Learning to Address Increasing Win Rates and Real Time Buyer Engagement with Alastair Woolcock


In his presentation, Alastair addresses the challenge of win rates and how to engage with buyers. Alastair further shares how to meet the need and solve the problems of buyer engagement before we ever get there.


Alastair Woolcock is Chief Strategy Officer at Revenue.io, an AI-powered RevOps platform that delivers real-time guidance in the moments that matter. Alastair is a growth bets and growth strategy expert and a public speaker.


“We always want to present using relevancy, simplicity quantification, and then make it shareable, aligned to the task and the differentiators. That’s what buyers need.” 

“Simply ask yourself, What’s your sales process today? What’s the customer buying tasks? And where do you have gaps or stall points? Those stall points are where we can create moments. Those moments to enable buyers is what actually increases win rates.”

Key Points

  1. It’s not your sales process. It’s a task process. And it jumps all around asynchronously.
  2. The irony here is to sell more, you need to sell less
  3. The future requires us to focus on helping buyers buy, not just our salespeople sell


Win rates continue to be a top challenge for every organization sales professional around the world. And we are spending more on sales technology now than ever before. And yet how do we engage with the buyers? What’s that look like? How do we do it in real time and how do we improve without just spending, spend, spend.

I’m Alastair Woolcock Chief Strategy Officer at revenue IO. And today, let’s address increasing win rates and look at this notion of real time buyer engagement.

The first thing I want to look at here is demand generation specifically, it’s absolutely and continues to be a top priority. In fact, 72% of all sales organizations would love to improve their pipeline. And of course, who doesn’t want to improve how they’re engaging with their accounts? 65% say that’s important, another 62% Say, hey, really running a more account-based strategy is critical to where I’m going in the future.

So, across the board, this is a Top initiative on all fronts. Those are the big three items. But you know, it’s also important to understand, well, what isn’t top of mind right now?

Well, I’ll tell you what the two bottom things are. If 74% of heads of sales are going look, please don’t come to me and tell me I have to completely change my go to market strategy. I don’t have the time, I don’t have the temperament, there’s too much already going on in the market. I just need to sell more. I need to win more. And by the way, if somebody else phones me up again, it says they got a new AI tool that helped me change the world and my win rates and my demand generation. They don’t want to hear it. So that’s the world. That’s where we live right now. Demand Generation is top priority, adding just tech for tech’s sake and AI and changing the models are not a priority. And so, you look at that landscape. We know that people need to change but it’s hard for all of us that are out there selling right now. It is very hard.

It’s hard to sell but you know what’s even harder, it’s harder to buy.

Remember, for sales professionals you’re doing it every single day. Demand gen specialists are doing it every single day. But buyers don’t buy every day. They buy very inconsistently. There’s an assumption that they know what they’re doing. There’s an assumption they know how to buy, that they know the steps, they know the sequences, they know the tasks that they should take on. And if this isn’t bad enough, where it’s hard to sell is hard to buy. And unfortunately, it gets even worse. Because of the complexities of buying, buyers are using all kinds of digital assets and going all over the place, and they actually are not spending a lot of time with sellers with vendors. In fact, only 17% of the entire buyers sequence statistically is the amount of time that they will spend with a vendor. And if that doesn’t frighten you enough at all vendors.

So, if you’re competing against three other companies, you’re getting right around for a little bit over 4% of that time. And then on the other side, you know we’d sit there and wonder why on earth, two thirds of reps are missing quota, two thirds. In fact, 1/3 generally are between zero and 50%, another third between 50 and 80% and then your top third makes it over 80. It’s a huge amount of cost. For people that aren’t engaging with buyers very effectively. And when they are, they’re missing the moment. The buying groups on top of this continue to grow and scale. In fact, deals that are below 1 million today you realize there are over seven people on average involved in that decision. If you sell things that are over a million dollars, that number gets as high as 13. And 77% of all buyers say it’s actually really hard to buy from a vendor. That’s one of those mind-boggling moments because I don’t think there’s anybody there’s a demand gen specialists that will never sit there and say you’re trying to make it difficult for a buyer to buy.

But are we really enabling them to buy? Are we just trying to produce more content, more channels, more volume of information, in hopes that we can cover enough people that they’ll buy from us? That’s not the answer, that isn’t what’s needed. The future of this requires us to focus on helping buyers buy, not just our salespeople sell.

So, let’s see how we do this. First of all, this would be a pretty common pipeline for any of us. You’d say there’s going to be a problem identification all the way through to the solution to now requirements on to the supplier and yes, we know they need to validate things and then they got to create agreement in the organization. That’s pretty normal. These are all things that need to happen as somebody buys a product or service. And across this of course, you’re there you’re thinking the buyers thinking about this is a bunch of tasks I got all of these things I have to get done. In demand generation sales we tend to think of this as Oh, I got to go from step one to two to three to four to five. Our forecast meetings, that’s how we think about it, as our CRM tools default our thinking but that’s wrong because that’s not how the buyer thinks. the buyer doesn’t phone up to say Oh, thank you Susan, the rep. Thank you for calling me today. I happen to be at the requirements building stage of solving this problem.

