What I learned as a CMO doing sales

Earlier this year, as the pandemic was heating up and lots of startups were facing lots of change and uncertainty, I found myself in foreign territory.

With ~20 years of marketing behind me, I was suddenly doing sales.

And being on the other side of the marketing-sales divide definitely taught me a few things.

My partner in this adventure was also not a salesperson. And by the end of the summer, things had gone so well, we were joking about writing a book: Dismantling the Sales Team: How two non-sales people had the best year ever. We still might. (Subtitle is a work in progress. But, world, that title is taken.)

I now encourage companies of all stripes to try hiring not salespeople to do sales. At least, if your market is similarly purpose-driven. Here’s why it’s different, and why it worked so well for us.

Just talk to people. It’s not that hard.

We quickly noticed how relieved people were that we weren’t selling to them. We talked to them. Like people. We didn’t follow a traditional sales playbook. (We’re still very non-salesy even though we constructed a playbook as we went. It’s why we were able to add a sales manager recently and keep scaling our successful approach.)

We kept our focus on who we were talking to. We connected as people. We’d introduce ourselves…like we actually wanted to get to know each other and were happy to be there. For instance, I’d often be real about the challenges of pandemic parenting, and note that an 11-year-old might be heard yelling for me or a six-year-old might wander in (and on one call, she stayed a while, seated on screen behind me in my comfy chair…good thing we’re talking to educators).

We’d ask what brought them to the call today, suggest a few things we thought made the most sense, and made sure to ask if that sounded like a good use of their time.

So, it felt more about connecting and learning from each other than closing a deal or pushing for a commitment on the next step…though we almost always ended with one.

When you believe in what you’re selling, people don’t feel like you’re selling them.

People trusted us because we trusted ourselves. We’d seen firsthand what a difference our products and services made. For real, not because we’re trying to manufacture stats or force a story to close a deal. We understood our customers well enough to be able to talk empathetically about how incredibly hard their jobs had become in the pandemic, and knew that what we were selling was even more important in this crazy challenging moment.

That came across in every conversation we had. In how excited we’d get when they asked a question as though we’d scripted it, because it was the perfect next feature to show them or strategic benefit to explore, it showed they totally got why we were doing this work the way we were doing it; that they were our people. (More on that below)

When you’re clear about who it’s for and who it isn’t for, things get way easier.

My focus from day one at this company was on aligning the whole team around a compelling (and true!) brand story, our good-fit customers, and who’s not a fit. We’ve focused in on who they are, what matters to them, when they’re ready for us, and when it’s not quite time for them to get started with us.

This is where I should at that my sales co-pilot is a leading subject matter expert. He wasn’t a sales expert who’d learned enough about the product and people to close a deal. He’s a trusted expert who was learning how to fold his expertise into a non-sales sales process.

So, we deeply understood who we were talking to, what their priorities were, and not only that what we had to offer fit in, but how and why it fit. We could talk about it in a language they understood.

And, when we were talking to someone we knew this wasn’t right for right now, we could say that. It happened very rarely, but people were always appreciative. Being consultative and without hesitation, we’d explain what we’re seeing, what next steps we’d advise, and when we think they should come back to us. (Our sales playbook actually opens with this line: “Our approach can best be described as selling without selling; sometimes known as a consultative sale.”)

When you’re transparent about pricing and process, it’s not that hard to keep the process moving.

When you readily show people, in a clear format, exactly what your prices are and explain why they work this way, people trust you. And they trust themselves. That keeps the process moving.

If you’re still on the fence about being transparent about your own pricing, here’s why I’d urge you to give this a try.

First off, you don’t have to put up a pricing page on your website tomorrow. You can start with something gated, or something people have to ask for. We started by presenting our pricing structure on sales calls, and as a trackable HubSpot sales document so we always knew who accessed it, when.

But more important than the tactics is the purpose. When you have a polished presentation of your pricing structure, people know you have a structure, which builds trust and adds to your perceived value.

You move towards a decision faster because you’re basically skipping the RFP stage. You’re empowering people to choose from set options instead of negotiating from scratch whatever options they imagine might make sense, which they can’t do because they’re new to you. And, you’re giving your champion something clear and simple to share with decision-makers, which is invaluable in the b2b sale, regardless of complexity. If your champion loses momentum because it wasn’t easy to get the right people on board quickly, you’re starting over from zero with them.

Doing sales gets easier with every conversation.

You get better with every conversation. I didn’t record any of my calls. (I know, I wish I had, too.) But I’m sure I improved with every conversation. At the beginning, I was surprised at how not smooth I was, especially giving people a good guided tour of our platform. By the end, I could blow through the key points quickly and have in-depth conversations that built connections. I was prepared for the questions most people asked, I walked people through our pricing structure with confidence that gave them confidence.

The best way to learn your own product is to sell it yourself.

Pointing back to that bit about getting better with every conversation, including the guided tours…I’d been marketing this platform for more than a year before I jumped in to directly selling it. I knew it backwards and forwards. But writing about it is different than talking about it, and is certainly different than talking about it while using it. I understand the product so much better now that I’ve been in that hot seat.

Sales works when the whole lifecycle works.

I so wanted to find a non-jargony way to say this. But it’s what it is. Sales works when every stage of the lifecycle works, and works together.

Sales works when you connect marketing to sales to onboarding; you connect what attracted them to what will engage them to what will convert them to what will delight them and keep it going.

By stepping out of marketing and into sales, I was continuing a unified process with each person. We’re a lean startup, so the people I was talking to were literally were hearing the same voice from marketing first-touch to that first call together. Even once you’ve scaled up, you can learn from this.

Part of what makes sales feel salesly is that almost imperceptible shift that people feel when they go from connecting with your company’s marketing voice to your sales voice. There are ways to make it all feel the same. From your brand story to your good-fit customer profiles, you can help make sure everyone is using the same voice (are you inspirational or doom and gloom? buttoned-down corporate or casually conversational?); that everyone understands the people they’re talking to in the same way; that everyone knows how to talk about your products and services in terms of what matters to the people you’re talking to.

And then, sales can still fall down if those wins turn into churns. So the continuity can’t stop at marketing -> sales. The same voice, promises, profile of who it’s for, and more, has to continue through the launch and continued customer experience.

All of this together is largely what led us to thinking about the evolution of my role from CMO to CXO.

I’d been customer-centric since day one when I relaunched the brand. Now that I had this first-hand knowledge of the sales process, it made sense to have my focus expand out to ensuring that the same premium experience we’d built from marketing first-touch to sales hand-off would be threaded through the sales experience, customer launch, ongoing success support, and the very product itself.

I’ll write soon on the story of that evolution, and what I’ve learned so far.