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Today I want to talk to you about building a data-driven win-loss program. But before I get stuck in, here’s a little background on me.

A bit about me

I’ve been at Toast for about two and a half years and I lead the product marketing, market insights, and partner marketing teams.

During my time here, Toast has gone from about 500 employees to over 2500 employees - it's been quite a ride. I joined to help the company scale its product marketing team; initially, product marketing was two people, one of whom had done product marketing before, one of whom had not; our team is now 20 strong and growing.

Beforehand, I joined EnerNOC as their first product marketer and grew the product marketing team until we sold the company. I also enjoyed an amazing year leading their enterprise sales team.

For those of you who are product marketers and who haven't had a chance to work in sales, I highly recommend it. I've done it twice in my career and it’s made me a much better product marketer.

Early in my career, I got my first job out of college in sales but also did competitive intelligence and pricing and these are really important parts of product marketing, too. So that's how I got into product marketing in the first place.

At Toast, we work with restaurants and they're a super fun customer base to work with. We get to interact with our customers daily, sometimes three times a day: breakfast, lunch, and dinner. We also spend coffee breaks with them too, but this depends on your caffeine habits.

As a result, I talk to both customers and prospects, whilst interacting with my product, as well as with competitor products every day. What's interesting about it is it's an industry that's changing quickly.

Most restaurants today still operate with a server in the back room of the restaurant and they're on technology that's 10-15 years old.

How are you all interacting with restaurants? How many of you all have ordered with a mobile app in the last week?

Starbucks’ mobile order-ahead, for example, has become a daily part of our lives. Therefore, a lot of what we do is we help restaurants adapt to that environment. We're teaching them about how consumer preferences are really changing their technology needs and then trying to help them take advantage of the tools that have been used in a lot of other industries for a while.

A bit about Toast

So, let me give you a little bit of information about Toast.

We're growing about 150% a year right now and we're hiring about 100 people a month. We've been around for about six or seven years, depending on whether you're counting from the first customer or when the founders started thinking about it.

Our headquarters is in Boston and we're just starting to get to the point where when I say, "Hey, you guys know what Toast is?", people are starting to say, "Yes". That's a fun place to be in as a startup pre-IPO stage and we're growing faster than almost any company out there.

So, if you think about it, there are some unique challenges for a product marketing team in this kind of environment. The vast majority of our sales team’s been here less than six months and we're growing fast. We were the fastest to 100 million among SaaS platforms that have gone public recently. It puts an extra strain on the programs that you're putting in place; I'm telling you this to give you some context as you think about what a win-loss program in this kind of environment might look like.

Typical challenges with win-loss programs

We had a lot of challenges when I first joined Toast around win-loss, and I wonder if anyone reading this is currently experiencing these challenges, or has experienced them previously:

  • At your company, understanding why you're winning and losing is driven by anecdotes or opinions.
  • Salesforce data isn't clean enough to use.
  • Win-loss fields don't make sense or aren't used.
  • Salespeople aren't motivated to fill out win-loss notes or reasons.
  • Sales notes have good info, but it's overly manual to get at it.
  • Win-loss calls are ad hoc, not done or only done by sales.
  • Your team or whatever team is responsible for this isn't trained on how to do win-loss calls.
  • Wins are communicated and celebrated but not losses.


While I'm not here to give you the magic solution, I can say that we had every single one of these challenges at Toast when I started and although we still have many of them today, we still have a successful win-loss program. So remember, there is hope.

When I joined Toast, what do you think our number one competitor was? It was 'other', and then Square. And then our number one loss reason was also 'other'. Okay, so one of the things we've done, and this is my first tip, is we took 'other' away as an option. We had a whole program to kill 'other'.

What key things make a great win-loss program?


Number one is buy-in. We didn't start with this amazing top-down buy-in where the executive team said, "Yes, here are all the resources to go do win-loss". Rather, we gradually got it as we got some small wins under our belts.

We also didn't ask permission. I've seen the power of win-loss before, so I never went out and said, "Hi, can I please call your customers and your losses and ask them questions?". Instead, we just started calling them.

This approach doesn't work if you're only doing 20 enterprise deals a year - don't do that. But we're in an SMB market and we do thousands of deals a year or tens of thousands of deals a year, so if we mess one up, it's low impact and doesn't matter too much.

However, always look at the risk profile of your company. In our case, we didn't ask permission, we just started doing it and that might work for more of you than you think.

