Leveraging Technology to Increase Adoption of Win-Loss Insight


Daryl Pinkal:                                            

Welcome to WinLossWeek, the world's largest online event dedicated to win-loss analysis. In this session, I'll be talking about leveraging technology to build an effective win-loss program. My name is Daryl Pinkal and I'm the chief technology officer for Clozd. I recently joined Clozd because I wanted to build world class technology that helps companies better understand why they're winning and losing deals, and then take action on that data to win more. Before coming to Clozd, I spent 13 years at market research giant Qualtrics as one of the founding principle engineers and later building out the product management function there.

At Qualtrics, we were relentlessly trying to figure out how to win more and bigger deals. It was a multi-team effort and everyone had to play their part, whether it was sales, building relationships with our clients or our marketing team, building a vision, crafting a story about the value prop of our products or our support team, our customer success teams providing world class service or our product and engineering teams building high quality products that helped our customers be successful. When we lost the deal, it wasn't a sales rep problem. It wasn't a problem with our pricing, it wasn't a problem with a specific product feature, it was a company problem. And each team really tried to better understand why we lost that particular deal and what they could do to better solve the problem within their own team.

Now, back when we were 10 people in a basement office, it was pretty easy for us to get together over a couple of pizzas and discuss every deal in detail and figure out what went wrong and what went right and what we could do about it. But those meetings didn't really scale with the growth of the company. Over time it became harder and harder for us to be on the same page across the company around why we're winning and why we're losing deals. In my role as product manager, I relied on the voice of the customer to understand what products and product features our customers needed.

I spent a lot of time talking to our customers and to our prospective customers, to better understand how to meet their needs. But as our customer base grew, I simply didn't have the bandwidth to be able to connect with customers at scale. I had to figure out how to operationalize that feedback collection. Problems that I faced at Qualtrics, weren't unique to Qualtrics. Organizations all over the world are finding it harder and harder to collect feedback at scale, and then use that feedback to help drive change. One of the reasons I was attracted to Clozd in the first place was the opportunity to solve that scaling problem through technology. I want to spend just a few minutes now talking about how I'm thinking about using technology to run a successful win-loss program.

What's the objective of your company's win-loss program? We believe at the end of the day, a successful win-loss program increases the company's win rate. Now, as I've talked to leaders in various roles at different companies, I've been amazed at just how many of them don't actually know what their win rate is. They say things like, well, our year-over-year revenue is up by 85%, or we beat our sales quota by 12% last quarter. Okay. But how many deals did you have to put through your pipeline in order to achieve those revenue numbers? Or more importantly, how much higher would your revenue be if you increased your win rate by say 5% or 10% or more.

In order to maximize the effectiveness of your win-loss program, you really need to take a look at your sales pipeline holistically. If your win-loss program doesn't look at your whole sales pipeline, you're probably missing something. You need to take an operationalized look into your sales pipeline. Now, what does that mean? An operational view means that you're programmatically looking at your whole sales pipeline in a way that enables your organization to identify problems or areas where you can improve. You should be slicing and dicing your pipeline data by segments, looking for bright spots and successes that you can expand on. The first place to start building out a successful win-loss program is through CRM analytics.

And CRM analytics can tell you your win loss rates, both current and historical. They can tell you win-loss rates broken down by region, by sales team, by sales rep, by product line, by skew or by customer segment and so forth. You should be able to see revenue you're winning and losing for each of those breakdowns. And then once you have visibility into where you're winning and losing deals, you can start digging into the why. In order to figure out why you're winning and losing deals, you should be going to the source. No matter how much data you've sifted through, your best insight will come from your customers, and secondly, from your sales reps.

Win-loss feedback paired with your CRM analytics, will help you see where your gaps are. As you start to drill into deal data, you'll discover areas of your teams, your processes, your products where your win rate is low, and you can improve. Ideally, you'll be looking at a range of feedback from both buyers and sales reps across deal size region, product line, sales team, tenure, et cetera, et cetera, et cetera. Now, one of the biggest challenges that our customers and even my colleagues have come to me with is simply knowing who to reach out to. Operationalizing your win-loss program means that you're automating the feedback collection process so that you can effectively reach out to your customers and get their perspective on why the deal had the outcome that it did. And whether you're conducting interviews or sending out surveys, you can leverage technology to help automate the process.

