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One important indicator is how many sales reps the startup has, what the total quota is that the aggregate group of salespeople is targeting, and how rapidly the sales organization has grown.
Ask, What was the sales quota attainment last year? If a company has added too much sales capacity too quickly ahead of its ability to make those sales people productive, its quota attainment is going to be at a low percentage—maybe 60 or 70 percent. Those are bad numbers. But if the startup is hiring in a measured fashion and is seeing aggregate quota attainment of 85 for 90 or 100 percent, those are really good numbers. Over 100 percent, of course, is fantastic. It means the company desperately needs more sales reps and, arguably has underhired.
Another question to ask is about the team’s win/loss rate;
If the win/loss rate is 70 or 80 percent, that is a great number. If the win/loss rate is 20 or 25 percent, that is a bad number. It means the company is investing time and energy into getting to the table and doing demos and filling out RFPs and answering questions, and yet it’s only converting one out of four of those situations into an actual revenue-generating event.
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having high emotional and social intelligence is critical. Being able to read people, to empathize with them, and navigate situations—these are all huge positive requirements and attributes of effective salespeople.
Independence/ability to think on your feet.
Competitiveness/confidence.
Not afraid of change.
Want to work as part of a team.
Not afraid to have work become a bigger part of your life.
Roberge, Mark. The Sales Acceleration Formula (New York: Wiley & Sons, 2015).
Ross, Aaron and Marylou Tyler. Predictable Revenue (2011).
“The Sales Learning Curve.” Harvard Business Review, July–August 2006.
If you are a risk-taker and enjoy the challenges and roller-coaster ride, then the jungle phase is for you, and you should bias toward seed-funded or recently Series A–funded companies that are pre-revenue and have not yet achieved product/market fit. If you are more conservative, want a good salary, and prefer to pick a “safe” winner, then a highway-phase company that is post–product/market fit and either pre-IPO or recently IPO’ed is the right choice.
For example, if you are interested in product management, then the earliest days may be a fit for you. Before a startup finds product/market fit, the product organization has a lot of the power, and Product and Engineering have a lot of the company’s head count. After the company finds product/market fit, Sales and Marketing grow in both head count and power, and the product organization becomes more focused on incremental improvements.
Even the best, most brilliant, and most experienced investors in the world are wrong over half the time. And while they have the benefit of holding a portfolio of companies, you only get to pick one to work for.
In selecting a startup to join, you ideally want to be part of a hot, dynamic company that has great momentum and potential.
One way is to ask a handful of insiders. Find the top three VCs, angels, startup lawyers, and headhunters in your target geographical market and ask them to name the three hottest companies that match the domain and stage you are interested in (and then the bonus follow-up question: Will you introduce me?).
Team: Is the founding team compelling? Can they articulate a vision that inspires you and others around them? Are they of high integrity? Would you want to work with them again in their next company?
Market: Is the market that the company is operating in massive (i.e., greater than $1 billion in revenue potential)? Is the market experiencing some kind of disruption that might lead to opportunity for a new entrant like this startup? How crowded is the market, and does this startup have a sustainable unfair advantage over the competition?
Business model: Are the unit economics (i.e., the comparison of revenues and costs of each customer unit or product unit) attractive? Is the company already able to articulate the lifetime value of each customer, the acquisition cost of each customer, and compare the two? Does the company’s business model contain network effects—that is, will the business get more valuable as the network of users grows such that initial market momentum will result in more momentum and value? If it ...
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Even if you are wrong (worst case, if the company you join fails), you can point to a thoughtful methodology when the next interviewer asks you “Why did you join that company and what did you learn from it?”
two. If you are willing to take more risk and operate with greater uncertainty, the quality of the experience at the early-stage startup can be superior to that of being a small cog in the larger, hot startup.
Be prepared, once you walk into the room, to have a point of view about the company and what you can do to be helpful to them.
Hey Jason, I’m really fired up about education technology and working for Codecademy would be a dream job. I think you are friends with Sandra, who works there. Then, with luck, Jason says, Yes, I know Sandra. We went to college together. She’s great. I’m happy to make the introduction.
Startup Institute, a vocational training program, advises its students to think through their personal motivations, strengths, skills, and experiences and to weave a career narrative that helps infuse the networking process with focus.
do your homework on Codecademy. Read everything you can online. Maybe even talk to a couple of the company’s customers—a couple of friends who are using the service. Try out the service yourself. Take a bunch of notes about ideas for how to improve the product. If you’re a designer, you may have specific ideas to make the product appear more attractive. If you’re a marketer, you may have an idea for a new campaign or message. Sign up for the newsletters and try to see what the patterns are for their email campaigns. Then, when you meet Sandra, you can walk in and say, It looks like you guys
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Instead of merely pitching your work, engage with Sandra in conversation about her work. Sandra—I guarantee—is going to get off the phone or walk out of the coffee shop and think, That was a great conversation with a great person!
Finally—and this one is a bit of a secret weapon that few people do well—come bearing gifts.
Hey, Sandra, how can I help? Anything you need? What are you looking for? What are you challenged with? Oh, you need to hire a designer? Actually, I worked with a great designer in my last job, I can recommend a fantastic designer for you.
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You can find the current version on my blog at www.SeeingBothSides.com. The blog post is entitled “Advice to Grads: Join a Winning Startup,” so just search for “winning.”
I find that people who work at startups are categorically happier with their jobs and with their careers than people who don’t. Startups provide a greater degree of freedom and autonomy. There’s the promise of a sense of mastery that people seem to really enjoy. And there’s a sense of purpose—a really clear sense of purpose—because your actions are linked directly to the ups and downs of the company. In a big company, it’s very hard to know how and what you should do to impact the greater whole. Yet, these are the key elements to happiness. And I think they’re much more prevalent in startups
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age. I was totally over my head at almost every job I took on during my startup career, and I got promoted faster than I was prepared to be. It challenged me. It pushed me to step up my game every year. Just like with dog years, every one year of “startup time,” as I like to call it, is like seven years at a regular company in terms of growth and responsibility, maturity, and growth.
