How have you used win-loss data as a sales leader?

Debbie uses win-loss data both strategically with the executive team to look at trends and the bigger picture, and tactically with sales teams by sharing specific reports and insights. It has become an integral tool in their organizational DNA.

How do you use win-loss analysis at the executive level, and what is most impactful?

Debbie believes a sales organization should have a culture of learning, using win-loss analysis to feed feedback into sales enablement, marketing, and product strategies. Looking at trends over time is important for strategic planning.

When should you bring win-loss analysis in, and what departments should be involved?

Debbie recommends involving the entire company in win-loss analysis, as different teams (competitive, executive, etc.) will interpret and use the insights differently. Applying these insights to strategy is a best practice.

How do you build a strategy around win-loss analysis?

Debbie suggests simply starting with win-loss analysis and treating it as a strong, third-party voice of the customer. The feedback should be taken seriously and used to inform company strategy.

How do you share win-loss learnings and ensure insights are acted upon?

Debbie shares insights through quarterly executive reviews and ad hoc sharing of specific interviews or reports with sales leaders. She emphasizes open communication and alignment across teams.

How do you use win-loss insights as part of the overall strategy, and what advice do you have for others?

Debbie advises feeding win-loss insights into the overall voice of the customer program and making them visible across the company. This helps teams understand their impact on customers and informs roadmap prioritization and strategic planning.

Dropbox Global Head of Sales on Win-Loss Analysis and the Buyer Journey

Q: What has surprised you the most about doing win-loss analysis?

Debbie was surprised that what customers reported in win-loss interviews often did not match what sales reps logged in the CRM system, which was enlightening and led to actionable improvements.

The content highlights Dropbox's Global Head of Sales discussing the importance of win-loss analysis and understanding the buyer journey, while promoting Clozd's AI-powered customer feedback platform and solutions designed to uncover reasons behind sales outcomes and reduce customer churn.

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Global head of sales leans on win-loss analysis to help her org improve the buyer journey from Clozd on Vimeo

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Global head of sales leans on win-loss analysis to help her org improve the buyer journey

Debbie McClure

Global Head of Sales

Debbie discusses the importance of getting to the root of why people choose to buy or not buy—and how win-loss analysis adds critical context and depth to her company’s internal CRM data.

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In this interview, Debbie McClure, Global Head of Sales at Dropbox, discusses how she uses win-loss analysis to inform sales strategies throughout the buyer journey. With 20 years of experience at Cisco Systems and 3.5 years at Dropbox, Debbie emphasizes the importance of understanding why customers buy or leave. Win-loss data plays a crucial role in shaping company strategies across sales, marketing, and product development. Debbie explains that she uses win-loss data both strategically with executives and tactically with sales teams. A key insight she gained is that what customers report doesn't always align with what sales reps log in CRM systems, leading to actionable improvements. She stresses the need for a learning culture in sales, where failure and feedback inform future actions. Win-loss data helps identify trends over time and drives company-wide strategies. Debbie believes that every department, not just sales, should be involved in win-loss analysis to ensure insights are shared and acted upon. Lastly, she advises companies to treat win-loss analysis as a critical part of the voice of the customer, feeding the data back into strategic planning and roadmaps. Regular executive reviews and open communication ensure that everyone stays aligned on customer needs.

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Q&A

Clozd: Today we're going to talk about how Debbie uses win-loss analysis in her role as global head of sales and how she's implemented it in different parts of the buyer journey.

Debbie: First of all, thanks for having me. Like you said, I lead global sales at Dropbox. I've been at Dropbox for about three and a half years, but I have a long history in sales and sales leadership. I actually spent 20 years at Cisco Systems prior to coming over to Dropbox. And in the sales world, the buyer journey and customer sentiment are everything. So it's all about the customer and understanding why customers buy, why customers don't buy, why customers stay with you, why customers leave you. That really needs to be at the heart of every strategy, not only sales, but sales enablement, marketing, product. It’s a company strategy, so it's super important to shape how successful we are.

