Sendspark Blog > Mastering Video Prospecting: Unlocking Six-Figure Deals in 5 Proven Steps.

Mastering Video Prospecting: Unlocking Six-Figure Deals in 5 Proven Steps.

Buyers today want a seller-free experience, but buyers who are assisted by sales spend more and have a lower chance for churn. Can video messages be the thing that gives buyers what they need and helps sellers hit quota? Let’s take a look!

“Seventy-five percent of B2B buyers say they prefer a rep-free sales experience, but self-service digital commerce purchases are significantly more likely to result in purchase regret.” - Gartner’s B2B Buying Report 2024

As a full-cycle rep I held a 1M USD annual quota on average and was selling five to mid-six figure deals. These were complex deals for two reasons. On one hand the product was highly technical. Secondly, between 10-20 people were involved in making the purchase decision. Imagine coordinating meetings with large buying committees with this many stakeholders in play.

I needed a way to get all the cards on the table, follow up with the right people at the right time, and enable my buyers during POCs and internal meetings I wasn’t invited to. I had little insight on what was happening outside of meeting with stakeholders. So much so that it often felt like I wasn’t in control of deals.

In the end I turned to video messages in hopes they’ll help me enable buyers and sell together with them.

In this post I’ll show you 5 ways I used videos throughout my sales cycles. Specifically how I used them to upsell an existing account of mine from 20k to 142K USD ARR.

How it all started

If you’ve been selling for a while you’ve probably had buyers ask you to send over pricing via email.

And every mentor you’ll have will tell you not to have pricing discussions over email.

Set a meeting instead.

That includes me, and yet in this case I broke my own rule and closed a 122k net new upsell deal a whole month before the fiscal year ended.

But this was the exception, not the rule - and it only worked because of the five points I’ll share with you in this post.

Each of them leveraging the power of video messages.

To understand why it worked, let’s go back all the way to how the opportunity started.

To make this post easier to read I’m going to refer to this account as “Shoppy” (not their real name).

Shoppy was an existing customer of ours that I’ve been working with for a year now.

During that time they’d agreed to roll out our platform to another team and double their annual spend from 10k to 20k USD.

At the end of that same year we introduced new plans with usage-based pricing.

These were priced much higher for power users such as Shoppy, but it also had clear benefits to them.

We just had to sell the value. 

Get complex ideas across visually

When you’re selling usage-based plans you’re going to have access to customer usage data. So even before reaching out to my contact at Shoppy I knew that this was going to be an 8-10x increase in spend for them.

What customer in their right mind would agree to an increase like that?

I needed to build a business case.

So knowing what their business priorities were I recorded a 3-minute video message using Sendspark.

My goal? Grab their attention by contrasting their current situation to what life could be like on the new plan.

Without any mention of price.

And that’s my most frequent use case for sending video messages.

To get complex ideas across visually.

Lead with a point of view and then validate if there’s a need for what you’re selling in the first place.

Pro tip: you can use this same approach when asking for an intro. Have a connection of yours forward your Letter on Behalf (LOB) to a prospect you’re trying to get a call with. Unlike emails, video messages help put a face to the name.

Start a conversation on social media

The video message landed me a disco call but my contact went cold right after hearing the estimated price increase.

I was feeling lost and with him being my only contact I didn’t know how I was going to get the opportunity back on track.

Should I go around him and contact the VP instead? Risky move and I wasn’t about to throw the trust I’ve built over the past year out the window.

But the challenge remained: my contact was a single point of failure and I needed to validate if others at Shoppy were open to the case I was trying to make.

My plan was to video prospect on LinkedIn. Have you tried sending short 1-2 minute video messages in DMs? They’re a great pattern interrupt and unlike when using links in emails you won’t land in the spam folder. I have a few other ways for starting conversations on social media in case you’re interested.

But then I got a lucky break!

A contact that I had worked with previously switched companies and landed a Sr position at Shoppy.

I congratulated him on the move calling out how happy I was we’d be working togehter. Then I kept in touch during his onboarding.

A month in I reached out again asking how his onboarding was going.

Turns out he was hired to speed up their processes and our new pricing plan fit in with that objective nicely. Having seen what our new plans can do at his past company I knew this opportunity was in good hands.

But does that mean this was a home run? Not even close. I needed to find a way to enable him. Short and punchy micro-demos do the trick here as long as you show the impact.

Pro tip: if you’re going to use video messages in emails, make sure your domain reputation is high and even then leave video messages to the 2nd or 3rd email so you don’t land in spam.

Putting all the cards on the table

We got the ball rolling again and I was ecstatic! My old contact was making good progress with the project and it was time to align the rest of the team. The goal was getting the org at Shoppy to back the change.

But while group meetings are great for bringing everyone on the same page they fall short when you’re trying to get all the cards on the table. See, no one likes looking bad in front of their peers so they’ll withhold unpopular opinions and information they feel they shouldn’t be giving out. All of these are silent deal killers.

So what I like to do after calls is send 1:1 emails to everyone who attended and get their take on the topic. Even better when sending a short video message. Not only do these make the message feel personal, there's an added benefit. You get notified when people click and watch your videos. This way you can find out which contacts are most engaged.

Pro tip: At this stage your goal should be identifying which influencers are supporters, whose voices you need to amplify, and which are detractors who you at the very least need to disarm.

Reduce time to value during POCs

Ever got ghosted as soon as a trial or POC started? I had my fair share of these too, and to prevent these I started building Mutual Action Plans (MAP) with my buyers.

The goal was to agree on the scope, rough price range, and who does what by when before we kicked off the POC. This way we knew that we as long as the product met requirements we had a good chance of closing the deal. This opp was no different and I asked my Coaches to loop in the Economic Buyer before kicking off the POC. The MAP was approved and we were ready to roll.

Shoppy’s POC was handled by my Sales Engineer because it was a six-figure deal, but what about smaller opps? The ones that won’t have the ROI to justify looping in an SE. For smaller customers I like using micro-demos for enablement instead of being hands on. Think 3-5 minute hands-on walkthroughs taking on a use case from start to finish. Then you link to these videos in the mutual action plan.

Pro tip: Instead of rerecording video demos every time, organize them into libraries and reuse for each POC you have. With Sendspark they have the ability to record one video and use it as a template, making it reusable again and again.

Get aligned async instead of waiting for the right time to meet

The POC was a success and we could finally calculate an accurate price. We measured the efficiency gains, what impact it would have on Shoppy, and contrasted it with the cost of inaction. I was excited to get the business case in front of my champion. But setting a meeting with him would have taken two weeks and December was rolling up quick.

You know how time kills deals, right? Me too! So I decided to take a risk and present the business case async in a video message - slides attached. You already know how this went, but why did it work?

It did the trick because:

  1. All user buyers were a fan of the solution by this time
  2. We had a clear business impact.
  3. We agreed with the executive buyer on scope and price before engaging in the proof of concept (and the final price was in the right ballpark)

Pro tip: Keep the executive buyer in the loop throughout the opportunity lifecycle. A simple update without input needed from them goes a long way. Executives appreciate being in the know and updates like these are a great way to turn them into champions. That also played a role in closing this deal successfully.

About the Author

Viktor has 10 years of full-cycle experience in tech sales. His latest contribution was helping Bitrise scale from 3M to 20M USD in revenue. For more enterprise sales tips and tricks, follow Viktor on LinkedIn.

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