5 selling tips from Kyle Asay
5 selling tips from Kyle Asay

B2B selling is hardly ever a quick, one-off task. Instead, you carefully engage and move prospects through different stages of the sales process until they’re converted into customers. 

However, successfully moving potential buyers through each stage and eventually closing deals depends heavily on your selling processes and strategies. As such, proactive salespeople are always looking to adopt sales techniques that can give them an advantage over their competitors.

If that sounds like you, then you’ve come to the right place. This guide shares effective selling tips from Kyles Asay, Regional Vice President of High Tech Acquisition at MongoDB to give you that extra edge to close more deals and reach your revenue goals. 

5 selling tips to win more deals by Kyle Asay

5 selling tips you can use

There are several factors that influence buying decisions in today’s business landscape. Your potential customers are less likely to take risks and make a point of arming themselves with enough information to ensure that any new products in their tech stack add value to their business.

This might make selling tougher, but that doesn’t mean it’s bad news for sales professionals. 

Instead, effective selling goes beyond simply pushing product features to nurturing quality personal interactions with your prospects and demonstrating a clear understanding of their needs in your sales pitch. 

Here are five sales tips from Kyle you can integrate into your sales strategy to win more deals.

1. Multithread your deals

As the average buying committees for B2B products continue to expand, depending on one contact to make a sale is risky.  

There are different stakeholders making buying decisions with different concerns and priorities, who you’ll need to prove your product’s value to.

This is why multithreading is so crucial to sales success. The more stakeholders you can build a relationship with, the more touch points you have to address their questions and concerns. 

Getting a lead or a previous champion to help connect you with other stakeholders can be a little tricky, but it’s worth the effort. Deals with previous champions have 54% bigger deal sizes, 12% shorter sales cycles, and your chances of winning the deal are 114% higher.

Kyle explains that the reluctance from your champions to connect you with other stakeholders is because “you aren’t just asking them to send a quick email. You are asking them to bet their credibility on you.”

He explains, “If they connect you with a coworker who doesn’t end up finding value in meeting with you, it reflects poorly on them. This is magnified at the executive level: no one wants an executive annoyed at them because they wasted their time with a poor sales call!”

So, how can you successfully multithread with your champion and potential customers? Here’s the framework Kyle uses:

  • Build their confidence by always adding value when you meet with them: Share new insights on their industry and how your product will help them grow.
  • Have a valid and specific reason for your request to meet with new stakeholders:  For example, this could be to address concerns they might have about your product.
  • Detail what will be expected from all attendees: Not just an agenda — specifically what role each attendee will play.
  • Share your plan with your champion beforehand to make sure it’s a successful meeting.

Kyle’s multithreading template

Kyle puts his suggestions into action using this template. Customize it for your product and connections to see how well it works!

Linda, it’s been great working with you to identify how MongoDB could help your dev team improve efficiency.

Last thing we’d want to do is begin a migration without a really clear picture of how our work would impact the broader engineering org - we want to optimize for the long term.

Typically, the CTO is the best person to speak to long-term architecture goals. We’d love to bring Angela onto the next call to bring her up to speed on our goals and planned implementation to see where she would recommend adjustments to fit with her vision.

We don't want to waste her time: we’ll prepare an executive summary she can review before the call so we can make the most of the conversation.

The main feedback we’ll want from her is related to the milestones we’ve discussed - now is the right time to change those definitions or timing.

To ensure the call is successful, we’ll also include an executive from our solution architect team - that way, any questions she has can be addressed during the call.

2. Dig deep to understand your buyer’s concerns

Every time you follow up with your buyer, they flood you with good news. For example, they might say they don’t have any concerns about using your product or that there are no further questions from the stakeholders.

This must be a good sign, right? Not necessarily. 

Hearing only good news from your buyer could mean that you’re on the verge of losing the deal. Kyle says that only hearing good news typically points to the following problems:

  • Your buyer is too far removed from decision-making to know the concerns. If your buyer isn’t hearing the concerns, they aren’t influencing the decision.
  • Your buyer knows the bad news but won’t tell you. This is a sign that they either don’t trust you or don’t believe you can help them navigate the issues they’re facing.

When a buyer doesn’t trust you with their problems, it means they still view you as a stranger who doesn’t really have their best interests at heart. And if nothing is done to earn the buyer's trust, the constant good news could turn into radio silence down the line. 

So what can you do in this situation? 

Kyle suggests, “Next time you have a deal that seems to be nothing but sunshine, slow down and dig for the bad news. If you still can’t find any, you know you have work to do to earn the trust of your buyer or need to go wider in the account.”

To dig for the bad news, Kyles recommends asking your lead questions like:

  • “I know how hard it can be to get everyone on the same page — who do you think is most skeptical of the value our solution can bring?”
  • “What other business priorities would we be pulling attention from if we moved forward with our solution? Who on your side is pushing to solve those priorities first?”

3. Leverage your team’s strength in sales presentations

Sales teams often get on a sales call and leave all the talking to a single team member. The same person does the demo, answers all the questions, and addresses all the concerns. 

