Five Challenges Facing CROs and Sales Leaders in 2024

9 minute read

What are the top challenges facing chief revenue officers and sales leaders today? And how can account planning help? 

There’s plenty of uncertainty in the economy right now. But also, a lot of opportunity. The best chief revenue officers understand that – and they take up the challenge of driving revenue regardless of the business horizon daily. Of all the challenges they face, however, there are a few that are the biggest and most top of mind. These include an uncertain economic landscape, attracting and retaining top-notch talent, crossing the digital divide, and staying relevant even as the competition grows fiercer. 

In this article, we’ll dive deeper into each of these areas to uncover what chief revenue officers can do to address some of their most pressing issues, and how an effective account planning practice can help.

#1 Chief revenue officers face an uncertain economic landscape

For someone whose job it is to grow revenue, having uncertainty in the market is never a good sign. There are a few major implications this uncertainty causes, and they seem to be taking businesses on all fronts at once. These issues revolve specifically around supply chain, increasing inflation, and tightening job markets. Together, these three obstacles are ramping up the already considerable pressure placed on CROs.  

One way that CROs can look to combat this triple threat is to focus on long-term relationships to increase retention with key, strategic customers, while using that as a launching point for growing revenue in both new and existing accounts.  

Sales leaders can use account planning to help bolster both their relationships and footholds within accounts. Altify’s latest book, Not Just Another Vendor, highlights one sales leader – Scott Jackson Senior Director, Sales Enablement, Comcast Business – whose team learned the valuable lesson of relationships over product or any other fit. Through account planning best practices, Scott’s team built a network of supporters within the account that ensured the ultimate defense.  

Solidifying strategic positions like these can go a long way in insulating a business from even uncertain economic times. While not impervious, focusing on relationships with customers is going to be a big trend for CROs moving forward into the next decade.  

#2 Attracting and retaining talent in an ever evolving, new world

Attracting talent has always been difficult, especially attracting the kind of top talent that organizations need to survive and thrive. Contemporary trends have compounded the difficulty of recruiting. Changes in how we work, for example, thanks to technological advancement have made it harder for employers to stand out. 

Whereas before offering things like free lunches, and trendy, downtown office spaces where employers could ensure the brightest minds worked for them, today, that dichotomy has entirely been flipped on its head. 

Employees value flexibility, remote work options, and with the economic hardships, financial stability over flashy titles at new startups, or nap breaks in the local pod room. 

Seller attrition is higher than normal 

Despite the news of high-profile layoffs, the job market remains tight across most industries and for the majority of businesses. CROs are not out of the woods yet regarding hiring and retaining talent. It is also unlikely that this shortage will end this year, next year, or even in five years. Due to changing demographics and a plethora of other reasons, experts predict that the shortage could last until 2031 (Forbes). 

As if a record-breaking tight labor market weren’t enough to cause friction when recruiting new employees, sellers are feeling burned out. 

Burnout is high 

According to Gartner, most sellers feel burned out. Burned-out sellers are less likely to stay at their job when something that looks better comes along. In fact, they might leave at the drop of a hat – a phenomenon labeled in recent times as “the great resignation.”  

While the great resignation may not be so widely talked about today, recent data shows that people are still leaving their jobs, if at a slightly reduced level, despite news of broad sweeping layoffs across high-profile industries.  

Sales leaders can help create cultures that avoid burnout by focusing their efforts on building a cohesive revenue team. One seller who achieved this in one of her previous roles, and also highlighted in Not Just Another Vendor, was Sarah Walker Managing Director, Enterprise, Cisco. Sarah created a culture of inclusion – a safe space where sellers could feel comfortable discussing the deals they had going, and whether or not they would close.  

Not only does focusing on the relationships with sellers internally help reduce churn, but it can also be key to unburdening the organization with common problems like sandbagging in sales.

CROs are forced to seek ways to retain employees, not just customers 

As important as it is to retain valuable customers, employers now face a new dichotomy – they must actively seek to retain key staff members or face the hefty costs of frequent turnovers. 

CROs know they need the right people to succeed, and the best ones are looking outside the box at how they continue a scalable recruitment process. Many, however, need look no further than their revenue team, and the relationships therein. 

#3 Digital Transformation and Competing in the Digital Space

Many businesses have yet to fully embrace the wave of digitalization that is sweeping the world. While the pandemic launched plenty of companies far ahead in this area, many still lag. This creates a large opportunity for businesses to excel where others have yet to succeed. However, the roadmap remains unclear.  

