How do you tell the best reps from the mediocre ones? In this week’s Workshop Wednesday, SaaStr Founder and CEO Jason Lemkin shares the 7 things the best sales reps get right and the 8 ways the rest make things worse.
#1: They listen to your problems and give you the best solution using their product.
The best sales reps solve your problems. Some spaces, like OpenAI, are on fire, so it’s order-taking to some extent. When you’re doing so well that you’re in order-taking mode, sales reps don’t have to solve a problem.
But for the rest of us, order takers won’t work today. The reason sales isn’t yucky or sleazy is because the best sales reps solve your problems. They ask you what’s going on, demo what you’re doing, and show you exactly why they can solve one of your top 10 problems.
The best sales reps don’t immediately go into discounting and pricing. To find the best on your team, listen to their calls, watch their Zooms, and see what they’re doing.
#2: They help you demo, pilot, or try the product.
The best reps help you get going. Jason spoke with a $20M ARR CEO with a pretty great PLG motion, but the sales side struggled. Why? None of those reps could demo the product, so they had to bring in engineers, solution architects, and founders.
The best ones don’t just talk about feature comparisons or discounts. They help you get started. Ninety-nine percent of products in business software have friction in deploying them, and ninety-nine percent of sales teams forget about this. Sales is just a moment in time. You need discovery, pilots, rollouts, deployments, and iterations for the next seven years.
Of course, it’s too much to expect sales to stick around for the next 7-10 years, but the best ones find a way to dramatically increase the odds that the demo, pilot, or trial goes well.
#3: They are fluent in and honest about the competition.
If your reps aren’t good at this, train them. The best ones are utterly fluent and honest about the competition. When you’re talking to a great sales rep, it’s not all about pricing. Arguably, pricing doesn’t matter much as long as it’s mostly transparent and generally fair.
But a very good rep in the competition will save you time and research, even if their information is biased. A mediocre rep may not know about the competition or struggle to find a tear sheet.
A great rep will say Datadog is one of the greatest products in the world for DevOps, and it does 98 things really well. But it’s gotten pretty big, so here are two things we do better than Datadog and how they will work in your business.
#4: They are honest about product gaps and weaknesses.
This is related to the last point. A great rep is honest about weaknesses. Recently, Jason got on a Zoom with a product we use, and it had a huge, fundamental bug that wasn’t fixed. Not only did the CRO argue whether it was a bug, but he said we had to pay $50,000 to fix it because it was a custom feature.
Maybe that’s a good sales tactic, but probably not. The best salespeople are honest about the product’s strengths and weaknesses and know how to backfill. They will let some deals go to the competition when you’re not ready, and the rest will struggle in a competitive landscape.
#5: They don’t play games with pricing.
This one isn’t crisply clear in 2024, but the best reps don’t create friction with pricing. You can play some games with pricing when you’re huge and at scale. But for anyone on the scaling journey, your job is to remove friction from the sales process.
The more friction you remove, the more deals that play. So, the best reps don’t play games with pricing. Once someone knows pricing is fair, it removes one objection. A mediocre rep spends all their time thinking about pricing and discounts.
But it doesn’t really matter if your app costs $5k, $5100, or $4200 a year. If a prospect chooses a low-end competitor, so be it. They can discover you out of the deal. If you’re reasonably priced, take out the drama.
#6: They are there for you after the deal.
This is one of the top ways to really differentiate the best reps from the rest. 99% of reps don’t care about you the minute the deal is signed. But the best reps somehow make you feel like they’re still there for you. Sometimes, it’s for the upsell or renewal, but you still feel like they care.
The best ones carry these relationships for years.
#7: They’ve done research on you before the first call.
We don’t see this enough these days. The best reps have done research before the first call. If you want to stand out in sales with a prospect, a renewal, or even finding a job, do 15 to 20 minutes of research before the call.
There are so many great tools out there, like Perplexity, ChatGPT, ZoomInfo, Apollo, or whatever. Do your research. How many employees do they have? Who is a similar company or competitor that is already a customer?
