You’re approaching a sales culture reckoning in 2024. Here’s how to prepare

Posted January 30, 2024

By Kevin Bognar

SVP of Sales at Outreach

Moneymaker: Selling in 2023 was hard. Kevin Bognar draws on his 30 years of sales leadership to break down how to save your team culture in 2024 so everyone can make more money — and you can keep board members off your back.


Once upon a time, commission checks were fat, President’s Clubs were bursting at the seams, and everyone had financial clearance to buy for expansive teams. And then, suddenly, they weren’t. Budgets were slashed, and the layoffs came; AI became part of the tech stack rather than an apocalyptic savior, and hitting goals became even more difficult. Morale took a dive, and boards demanded answers. Selling in 2023 was hard and won’t magically become easier in 2024. It’s going to take work.

Here’s what I’m prioritizing in 2024:

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Redefining expectations: Minimize churn, select industry plays, geographical alignment, equitable books

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Return to selling basics: Conscientious outbound

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Coach like you mean it: Communicate your expectations, run defined meetings, and reward and share great work

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Return to management basics: Coaching, retaining, and taking care of talent, setting people up for success with clear KPIs, transparent communication

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Get used to being unpopular (for now): Restructuring and enforcing may not be as well received, but it will pay off

Anti-radical 2024:  Focus on getting sales teams what they need

My top priority as a sales leader: to do everything I can to make sure every single team member hits their numbers so they can win the prize, earn the commission, and land their OTE target. Because it is that drive and that reward that structures team culture. An old boss told me early in my career that it was “okay to be coin-operated,” and I’ve never forgotten it. No amount of happy hours and trust-building exercises will override a low base salary and trickling commission.

In 2024, that means redefining expectations. Here’s where I’m putting my focus:

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Minimizing churn of existing relationships with customers: Company growth doesn’t happen without your current customers.

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Selecting focused industry plays: I can’t reveal all my secrets, but 2024 will require a shake-up

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Alignment of geographies for quality of life for sellers and customers: Increasing customer cohesion (and renewal) means aligning them with the right sellers

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Building equitable books so hard-working sellers succeed: In this sales climate, it pays to value new business, expansion, and even renewals equally — we should ensure that compensation programs reflect that.

I want my teams to spend their time where it will actually matter in 2024. Nothing I’m implementing is incredibly radical, and it shouldn’t be. The past few years have been crowded with bells and whistles, and the continued ebb and flow will require a solid foundation: a return to good, old-fashioned selling. 

Doing the work matters. No shortcuts, no elaborate tech stacks, just maximizing what we have and pounding the pavement. We’ve all been distracted by more prosperous times. Now, we’re locking into focus.

To get your sellers back to basics, you’ll need to get back to basics as a leader. And that means coaching.

Back to sales (and management) basics

Buffet said it best: you can’t see who’s swimming naked until the tide goes out. Boom sales times masked all deficiencies. Now is the time to make sure your team has the basics covered. 

To be able to meet my goals, I’m going to need to coach accordingly, and so will you.

Your greener sellers are going to need more time and attention in 2024, especially if they entered sales in a remote environment. Remote work does not make bad sellers, they just weren’t given the same selling education. They didn’t observe techniques from across the bullpen, absorbing hustle via osmosis. They didn’t get the chance to ring the gong or cut a tie for a raucous team. They didn't visit customers on-site, sit across from a difficult client, or walk the halls and spontaneously meet more contacts. What they did get was entry into a booming sales market, where anyone with enough gumption and an internet connection could seal the deal.

Now, that luxury has evaporated, and the tide has receded. It was up to sales leaders to go beyond standard onboarding, but they got distracted by winning — the boom market masked leadership deficiencies as much as it did on the floor. And it will be up to sales leaders to make it right.

This is not a reason to abandon remote work or only hire seasoned sellers. The future of sales doesn’t just lie within its plucky upstarts, it depends on how effectively veteran sellers can build the foundation for new talent to stack on top of. 

Coach like you mean it

Only those who have been around long enough really know how to navigate the cycle of feast and famine. This will be the year when leaders and sellers get back to basics, and that means quality coaching to achieve a more conscientious approach to outbound.

I’m biased, but this is where tools like Kaia make a difference in coaching. Kaia is Outreach’s conversational intelligence tool, providing conversational insight and guidance, transcribing, bookmarking, and analyzing in real-time. Kaia users are 36% more likely to secure a follow-up meeting compared to non-Kaia meetings, supporting sellers and account reps in real-time while recording and monitoring progress for me to review and follow up later. I know exactly when and where sellers need guidance. It’s old school meets new school.

If you’re looking to improve coaching without the Outreach platform, stay close to the data you have available to monitor where your team is losing momentum. Create actionable onboarding and training programs with clear and deliberate goals to support and guide your sellers. Communicate your expectations, run predictable and defined meetings that measure progress, problem-solve issues, and reward and share great work. 

When so much of the culture conversation gets weighed down with perks, it’s easy to forget that the foundation of any culture will always be making sure your team has what they actually need to do their jobs — and that includes the right knowledge, training, and coaching.

Get used to being unpopular… for now

It’s not going to get easier any time soon. But if you do it right, your sales team is about to get stronger. 

2024 will still be a grind. Incoming and veteran sellers have been dazzled by the rise of the LinkedIn Sales Influencer. Scroll through your feed, and you can’t help but see how many faces seem to have it all figured out. But social media followers don’t equal bottom-line dollars as a salesperson, and it has been infuriating to watch so many flex without substance. Their popularity is an omen: it’s time to get unpopular. 

Sellers are looking for guidance during this time, it’s why they tune in and follow. Don’t let the internet overpower real insights and technique.

The basics matter: coaching, retaining and taking care of talent, setting people up for success, clear expectations of KPIs and performance management, transparent communication… These will be at a premium in 2024. And restructuring and enforcing may not be as well received, but you will need to make the tough, and sometimes boring, decisions to lead your team through this. Don’t be cruel, be smart and resilient. When your sellers start winning again, you won’t be unpopular for long.

To avoid another 2023, you’re going to have to do it on purpose. Veterans and rookies learned a lot this past year. The wise ones will act, the foolish will wait for the market to shift. The market is the market, the wind will not always be at your back. If you’re serious about leading successful teams and hitting your goals, you’ll need to beef up resiliency – and your team can’t do it without you.


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