Things I'm learning about in sales

26 August 2019
5 mins

(This is an archived copy of a post originally published at

As I’m diving deeper into my role at Hack Club Bank, I’m trying to learn more about sales and working with customers, and I’m also learning a lot every week about leading a B2B product. This is a place for me to collect the things I’m learning in the process. I’m going to keep this up to date over time, and I thought it would be nice to make it publicly available, in case you might find it useful as well.

With that, here’s what I’ve learned, from most to least recent.

The customer should really believe that I, as the salesperson, can close my eyes and step into the shoes of the customer and feel their challenges and wins. A huge part of an enthusiastic yes is the customer’s trust in the company and the salesperson, and that trust can’t exist unless the customer really believes that the seller can empathize with them as a person.

More tactically, in a sales conversation, anchor the conversation early around expectations and price point, and make sure that you, as the seller, is leading the conversation. One good way to do this is to learn about the customer in the conversation and ask lots of question, to lead the conversation rather than follow where the customer leads. Especially early on in the conversation, anchor the conversation to the main points you want to drive home.

Talk at the upper edge of the Overton Window of sales, but also make sure that the customer always feels like they’re in control of their decisions. If they feel as if they’re being led on by the salesperson or if they have no choice but to say yes, it won’t be an enthusiastic buy-in. Even if this means that the customer has to say no to some things, give them that freedom, so they feel great about the yes-decisions they do make.

Selling to a team requires more than selling the decision maker. In a consumer business, there’s usually a few people involved in a purchase. In selling to organizations or teams, it’s important that sales become a more continuous, collaborative process. We want to find people who have authority within and over the team who may be feeling the biggest pain points, and help them become strong internal advocates of what we’re selling. Help them build a strong case internally for why they should buy or adopt something new. And as the argument internally becomes strong, it becomes easier to convince the decision makers and buyers. As a corollary, we also need to understand how the organization or team works internally to sell well. Who are they people who have voice and/or authority within the team, and how do decisions get made? How do they measure success?

Use previous customers’ case studies to help potential new customers find their product fit/value. Testimonials serve to build trust with new customers that the product they’re buying into is going to solve their problems, but I can build an even more powerful case by talking about how previous, similar customers have faced similar challenges, and how a product I’m building helped them overcome those challenges. And as we sell and get more customers, we can start to accrue a larger and larger body of customer stories, that we can then build on to make the story of the product itself much more convincing.

Understand how each team is different, organizationally and in internal goals. Each team might be structured differently, and each organization cares about a different set of priorities. If two teams are different in this way, trying to pitch the same value propositions to the same people won’t work.

Sales is a continuous, ongoing process, even after the transaction. This is especially true for subscription-based products like Hack Club Bank. Sales works better when we view it as a continuous process. It’s not over when the transaction takes place; every interaction the customer has with the product, with us, with the company, and with other customers is an opportunity to provide more value or convince them that they paid too much.

Build habits, not just value. The easiest way to growth in a product with market fit is to raise retention, and a great way to raise retention is to build product in ways that build habits in their users. If a product makes something easy to do, it’s sticky, but if it becomes a part of a daily or weekly routine, or if it becomes a part of an established, internal process, it becomes much harder to switch away.

It’s not enough to build a case for value; selling requires building a case for urgency. This is as true for selling products as it is for selling equity in startups (pitching), and the best pitches for companies and products alike don’t just build convincing cases for why a product offers great value, but why the moment is now. Usually, this is some combination of saving more money, cutting more losses, or timing.

Selling a product is really selling a combination of two things: the value provided by what the product is today, and dream afforded by what it could help them become. Each organization or team weighs these two things differently – younger organizations or fast-growing ones will bias towards future potential, while established, larger teams bias towards present value. It’s important to understand where a group stands in this spectrum, and build a case for the product that incorporates both present value and future potential.

Thank you, Hello Hack Club

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