Will Wissing is the Sales Lead at Pinwheel, where he’s been for the last couple of years. He started his career with an exterior painting company, but after a few years doing that, he transitioned to tech sales — at MRI Software, Blend (a VC-backed digital lending platform), and Pinwheel.
Here are his top ten principles for how to be awesome at sales. Two decades of reps and wisdom, distilled into a two-minute read. You’re welcome gang gang:
(1) 2% edge. Especially in a market where competing products are quite similar, a customer might choose to “buy” if you can get even a tiny (2%) edge. There are a number of ways you can generate this edge — running a strong discovery process, presenting well, being likable and trustworthy, etc.
(2) Curiosity. Will mentioned that he got really into investing in college, and reading companies’ annual reports. If he is going after an enterprise customer, he will read their annual reports to really understand their company priorities.
(3) Being methodical. “You have to be very process-oriented, and very organized. That’s where sales can often be somewhat boring, in a sense that the best sales people are very methodical in the things that they do over and over and over and over.”
Some of the processes that Will follows are to read the annual report of companies that he’s targeting, and then map out their organizational chart to understand the relevant stakeholders, and the mutual connections that he has to them.
And when he was an Account Executive, Will would be pretty “religious” about blocking time on his calendar for prospecting, doing a weekly sync with his SDR, diligently sending follow-ups, etc.
(4) Active listening. Actually listening to what someone is saying, rather than thinking in your head about the next thing you are going to say. Both to really deeply understand what the customer is saying. And also to pick up on body language and “reading the room”.
(5) Adding value. The trickiest part in sales can be navigating through mid-stage deals. Something Will has found useful in keeping momentum is to be super prescriptive in terms of what needs to happen next. Rather than saying something vague like “Hey, checking in…”, say something specific like “Hey, here’s a project plan we’ve put together to help you start thinking through xyz. Can we connect this week to walk through it live?”
(6) Be yourself. Previously, Will thought that in order to be good at sales, you had to be extroverted, loud, bombastic, pushy. But over time he’s come to realize that you don’t need to conform to that stereotype — you can succeed by just being authentic to who you are. When buyers have more and more information at their fingertips, their “trust” in you is increasingly important, and if a customer doesn’t believe you’re being authentic and geniune, it’s going to be very hard for them to trust you.
(7) Focus. “Sales is the type of thing of thing where you can easily get pulled in a million different directions. But when I talk to Account Executives now, I always tell them to focus as much as possible on the things that are going to help them hit their target”. And that’s true both from a quarterly / long-term perspective, and also on a daily basis.
(8) Say Do. The idea here is simple — just do what you say you will do. If you say “I will get you that pricing proposal by December 31st”, then make sure you hit that deadline. This is a very easy, but critically important, way to build trust with customers.
(9) Unemotional about No’s. Will meant two things by this. Firstly, that sales can be a brutal job. The majority of your day you’re being ghosted, or getting rejected, and hearing no far more often than not. And so you need to have a very thick skin, and an emotional resilience. But secondly, that through the rejections from customers you can start to understand what their objections are, and how your product / company needs to improve and evolve to win more deals in the future.
(10) Challenge early and often. This also aligns with the “be yourself” point above. Part of being yourself is that — if you disagree with something the customer is saying, tell them that! See yourself as a peer to the customer, rather than framing it as “I am the sales person, and you are the customer”.
Have any ideas for who I should interview next for Closing Time?
Or any feedback on how to improve the format of the episodes?
Feel free to email me at jonny@wefunder.com.
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