It’s Time To Start Getting an Uber/Lyft Rating for Sales Reps. And Paying Them Based On It.

This year we’ve had a string of fairly terrible experiences buying software at little ol’ SaaStr:
  • With one well-known SaaS vendor, an employee e-signed a 2-year contract without permission.  We never deployed the software, and yet the vendor threatened to sue us if we didn’t pay for Year 2.  Even though we never used the product, paid in full for Year 1, and the signor had no signatory authority.
  • Another vendor, the sales rep was so aggressive it took us 14 months to buy.  We would have bought the prior year, but the rep was so insistent on rip-off pricing we gave up.  The rep also shut off the trial repeatedly before we could even put any data in it or use it. It took intervention at the C-level to get the deal done, and it took more than a year.
  • A third vendor, the rep
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The Top 3 Critera for Hiring Your First Head of Sales

We’ve talked a lot on SaaStr about hiring that first VP of Sales.

But what if you can’t find the right person, and you’ve spend months looking.  What risks should you take when you’ve realized Ms or Mr Perfect just isn’t going to happen rigbt now?  At some point, you have to take more risk.  I’d boil it down to 3 factors.  If your risky candidate passes all 3 critera, and you haven’t found your “true VP” after 4-5 months (possibly less), I’d go ahead and make the hire:

#1: Have they hired 2+ quota-meeting/exceeding reps before?  This is #1 by far. If they’ve never hired 2+ great reps before, you are taking on a lot of risk making them your director of sales or first “head of sales”. 95%+ of great individual contributor reps have zero experience hiring. Do you want to be the company Continue reading "The Top 3 Critera for Hiring Your First Head of Sales"

What’s Your Loss Rate? You Really Should Know.

A ways back on SaaStr, we wrote a classic post, Beware of the Confidence of High Win Rates.  It’s something I see again and again, especially below $2m in ARR or so.  A start-up says they have a lot of problems, but winning deals isn’t one of them.  That they win every deal they are in.  Well, of course these early stage start-ups win all these deals.  Because they are only invited to just a very small percentage of the dances. So ultimately, it’s healthy and positive to see win rates decline after $1m-$2m.  That means your mini-brand is coming into its own, prospects are starting to hear about you, and that marketing, one way or another, is starting to work.  You are getting into more deals that you aren’t ready for.  That’s OK.  You’ll learn from the ones you lose,
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7 Of The Most Common Mistakes Made Building Your First Sales Team

A few key mistakes I see start-ups making > 50% of the time:

  • Hiring Early Reps (#1 – #3) That You Personally Wouldn’t Buy From. Don’t hire someone with the right resume. Hire someone you’d buy your own product from. Later, once you have a real sales leader on board, she may hire folks you personally wouldn’t buy from. And that’s OK. But it won’t work out while you are Interim VP of Sales.
  • Hiring your first VP of Sales from a Fancy Tech Company That’s Actually Not Remotely a Startup Anymore. They almost certainly haven’t actually done what you need them to do before. A little more here: The 48 Types of VP Sales. Make Deadly Sure You Hire the Right One. | SaaStr
  • Hiring a Stretch VP of Sales Who Has Never Hired Quota-Hitting Reps Before. A stretch VP is fine, but someone who has never hired a Continue reading "7 Of The Most Common Mistakes Made Building Your First Sales Team"

WebSummit Presentations

I presented on two topics at WebSummit 2018 in Lisbon on November 6th. The slides and videos of those two presentations can be found below. The videos are provided courtesy of WebSummit: 9 Secrets for Startup Success, A roadmap for B2B Founders Lean Startup taught the world how to find product/market fit, but in the...

11 Simple Questions to Assess the Maturity of Your Sales Team

In my experience, at the $1 million ARR stage, most SaaS companies find themselves in one of two buckets. Either their sales organization is firing on all cylinders or falling apart at the seams. You can guess what happens to the companies who have sales teams that are knocking it out of the park. Customer acquisition increases as they continue to execute strategies and tactics that they know work well and shed the ones that don’t. These teams don’t have it all figured out, but they know enough to deliver consistent sales results. On the other hand, the companies who find themselves stumbling at this stage have to act fast. Getting to $1+ million in ARR is a significant achievement, but continued growth isn’t a given if there are severe cracks in the foundation. These teams tend to have stumbled into early success without being able to attribute it to
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If Your Sales Process Looks Like This, You’re Blowing Deals

I got on a call with an SDR recently who was nothing short of lovely. He asked great questions, talked about my goals, what I was looking for, what I wanted to see in their technology, etc. He listened well, was authentic, and was helpful from start to finish. Then I asked to see the technology. Which is when he told me it wasn’t his job and that he’d have to get me scheduled with an Account Executive because he wasn’t allowed to show me. I actually had no idea he was an SDR… talk about killing the momentum! Fast forward to the next call. The first thing the Account Executive asks me: “So… tell me about your business and why we are talking.” Really? Did you all not talk behind the scenes? The LAST thing I want to do is to have the same conversation again… … and
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Lessons from ZipRecruiter: Building a Sales Org From Scratch in a Product Led Company

When Kevin Gaither was hired as the forty-ninth employee at ZipRecruiter, the closest the organization had come to talking about sales was to say that they didn’t want to have a call center. A leading online employment marketplace, ZipRecruiter had experienced astronomical growth since launching in 2010. To-date, the company has helped more than 1.5 million businesses of all sizes find great candidates, received more than 430 million job applications, and currently has more than 8 million jobs listed on their site. But, five years ago, as Kevin was coming on board to build—from scratch—what is now a 300-person sales team, the company hadn’t even begun to tap into sales as a way to grow the business. A product-led company, ZipRecruiter initially started out leaning heavily on improvements in product design and engineering to increase their conversions. But at a certain point, the team was able to look
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How the Growth of SaaS Makes Life More Difficult for Customers and What to Do About It

When I was the sales leader at ion interactive, even our smartest customers sometimes asked me questions that, at the time, seemed pretty clueless. For example, I’d often get calls from prospects asking “So wait, how are you different from Google Analytics?” In my head (though thankfully never out loud) I’d be screaming: “I just told you! We’re nothing like them. We’re a software that makes a calculator or a logic-driven assessment without code. You can’t do anything like that with Google Analytics!” I would get off calls like that and immediately go to our homepage. Yes, right there on the home page it was clear. What our product did, the challenges it solved, who it solved them for, the benefits of it. Clearly spelled out. How could a buyer be confused? Then, our martech SaaS company was acquired, and I accidentally became a SaaS consultant. Suddenly I
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