What is clear, however, is the importance of winning in regard to the digital space. As most of the buying journey takes place online (Gartner), winning digitally has become synonymous with winning in sales. To do this, CROs need to double down on content, social media presence, and pay close attention to the impression potential buyers are experiencing while using digital channels to learn about their products and services. 

At the same time, it places a premium on the interactions sellers have with buyers. It takes a comprehensive vision of the account at hand, and the people, problems, and relationships within to maximize these few interactions. Without account planning that enables sellers to build this cohesive view, all the work in the world toward bolstering digital channels is fruitless.  

Remote Collaboration 

Enabling effective remote work situations is a challenge that should be near and dear to just about every CROs heart. Not only is this because the world is largely remote, and enabling effective collaboration has the ability to unlock performance potentials, but ensuring their business has what it needs to help sellers work remotely can impact recruiting efforts. 

As many employers pull back on remote work, and return-to-office becomes ever trendier, businesses can stand out by continuing to offer flexible work arrangements, or even enhancing their already existing programs. 

#4 Artificial Intelligence (AI)

If digital transformation wasn’t a strong enough challenge facing CROs, they now must contend with artificial intelligence. Not that AI is a threat to them as workers – but it is a real potential hurdle for their organizations and the people within.  

Will CROs embrace AI? Will they shun it? There are compelling reasons for either course of action. Ultimately, however, CROs need to decide which makes the most sense for their business, and which will better future-proof their organizations. This includes things like guardrails to implement in the use and integration of AI, as well as proper education and continued learning in order to ensure the success of their business in the long run.  

In some ways, ironically, however, artificial intelligence shines a light on the fundamental importance of the human touch. Several studies have been performed to ascertain the actual quantifiable value a seller brings to the table in a world where people are turning to digital channels more frequently instead of sellers.  

What was found, unsurprisingly, was that when it comes to the big decisions, you had to go with a seller. When the cards are on the table, budgets and jobs are on the line, buyers go with human sellers, time and time again.  

As Nigel Cullington, VP of Marketing for Upland Software’s Sales Effectiveness division, explains the phenomenon in his recent eBook, The Practice of Account Planning: 

“In the digital age, it can sometimes seem out of touch to say that the human touch is the most valuable aspect of a B2B sales interaction. However, increased digital transformation has, if anything, heightened the need for sellers.”

Nigel Cullington, Upland Altify

In fact, recent Forrester studies have found that not only is face-to-face selling on the rise post-pandemic, but buyers are more likely to turn to face-to-face, in-person meetings and rely more heavily on sellers when sales are large and complex.


Top Challenges Facing CROs

#5 Competition is fiercer than ever

To top it all off, your competition isn’t sleeping. The wolves are at the door, and nobody knows this better than CROs. However, a few principles can help their teams of sellers stand out.  

While it might be tempting to go for a quantity-over-quantity approach, many sellers are finding just the opposite works best. In fact, most buyers in a B2B business world are accustomed to receiving basic pitches with minimal information from sellers who treat them transactionally. However, the transactional sale is quickly becoming outdated.  

Setting yourself apart means understanding your customers 

In our blog – Forget the Ferrari – Earn Trusted Advisor Status Instead – we highlight the inspirational story of sales legend, Todd Adair, Southeast Zone Commercial Manager | GE Healthcare, and how he was able to turn things around with his customers by simply going to them and seeking to understand their business.  

The standard he set for himself to meet? He had to understand his customers’ business as well as they knew it themselves. 

Becoming a trusted advisor helps chief revenue officers fend off competition 

Whether it is in wooing new customers, or defending vital footholds in strategic accounts, sellers must seek to become more than just another vendor to their customers. They need a seat at the strategy table. 

Trusted advisors are the sellers who get the call when a new project comes through. Sarah Walker, the sales leader we highlighted earlier, understood this well. She leveraged a land and expand sales strategy to grow business in a vital new sector, become a trusted advisor, and gaining unparallel growth to her previous business.  

Through effective account planning practices, a cohesive, revenue approach to account-based selling, and putting the relationship at the center of the deal, chief revenue officers can face the many challenges present in an uncertain business horizon, and hope to not only survive, but thrive. 

Reliable products. Real results.

Every day, thousands of companies rely on Upland to get their jobs done simply and effectively. See how brands are putting Upland to work.

View Success Stories