Okay, I love that. In this journey as a sales leader, how have you used win-loss data?

‍ So I use win-loss data a couple of different ways on an ongoing basis. The first is looking at it strategically as an executive with the executive team and taking a step back so we can really look at trends and the bigger picture. Then there are times I'm just looking. A report comes in and I'll take a look and I'll do a screenshot, send it out to the teams, ‘Hey, why did we say this? Does this person know this? Can we train folks on this?; And so it's just a tool that has become part of our DNA.

The way you think about win-loss is probably much different than a sales rep. What has surprised you the most about doing win-loss analysis?

Oh gosh. Okay. So when I started doing win-loss analysis, I think what surprised me the most was that what our customers were saying was not what our reps were putting into our CRM tool, so it was really enlightening. I'm like, ‘Whoa, wait a minute.’ So I thought this all the time, and it's really this, so I think that's what surprised me the most.

Okay. Stepping back, looking at win-loss analysis at your level, how do you use it? What's most impactful to your organization as you share it out?

I think that any culture in a sales organization should always be a culture of learning, and because you have to fail fast and learn from it and go to the next, and salespeople have pretty thick skins because you have to hear ‘no’ a lot to hear ‘yes,’ right?

Or they don't last very long.

Yeah, exactly, and so I think that really feeding that analysis and the feedback into learning and evolving as a company is paramount. So into sales enablement, like I mentioned, marketing, account-based marketing, understanding at a higher level to take a step back, what are the trends? So if you did implement different enablement points or marketing, are the trends changing? So I think it's important for you to look strategically over a period of time, versus myopically at a point in time. It needs to really be an evergreen strategy. That's a company strategy, I would say. Sales is a team sport, so it's a company strategy.

Is there a specific point when you should bring win-loss analysis in? Or what departments should be involved in win-loss analysis?

‍ The company should be involved in win-loss analysis. I think that there are multiple conversations in win-loss analysis, so I think that the competitive teams are going to look at it differently than the executive team. So the importance of being able to either zoom in or zoom out and really understand what the win-loss analysis is telling you, and then apply it back to the strategy, I think is really a best practice.

Could you share any examples or ideas to help others that are looking to build this out? How do you take it and build a strategy around it?

Yeah. Well, I think first of all, just do it. And then you use the information as the voice of the customer. It's a strong voice of the customer because it's a third party. It's not you asking that customer where maybe the customer's a little guarded, but it's somebody that the customer's comfortable talking with, so it should be taken very seriously.

In your role, how have you found it's best to share these learnings with other people and to make sure these insights are acted upon?

Yeah. Gosh, I do a couple of different things. I think that it's important on, say, a quarterly basis, to have an executive team review and look at insights and trending and themes, and have a qualitative discussion based on the facts and data. And then there is the, I'll get an email of a certain interview or something and I'll just click in and say, ‘What's going on?’ And then I send it off to my sales leaders like, ‘Hey, why didn't we do this or that?’ And so that's always fun. But it really just depends. I use it in so many different ways, and then my teams are using it. My team, the sales teams, are using it and they want more interviews. I'm like, ‘Wait, hold on. What are we doing? What are you guys doing in that?’ So I’ve got to make sure we're all aligned, but it's something that the sales team really, really appreciates and loves.

One last question that we’re curious about. In your role, how do you take win-loss insights and use them as part of the strategy? At the executive level, what are some ideas that you could give to others looking to bolster their programs?

Yeah. Well, I think it's an important voice of the customer and input into an overall voice of the customer program. There are so many people, in sales, we're so fortunate to talk to our customers every day, but there are a lot of people across the company that maybe don't talk to a customer every day, and they love hearing these insights, these verbatims, because it gives them a better idea of either what they're building or whatever their role is within the company, what impact they're really having on our customers. So, just feeding it in and giving visibility to the company, feeding it into the strategy to roadmap prioritizations, like I mentioned, is really the heart of what win-loss is.

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