Welcome to Season 3 of 10/10 GTM: The Podcast for Revenue Leaders!

Our guest for Episode 66 is Kathleen Waid, a Fractional CRO working with companies like SilentEight, Themis, JUMO, Valid and Solo.one. Kathleen is a sales and revenue expert who brings more than two decades of experience to the conversation.

In this episode, Ross and Kathleen discuss the importance of accountability, empowerment, and measurement in driving execution excellence. They also explore how to motivate teams with clear comp incentives, and why understanding why customers buy and renew is crucial. 

Listen to the episode here, and get the key takeaways from our conversation below.

Accountability, Measurement & Empowerment

When it comes to forecasting, accountability, empowerment, and measurement are crucial. Here’s why: 

• Accountability: Clear expectations are foundational. When each team member understands and commits to specific targets, there’s clarity about what’s expected of everyone. This transparency ensures that each person knows their responsibilities and can be held accountable for their contributions to the revenue goals.
• Empowerment: Treat each territory like its own business. Empowering your teams in this way means providing them the autonomy to make decisions and giving them a platform to be heard. By empowering your GTM teams, you will motivate them while also driving ownership. 
• Measurement: Data is your compass. Use your CRM as the source of truth. It should be the go-to reference for everyone in the organization, with leadership using the insights from it to learn, adapt, and make changes as necessary.  

Questions that will help you hold both yourself and your teams accountable, while also empowering them and measuring their outputs, include:

• Are we hitting our targets?
• Is something not working?
• If yes, how do we fix it? 
• Are we spending money wisely or not?

These questions will help you measure your progress and hold people accountable to what they’ve signed up for and agreed to. This empowers them to redirect their efforts if they’re on the wrong track and course correct. 

“I find that a lot of people stray from the hard discussions, but you have to have them,” says Kathleen. “It’s not fair to the receiving party if you catch them off guard. There has to be this culture and environment where people can say, ‘Yeah, I messed up. And here’s what I’m going to do to fix it,’ because it happens.”

Another key aspect of accountability and empowerment is a method Kathleen describes as “see one, do one, teach one.” The idea is simple: if someone hasn't performed a task before and you possess the expertise, your role as a leader involves demonstrating the task first. You'll show them how it’s done and then the next time, they do it on their own. Eventually, they'll pass on this knowledge to the next person. This way, your team isn’t just waiting to be guided; they know how to solve problems independently and can teach others to do the same. 

Clear comp incentives 

No one likes to be confused; especially when it comes to compensation. That’s why Kathleen’s third tip for execution excellence is to outline clear incentives for your sales and CS teams that are aligned with company goals. When doing this, make sure your teams understand how they will earn money and get paid. 

“A lot of people have a lot of opinions on compensation for salespeople,” explains Kathleen. “But many of those people have never worked as a salesperson.” This disconnect can lead to compensation structures that are not aligned with the realities and demands of the sales roles. When those setting the policies do not understand the daily pressures and challenges faced by reps, they may create incentives that do not motivate the right behaviors or adequately reward effective performance.

When creating comp incentives, think like a salesperson. “Early on in my career, I had a sales leader that told me, ‘Plan your work and work your plan.’ That stuck with me throughout the years,” says Kathleen. “Now when I’m writing comp plans, I am very explicit about outlining what the company goals are, how people will be incentivized to achieve those goals, and I make them very simple and clear.” 

The challenges encountered in compensation planning often revolve around the concept of capping earnings. Some leaders are hesitant about sales reps earning substantial amounts, yet Kathleen argues against this mindset. She emphasizes, “If we paid a person a million dollars, what would we expect in return for the company? It isn't a bad thing if one person earns a lot. It’s good because when you see one person making a boatload of money, you’re motivating the rest of the sales team to behave like that person.” She also emphasizes that when comp planning, don’t lose sight of company goals through some exception process. Pay your reps the full commission they’re expecting, based on the goals they’ve delivered against. 

The ‘why’ behind purchases 

Based on Kathleen’s experience, one of the things organizations get wrong almost all the time is understanding the “why” behind customer purchases. “When I talk with new prospective clients, I ask the sales leader, head of product, and CEO to give me the top three reasons why someone bought their solution,” says Kathleen. “I’ve never had a consistent answer and it’s rare for me to find a company that gives me the ‘why’ from the clients perspective” 

This is a problem because when organizations can’t articulate why customers buy their products, they aren’t able to accurately market or sell their solution in a way that resonates. This means they’re leaving a lot of money on the table. 

To understand the “why,” ask questions to uncover the material reasons why clients actually buy. That’s the foundation of your ROI. For example, if you promote a “time-saving solution,” what specific activities does it save them time on? How does this impact their day-to-day operations? What does it mean for their bottom line? The key is to keep asking questions until you can clearly articulate the reasons behind purchases. Once you have this understanding, Kathleen recommends interviewing five different people in your organization and asking for the top three reasons why people buy your solution. “Everyone in the company should have the same darn answer — if they don’t, engage in some team-building exercises to build consistency around your value proposition messaging.”

About Kathleen

Kathleen is an experienced GTM and revenue leader whose career spans eight startups and 20+ years. As a fractional CRO, she spends her days delivering direct and actionable guidance for all aspects of revenue generation, from marketing to sales, integrations and CS.