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Working for a startup offers many advantages.

Opportunities for growth and learning abound. The chance to wear many hats, to be on the ground floor of something new and disruptive, and to know that your contribution has an immediate and lasting impact on the business all make working at a startup attractive. Generous equity packages are nice, too.

But not all startups are created equal. The vast majority fold within three years, churning through capital and employees. Even in the best startups, long work hours, shifting priorities, and a relentless pursuit to dominate the market can create an untenable work environment for some.

We reached out to startup founders, CEOs, consultants, and some of the WELL team to learn what potential candidates should consider when applying for a job at a startup. Here are their top recommendations:

#1 Do the values of this startup align with my own?

“Startup work is tough — long days flow into nights, getting off the ground can be hard, and it’s important to make sure the company you’re giving your all to has the same beliefs as you.”
— Adam Csillag, Director of Contracts & Business Development, Incentive Technology Group

#2 Does the product or service have product-market fit?

“I have seen tons of great ideas that lack product market fit or some components of product-market fit that they languish in the initial revenue to $500K per year range. That’s a horrible place to be since you don’t know what you need to do to achieve growth. That’s why having a plan for determining product-market fit is so critical. As a future employee, you need to know that what you are building someone will actually buy.”
— Jarie Bolander, Founder, Lab Sensor Solutions

#3 What is the cash runway and what plans does the company have to manage it?

“Understanding how a business manages its cash flow and cash runway are critical to learn before you join, but especially when it comes to start-ups. Cash runway can be a determining factor for how long a business will stay viable, and its important that a CEO has a strategic plan to ensure maximum cash runway and what the plan is for when the cash runs out. Do they intend to pursue equity financing? Do they have plans to take out a debt line? There are many ways to stretch cash and secure new funding and each require extensive planning ahead of time. Understanding if your CEO has a plan in place for cash runway lets you know that they have a growth plan, a budgeting plan as well as intend to take care of their people by ensuring their company stays alive.”
— Savannah Hart, Financial Analyst, WELL Health Inc.

#4 What is the CEO’s ultimate vision for the company?

“Before joining a startup, find out what the end game is, the CEO’s ultimate vision for the company. In Silicon Valley, there is often a rush to ‘turn and burn’ companies, build quickly and sell, leaving the original employees out of jobs. A quick thrill ride may not be what you seek.”
— Ray Zinn, Founder, Micrel Semiconductor, and author of Tough Things First

#5 What is the biggest risk for this startup?

“Being aware of the challenges and risks gives you a general idea of how the founders of this company evaluate its certainty or uncertainty. It can give you insight into how the CEO is thinking about the future and the biggest risks [they] think might affect the company.”
— Jordan Wan, Founder and CEO, CloserIQ Link

#6 How will I be measured?

“The reality is that an employee at a startup gets pulled in a lot of different directions, and rightfully so — the company has to look for opportunities to make both existing and potential customers happy. Despite the fact that you’re trying to work agilely and change focus all the time, you need to know that all of your activity counts and is recognized. That’s harder to do in a startup. As long as you’re in agreement with management that there are specific goals you’re trying to hit and what your overall contribution is, that’s a good sign. You want to know your work counts.”
— Tom Christensen, Head of Marketing, WELL Health Inc.

#7 What is the average tenure of your workforce?

“This question is a clever way to figure out whether employees are happy or not. If the current employees have been with the company for a long time, it’s usually a good indicator that they are happy and the company has a positive and fun culture. Even though the company may just be a startup, if the hiring manager says less than a year or talks about high turnover rates, then it’s a clear red flag.”
— Matthew Ross, Co-Owner and COO, The Slumber Yard

#8 What type of employee has struggled at the company?

“Startups are different than more mature companies. Change and uncertainty are the norm and not the exception. This question will help the candidate determine: are the issues that struggling employees had something that might also be an issue for them? I say a good startup employee is more willow (flexible) than oak (rigid).”

“A good response to this question from the interviewer would take some responsibility for the failure of certain employees such as: ‘Early on we weren’t as clear about expectations around the need for everyone to wear multiple hats, the culture we want to have, or the number of hours that will be expected during the interview process and some employees came in with the wrong expectations,’ or ‘We didn’t have a formal onboarding training program and it was mostly ‘OJT- on the job training’ and that just wasn’t enough training for some of the employees we hired.'”
— Kristie Jones, Principal, Sales Acceleration Group

#9 How does the company help employees stay engaged and productive during the work day?

“Finding new ways to get your job done can be difficult, but it turns out the best approach to staying motivated might actually be to take a break from the computer and pet a dog. Having that best friend with four legs around actually decreases stress throughout the day and makes the office a happier place.”
— Jennifer Young, Co-founder and CMO, Outdoorsy

#10 What are the options grants worth?

“While working for a startup is an inherently risky venture, option grants can become a meaningful source of wealth if the company succeeds. Option grants have always seemed to be cloaked in mystery — many companies are unwilling to help prospective employees understand the value and structure of the grant they are receiving, and unlike salary data it can be very difficult to compare competing offers. Prospective candidates should make sure they understand the current and potential value of the grant, as well as what the underlying data tells you about the health and future prospects of the company.”
— Matt Cooper, CEO, Skillshare

#11 What are my personal goals in joining a startup?

“Finally, here’s advice that I’ve given to my own kids. If you’re between 22 and 30 years old and looking to join a startup, you have one major advantage on your side: time. You’re young. Trust your gut and put your energy/talent into something that moves you. If you’re bright and you work hard, the money will eventually come your way… you’ll gain essential knowledge, maturity, and insight by being part of a company that you believe in. The experience of watching it succeed — or possibly fail — will be invaluable to your career and your professional worth over the long term.”
— Dr. David Lenihan, Founder, Tiber Health

Why work at WELL Health Inc.

At WELL, we are well funded with rapidly growing annual recurring revenue. Our product has demonstrated market fit and is trusted by many of the leading healthcare organizations. And, our employees are thriving in their jobs, resulting in a five-star rating and rave reviews on Glassdoor. Visit the WELL careers page to find the perfect opportunity to join our fast-paced startup in Santa Barbara, California. ♥

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