As the title says, these are my top 7 tech sales lessons of 2024:
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Big deals happen when big problems are solved and the business impact of the solution ($$$) is high. Vice versa, if the business value is low, the price is the deciding factor and the deals automatically get smaller.
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Small deals often take as much time as medium-sized deals, so it is important to set the right focus, both as an Account Executive and as a company. For Account Executives, one of the most promising ways to maximize commercial success is to close large deals with large companies and high complexity.
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Be careful with roles like “First AE on the ground” etc. - Many founders have no or unrealistic ideas about sales and sales quotas, in addition I realized how important it is to qualify the company (not just startups) in job interviews and to ask about quota attainment, development opportunities and culture in the revenue team.
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The Importance of Product-Market Fit for Revenue Organizations - Being in an organization that has already found product-market fit is as important, if not more important to commercial success as an AE than your own skill set.
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AE as quarterback: As a revenue organization, you are a team, but one person has ultimate commercial responsibility, and that has to be the account executive. Revenue organizations need to ensure that AEs have access to resources such as solution engineers, that customer success managers and IT support handle operational customer issues that are not strategic and commercial in nature, and that revenue operations maintains the systems and processes to keep things running smoothly.
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How crucial your own book of business and territory can be for your own success. I am a big fan of meritocracy and believe that everyone is the master of their own destiny. However, you can see the impact of external circumstances when you have a Book of Business or Territory that offers little in return for all your hard work and dedication.
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Retention is so important for organizations to grow exponentially. That is why it is so worthwhile for established organizations to include it in their commission plans.
Do you agree/disagree?
What are your key learnings of 2024?
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Great insights! As someone who’s been in enterprise sales for quite some time, I strongly resonate with many of these points and want to share my perspective.
Regarding #2 and #6 - there’s a fascinating paradox here that I’ve observed. While I agree that large enterprise deals often offer better ROI for time invested, I’ve also seen how a well-structured territory strategy can make mid-market extremely profitable. It’s about finding the sweet spot between deal size and sales cycle velocity.
I particularly want to double down on #4 about product-market fit. In my experience, even the best sales professionals can’t consistently overcome a product-market fit gap. It’s why so many companies spent so much time in their early days to ensure they’re not just selling software, but delivering real business transformation.
On #5 - the “AE as quarterback” analogy is spot-on, but I’d add a crucial nuance: The best quarterbacks know when to hand off the ball. I’ve seen top AEs excel not by controlling everything, but by orchestrating their resources masterfully.
My key learning from 2024? The rise of what I call “ecosystem selling” has completely transformed how we need to approach enterprise deals. It’s no longer enough to just understand your customer’s immediate needs - you need to grasp their entire technology ecosystem and partner network.
I’ve watched deals completely transform when our teams mapped out not just the customer’s internal stakeholders, but their key technology partners, system integrators, and even their customers’ needs. In one case, what started as a big deal expanded to a huge deal because we identified how our solution could create value across their entire partner network.
This means sales teams need to think bigger and broader. It’s not just about selling to a company anymore - it’s about understanding and adding value to their entire business ecosystem. The most successful AEs I’ve seen this year are those who can navigate and leverage these complex relationships.
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Thank you. I appreciate your detailed response.
Re: 2 & 6: I agree with you that even a mid-market strategy can be very profitable and enterprise customers require a lot of customization and hand-holding. Generally, I believe that if one has enough inbound leads or a high opportunity flow, transactional business models can work great. However, as an Account Executive, I still think it is more attractive to be in Enterprise or Strategic Sales under the right conditions, because you can simply blow up your quota with one big deal.
Re 5: You are absolutely right. Nobody can do everything alone and teamwork makes the dream work. As always, you need a good team for this to work - delegating should not result in major quality losses.
Re: Ecosystem Selling - I think this is a very interesting point and I have been in contact with it when trying to solve the problem of my customer’s customers with our product and thus create a strategic advantage. Ecosystem selling, on the other hand, is very complex and probably only makes sense in the enterprise segment. What do you think, and do you see a way to make this work for SMBs/Mid-Market and smaller transaction sizes?
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Your point about enterprise sales and quota acceleration through big deals resonates. That said, I’ve also seen AEs get stuck waiting years for the “big whale” while the mid-market team always hit their quota.
Your observation about the complexity of ecosystem selling in smaller segments is true. Here’s what I’ve learned: While full-scale ecosystem selling might be overkill for SMB/Mid-Market, there’s a “light” version that can be incredibly effective. Instead of mapping entire partner networks, focus on identifying one or two critical integration points that can multiply value.
For example, we’ve seen mid-market teams have great success by simply understanding how their solution connects with their customers’ most-used platforms. It doesn’t need to be as complex as enterprise ecosystem selling, but even knowing how your solution impacts your customer’s relationship with their key suppliers or customers can transform a transactional sale into a strategic one.
The key is scalability - in enterprise, you can invest weeks mapping complex ecosystems because the deal size justifies it. For mid-market, you need a more streamlined approach that can be replicated quickly.
The point about team quality in delegation is crucial. I’ve always said that the best sales leaders don’t just delegate tasks - they delegate opportunities for growth. When you have the right team, delegation becomes multiplication rather than division of effort.
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