What I Learned Scaling From 2 to 80 Salespeople in Under a Year

*Editors Note: Live updates from the Sales Hacker Conference San Francisco are brought to you by PipelineDeals. PipelineDeals is sales and CRM software trusted by thousands of companies to increase sales. Follow us @pipelinedeals.

This session is titled What I Learned Scaling From 2 to 80 Salespeople in Under a Year by Sam Blond, VP of Sales at Zenefits.

There were many things we learned along the way that took us from 2 to 80 Salespeople in under a year, and today I will share some of those with you.


  • What to look for in a rep:

Look for synergy between what they have done in the past and what you are doing now. Make sure they have seen an early stage startup and can make an impact without having to invest extensive training.

When you bring on new sales reps, remember hitting numbers should be a definition of success. For myself, I always shot to be number one. When I look for candidates I see how they rank against their peers. If they aren’t number one, are they passionate about being number one, or do they show the desire to improve?

Finally, always ask for 5 references. Anyone can find 3 people to speak positively about them. Once you dig into number 4 and 5, you tend to get more accurate and complex information. It helps to position it as, “We are thinking to hire John, what can we do to help make him successful?” This leads the way for their references to surface any weaknesses that may change your hiring decisions.

  • When is it time to hire a VP of Sales?

First, get a few sales reps and a million in revenue. You want to find someone who will be a good leader but also have the right amount of talent. The VP should also collaborate well with the existing team.

  • When should you use Outside recruiters?

In the beginning, outside recruiters can be very helpful in helping you generate a pool of candidates with the right talent. Use a variety of recruiters for diversification.

  • When should you hire an internal recruiter?

If you are hiring 2-3 people a month, it is probably time to hire an internal recruiter.

Quotas and Compensation

Quotas should be challenging, but attainable. A good goal is to set your quota so 70% of your sales reps can hit it.

Remember, you get what you pay for. Be more aggressive on the variable compensation side and aim for above the market rate. Make people want to work for you, then you can be selective when hiring.

Controlling Cycle Times

Controlling your cycle time is incredibly important because if a sales rep is taking extensive amounts of time to close an opportunity, they are unable to focus on new opportunities and you are missing out on revenue.

The role of discounting will play largely into this. Be creative with how you position offers. What we did, is every few months we would tell customers we were losing the ability to discount and they needed to take advantage now.  You must be creative in your approach.

Finally, don’t back down. Don’t extend a discount or offer, they will usually end up closing anyways. If you say yes, they will have that expectation in future negotiations.

Specialization and Sales Development

Specialization allows reps to be more efficient. For example, if you keep one sales rep for prospecting and one for closing, they become experts in their field. If your margins support specialization, do it.

Hire strategically. You should not be spending time training reps on how to sell. You want to be training them on your product. When you begin hiring more than 2 reps per month, hire them in groups and invest in training classes. Over invest in the beginning, because it will pay huge dividends later on.

Make culture a priority, and include that in training as well.

Organizational Structure and Promoting

Each closing rep manager should have 8-10 direct reports. SDR managers can handle a bit more. Be sure to keep the org chart simple. Additionally, promote from within if it is the best option, but don’t force it.

Be careful not to set unrealistic expectations around promoting. We started a trend where we were promoting people after 3 months, then as we grew and hired more salespeople, they were expecting to be promoted after 3 months when the positions weren’t available. Be sure to communicate and set realistic expectations in the beginning.

Sam is currently the VP of Sales at Zenefits. He also became the Director of Sales at EchoSign, the biggest e-signature provider in the world and the fastest growing business unit within Adobe, he manage Sales Managers, Field/Territory Account Executives, and Inside Account Executives.

Join Us Today

Insider access to the GTM network and the best minds in tech.

Join Us Today

Insider access to the GTM network and the best minds in tech.

Trending Now

You may also like...