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A startup’s “gnarly” problems: hiring and marketing

Sometimes it pays for startups to be a little risk-averse.

A startup’s “gnarly” problems: hiring and marketing
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Editor’s Note: Each week, Maynard Webb, former CEO of LiveOps and the former COO of eBay, offers candid, practical, and sometimes surprising advice to entrepreneurs and founders. To submit a question, write to Webb at dearfounder@fastcompany.com.

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Q. I have two gnarly problems right now . . .

  1. Who should I hire as the first sales person in a SaaS company? Do we hire a senior person, who might be expensive and risky, or junior people, who might need a lot from us?
  2. Our product is a flipped interactive survey, and the category does not yet exist. Do we lean on an existing category (“survey”) and risk being mislabeled, or insist that we are different and completely new–a project intelligence tool? 

–CEO of a project intelligence software company

Dear Founder,

Some of my biggest mistakes have come from hiring a person who was too senior for where the company was at the time. Don’t make the same mistake I did! Especially in the beginning, don’t hire someone who is seasoned and focused on building a team and requires guarantees on pay. Instead, hire somebody who could be a growth hacker and who has the potential to grow into an effective leader.

Your first sales hire should not be an experienced sales exec, but a sales person who’s scrappy and doesn’t need a lot of direction. Look for someone who has seen the movie and has some methodology. A scrappy person can be inspired and excited to help build something big. It’s possible that this person may not be the one to lead a sales organization when you are 50 or 100 people, and you might ultimately need to bring in seasoned experienced help to scale. But you can make good inroads with a scrappy team. One story I love from Salesforce is how they didn’t even have sales people in the beginning and everyone sold the service. Their product marketer signed the company’s second customer while waiting in line at the supermarket!

On the question of categorizing your company: My gut feeling is that when you are brand-new it’s better to be mislabeled and recognized rather than perfectly labeled and not show up anywhere.

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Once you get people to your site, you can use whatever wording you want, but you first need to get them there. To do so I would lean on the existing category–and then work to differentiate your offering.

Rather than be too narrow, it’s always better to pick a category that’s big enough to describe where your dreams are. Again, Salesforce offers an interesting example. The company does so much more than Salesforce Automation (SFA), but it never changed its name because of the logistical nightmare that would have been and the branding ramifications they would have faced. However, when Salesforce picked its ticker symbol when it went public on the NYSE, it chose “CRM.” CEO Marc Benioff thought it was a “home run” because Salesforce wanted to be in the customer relationship management (CRM) business and do more than SFA. It’s funny now because Salesforce does so much more than either of those categories describe. But it’s better to always broadcast the bigger picture. Think about where you are going–not where you are. As that famous quote attributed to Wayne Gretzky goes: “Skate to where the puck is going to be, not where it has been.”

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