impossible to be wildly successful at a startup if your only motivation is external, e.g., money or what others think of your job. Why do you want to work for a startup, particularly, this one? The most successful people I know are internally driven; they do it because they want to prove something to themselves.

Generally, startups are looking to preserve cash and, especially if they have not raised a large round, may not able to pay top salaries. You should have realistic expectations, but if you’re ready to take the plunge, make it easier on yourself by planning for your future. Have some savings in the bank and keep your expenses down and flexible.

Equity can have huge potential. However, understand that companies often reserve equity for senior hires. Remember that equity has a vesting period, so you’ll need to hang around for years to get your full share, plus don’t forget shares only convert to cash when you can sell. Be aware that the likelihood of any startup making billions in the short run is unlikely.

2) Do you understand the product, business model, and company financials?

Before joining any startup know the answer to questions about the product and business model, plus understand the financials. What are the startup’s strengths? 

First, look at the product. Would you pay for this product/service yourself? Do you find it superior to what is in the market, and do others feel the same? Spend time reading customer reviews online to get a sense of how well the company is addressing customer needs and where things need work. Your passion for the product will be a significant determinant of your success. Startup teams are too small to coast, and you will be pushed and stretched – it’s impossible to fake passion if you don’t believe in the product.

Next, consider the business model and economics. Are the fundamentals sound? Do you see this company being profitable within a specific horizon? Even well-funded startups need to be driving towards profitability to remain viable. Ask a lot of questions about growth, margins, CPA, and LTV to understand the key metrics that drive the business.

Figure out how much money they have raised and how much is left in the bank. Check on Crunchbase. Investigate who has invested and ask who the target investors are. Is the company being strategic in their fundraising or just taking any random check?

 3) Can you thrive in chaos but work towards structure?

Startups offer enormous opportunities for growth and impact, but also challenges. People who can navigate the chaos of startups and yet strive towards creating structure are the most successful.

Startups are lean. Unlike corporations, you may not have any colleagues that do what you do, and often you are the first person doing this role in the company. This means figuring out things by yourself without many resources. Does that sound fun or daunting? Would you prefer having a team of specialists to bounce ideas off? Also, consider training. Most startups have not yet had a chance to build skills training. 

Make sure the role makes sense for the company, and for your growth. Particularly if you’re experienced (expensive) ensure you add value right away. Change is the one constant in startups–expect that no matter what your job is, it will evolve.

4) Do you fit with the people and culture?

Culture is one of the most indicative determinants of whether you will be happy in your startup job. Think about your work style, collaborative or independent? OK with long hours? Do you have what it takes to succeed at a startup? 

Take a hard look at the founders, especially the CEO. Do they have experience or have they hired people that know how to put together a team? If there is more than one founder, what is the relationship between founders? Does the CEO have a reputation for firing people at the drop of a hat? Also, the CEO is your pitch person for the company. Do you think this person will be successful at raising money now and in future rounds, representing the company in media and PR?

Make sure when you interview that you are listening and observing as much as you are talking. Pay attention to the office – is it quiet with people working alone, or noisy with folks working in groups? Are there too many Post-its on the wall with too many projects? Particularly if the team is international, do you feel a cultural fit? 

Talk to current and past employees, but be tactful. It’s a small world, and you never know what is on the other person’s mind. Check out sites like Glassdoor, but always come to your own conclusions.

“From the start, have a plan of exactly what you want to get out of this experience, and your next steps afterward…”

Credit: Pxhere

5) Do you have an exit plan?

Startups are a fantastic opportunity for career growth and gaining experience. As much as you are unlikely to hit the jackpot and make millions, you are almost guaranteed a job that will stretch your skill set and take you into new directions.

From the start, have a plan of precisely what you want to get out of this experience and your next steps afterward, and be prepared to learn and grow. Learn from the experience of others who have worked at startups.

After all is said and done ask yourself one last question: Does the startup offer you the chance to do something you will love doing? It may sound cliché, but I believe the most important thing is to love what you do. Startup work is hard but can be incredibly rewarding. Finding the right fit is critical. 

Good luck!


About Rachel

Rachel ten Brink is a startup advisor and the co-founder and former CMO of Scentbird. She helped scale the fragrance subscription to over 250,000 subscribers by making beauty discovery simple and affordable.  She is a Columbia Business School and Y Combinator alumna.

In her role, she led brand marketing and growth, editorial, influencers and social, email, off-line media, and PR, as well as business development. She started the company in 2013 after working for over fifteen years in global marketing leadership roles at Estee Lauder, L’Oreal Elizabeth Arden, and Procter and Gamble. She is passionate about consumer brands, beauty, product development, technology, and entrepreneurship.


April 17, 2019 at 12:03PM
Forbes – Entrepreneurs