Don't do it manually. Integrate with your CRM to pull information on who to reach out to. You can use technology to utilize scheduling integrations to make sure that your team can actually connect. Use transcription software to most effectively use the content from your interviews. There's a lot to win-loss programs, and the more that you can focus on the jobs that matter and automate the jobs that are tedious and time consuming, the more successful you can be. All of the pipeline data and even feedback in the world, isn't going to help you unless it gets to the right people in your organization and they can take action on it.

Well, who needs win-loss data? The obvious answer might be the folks selling your product, right? But it goes way beyond that. Everyone is a stakeholder. Every role in your company can play a part. From the executive team to the product marketers, product managers, customer success, the engineering teams, everyone needs to know why you're winning and why you're losing, and then they can decide how they can best take action on it. So how do you get this data to the right stakeholders? Well, executives are relying less and less on paper reports on their desks these days. I know from experience that today's product managers and engineering teams, are definitely not reading through a stack of paper reports or PowerPoints, so give them another software tool to use, right?

Well, no. So you're probably wondering why the CTO of a software company is telling you not to buy another software across the organization. Well, there was a recent study that found that on average businesses use 37 different software tools or platforms to run their day-to-day operations. Your key stakeholders are already using the tools they need to take action on win-loss data. So rather than give them a 38th tool to log into, you're going to be more effective getting most valuable win-loss data to the top of their email inbox, or popping up a message notification, a Slack notification on their phone.

Before you go inundate everyone with win-loss data, make sure that you're thinking about what data matters to each role and filter your data accordingly. If you're spending all your time putting together a PowerPoint presentation and stuffing all the data about your win-loss program into it, there's probably room for improvement. If a potential customer's talking about a missing feature that's a must have for their business, make sure that that feedback is the feedback that gets to your product team not the feedback about the pricing in the European market. If the pricing in the European market is the problem, then send it to your European team. Or you want to make sure that the win-loss data that you send off goes beyond anecdotal and it goes beyond one-off comments from customers. Make sure that you spend the time aggregating this data both by impact in terms of the number of deals, but also by the total amount of revenue won or lost because of this particular feedback.

If your customers, for example, are telling you that they're not renewing because your support team is too slow, make sure that your support operations leaders are seeing the lost revenue and tying that back to the work that their team is doing. Then lastly, set up push reports that provide your stakeholders the view into the data that matters the most to them. So you're getting the data to the right people, you can just sit back and watch the deals roll in, right? Well, it's not quite that easy. You need to increase visibility, but that's just the first step. Once key stakeholders have visibility into the data, the next step is to set some goals around improving specific metrics. Transparency is what drives accountability, so set up notifications triggered by changes or the lack thereof to the specific metrics they're working to improve, and then send out those notifications to the key stakeholders that can make the changes.

You want to standardize your data across all feedback, regardless of what channel it's coming from, whether it's coming from an interview, whether it's coming from a survey, whether it's coming from a customer or from a sales rep, make sure that you're tracking the data over time and then focus in on the data where you're implementing improvements. Implementing a win-loss program, as you might know, can be pretty challenging. And getting the executive and organizational support is often an uphill battle, especially when the upfront investment is high.

And once your team has implemented improvements and you start seeing a return on that investment, make sure that you quantify those returns in terms of new business, in terms of renewal revenue, in terms of things like ramp times for new sales reps or long-term improvements in sales productivity. Look at customer satisfaction and retention rates, look at incremental revenue that's tied to different product improvements, and then make sure that you're pushing those win-loss insights out to executives and help them understand the value of the investment that you've put into it so that you can continue to build out a holistic win-loss program.

Are you feeling overwhelmed yet? Well, if you need help finding or implementing the technology to run a successful win-loss program, please reach out. Clozd is your technology partner. We're building a new platform now to bring all of this technology into one place to enable you to run an effective win-loss program. I'd love to hear about the challenges you're facing and help solve them together. Thanks.