Risk vs. Reward - Choosing Your Startup #2

For the next few weeks, we're going to be featuring a five part series by Sally Bolig, Head of Talent Acquisition at Yotpo. Stay tuned to learn more about how to decide if the startup life is for you!

First-Tier
These are the key components that you want to prioritize. All of these first-tier questions are not only appropriate to ask, but interviewers will respect that you have thought to dig so deep. It demonstrates your commitment to understanding the ins and outs of their organization.

1. Does the company want to be purchased or to IPO (go public)?
There isn’t a right answer but depending on what you’re hoping to accomplish at this company, it matters.

If a company is working toward being purchased, this purchase could occur in 4 years but it could also occur in 6 months. There is a lot to be said for being with a company that was acquired and therefore successfully demonstrated true value. You knew how to choose a high-quality company and contributed to the company’s accomplishment. But it also means that your company is no longer a startup. This could result in you now having a gig at a big name company, or losing your job all-together.

An IPO typically takes a longer time to attain. As long as you’re happy and performing, you’ll have the ability to work with this company for the foreseeable future as it grows and proves value. Typically companies looking to IPO are extremely passion based. However in order to IPO, a company needs to demonstrate a value-add more appealing and accepted than any competitor of theirs does and, of course, there are few companies that successfully do so.

2. How long has the company been trying to fill the role you’re interviewing for, and why is it open in the first place?
Much of the time the reason will be because the organization is going through a growth stage and this is a purely new position. Sometimes, it’s not so simple.

It’s important to understand whether this position has been open for a long time. If so, why is that? What about the other candidates proved to not be a fit? Has the spec for the role changed a number of times? Dig.

It’s also important to understand whether the previous person in this role was fired or quit. If so, why? What has the company learned from the departure of that employee? How has that impacted who they’re looking to hire this go round? Dig.

3. How often do people leave the company of their own volition? How often are people fired?
In many startups, there is high turnover. Those are not the sorts of startups you want to join. Ask questions around who is leaving, how often and why.

Also, if you’re interviewing for a sales role and are told that the reason people are leaving is simply because “it’s sales” and “a hard job,” know that you’re being misled. There are many companies where salespeople remain for a long time.

4. Talking sales roles, how many reps are hitting quota?
When it comes to any sales role, you will never find a company where 100% of the team is to quota. If you do, either the person you’re speaking to is lying or leadership has done a haphazard job of creating goals. Look to hear that somewhere between 70-90% of reps are hitting quota. Those are healthy figures.

5. Are promotions tenure or merit based?
If you’re exploring startup, the answer you want to hear here is that promotions are merit based. Of course there will always be guidelines around how early you could expect to be eligible for a promotion (9-14 months is typical), but in a startup environment you should be somewhere with management that takes into consideration not only tenure but performance, hard work, initiative and positive influence within the organization.

6. Will you have at least one key manager who has done your job before and who has influence in creating your goals?
In simpler terms, if you’re a SDR, is there someone who has actually cold-called people for a living who is a key player in making decisions about your future quotas and growth?

This is important because you want to be led by individuals who know the reality of your day to day. They can sympathize with your struggles and be your champion, but they can also call you out when you’re making excuses.


7. What is the company’s anticipated growth in regards to head-count?
Look for growing companies but be wary of companies that are growing too quickly. But what does realistic growth look like? There is no true rule of thumb, but if a company of 100 employees is telling you that they’re scaling to 400+, that’s reason for concern. It isn’t a deal-breaker but ask probing questions around what has inspired that growth. There is such thing as growing too quickly and sometimes it can result in layoffs.