What I Wish I Knew: Leading a Sales Team Through Uncertainty

In the latest episode of What I Wish I Knew, I spoke with special guest Amii Stephenson, VP of Sales at Maple. Growing economic pressures, inflation, supply chain issues… it’s a market full of uncertainty. We had a conversation about the changes and challenges facing sales professionals today.

How do you keep your sales team focused?
How does technology impact your organization’s culture?
How can you place your bets when everything is so unpredictable?
Amii and I explore it all.

Here are 3 key takeaways from our chat.

1. Sales is harder than ever

The buying process has completely transformed, especially in the past several years. With the shift from face-to-face to remote interactions, buyers expect to engage across 10 or more channels. They do more research without the help of a sales rep. They’re more risk averse. There are more decision-makers involved increasing the complexity and length of a sales cycle. Knowing this, Amii discusses how it’s beneficial to leverage partner channels.


Growing partner ecosystems and capitalizing on as many channels as possible allows you to maximize on market penetration. As Amii discusses, you need technology to do that. What is she looking for from her tech stack? Watch or listen the episode to find out.

2. Buyers aren't buying it without the data

Searching for insights from data is nothing new – someone has always spent time, energy and creativity to uncover trends to support decision making. However, with the evolution of data enablement tools and AI, the right provider with the right data can reveal a treasure trove of actionable insights with far less effort and time. This is one way your tech stack becomes crucial. Not only can you leverage data internally to support and accelerate decisions, but sellers can also share the insights with potential buyers to accelerate the sales cycle forward. Gartner calls this ‘buyer enablement.’



Technology also plays a key role in planning and assessing what lies ahead. Amii discusses how technology can enable you to be less reactive, and make more informed, confident decisions. Watch the episode for a deeper dive into this conversation.

3. Think of tech as a coach

I asked Amii whether she thinks sales technology can negatively impact seller morale. It is reported that the average sales organization has 10 sales tech tools, and plan to add 4 more. Does it become overwhelming? She emphasizes that when introduced to a sales technology, sellers want to know ‘what’s in it for me?’.

Technology should make a seller’s job easier, make them more efficient, and make it easier for them to have higher quality meetings with their leaders. More importantly, tech should help sellers hit their goals. Naturally, people want to be part of a winning team. Look at technology as a coach – another way to facilitate a winning culture across the organization.

Uncertainty is full of opportunity

I’ll leave you with one more insight from Amii. Something we all need to remember as we ride this roller coaster of a market. While a rise in uncertainty and volatility creates a sense of unease, it should not be feared. Look at it as an opportunity. After all, disruption leads to innovation!

Did you know What I Wish I Knew is now available on Spotify and Apple as a podcast? Follow us, so that you won’t miss our next episode. That’s not all – each episode will debut live on LinkedIn. Follow Varicent to get updates on when the next episode will be going live.