10+ Of The Most Common Mistakes in Early SaaS Sales


Q:  What are the common mistakes in B2B sales in the early-ish days?


The list could be endless, and it can vary a lot based on type of customer, type of sale, etc. And some of these mistakes are seen by some as best practices, or at least OK practices.

But let me outline some common mistakes that mean you are leaving money on the table, either now or in the long run:

  • Not training reps 3–300. The first couple of reps you often can train by osmosis. But after that, you have to build systems and processes to train them. It doesn’t take too long for a product to get so nuanced, so complex, and with so much competition, that a rep can’t wing or. And can’t just learn by sitting next to the CEO. As soon as you don’t have time to work every day hands-on with your reps, at least by then — you have to train them. Much more than you might have planned. More here: You Have to Train Reps 3-100+ They Won’t Train Themselves. | SaaStr
  • “Firing” prospects. Do not fire a prospect. Do not break up with them. No prospect enjoys going through a sales process for fun. If a rep can’t get engagement, but a prospect has registered some interest, marketing can at least drop them into a long-term engagement campaign. No one likes to be broken up with, folks. This does nothing for your brand.  A related post here:  10 Things New Sales Reps Are Taught. That Maybe They Shouldn’t Be.
  • Too many cadences and automations. Yes, use Mixmax, Salesloft, etc. to automate outreach for sure. They give you scale. But — do not do this for larger prospects. Larger customers deserve personalized outreach. No one is going to make a $100k purchase without personalized discovery and a solution sale. Spend the time to get to know your prospects and customers’ needs. It always pays off.
  • Not segmenting your prospects and customers. If you have your reps work on every type of prospect, they quickly default to spending most of their time on whatever type of lead they get the highest personal ROI from. Sometimes, that’s the whales. Sometimes, it’s the ones that instantly indicate intent. Almost always, SMBs suffer. They are a lot of work, and pay the least. So at least send the SMB leads to a rep just working those ones. She will close a lot more of them. A lot more.
  • Impossible quotas. You want at least half, ideally 60%-70% of your reps, hitting quota. Sales is hard enough as it is. If you have a terrible sales team, maybe that’s not possible. But you have to make sure good, well-trained reps can hit quota and be paid fairly. Anything less is demoralizing. And folks leave.
  • SDRs (and AEs) that blow the deal.  See the tweet above.  In our rush to qualify prospects and improve efficiency, we can push some of our most engaged prospects away.  SDRs are great, but they shouldn’t be adding friction to a potential deal.  Are they?  And an AE should be a prospect’s best ally in the discovery process.  If an AE is breaking up with too many prospects, that AE probably has too many leads.  Maybe move to more of a “lead poor” sales environment.  Or at least consider it.
  • Not following up in minutes to every inbound request.  Every sales study with data out there shows the faster you respond to an in-bound request, the higher your close rate.  Why can’t every prospect be called back in 1 minute, or at least 5?  Are you sure they can’t be?  Tomorrow just isn’t good enough.
  • Expected reps to do it all — prospecting, outbound, inbound. You can sometimes start here. But quickly after that, you want to specialize. You want reps doing what they are best at. SDRs just doing outreach. AEs just closing. Field reps just hunting bigger deals. If everyone does everything, no one will do anything particularly well. And they’ll get overwhelmed doing things they are less good at.
  • Not measuring actions per day. All reps think they are working hard. Even when they leave at 3:30 to go play tennis. Have an actions quota, too. Say 150 actions a day (calls, emails, etc.). You’ll be surprised how many reps don’t hit their actions quota at first. This works.
  • Not listening to reps’ calls. Please use a product like Chorus, Salesloft, Gong, etc. here. You have to make sure your reps are saying the right things. Especially if you aren’t training them well. You’ll be shocked with some of the things you learn here as you scale.
  • Churn-and-burn contracts. Signing deals you can’t fulfill, or exaggerating functionality to such an extent the customer will never deploy, is highly ROI negative. Yes, you hit the plan for the month or the quarter. But then the customer doesn’t renew, doesn’t say positive things, and tons of energy is wasted. Even if the sales rep gets their commission.  A bit more here: 5 Tips To Minimize “Churn and Burn” Behavior in Your Sales Team.
  • Hiring folks that can’t do competitive sales. If you hire reps from companies that dominate their market (80%+ market share), they usually lack the toolkit to compete with other vendors. They learn how to compete for budget, and for urgency. That’s sales too, and it’s hard. But then tend to just melt when there are other, ultra-competitive, strong vendors in the space. This is one of many reasons why “Big Company” reps usually fail at start-ups. It’s not just the lack of processes and infrastructure. It’s the lack of a toolkit to compete with 2–3 other peer vendors of the same size and brand equity.  A related post here:  5 “Sharp Elbow” Tactics That Do Work in Competitive Spaces.

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