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We were lucky to get a chance to chat with Meredith Doty, an Account Executive at Contentful.  Meredith began her SaaS Sales journey at ​​LogMeIn and has been selling SaaS products for over 7 years. For those who don’t already know about Contentful, it’s one of most popular headless CMS and was recently valued at over $3 billion.

What types of leads do you work at Contentful?

Majority of our opportunities are inbound leads and hand-raisers. All of them have varying levels of product usage.

The tricky part is that product usage is all over the gamut. So it’s our job as salespeople to understand from the get-go where the customer is in their product adoption journey. Their familiarity with the product very much influences how long the sales cycle will still be.

How does product usage affect the sales cycle?

People who’ve tried the product are going to move much quicker. They already have a high level of education and understanding of the product. At that point, all that hard work is done for me.

In cold outreach, I have to pitch the concept of headless CMS versus a traditional CMS. That’s a new concept for many still. Then we figure out how to work with developers to build out the stack and manage the implementation timeline. We have to develop the whole conversation. There's a huge time cost that comes with that.

What do conversations with product qualified leads look like?

Rather than a hard sell, it’s more teasing out how far we can take this opportunity. There's a lot you can learn by asking about the different projects within the organization. That helps you uncover a couple more use cases.

Depending on how large the business is, I also ask for introductions among the organization to meet different teams and see what's on their mind and any projects on their roadmap that could be a fit for our product.

From there, we talk through what ROI they can expect by using Contentful and a Jamstack architecture, plus what’s in it for the people working on the projects–whether it be from the builder's side or the content creator side. Ultimately, the more projects an organization rolls Contentful out to, the stickier it will be to the client.

Your sales are going to exponentially grow if you take that time to dig a little deeper.

Do you focus on product usage before signing contracts?

It's definitely a land and expand play. That's my MO here. Because once you kind of get people going and prove it out, the sales friction dramatically decreases.

First they get their systems developed and up and running. Then from a sales perspective, teams start talking internally and the legal process is already done. So all you have to do is send over an order form when they’re ready to buy.

So if customers can build on their own, what’s the role of Sales?

There are two key roles.

First, we need to give them ideas of what other companies have done, and what the other use cases are. They could just be thinking in one way, but another company is using it in a completely different way that they would have never thought of.

A big part of my job is to educate them on the possibilities. It's helping to build the vision together and letting them dream a little bigger.

Second, expansion deals require building relationships from the very beginning. It starts from that initial call. The relationships you establish from education and rapport are the key to spiderwebbing through an organization. Sales has the unique ability to discover and solve for pain points throughout an organization and it would be doing everyone a disservice to not have that human connection.

What’s the toughest part about moving an account from a self-serve plan to an Enterprise plan?

It typically is a pretty big jump from the credit card plan to the invoice plan. With the Enterprise tier, you have to be more strategic. That’s why customers buy through the sales rep.

What I'm finding is the buyer of the credit card plan is not usually going to be the buyer of the enterprise plan. So you've got to be able to spider web through the organization and do some digging to uncover a larger use case. Just upselling them for the project that they need the credit card plan for is not the play.