Quantitative data is really important. This is because it tells you what's happening and where, what segments, what competitors, what markets, and it also tells you whether what you're doing is working. However, it doesn't tell you ‘why’, so that's why you need the qualitative side too.

So you need buy-in, that quant side and you need qualitative because, with quant alone, you'll never answer the question, ‘why?’. I'm going to give you guys the tools and tricks to build this. No theories, just what I did - the spreadsheet I pulled, the email I sent, so that hopefully you can take one piece of this and use it when you get back to your offices tomorrow.

How we built it

I boiled it down to eight things - it just happened to be eight, there's no magic number. Firstly, we did all the manual work which starts with pulling a Salesforce report. We aligned on categories and metrics:

  • How are we going to categorize things?
  • What are the metrics we're going to measure?
  • How do we know if we're being successful?

We got really deep in Salesforce and we spent a lot of time with sales. No question there. We called a lot of customers ourselves but we also needed extra help, so hired a win-loss firm. We're going to do it again next year and that'll be in my budget forever. We did automated surveys. Then, of course, we used all of this information to generate insights and enablement. And then we shared the results every week, every month, every quarter, for the last two years.

The manual work

Here’s how we started the manual work:


This phase started with the conversation of, “the Salesforce data is really, really messy, and the sales reps don't fill out the categories right, but we did have a lot of good sales notes”.

That was the one thing we did have and this turned into a game of chicken between myself and the founder. I said, "You know, we’ve got to figure out this category first, then we need to update Salesforce and three months later, I can give you the results".

And he said, "I dare you to sit in a room with me and read them all. And then we'll know why we're winning and losing". And I said, "We do thousands of deals a month." And he said, "Yes, we do". On a Friday afternoon, I sat in a conference room with the founder of Toast and we read hundreds of opportunities.

We started to see that there’s a lot of great stuff there. For the first six months of our win-loss program, we read all of the wins and losses, every single one; there were 1000s of them, and you can do that too. It was the best education I could have ever gotten into Toast; it told me why we were winning, why we were losing and what was happening in our market. It was time incredibly well spent. It was sometimes painful, but it was time incredibly well spent.

What we started doing was recategorizing things. We said, "Hey, this last note says we lost to Square, but the field says we lost to TouchBistro". And so, we started creating our fields. Then, we mass uploaded all of our manually corrected opportunities into Salesforce. This gave us a quarter of good data to start with and we learned what was actually happening, what win and loss reasons potentially were real, giving us the confidence to kill 'other'.

So, our first job was to beat 'other'. We did that because we had done enough digging to understand what was really happening. As a result, we didn't need to have this category of, "Oh, I don't understand this about my market yet", because we knew what sales were saying. That was how we started.

Any of you reading today could probably download your most recent 10, 100, 1000, whatever is relevant for your closed business opportunities, and start reading.

Aligned on categories & metrics

Secondly, we said, “Okay, based on all of this learning, we aligned on categories and metrics, how are we going to categorize everything?”


For win and loss types, that's like the highest thing in our hierarchy, you can be five things at Toast. You can be a win - it's actually the simplest one. We can lose you to a competitor - i.e. you chose someone else. You can be lost to upgraded existing - that's a weird phrase and I will tell you why we needed that because we did four different names of that category. No-decision, or ghosted - the prospect just stops picking up the phone, returning your emails and you don't know what happened. Lost a competitor means they actively chose someone else. And the difference between lost to upgraded existing, and no-decision is that an economic buying decision was made and money was spent.

If you upgraded existing, you spent money to upgrade your existing system. If you decided to just stay with your existing system - status quo - that's no-decision. That's a really important distinction for us because one of the things my team is tracking closely is how many decisions are happening each year in the market. After all, we think that's our limiter to growth in the medium term.

For example, let’s say there are 700,000 restaurants in the United States, and about a quarter of them are buying every year, we actually know how many decisions are being made every year. Moreover, we know how many decisions we're in, wins plus losses plus upgraded existing, that's how many decisions we're in. Then, we can compare that to the total market, and so this is the kind of stuff that we're tracking from a win-loss perspective.

Then we took the top 10 loss reasons for each, and they're different whether you lost to a competitor, lost to existing, no-decision, ghosted, and coded them in - you have to pick one, and then we have fields.

We also did another thing, which is, as we got maybe six months or a year in, the product team said, "Hey, we're not losing based on product features enough. And so we're not getting good enough data". So we added another field that's like, even if you say, "Oh, I lost on price", because every sales rep says they lost on price, right? We also said, "Okay, were there any features that were important too?", so they also added that.