It’s not impossible for one individual to do a good job of it. But with how competitive the B2B industry is, you want to do more than just “good”. 

Team selling allows you to tap into the expertise of each of your team members to provide prospects with in-depth answers to their specific concerns. This allows you to build trust with new customers by showing them you have an understanding of their business needs and the expertise to provide the best service possible.

Kyle outlines some steps to take to improve team selling and drive revenue alignment

How to take advantage of your team's selling skills during sales prospecting
  • Identify strengths

Knowing where each team member excels helps you determine where to leverage them at different stages in the sales process.

“Ensure every agenda item is covered by the person best suited to impress your customer,” says Kyle. “A senior leader may shine at painting the vision of the product roadmap. The account executive may be best at telling stories that tie back to the customer’s use case. And the customer success manager (CSM) may be best for walking through your plan to ensure long-term value for the prospect.”

Identifying your team’s strengths also shows you which sales skills they might be lacking and guides future sales training.

  • Define roles

“Everyone joining the call should know exactly what outcomes they are responsible for driving and how they plan to execute,” notes Kyle.

“No mid-call juggling, and please, no panicked slacks, ‘How do we get Kyle back on track before he blows this deal?’”

This ensures everyone is aligned on what needs to be done to move different personas down the sales funnel.

  • Remember your external team

“Few things are more effective than your champion pitching your solution to their team,” Kyle notes. 

“Involve them in call preparation and assign them an active role where you make them look good. Make them look good on the call, and they’ll be happy to make you look good after the call.”

He adds, “Conduct deal reviews so the team can function efficiently and keep the deal on track. During these reviews, team members can provide feedback to help the team understand what’s working and what’s not. This enables the team to remain adaptable, learning and improving with each account.”

4. Maintain an enterprise mindset 

Having an enterprise mindset means filtering everything through the lens of your customer’s pain points, goals, and priorities. This mindset can guide the outcome of discovery calls and the overall customer experience. 

An enterprise mindset puts you in the frame of mind to focus on your prospect’s business and gives you an opportunity to genuinely understand their pain points and business goals. 

As Kyle puts it, a sales rep with an enterprise mindset would ask, “What change is your company making that has you looking at new solutions?”

With this question, you’re more likely to have a better sales conversation.  

On the other hand, a transactional mindset is often too product-oriented. This causes the salesperson to focus on the product and its features instead of how it adds value to the prospect’s business. 

During discovery calls, a transactional perspective leads to asking product-focused questions. 

Kyle gives an example: “How do you want to use our product?” 

This mindset and the questions that typically follow signal a one-sided value extraction, making building rapport and long-lasting business relationships difficult. 

5. Find a warm path into an account 

A key selling tip is to align the prospect’s business goals with your product’s solution. And this requires having a good knowledge of the business, which can come from an unusual source, as Kyle found out. 

“As an AE, I spent months trying to get into an account at ‘senior” levels,’ says Kyle. “No one responded. I started reaching out to entry-level professionals and one agreed to meet. I could have quickly disqualified them as they were clearly not the right contact. Fortunately, I still decided to run a full discovery. They gave me insight into a C-Level goal (NPS at 60 by 2021) and a breakdown of internal systems.

“Using this information, I created a business case for how we could help them achieve that goal within their current internal systems,” Kyle says. “I sent a message to the CEO with the subject line, ‘NPS to 60 by 2021?’ and attached my business case for how we could help. He responded immediately, and we kicked off the evaluation.”

“Here’s the lesson: Stop thinking that initial conversations are only valuable if they convert into an opportunity,” says Kyle. “Your first conversation with an account is probably not with your eventual buyer. If you worry only about “converting” the opportunity, you’ll leave the call without being any closer.

“Shift your mindset from ‘how can I qualify an opportunity’ to ‘how can I better learn the value I can add to this company,’ and you’ll end up with the strongest opportunities of your career.”

Apply these selling tips to win more deals

Although economic conditions are always changing, focusing on aligning your buyer’s needs with your product’s solution and building a relationship with key decision-makers is always a great strategy for hitting your metrics. 

But achieving this requires you to be an active listener, able to grasp the buyer’s needs and build a case for your product for the different stakeholders in a buying group.

That’s why you need to 

  • Multithread your deals
  • Dig deep to understand your buyer’s concerns 
  • Leverage your team’s strength for better selling
  • Maintain an enterprise mindset
  • And, find warm paths into your target accounts.

Why UserGems?

UserGems tracks your past champions, buyers, and prospects when they move to new target accounts and surfaces them in your CRM so you can automatically reach out to them. This helps you stay top-of-mind and keep the conversation going, which can lead to repeat business. We also make it easy to build relationships with the entire buying committee by capturing key contacts in an account and including them in your campaigns. 

Try our self-guided demo to learn more.

UserGems is pipeline generation software that helps revenue teams generate and protect revenue efficiently. With UserGems, companies can track and automate outreach when their champions change their jobs, and capture the buying groups to find the warmest path into every account.

Companies like Mimecast, Greenhouse, and Medallia use UserGems to reach their revenue goals quickly and efficiently.

Want to get more pipeline with less work?