You can reach out to Vanta and say, “Hey, Drata has been a super happy customer for two years, and this is how they use Vanta.” They’re going to take that call.
You don’t need to know everything because there isn’t enough time, but the best reps do a little and make you feel like you’re a trusted vendor for them.
The Ways the Rest Make Things Worse
Let’s look at eight ways the not-great sales reps make things worse.
#1: They play endless games with pricing.
You have to root this out or move on from these folks. As founders, it may take a while to figure out that pricing is important, but not that important. It won’t be a huge issue if it’s priced fairly and in line with the competition. Taking a product no one wants to buy and discounting it 50% very rarely gets the deal done.
#2: Fake and pressure-filled urgency to buy now.
Mediocre reps use the obnoxious urgency-to-buy-now tactic. If people don’t renew for a multi-year contract today, you threaten them with a price increase next year. Getting this right is hard, and 90% of salespeople can’t create urgency. The same is true for founders.
The best way to create urgency is to add so much value during discovery, pilots, and discussions of the competition and feature sets that when a sales rep asks to get it done in July or December, the prospect is willing to say yes because of the value the rep brought.
#3: Lies about the competition.
The best reps are good at knowing the competitive landscape and how to spin it a bit. But to be good, you have to admit where the competitor is good to build trust. Weak reps lie and make stuff up about the competition because they’re lazy or don’t know the answer.
When you see this, pull them aside or get rid of them. It doesn’t work. Prospects can smell it when you lie. The best reps make the discovery process easier, and the worst make it harder.
#4: Not understanding your budget and situation.
The worst reps don’t understand your budget and situation. Too many folks are trying to force deals under stress, but it’s ok to ask if there is budget and what it is. If there isn’t budget, you have to realize you’re probably coming out of a small or experimentation budget.
You have to ask questions, listen, and play the long game. You might quote someone $3M a year because they’re a VP at a major company like Adobe. But if that VP only has a small discretionary budget, you’ve lost them. Even MongoDB takes three years to build up to a big deal.
#5: Too few check-ins.
This has been an issue forever and has only gotten worse. No one checks in to help anymore. They only check in to threaten you, tell you prices are increasing, or pay $50k to fix a bug. Even worse, customer success has been weaponized and turned into part of the sales team.
Customer success doesn’t even check in anymore because they all have opportunity commits. The best reps don’t ghost you. They may not do as much, but they’ll take some time for their top accounts to get you the help you need.
#6: Too many check-ins.
On the other side is the upsell world of weaponized customer success. A few do too many check-ins, but not to help. You don’t need a check-in every week for an upsell. So many folks are doing 10-step endless break-up email cadences. Three is enough. If someone opened your emails 28 times and didn’t respond, the 11,000th won’t help.
#7: The breakup email.
It’s a sign of weakness. It might have worked in 2015 or 2018, but not today. Why? Because today, it’s not all about you and pricing. Most founders know this next piece of wisdom, but so few sales folks do. You’re lucky if 10% of your prospects are in market at any given time.
Do you want to send a breakup email to someone who doesn’t have time and isn’t in market yet? No, you don’t. Ghost them if you have to, but don’t break the relationship. Good breakups can mark the deal as lost, but it also moves good deals to lost that aren’t lost.
#8: Playing games on renewals.
This has become the worst of all in SaaS. So many renewals are ripoffs, and price increases are laced with threats. It doesn’t work unless it works. So many folks are under stress. It’s hard to find new logos and deals, so more energy is going into monetizing the existing base.
Done right, it’s a gift. You can earn it by giving the customer more value. Otherwise, you risk running your company into the ground. So many startups are seeing net new logo growth slow to zero. All the energy needed to get new logos is offset by logo churn, so where do you go? Your base.
Make sure you’re going long. A weak rep who can’t close new deals and doesn’t know the product will pressure the base to the detriment of your business.
