March 20, 2023

4 Challenges Facing Sales Leaders in 2024

Sales leadership can be a tough job. You’re constantly managing competing priorities and personalities, all while trying to hit targets and grow revenue. But as we navigate a shifting economy, sales leaders are facing a new set of challenges that require a different kind of leadership. In a recent webinar featuring top execs from New Breed, HubSpot, Semrush, Teamwork and SaaSWorks, we discussed the top challenges facing sales leaders this year and insights on how to tackle them strategically that motivates teams and drives results.

Approaching the Cautious Customer

Customers have become more deliberate in their purchasing decisions than ever before. This has led to a shift in company-customer relationships, where customers are now expecting more value and more personalization earlier in their journey. In this landscape, sales professionals who prioritize empathy, curiosity, and solutions for their customers in the pipeline will continue to thrive.

In other words, empathy is key to selling in 2023 more than ever. Tara DiCristo-Schmitt, HubSpot's VP of NAM Small Business Sales, emphasizes the power of empathy in uncertain times:

"By saying, 'we know how you're feeling, we're feeling and going through those things, too. Let me tell you what we're learning and what's happening and how other businesses are making decisions,' sales reps can truly connect with buyers and build trust." Tara DiCristo-Schmitt, HubSpot's VP of NAM Small Business Sales

Building Trust with Executive Decision-Makers

Getting buy-in from executive decision-makers has always been a challenge for sales leaders, but in 2023 it's more critical than ever. Reps are now facing larger and more diverse buying committees as finance and operations leaders take a more central role in company budgets. According to HubSpot's 2023 Sales Report, the average number of individuals involved in the sales process from a prospect's organization is now around four or five, including up to three decision makers.

As a result, larger buying committees can lead to longer sales cycles and tougher negotiations. Reps must engage each stakeholder effectively, anticipate objections, and pivot quickly when priorities shift or new stakeholders enter the picture.

For example, CFOs are now playing a more direct and significant role in the decision-making process, often getting involved earlier and with broader go/no-go authority over spending. Anticipating their needs and modifying your approach to win these key stakeholders can be a huge difference-maker for your overall effectiveness.

By building trust with executive decision-makers, sales leaders can make their case more effectively and win more deals. As Suneet Bhatt, Chief Customer Officer of SaaSWorks, points out, CFOs are increasingly involved in the decision-making process, and leaders need to understand their priorities and constraints.

"We approach that conversation, we equip the buyer is with, 'hey, get preapproval' or 'let the CFO know that you're moving at this cadence, presuming their blessing."Suneet Bhatt,Chief Customer Officer of SaaSWorks

Navigating Longer Sales Cycles

As a result of indecision and involvement of more stakeholders, deal velocity continues to be a challenge. The pressure to close deals and generate revenue can lead to demotivation as cycles lengthen. Sales reps can feel like they're not making progress, which can impact productivity. To make matters worse, forecasting can become more difficult, creating more uncertainty around closing plans and contract terms. It's a tough environment, but teams must adapt to build customer relationships that can withstand the longer deal lengths.

As always, creative problem-solving is the key to overcoming challenges. Joint evaluation plans have become a game-changer for increasing deal velocity and can be a powerful tactic in a difficult economy. Collaborating with decision makers, reps can create a detailed plan for evaluating and implementing solutions while building consensus around the path forward. By doing so, reps can reduce uncertainty on both ends of the deal and close a deal faster — or abandon ship when necessary.

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Building a Predictable Sales Pipeline with Data

Sales leaders are starting to re-evaluate their approach to management and focus on metrics that are most relevant to deal velocity. One of the key takeaways from the webinar was the importance of rebuilding reporting structures if necessary to apply pressure to sales efficiency. This involves modifying traditional reporting structures and incorporating pipeline hygiene and team performance metrics to predict and improve performance, such as deal cycle length and push rate.

According to Beau Brooks, VP of Worldwide Sales at Teamwork, one way to improve performance management this year is through weekly film reviews.

"We pull the sales team together every week, and listen to a call together. Then, we tear it down. That really helps me to get alignment with the team and to interject positivity into what can be challenging on a day-to-day basis."  Beau Brooks, VP of Worldwide Sales at Teamwork

By keeping the team engaged and accountable to their share of the pipeline, managers can help their reps succeed in a remote, high-pressure environment. They also need to embrace a growth mindset and be willing to learn and pivot as needed. According to Channing Ferrer, Chief Sales Officer at Semrush, this means being open to new ways of working and new technologies.

"The ability to adapt to different communication methods is a big deal. We need to be open to new technologies, we need to be open to new ways of selling." Channing Ferrer, Chief Sales Officer at Semrush

Channing also discussed the importance of driving efficiency in the sales process and creating a buying experiences that allow customers to engage at their own pace. This can be achieved by minimizing human involvement through the right data-driven "self-education" engagement model, and the use of automation such as email, chat, and SMS automation. Channing emphasized the need to put humans in the sales process only where they are needed, and to automate the rest.

As another example, Teamwork's Beau cited Distributely, New Breed's lead routing app built on top of HubSpot, as a key driver of becoming more creative and nimble in the sales processes. By skipping unnecessary steps and getting qualified leads directly into the hands of account executives, Distributely has shortened the sales cycle and added efficiency to the bottom-of-the-funnel engagement.

Fast-Track Lead Routing to Inject Efficiency to Deal Velocity

If you're aiming to achieve long-term success in a shifting economy, focus on empathy, build trust with executive decision makers, find ways to streamline longer sales cycles, and build a predictable sales pipeline with data. But it's not enough to simply know what to do; you need the right tools and strategies in place to execute your plan.

That's where Distributely comes in. This powerful lead routing app built on top of HubSpot allows you to simplify lead distribution and automate your sales processes, freeing up time and resources for you to focus on what really matters: growing your revenue. With Distributely, you can easily assign leads based on criteria like availability, location, or expertise without manual updates to existing workflows.

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Elizaveta Shkurina

Sr Creative Strategist specializing in B2B brand creation, sales enablement, and SaaS demand generation. With 8 years of experience, she excels in driving ROI and revenue-driven KPIs through collaborative innovation.


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