They don’t talk like that. They don’t think like that. They just think I got all these tasks to get done. And then across that I got to get a bunch of people inside my organization aligned to actually solve this problem. As a buyer. As a buyer, I have to deal with all of these buckets. I got to organize all these people. It’s like a really horrible game of telephone. Remember that kid’s game we all used to play where younger you pass a message from person to person around the circle, buyers are trying to figure out and if you aren’t helping them with each of those tasks every single time.

Again, good quantifiable helpful advice. Do you think that message is going to sound like when they get through person number seven or person number 13? Probably not what you hoped. As soon as we look at this, when you start to think about this is a series of moments, tasks and activities and experiences. And there’s four big buckets: the problem, the solution, the requirements and yes, the supplier you it’s okay to think in those buckets. But just think of those jobs within those that need to occur. And they require continuous validation all the way and they can try to create continuous agreement with the buyer all the way. And so, as we kind of blow that apart. I know this looks horrendous, but you have to think in terms of these bidirectional flows. Don’t think linear. Think of how all these distribute distinct moments of guidance and enablement of learning.

When we look at how we create our outreach and our inbound strategies and all that we add the customer engaging How are you applying hyper personalization to help them see the problem for their role, their industry? How are you helping the buyer engage to many different channels using many different assets? Not exclusively, always getting on the phone and then when we are on the phone how you are guiding them effectively in that moment. Not just saying I got them on the phone, job done all the way through this right info right time is what we’re looking for across the stages and this requires real time data synchronization, it requires us to think in these buckets.

So, I’m going to break this down really very tactically for you. As an example, when you keep our four buckets and we’re going to go through what are some things we can do, some tips and tricks if you will. So, when you think of the problem identification stage, when you think of the buyer what they’re trying to do is verify all of these things from the vendors. Think of what’s happened at this point, they agree they have a problem. And now they’ve gone and talked to third parties, they Google things, they search things, and they’ve come up with a shortlist of people that they think might be useful. Maybe you’re the first person they contacted, maybe you’ve helped them identify the problem, but they’re still going to compare the market and think about that every single time they go compare you and other vendors, what’s every vendor do? What’s every demand gen team do? Here’s our differentiators and solving the problem our way is better. And you may be right. But that poor buyer is still trying to figure out well you’re all telling me kind of different ways to solve the problem. I’m not sure which one I should choose.

So, they’re trying to confirm the claims of what’s going on. And they’re trying to quantify the benefit of an action versus inaction relative to you as a vendor. So, the vendor’s response here, the demand gen response here is really about how do I organize this problem and this issue around the role and function. Well people are tasked with solving big problems for organizations’ individual jobs and individual buyers look at it from their role and function predominantly. Far from procurement specialists who are tasked with looking at a variety of issues to sort out the pricing which happens downstream. The initial buyers’ line of business buyers often are looking from their lens, their vertical, their role, contextualize and help them understand that and see the problem in the light. From there of course, then the buyer wants to learn from their peers. So how do you help them explore and coordinate other things? And I’m not talking here about those checklists that we all hate. You know, the ones where people put them up and demand gen specialists for that are going well. Here’s our list. Look, I have five more checkboxes than all of the other competitors therefore I’m better. I have five more features therefore I’m better. Throw those things away. Help them understand what others are doing in their network in their market, amongst their peer groups.

Be a value, be of service.

Remember, they don’t buy every day, but you sell to those industries and similar personas every single day. How are you bringing them together and helping them explore and learn and understand from one another? Demand Generation and selling is networking. Help them do the same. And then as you’re doing that, of course we’re helping them compare a network and of course you’re helping them narrow down the field. Now that’s tricky because we want to go well us, us, buy from me. Fair enough. But don’t get too ahead of yourself on the selling. This is about enabling a buyer, in fact, challenge yourself not to sell and solve efficient solution exploration stages.

Challenge yourself to actually just help the buyer analyze what’s going on. And narrow down the scope so they can make an effective decision relative to the first step which was the problem then from there. It’s going to be about the validation that requirements and how we’re what are the things that they absolutely need to get done? Not all the things they must do relate to the problem they’re solving for because at this juncture, they’ve been bamboozled by clever marketing and clever selling.

So, if you overload the choice and scope and the problem, all you’re going to do is actually lengthen the sales cycle. Or worse, you open it up to even more competition. So, the irony here is to sell more, you sell less, and we sell less, and we validate it with the bottom point which is super key quantifiable data. Selling based upon opinions, demand generation articles without quantifiable evidence, are not of use to buyers. Be ruthless in your use of data and quantification. And then ultimately, how do you help them understand well, what’s this going to look like? And how long is this going to take me to get value? You know the pandemic really changed that landscape. You know, we used to be able to get away with value equations that were 12-18 months.

