Motivating Sales Teams Through Tough Times

Timestamps:

2:49 - How Sherpany got acquired

18:05 - Discounting vs additional free features

23:20 - Should you hire salespeople or marketing people first?

32:03 - Where to hire salespeople

45:47 - The fixed/variable salary split

About Tobias Häckermann, Lars Mangelsdorf & Laurent Decrue:

Tobias Häckermann is the co-founder and CEO of Sherpany, a provider of meeting management software for leadership meetings that was acquired by Datasite in 2024. He holds a Master of Laws from UZH.

Lars Mangelsdorf is the co-founder and CCO at Yokoy, a spending management software company which enables companies to automate their expense and credit card processes using artificial intelligence. Yokoy was acquired by TravelPerk in 2025. Lars previously worked as Senior Account Executive at Beekeeper.

⁠Laurent Decrue⁠ is the co-founder of the moving company ⁠MOVU⁠ and the software company ⁠Holycode⁠, and the former CEO at ⁠Bexio⁠. Currently he is active as CFO and co-CEO at Holycode. He holds an MBA from the University of Basel and previously worked at DeinDeal.

During their chat with Silvan, Tobias, Lars and Laurent shared their insights on how to scale your sales team from founder-led scales to a fully operational sales army. When asked about KPIs to track early on, they stressed the importance of AE efficiency (2 AEs bringing in 90% of your revenue is bad) and also talked about sales cycles:  if your average deal size goes up by 200% but your sales cycle goes up by 400%, you’re clearly doing something wrong.

Laurent recalled a lesson he once learned from a fellow entrepreneur about how discounts, despite their attractively lower pricemark, ultimately signal that you’re giving your customers the same product for less money, which insinuates that you were overcharging them before. Laurent’s friend encouraged him to add additional free features for the same price, instead of lowering the price with discounts. 

Still on pricing, Lars shared that since some markets have a competitive price pressure, it may sometimes pay off to go into them with a lower pricing number and increase your price by 15% every year. It’s easier to get people to pay more once you’ve already started to earn their trust. This will allow founders not only to branch out into different markets but also to ultimately increase their deal sizes.

Another topic discussed during this episode was the old chicken and egg problem of whom to hire first: sales or marketing people? Here the guests held different opinions. Laurent said that because you need lead magnets first, you should hire marketing people before sales people. He added that your sales should go from founder-led, to hiring a couple of people to build a really great pipeline, to then hiring a larger number of salespeople. Lars, however, argued that doing sales first allows you to test whether there is a strong demand for your product in the market you’re targeting, and whether your messaging is properly crafted. Finally, Tobias added that marketing is much less relevant for B2B businesses than it is for B2C, since you only need to reach a couple thousand people, as opposed to millions.

When it comes to actually hiring salespeople, Tobias encouraged listeners to start hiring way earlier than necessary “in their head”, meaning that they should build relationships proactively (including with competitors) with the goal of later on acquiring great talent. This is especially important considering that the likelihood of making the wrong hires early on is very strong. He finished by sharing that founders should hire their sales team themselves, instead of outsourcing the job.

The cover portrait was edited by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.smartportrait.io⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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