5 Challenges Keeping Sales Leaders Up at Night and What They’re Doing About It

The sales industry is advancing more quickly than ever before. Both the pandemic and full adoption of digital selling have rapidly improved the way that we are looking at workplaces and teams, how we communicate with customers, and ultimately how we sell. These changes are positive, but now sales leaders have new challenges that are keeping them up at night – myself included.

Three top European sales leaders recently joined me to chat about these topics. We are all facing similar challenges and they gave me a lot to think about – from reducing time in the hiring process to how we can train managers differently. 

Here is the incredible panel of leaders and the insight they shared: 

• Henrique Moniz de Aragao, VP of Sales at Ultimate.ai
• Penny Orme, Commercial Director at iManage
• Natalie Barrie, Head of Sales at Mention Me

1. Preparing sellers for a compressed sales cycle

We all know that with the lack of in-person meetings, buyers are able to meet with a lot more vendors than they used to. The buyer is a lot more skilled in doing their own research. That means sales cycles are shrinking. It’s harder to get in front of clients and it’s harder to get the commitment. It is more critical than ever that we find ways to get their attention and build the messaging to make the most of the time when we are in front of them.

Henrique Moniz de Aragao: The window of opportunity is much smaller than it used to be — no more one-hour demos and two-hour discovery calls. If I’m fortunate enough to get some time with a prospect during a sales cycle, I need to be sure I can add real value and that they will remember this interaction. Sellers need to come prepared, they need to have credibility, they need to have done their research, and I believe more and more sellers need to come with a point of view. Prospects will value that.

2. Focusing on the champion

More and more, sales teams (mine included) are spending much more time prepping the deal champion because there will not be an opportunity to present to the economic buyer. If you’re still pushing to get in front of the economic buyer, it’s important to realize that you’re battling a fight that can’t be won. Make the most of the time you are spending with the champion.

Natalie Barrie: We’ve really stepped up our game with the design and brand team to make sure our product is coming across as mature and professional visually. We know that it is unlikely that we will be able to present that proposal, so we need to give our champion a really amazing piece of content to take to the board meeting. We are finding ways to stand out when we aren’t necessarily in the room anymore.

Penny Orme: We found that our champion is more likely to remember and share a story with the economic buyer. They do not remember features, functions, and facts. We have invested in storytelling workshops for our team in hopes they can share stories the champion will remember when presenting. We have also had to teach our sales teams how to get the champion excited before the meeting since we aren’t there to build energy.

3. Putting greater emphasis on cross-departmental collaboration

It was encouraging to hear a renewed interest in alignment between sales and marketing. Lead and revenue generation can explode  when your marketing automation and sales engagement platforms are integrated. Each department will have the tools that help make their jobs easier so sellers can appreciate marketing for the inbound leads they supply, and marketers will be gratified when they see sales converting those leads into more revenue. 

Penny Orme: For the first time we’ve created a joint marketing and sales go-to-market plan that is part of our new OKR (objective and key results) process. We’ve invested in content specialists to build rich content and focused on the voice of the customer. We completed interviews with customers and then heat-mapped the most common words so the sales and marketing teams can use the terms to more quickly relate to the prospect.

Natalie Barrie: We are focusing our entire go-to-market strategy on ICP (ideal customer profile) selling so we are collaborating more with marketing than we ever have before to make sure we are using the right collateral, the right testimonials, and video case studies. We also re-wrote our entire sales playbook around our three top ICPs and changed how we enable the team, sales plays, how to market to them, and objection handle. At the same time, we have started rolling out 4DX (The 4 Disciplines of Execution), which really focuses on cross-departmental collaboration working together toward important goals. 

4. Making the most of a hybrid work environment

Most companies are now moving to a hybrid workplace. While the obvious answer might seem to add more sales technology, the process of digitization isn’t as straightforward as it may seem. Almost daily, I talk with sales leaders who are feeling tech bloat – they’ve adopted disparate systems that were meant to make them more efficient but have actually resulted in less focus. I foresee there is going to be a strong demand for technology platforms that simplify tasks for sellers. 

Penny Orme: Since we will keep the hybrid model, we need to make people who are remote feel included even when they are dialing in. We’ve established meeting room etiquette for the people who are there in-person. For example, in a meeting room people can get chatting amongst themselves and forget someone is on the screen. We’re asking people in the room to look at the screen, arrive on time (it’s much easier to get sidetracked in the office), and ensure there is an agenda.

Henrique Moniz de Aragao: As a sales leader, you need to be thinking about technology. What tools are available that you don’t yet have for your team, but will allow them to add value for prospects and make memorable interactions? How are you going to make sure you can reach as many more buyers as possible? I’m talking about sales engagement, sales enablement, data tools, and AI. 

5. Recruiting sales talent in a highly competitive environment

Sales talent is in high demand and the job market is as competitive as ever.   The hiring process has  very much become a two-way process. It’s no longer just “is the candidate right for the job?” but also “is this company right for the candidate as an employee?”

Henrique Moniz de Aragao: We are hiring quite aggressively, so we can’t have long, drawn out hiring processes. We now have SLAs (service level agreements) from first screening call to offer/no offer within 10 days. And we are finding we can turn more junior roles around even quicker.

Penny Orme: We are being more intentional in looking for specific attributes, like resilience. And thinking through how we test for those skills and attributes. We are ensuring there are no more than three people in the interview and that the interviewee and interviewer know exactly what the outcome of the meeting will be and that it is a quick and easy process with a feedback loop.

Natalie Barrie: The thing I think is missing from remote interviews is being able to have the time to determine whether it is a culture fit. My first part of the process once the candidate has met with the recruiter is to schedule a 30-minute call that is completely informal to get a sense of the person and their personality. I’ve found this informal chat is working very well because I can do it one day before the formal interview so it isn’t adding time to the process, but puts our company in a more positive light and helps the candidate feel more aligned with us.

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