Selling Smarter

Recap of Selling Smarter Fireside Chat with Craig Jordan of SaaScend

Recap of the Selling Smarter Fireside Chat on issues impacting sales leaders, sales optimization, and revenue operations. Read more.

Last week, we held our inaugural Selling Smarter Fireside Chat. During these 30 minute chats, our CEO and Co-founder, Jinal Jhaveri, speaks with industry experts on the pressing issues impacting sales leaders, sales optimization, and revenue operations. 

Our first guest was Craig Jordan, CEO and Founder of SaaScend. His company helps GTM organizations grow and scale their businesses.

Watch the Selling Smarter replay:

  • 00:00 - 3:30 - Introductions
  • 03:30 - What are the key challenges for sales leaders
  • 06:53 - What techniques are there for coaching sales?
  • 10:10 - What tips do you have regarding the manual tasks for sales reps?
  • 15:30 - Where should sales leaders invest to help with sales qualification and processes?
  • 24:30 - Final tip for sales leaders?
  • 27:44 - What is an upcoming trend that sales leaders should watch out for?
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Key Challenges for Sales Leaders and Organizations Today

To kick off the chat, Jinal mentioned that Craig works with many sales leaders and revenue operations teams. Based on Craig’s conversations, Jinal inquired what sales leaders were most concerned about. 

While many companies are experiencing the impact of macroeconomics on the progress of deals in the pipeline, not all companies are experiencing it in the same way. With that said, the common themes he’s hearing are related to:

  • Tech stack bloat
  • Lack of sales process
  • Lack of foundation
  • No data to report on
  • Ability to coach teams
  • How to do more with less. 

As Craig elaborated, “We're seeing a lot of consolidation in terms of tech stack and process and structure. So that way, it's like we know where we're going, and we know why we're going there, and we have a certain degree of predictability to be able to hit that with confidence.”

What Techniques are There for Coaching Staff?

After setting the stage, Jinal double clicked into the coaching techniques that sales leaders should consider. 

Craig highlighted that a lot of sellers are moving toward consultative selling and relationship building. This means transitioning from feature / functionality selling to value selling. Sales organizations are using an account-based approach, as well as the changing role of SDRs being outsourced or reporting under marketing. 

Rather, he would focus on how to up-level AEs to close more and accelerate the sales cycle.

“How can I up, level my aes to close more and have a faster velocity of a sales cycle that has more end state output. As long as you have a good deal flow.”

How to Drive Sales Behavior Change for Data Completeness and Accuracy

While data and analytics are needed by sales leaders and revenue ops to forecast revenue, Craig mentioned that manual updates are a blocker for most organizations. 

While Craig admitted he, himself, doesn’t enjoy inputting data, it’s a necessary evil. What many leaders tend to do is over engineer the process. Rather, he urged sales leaders to work collaboratively with AEs and users on understanding how the data will be used. 

His two tips for driving sales behavior is:

  • Align sales to the vision
  • Provide incentives - both positive and “shame” focused
  • Incorporate feedback loops to highlight negative behaviors
“Align people to that greater vision of the importance of this is going to allow me to help you win more business. Because I'm gonna be able to see things within the system that it enables me to coach you better. That way, we can kind of get ahead of it before we kind of get to a split in the road, and we don't know which direction to drive. And two. Commission is a pretty easy incentive.”

Craig further added that “the wall of shame” is another way to approach incentives. Since sales reps are competitive, they dislike seeing themselves fall behind or their name in “red”. This “public” shame may also drive change quickly within the organization. 

With that said, Craig stated that sales is spending upwards of 30% of their time inputting data. Beyond behavior change, he urged leaders to find tools to help optimize sales. Tools like Enable Us (thanks for the mention!), Scratchpad, and Dooly.

Doing More With Less - How to Focus on Deals that Will Close

Operationally minded sales leaders may lean toward data. While that is important, Craig urged a combination of art and science. 

From his perspective, it’s providing reps the opportunity to leverage their “gut feeling” to dig into the underlying factors of what’s happening with a deal. Sales leaders can then coach reps on these “positive or negative signals” based on data and how to communicate this accordingly. 

When looking at the science component, there is a lot happening in the sales intelligence and conversational AI spaces. These technologies can help sales and operational leaders to better identify “lead zombies” and better evaluate historical data to support sales. 

These technologies, along with sales “gut feeling” can help optimize how and where sales can focus their energies. Moreover, this can help sales leaders understand how to guide and coach their reps for smarter selling. 

Continuing the conversation on the “science of sales,” Jinal highlighted how Enable Us’ digital sales room helps shine a light on the “deal status” black box for the upcoming quarter. For example, instead of wondering if the CFO has viewed the document, a digital sales room provides insights on who, when, and how long the buyer has interacted with the room. This helps the sales teams better forecast the likelihood of a deal closing based on engagement. 

Final Tips for Sales Leaders

Like a professional sports team, each sales rep has their different strengths. There are two areas to consider. 

First, as a leader, provide “personal coaching around the strengths of your reps and how you can effectively get them to the Shangri-la state, which is closing as much business as humanly possible,” explained Craig. 

Secondly, augment technology to optimize the sales process. But the process has to be repeatable, while layering coaching to enhance the sales rep’s potential. Ultimately, Craig concluded,My advice is, combine the art with the science, but have kind of the consistency to be able to recognize folks that are gonna win and folks that are not.”

Conclusion: B2B Sales Trends to Watch

Before concluding the fireside chat, each speaker was asked to provide the one trend that sales leaders should think about in the coming year and beyond. 

Craig responded first:

“Look at inbound outbound and especially channel. I think the channel within 2023 is gonna be an area that’s going to have its coming out party a little bit. I think there's a lot of organizations that we see that are under leveraging channel partnership and that motion.”

With Jinal adding:

“Really empathize with your customers. They're gonna have a tough year budgeting. They're gonna have a tough year selling. They still have bigger goals. We have to do more with less. And then asking yourself like, first genuinely, is there something within your product within your services that you can reach out to and talk about? Can you offer more recession- proof discounts right before they have more liberty to spend more. So those are some of the things that we are doing ourselves. Because look, I mean, if you are with them in the bad times, they are going to be with you in the good times.”  

Watch the Selling Smarter replay:

Selling Smarter Fireside Chat image

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