I'll talk about why we still use Salesforce coding for this, we also do win-loss calls - they're important, they're both important. And then, of course, things like competitor segments. The other really powerful thing we've done is we've said, we're not relying only on sales to make sure our data is clean.

We've brought in a bunch of external sources to complement our Salesforce data and integrated with third parties like Yelp. Also, we have offshore teams calling into restaurants updating things like what kind of restaurant are you? What point of sale are you using? That basic information is really clean and we think we have the best database in the industry; it's become a real competitive advantage for us from a win-loss perspective.

As far as metrics are concerned, we said we're going to track all of this per ramped rep. So per ramped salesperson, so a person who's out of training. For us, it's really important because we have so many reps in training every month, every quarter, so wins, losses, no-decisions, and ghosts per ramped rep. When we give you 15 opportunities a month:

  • How many of you turned into wins?
  • How many turned into losses?
  • How many are no-decisions? And,
  • How many have ghosted you?

This is crucial: For a competitive win rate, it's what percent of those decisions - wins plus lost to competitors, plus lost to upgraded existing - did you win? So, of all the decisions you were in, how many did you win? And then opportunity to deal conversion is of all the opportunities, including ghosts and no-decision, how many did you win? Because guess what a no-decision is? It's someone who the salesperson didn't show enough value to.

Maybe we could have gotten a decision out of that, perhaps we could have turned that into a buying opportunity, so we're not ignoring those. And we've found through our work that about half or more of the ghosts bought something, just not from us.

Got deep in Salesforce with sales

So we made all these beautiful categories. We had done our homework, we had read everything, we had talked to sales reps, we'd got feedback. We've put it all into Salesforce and we automated it. Everyone must fill this out and then the manager must review it. It's controversial, but we did it. And part of how we did this is we shared the why a lot.


I go around to the sales team twice a year, we go to all the different regions, we do training, and I get up there and I say things like, "I read every single one of your sales notes". I do, I still read most of them. I get an email every time we win a deal. And I get an email every time someone fills out a why not Toast. I read them. I read them all.

I tell people that and they're like, "Oh, really someone's reading my sales notes?". And you know, people take it seriously, if you tell them they’re using the data, and we show them the results. We say here's the graph of your territory. And here's how many won and lost and why and what's going on and they're like, "Oh, wow, this is like real", so people start doing it if you show them the results and we show it to them at the RVP level, the district manager level, and the rep level, we share it back out and so they're like, "Oh, this is real data, we have to fill it out", and it helps with the quality. And then also tweaking it and getting feedback on what's working, what's not, and changing all the time.

We called wins and losses ourselves

Then we started calling wins and losses ourselves and we created an interview guide for the teams, it's kind of a basic one that they can work off of. But then every product marketer in the team focuses on a product line pretty much and so they're usually working on some project. And so part of this win-loss program is just part of their day-to-day work.


So I'm preparing for the launch of a new product. I make sure I do win-loss as part of that and then that counts towards their quota. So everyone in product marketing has a quota for how many win and loss interviews they have to do per quarter, and how many sales ride alongs they have to do per quarter to make sure they're out talking to the team.

At my last company, it was an enterprise which is harder, because it's harder to get in touch with the C-suite buying decisions, at SMB the team crushes through their goals, it's really easy. But in both environments, we set quotas and found that’s helpful to keep that discipline up.

And then we do a monthly dashboard of what's happening in the business. And the insights from these become the 'why' behind that dashboard. So we're seeing this trend, we're seeing this competitor spike, we're seeing us winning or losing more in the segment, and by the way, I did three interviews this month about this so here's some of the why behind it. So it's really helpful to bring that context and that credibility to the product marketer.

We called in pros to help


We have a third-party consulting firm that does about 20 interviews for us a quarter and we pick themes each quarter based on what we're seeing in the data. We go quantitative first, we say, "Oh, gosh, this one competitor is starting to spike in our market", or, "We're seeing no-decisions go up", or, "We're seeing in this specific segment we're not going doing as well as we think".

We pick a focus area every quarter and we give it to the pros and they do 20 interviews. This does a couple of things for us. One is, it gives us scale. Realistically how many of you reading have free time? Extra time in your day? Product marketers are busy. And in a high growth company, we're always a man down because we're always hiring. So we actually always have more budget than we're able to spend because we're always hiring. And so we just need that extra bandwidth. That's the number one reason we do this.

