How to Recruit Your First Top-Notch Sales Rep for Your Startup

Most startups suck at outbound sales recruiting.

They either recruit too early or too late. Too aggressively or too passively. They pursue the wrong candidates or no candidates at all (FYI: good salespeople are not going to come to you).

The good news is they don’t have to. Create an outbound recruiting machine and you’ll have a pipeline of high-quality sales candidates. Here are the steps to start building your recruiting process today.

When is the Right Time to Hire a Salesperson?

Hiring your first full-time salesperson is a huge step. Are you sure the timing is right? Too soon, and you risk losing touch with your market.

Ask yourself these three questions to find out if your startup is ready for a full-time sales hire:

  1. Is my customer lifetime value high enough? You should have a CLTV of at least $5,000 before you consider hiring a full time salesperson.
  2. Are my larger customers struggling to convert? If larger trial accounts convert at the same rate as smaller accounts, you don’t need a salesperson.
  3. Is there complexity in the sales process for my larger accounts? A salesperson probably won’t make a difference in a frictionless sales process.


If you can answer “yes” to all three questions, you’re ready for a salesperson! But where do you start?

Talent Trumps Experience

It might be tempting to browse job boards like Craigslist or Indeed to find a qualified salesperson with 10+ years of experience.

Don’t! That’s the biggest mistake founders make with their first sales hire.

Good salespeople aren’t looking for work. The kind of candidates you’ll find on job boards aren’t salespeople; they’re scam artists who are great at selling an inflated resume.


Instead of looking for sales experience, look for sales talent. Here are some of the key characteristics of successful startup hustlers:

The best place to find people with those traits? Your immediate network.

How to Recruit Sales Talent Within Your Network

Who do you know with hustler DNA?

Don’t limit yourself to salespeople. Your next great sales hire may be working as a teacher, engineer, or mechanic. Identify the people in your network with an entrepreneurial spirit and talk to them about joining your startup.

Ask for referrals if you can’t find anyone in your immediate network. Explain what you’re looking for in a salesperson and ask your contacts for introductions.

If that doesn’t work, start looking outside your network.

How to Recruit Sales Talent Outside of Your Network

Forget job boards. When recruiting outside of your network, start with businesses in your market that are a couple of years ahead of you.

Find one with an established and successful sales team and reach out to one of their junior reps. Say:

“Hey John, this is Steli from Close. I really admire what your company is doing, and I’m hoping you could help me out. You’re part of an incredible sales team, and we’re trying to hire amazing sales talent like you for our inside sales CRM. Would you be willing to hop on a call with me this week and tell me what you were looking for when you joined a company?”

Most reps will be flattered and take the call. Use that opportunity to explore whether or not they’d be a good fit. If it seems like a match, be upfront. Say:

“This might sound crazy, but is there any chance you’d join our company? You’re exactly what we’re looking for.”

If they’re interested, keep the momentum going by setting up a formal interview. If they aren’t, thank them for their time and ask one final question.

And if local hiring options are limited, consider hiring internationally with Employer of Record (EOR) services. EOR takes care of payroll, tax, and HR tasks, letting you hire the best candidate regardless of location.

Turn Rejections into Referrals

Some of the best hires start as referrals.

If the rep rejects your job offer, that’s okay. Thank them for their time, and just before you get off the phone, ask for a referral that’s totally out of your league. For example:

“Thanks for your insights, John. Before I let you go, I have one more question. Now that you know what we’re looking for in a salesperson, who do you know that’s so insanely talented at sales that they’d probably never work for us?”

This twist on the standard, “Who do you know who would be interested?” makes people really think and leads to higher-quality referrals.


Create Long-Term Relationships

When you reach out to this referral, keep in mind that the goal isn’t to hire them on the spot. If you rush it, you’ll lose the opportunity. Approach the conversation like this:

“Hi Mark, this is Steli from Close. I was speaking with John about building an amazing sales team, and he said you’re the best salesperson he knows. He also said I’d never be able to hire you so that I won’t try. But would you be willing to talk about your sales experience with me?”

If you’d be interested in working with this person in the future, start building a relationship immediately. Find a way to consistently provide lasting value and check in with them once or twice a month.

It may take a while (I knew my Close co-founders for five years before I could convince them to start a company with me), but if you’re willing to invest the time no one else is, you’ll win them over.

And if you don’t? You still developed a powerful relationship that can be valuable in other ways.

Always be Recruiting

Outbound recruiting resembles outbound sales, forming a parallel that underscores the value of strategic preparation and innovative outbound sales tools.

You identify a prospect, qualify them, and go for the close. If you don’t get it on the first try, you follow up relentlessly.

And if you don’t start looking for prospects until you really need them. Don’t wait until you need to hire to start recruiting. If you start making those connections today, you’ll have a list of highly qualified candidates when you need them.

Like sales, recruiting is a never-ending cycle. Start preparing today for tomorrow’s crisis; there won’t be a crisis.

Want my complete A-Z guide on hiring and managing a high-performing sales team? Download a free copy of my book today!

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