The average sales email uses “I” a bit much.

As in, I’d love to get time on your calendar. I’d like to chat. I was wondering. It’s like getting a terse “sup” from a stranger on a dating app. Prospects deserve better. Don’t you think?

Here at Vidyard, we’re always seeking the most creative and compelling ways sales reps can bond with prospects using video so we assembled a superteam of sales and marketing experts for our Videoify My Pitch program.

These experts took real email templates and phone scripts submitted by real sales reps and showed how they could be transformed into engaging video pitches.

The Videoify My Pitch Panel:

Marilyn Cox, VP of Marketing at Cubeessential HoldingsMatt Heinz, President of Heinz MarketingMorgan Gillespie, Account Executive at FullstoryTyler Lessard, VP of Marketing at Vidyard

The panel of experts helped Videoify My Pitch webinar contestant Jacki Leahy, Director of Business Development at LinkSquares, generate a ton of creative ideas for breaking through to a notoriously difficult audience: legal professionals.

THE SITUATION: Selling to Proud Prospects

LinkSquares sells AI-powered contract document management solutions to general counsels and CFOs, who aren’t always the easiest to work with. Or patient. Or forgiving.

In Jacki’s words, “They’re like a proud lion with a thorn in their paw,” and it takes a lot to earn their respect and attention.

The team of sales video experts agreed that there are two factors at play for Jacki when she’s working to earn her prospects’ confidence: who her prospects are and who she is.

Good creative outreach is about playing up characteristics that are true to Jacki because she can’t be expected to keep up an act. Your first video is a preview of working with you. Whatever you start, you must finish.

Who are LinkSquares’ prospects?

LinkSquares prospects are general counsels and CFOs. They’re dominant, risk averse, knowledgeable, and prize their time.

What are their pain points?

Searching for contracts. So many contracts. They often work late looking for files and miss out on valuable time with family or activities they love. Whenever a regulation changes, they manually scour contracts to find clauses that require updating.

What makes the sales rep special?

Jacki is a real character. She loves to help others, runs distance, says yes to improv, and takes her volunteering as seriously as her work. In her words, “Selling like a boss.”

What is she selling?

LinkSquares provides an AI-powered cloud storage and tagging system that relieves people’s contract pains, if only Jacki can break through.

THE ADVICE: Be Human and Use Humor to Stand Out

It’d be easy for Jacki to emulate the reserved style of her prospects, but if Jacki’s going to be noticed, she has to interrupt their pattern. Where other sales reps zig, she needs to zag.

“Buildings don’t write checks, but people do,” says Matt. “Even general counsels have a sense of humor and are interested in seeing interesting things.”

A keen understanding of your audience’s habits, needs, pains, and pet peeves can give you plenty to work with when creating videos. And knowing who you are and how you can relate to them makes for interesting, story-driven videos that create a real connection.

The team came up with eight different video pitch ideas—complete with mockup videos—for Jacki. These are three of their favorites, with Tyler playing the role of Jacki.

Option No. 1: Frame it as a Story

One way salespeople can generate a human connection is by framing their prospect’s pain as an archetypal story, made up of heroes, villains, and a status quo that gets flipped.

In Jacki’s case, the hero is the prospect, valiantly hacking away at an unending backlog of administrative work with their trusty sidearm—the Control and F keys. The villain is the process—rolling hills of paperwork, files, and documents. When the government changes a regulation and the process threatens to keep the hero from their family or beloved volunteer time, what are they to do?

Option No. 2: Prop it Up

Another approach is to employ props. Get meta, says Tyler. Gather props from around the office to assemble a visual analogy like an idea the team had around nappuccinos—a theory that downing a coffee before a short nap boosts your creative energy—and the fact that Jacki’s prospects don’t have time for that sort of luxury.

Option No. 3: Punch the Shark in the Nose

Bluntness also sells. “What do you do when a shark swims up to you?” asks Morgan. “You punch it in the nose.” Try videos that get right to the point, which is something Jacki’s prospects, with the premium they place on time, are guaranteed to appreciate.

Want more inspiration? Watch all eight videos the team generated for Jacki. As you can see, the production value needn’t be unattainably high. All you need is you on camera talking about things your prospects care about—instead of just saying “sup.”

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