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Women in Enterprise Sales Forum: 3 Technical Sales Myths Dispelled

We’re excited to see our #womenterprise community continue to grow! This month, we held our Women in Enterprise Sales Forum alongside our NYC neighbor Datadog, and focused on the complexities of selling a technical enterprise product.

Our panel of women got into the nitty gritty tactics on how to not only break into technical sales, but thrive in the role, and included sales leaders: Kelsey Kraft, Enterprise Account Executive at Datadog, Sheila Moghadam, Enterprise Account Executive at FireHydrant, and Brianna Kelley, Sales Director at Snyk.

If there was one sentiment to takeaway from the event:

“Don’t be afraid to step outside your comfort zone. It’s easy to get comfortable in a repeatable process, but don’t be afraid to challenge the people you’re working with, ask those hard questions, and really push people. It’s a hard skill to build, particularly as a woman in a very male dominated conversation, but it’s important to do.”

— Brianna Kelley, Snyk

The panel also dispelled common myths about the world of technical sales. See a full recording of the panel here and the 3 top myths below:

Myth: You need a technical background.

Truth: You don’t need a technical background at all. In fact, our panelists come from a wide spectrum of backgrounds. Sheila has extensive engineering training, while Brianna’s role at Snyk is her first stint in the technical world.

There’s a learning curve with any role, and technical sales is no different. Brianna admitted it took her a few months to get up to speed on Snyk’s product and true value proposition, and her biggest breakthrough was when she was connected to a Sales Engineer and given the opportunity to ask questions. As the sales teams’ technical counterpart, Sales Engineers should take on most of the technical aspects of a sale — it’s much more in their wheelhouse and it’s their responsibility to form that technical credibility with customers.

What’s more important than a technical background, is to have a solid foundation of sales skills on your resume. These skills translate no matter what products (technical or not) you’re selling, and will go a long way in successfully closing deals.

It’s also deeply important to know how to storytell. Technical sales leaders should sell to the value, not necessarily the features of the product. To do this, you’ll need to first dig into the customer pain point and top challenges. Then, make sure you can answer exactly how your product solves this pain point and the larger “so what?” question.

“I love storytelling. It’s such a powerful way to explain what your product does. One of the methods I like to use, which is similar to traditional objection handling and the “feel, felt, found approach,” is being able to share how other customers have leveraged our product and used our product to solve challenges. People buy based on emotion and the ability to relate. So striking those chords is extremely important.”

— Sheila Moghadam, FireHydrant

Myth: Bottoms up closes all of your sales for you.

Truth: Bottoms up sales can be an important way into companies, but it’s still critical to have a sales team expand those opportunities. These days, it’s easier than ever for developer-focused tools to offer a free or credit card-enabled trial on their website and then let “land and expand” take over. However, it’s rarely that easy of a process as the full-picture sales motion is much more complex:

“It’s definitely a case by case basis, but the developer is at the heart of technology these days…So as long as you can get in somehow, someway, that’s usually a successful first step then you can go from there.”

— Kelsey Kraft, Datadog

Kelsey expanded that the real success for Datadog is a dual sales motion: Building champions from the ground up, while also tackling leaders within these large enterprises.

Similar to Datadog, most sophisticated enterprise companies use a split bottoms up and top down approach these days. The panel elaborated that bottoms up allows you to get into the organization and get a master service agreement (MSA) established, which then opens the doors to have a sales hunting license within the organization. This model can be highly effective because it allows you to leverage internal resources and have customers selling additional products within their own organization (to higher up management or other business units) on your behalf. However, our panel was clear that sales leaders need to be on the other end of that bottoms up approach to chase and close those larger deals.

Myth: Customers aren’t human.

Truth: Customer relations require a lot of personal elements and some professional stalking. They often say that the key to success in enterprise sales is being able to build an authentic relationship with your customers and our panel doubled down on the importance here. Each of our panelists had their own unique way of foraging connections:

  • Brianna prefers a texting relationship. While this can be awkward at first (and maybe feel a little intrusive), it allows you to become part of the prospect’s day-to-day life vs. just another voicemail or face in a Zoom box.
  • For customers already engaged in a POC, Kelsey sets up a joint Slack channel. It’s a fantastic way to connect everyone involved in the POC process and allow for instant communication.
  • In initial outbound emails, Sheila likes to offer whiteboarding sessions vs. asking for the prospect to watch a demo. She feels this is a great way to learn about their business and current processes without scaring them off with an overly salesy tone.
  • Sheila also mentioned she likes to make deposits to her prospects, meaning she’ll reach out with information helpful to them (ie. relevant webinars, white papers, news, etc.) without asking them for anything in return.

However, in any approach, it’s critical to personalize the message and reach the person on a human level. During your research phase, make sure not to just look at the prospects company and professional work, but what motivates them as a person: Do they have pets? Do they live somewhere unique? Do they have a hobby? And upon meeting them, dive into some personal questions about their career: Do they like what they do? Who do they like to work with at the company? What’s life at the company like? Etc.

BONUS Truth: Zoom fatigue is real and worse than ever.

Our panel had some creative ways to connect with prospects while trying to work around the overused and dreaded Zoom meeting:

  • Hold 1:1 virtual coffee / lunch meetings where the conversation focuses on personal questions rather than sales talk. Add an extra touch by sending them a gift card to order food or a drink for the meeting (this also makes it less likely they’ll cancel or reschedule).
  • Host virtual whiskey or beer tasting happy hours. The Work-Bench team has also explored this idea and so far, our favorite has been hosted by Aberlour.
  • Have people turn off their Zoom camera and use audio only. This takes us back to the heart of phone calls and makes the conversation a little less awkward and forced.

If you don’t already, sign up for our #Womenterprise newsletter to stay informed on upcoming Women in Enterprise Sales events. Also sign up for our Enterprise Weekly Newsletter (below) for all Work-Bench community events. We hope to see you at the next one!



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Kira Colburn

Kira Colburn

Head of Content at Work-Bench, leading the firm’s content vision, strategy, and production!