The Future of Sales Development [Webinar Recap + Recording]

future of sales development

The last few months of 2020 have shown us firsthand the true meaning of disruption. Across industries, especially for B2B sales organizations, leaders and teams have gone to great lengths to survive. The future of sales development and prospecting is an important topic for sales teams right now in order to understand how to best move forward and build their outbound and go-to-market strategies.

At Skaled, we’ve been hearing lots of discussion around things like modern outbound, the back-to-market process, and the right messaging and strategy. 

Related Content: Building Your Back-to-Market Strategy

Our CEO, Jake Dunlap, and Outreach VP of Sales, East, David Rubinstein, made time this week for a candid Ask Me Anything (AMA) about the current sales climate and what we can expect beyond 2020. Over 100 people sent questions in advance of the AMA, with many more coming in live during the webinar. 

The conversation was a healthy mix of high level and tactical details that reps to leaders would find useful. Below you’ll find the full recording of the webinar and a recap of the most informative answers provided to the industry’s most pressing questions.


Q: What are the critical trends for sales development going forward?

This first question on the future of sales development is by far the most common among B2B sales reps. With so much upheaval in the global economy, even a basic idea of how things will unfold over the rest of 2020 and 2021 is considerably useful. David was more than happy to give his take.

“Sales is competing with a lot of noise right now. Everyone is hosting a webinar. It becomes that much more challenging to figure out how to get someone’s attention, how to get out of the fray, and use other channels.”

Even so, David also made the point that there is still excitement from sales development leaders, noting that much of the world is now coming directly to the SDR. That sales engagement is an opportunity for enterprise sales to step up with technology. This widespread adoption of sales tech by sales organizations of every caliber will be a key trend to watch.

Jake added that while many sales reps think that automation is not for them, the pandemic has upended person to person sales, and salespeople will have to adapt. Too many people don’t look at automation as workflow management. But no one can nurture every single connection they make during the sales process.

“Automation is with the people you’re not talking to… You automate remembering.”

Pro tip: With sales engagement and automation, it’s not about knowing how many respond to your messaging, but also what the sentiment is in the response.


Q: What are the next major changes in the sales process?

Being able to anticipate further disruptions and manage the ensuing risks is something every sales team strives to do.

The short answer is selling remotely.

David put a spotlight on the change in hiring. Sales teams have been so used to hiring people to come into the office, but the world has got a lot bigger, and remote work has become more acceptable and prominent. Jake added that the way you interact with customers is now digital as well and is forcing executives to be comfortable building rapport without meeting face to face and rely on technology to make more deals. 

David and Jake agree these changes have and will continue to humanize prospecting. Sales leaders will have to become more comfortable being real with people on Zoom calls, and in essence, inviting prospects into people’s homes. Authenticity in those conversations will be key and have to take place much earlier in the sales cycle.


Q: How do you accelerate a sale?

This question on the future of sales development spawned perhaps the most important advice in the entire AMA, courtesy of David Rubinstein. (They are so key, that we encourage everyone reading this to take it down in your notes.) He provided four questions that he and his sales team asks on every deal. And they are:

  1. What problems are we solving?
  2. Why is that a problem now?
  3. Who is looking to you to solve the problem?
  4. When are they expecting it to be solved by? 

Right now, most prospects’ response to the last question is ASAP, but it’s critical to ask more questions and dig deeper in your conversation to come to a more realistic date and deadline. Never assume an answer. You can always get more information.

If you answer the four questions with your prospect, you can build a plan with your customers. More important, you’ll have a real opportunity, and your win rate will be higher in these challenging times. You’ll also spend less time on the prospects in the “Maybe” category.

Jake agreed and pointed out another nuance in the sales process he has noticed, but one that cannot continue if sales leaders are to succeed in the current business climate. That is, not researching to understand your prospect well enough before meeting with them.

“Always know how your prospect makes money. If you don’t understand how a company makes money, then you can’t understand the nuances of the business.” 

Consequently, you can’t make a customized message. And as a result, most sales leaders and reps, according to Jake, don’t know their ideal customer profile (ICPs ). His immediate advice is to know your buyers’ industries more than ever and how they are being affected.


Q: How is your team using LinkedIn in your sales sequence?

It wouldn’t be a conversation on modern sales if the importance of LinkedIn didn’t come up in a Skaled discussion. 

Jake explained how and why our team at Skaled starts a lot of sequences with LinkedIn. “We have to build some amount of relationship capital as opposed to going straight into emails and calls,” he said. He also noted that Outreach is very useful in this process

David followed up with a quick strategy on using the sales engagement platform in conjunction with LinkedIn. 

First, build out a list of current customers, import that list into Sales Nav, and look for people who came from your current customer list and used your product. This search will give you a list of potential customers who are already familiar with your product.

Jake was so impressed with this strategy, he summarized it:

“All you do is upload your customers and do a search by previous company equals in your search. And then you just look. You’ve got a hundred target accounts.”

This wasn’t mentioned in the webinar, but you can also automate most of these LinkedIn Sales Navigator tasks within the Outreach platform if you have it!

Related Content: Using LinkedIn Touchpoints to Increase Sales Performance

Using LinkedIn as an Additional Touchpoint X5


Some of our favorite snippets of advice

Jake and David covered a ton of topics in the AMA on the future of sales development, so if you haven’t watched the recording yet – grab a pen and do so because we only covered the gist.

A few insightful words from our speakers that we’ll leave you with:

David: In sales, you either have momentum or you’re chasing.

Jake: Small, unique touches are a great way to stand out. Direct mail is also an underutilized channel. The Sendoso sending platform helps with those unique touches.

David: Make it a conversation, not an interrogation. 

Jake: Circle executives and their content when building your LinkedIn strategy. 


Submit your own questions

There were even more questions that were submitted for this AMA that Jake and David couldn’t answer during the webinar. The good news is Skaled is always available to answer your questions on all things sales and LinkedIn. 

Have one in mind right now? Don’t hesitate to contact us!

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