How to Unblock Your Startup’s Sales Cycle: Insights from Founders

David Paul
3 min readMay 12, 2023

Startup founders are always navigating their way through unchartered territories and learning how to overcome critical obstacles. One of the trickiest parts of any startup’s journey is to unblock the sales cycle. Recently, I had the privilege of having dinner with Amy Jackson, founder of DWP Capital’s portfolio company, Statera. During our conversation, we discussed how finding the customer’s compelling event is the key to unblocking the sales cycle. In this blog post, I will share the insights, tips, and takeaways from my conversation with Amy. If you are a startup founder or venture capitalist, this post is definitely for you.

As we dug deeper into the conversation, Amy highlighted the importance of knowing what the customer’s pain point is. It is essential to listen to the customer, understand their needs, and identify their current challenges. Once the customer’s pain point is identified, the sales person can then pitch a solution that meets the customer’s needs. This will create a compelling event for the customer, and they will be more likely to make the purchase.

Furthermore, Amy emphasized the importance of having a deep understanding of the customer’s buying process. It is always helpful to know who the decision-makers are, what their decision-making process entails, and what objections they may have. By having this knowledge, the sales person can tailor their pitch and address any concerns the decision-makers may have. This enables them to be more effective in closing the sale and unblocking the sales cycle.

Another key takeaway from our discussion was the importance of follow-up. It’s common knowledge that it takes multiple touchpoints before a lead converts into a sale. However, many salespeople and startups falter by failing to follow up effectively. Following up provides the necessary continuity in the sales process, and it assures the customer that their needs are being prioritized.

Amy highlighted the role of data in sales. Using data-driven insights when engaging with customers can be an effective way to identify patterns that lead to successful conversions. By analyzing data, startups can be more effective in refining their sales strategy, and this can help to unblock the sales cycle.

Lastly, it is essential to keep the customer engaged and happy even after they make a purchase. By ensuring that the customer has a great experience, they become not only repeat customers but advocates for the brand. Satisfied customers create buzz, and this can be the key to unlocking further sales opportunities.

In conclusion, unblocking the sales cycle is one of the critical challenges that startups face. However, by understanding the customer’s pain points, knowing their buying process, following up effectively, using data-driven insights, and keeping customers engaged, startups and salespeople can be more successful in closing sales. I hope this post has provided you with useful insights into unblocking the sales cycle. Remember that each sales opportunity is unique, and finding the compelling event is the key to success.