Now if you can’t prove value, cost of revenue reductions, key metrics like that, in under six months, ideally under 90 days, you’re going to be in trouble. And inside that, that means you better help the buyer understand the implementation, the security ramifications, all of these other things. Those aren’t necessarily value-based steps. They are differentiators. They’re the realities of buying and a task they have to go through. Bring those forwards in your demand gen and sales cycles, and you’ll shorten them, you’ll win more because you’re giving the buyer confidence this can be done and confidence that they can achieve solving their problem. And you see down there I put down there as an idea to be proactive on security.

Do you realize that 67% of the time vendors and buyers overlook security and I’m not talking here to be clear, hey are our product is sec SSAE compliant, sought compliant yada yada all these things are HIPA compliant. No, no, no what’s the causality of putting your product or service in that buyer’s environment? Not just you build a wonderfully secure product, but what happens, the ramifications, what happens to IT and operations and all those other key stakeholders and systems and applications? What’s that look like? That links back to the implementation. So, this is just a sample we could spend hours here mapping this all out but think of these functional tasks of what buyers need to do. And that’s how you help them and then you map it into how we present this, and we always want to present using relevancy, simplicity, quantification, and then make it shareable, aligned to the task and the differentiators. That’s what buyers need.

Now, then, I’ve got a sample down here for you of things that you can use right from self-driven demos, implementation guides, we’ve discussed short form videos, there’s a variety of ways in which we can aggregate and use these things but do think of assets based upon buying tasks.

Now we have one more big thing to do here. And this is how we engage, and this is an example of the moments when you’re in that conversation in those critical moments. How do we help ensure the right message at the right time remember I said the guidance piece is key here. Guidance from demand gen to the seller to understand the buyer moment the buyer tasks, whether it be a conversation, a pricing thing. Maybe it’s interruptions with questions that they’re asking, and the reps don’t know, how are you guiding them in that conversation to be better? So, remember, most of those conversations are not valuable and sharing the right assets based upon the buying task, i.e. implementation or security guides. That’s critical.

And then finally, this. Let’s look at the channels and how we help them buy across multi channels. I will forewarn you this is a doozy of a slide. Here you see again our standard sales stages at the top going from problem all the way through supplier selection and consensus etc. But then look down the other side of the vertical axes we have a bunch of different ways of engaging. This is really important for demand gen right as we know we got our marketing efforts we got our websites you know we have sequencing and dialers and digital selling rooms we have then way we’re texting or maybe we’re using video to connect all of these other formats. We got the salespeople themselves as the seller moments.

And then of course we have all of these microsites and other things we’re going to build out. Now, this wouldn’t be terrible, if we were only selling to Bob, and Bob comes along, tracks on he sees our marketing campaign goes to our website, then he starts talking with a seller further down, then eventually nobody’s losing some digital assets and then he’s coming back and working with the seller again. That’s how the primary engagement model works. And that’s what most of us drive demand around. But the reality is that Bob, our buyer, is also doing a bunch of secondary things. He’s jumping over to the website throughout the buying journey. He’s moving in and out of different sequences. Boy, he’s jumping around different omni channel engagement mechanisms. He’s going up and down with the seller and if that isn’t bad enough, remember, it’s not just Bob, is it? If you remember how many people I said earlier, when we sit there and we see today, seven or more people for a million deals a million and below 13 for Million and above. And then these additional buyers and influencers aren’t following Bob’s track. They’re coming in at different moments of these journeys.

My finance team is probably coming in around my supplier selection, wouldn’t it be great if they just met with the seller and learned everything, but they don’t? They’re going to start with the digital sales room. They’re going to look at certain sequences of activities, I’m going to jump down to the microsite. And by the way, from there, they’re probably then going to go over to Okay, well now talk to the seller, see what’s going on. And by the way, I had the rest of my buying committee, the other six folks, who came in somewhere around solution exploration to requirements building, and they’ve jumped all over. They’ve been looking at our digital assets and they’ve been reading marketing content. They’ve been jumping to digital selling rooms. And so all of this requires orchestration. This is the future demand generation, and you have to be able to enable the key moments that we can influence. So, all of them, their critical moments. And those are unique to each of us- every vendor. And if you’re wondering how we decide, simply ask yourself, What’s your sales process today? What’s the customer buying tasks? And where do you have gaps or stall points? Those stall points are where we can create moments. Those moments to enable buyers is what actually increases win rates.

So, as I wrap this up, it’s all about meeting the need. But meeting suggests that whenever we meet the moment, we’re rising to the challenge. I’d rather you actually meet the moment. Solve the problem before we ever get there. Think of the moments, the experience and the tasks. The moments in terms of the interaction are limited. And we must focus on the buying task on that journey, the experiences multichannel think about how you’re driving demand and organizing all those steps finding where you have the friction stall points. And then remember, it’s all about a series of tasks and buying jobs, to your customers. It’s not your sales process. It’s a task process. And it jumps all around asynchronously.

Thank you so much. Here’s some summary recommendations, which you can read offline. I’m happy to talk with any of you in the future. It has been a pleasure to meet today. I hope that gives you some quick insights around how we improve win rates where the market is at and what we mean when we talk about buyer enablement.

I’m Alastair Woolcock, Chief Strategy Officer of revenue IO. And let’s crush every moment in real time going forward.

Thank you so much.