The number two reason we do this is that we can get an unbiased view. We try to tell the product marketing team 'don't ask leading questions, be unbiased, ask about their process'. But everyone comes in with an angle, you try hard not to but you can't help it. It's your product, you care about it. Having an unbiased interviewer is helpful to make sure we're getting the real answer as to what's happening.

I've heard people say, "Oh, people are more willing to talk to a third party than to a product marketer". I found as long as you open your interview with 'I'm not from sales', then the guard goes down immediately, and they'll talk to you, they'll tell you anything you want to hear as long as you open with that, we actually have had better results getting people on the phone as Toast than the third party has.

And then they also do a lot of work. So they're doing the quarterly presentation, they're putting the themes together, they're helping you with the 'why', it's just that extra bandwidth that’s helpful.

If you think about the costs of this versus hiring another product marketer, it's usually more efficient to outsource this at least in part, so I wouldn't hesitate in doing that.

We automated surveys - why not Toast?

So we have an email called ‘Why Not Toast?’. This is the HubSpot screenshot of an example.


We took those same loss reasons that we had from sales, and we put them in here and then we put a free text field. Everyone fills out the free text field. Everyone. They'll have a strong opinion about Why Not Toast, I guarantee you, they have a strong opinion about ‘Why Not Your Company?’, too.  

I get a handful of these a day come through, and I read them and then they go into a report where we can go through and we can slice and dice and say our customer's saying, Why Not Toast the same loss reasons as sales is saying Why Not Toast, and it's a good check.

We can actually go back and match the Salesforce opportunities and say, "Hey, salesperson, you said it was pricing, but they said it was this feature." So we can create that feedback loop. We aren’t great at that feedback loop yet, it's one of my goals, but we can do it. So this is something that goes out to every single lost deal. We get enough of these back that it's valuable. This is so easy to do. This is one of those things that I would do tomorrow if you don't already have this in place.

We automated surveys - deeper dive

Okay, and then we also conducted a 20 question survey. This works for us because we have a lot of volumes. So we used to pay 25 bucks per survey until we got a good amount completed back. Now we do a monthly raffle for a $100 amazon gift card.

We ask 20 questions to the same group. They've received the ‘Why Not Toast?’ survey and whether or not they fill it out, we email them again. And we say, "Hey, you can enter this raffle for 100 bucks if you'll answer our 20 questions survey".


The 20 questions basically cover, did you buy something? So the first piece of data we collect ties back to those categories I talked about, we collect that same information, and we found out things like the ones that we think we lost to a competitor, 80% of the time that's true. Of the ones we think it's no-decision, 60 or 70% of the time, it's true.

We can go back and check and see what we thought and what actually happened. We asked them who they bought and how much they paid - so we got pricing information. There's a lot of discounting in our market, so we can't just look at our customers or competitors’ websites and know what price they're paying, therefore, we actually ask them:

  • How much did you pay?
  • What did you buy?
  • What was your configuration?
  • What were your key purchase criteria?
  • How did you evaluate this person you bought, and us, against those key purchase criteria?

It's pretty thorough from a survey perspective, but we get 100-150 of these back a month. We've been running it for about a year, so we've got a couple of thousand responses; this means we've got a pretty robust data set off which to do this and it's also a great gut check for our sales-driven data.

Don't rely on your sales team alone to tell you why you're winning and losing. But if you pair that with some additional work, you can start to get a good picture of where the gaps are.

We generated insights and enablement

Next, we generate insights and enablement off the back of that. If you think about all of this, it’s to get to a 'why', and then what do you do with it? We use Crayon for our competitive battle cards and we use the data from our win-loss notes to power those battle cards.

We actually look and say, literally, "Why are we winning and losing against Square?", or, "Why are we winning and losing against NCR". And we've got all the data now from our win-loss, we've got the quotes from our interviews, and we really use that to drive the competitive battle cards.

That's a really helpful way to get this in the hands of sales in an actual way - use it to write scripts. We use it to come up with language that they can actually say in front of a customer.

We do quarterly sales training that always has a win-loss component. Right now, we're doing our sales training in-market, and there's a whole panel around the five top reasons we win and lose and reps talking to each other about why they're winning and losing based on these factors, and then we do what we call competitor takedown plays.

If we see a competitor trending in our data, we go with the targeted campaign across sales and marketing against them, and include sales enablement, updating the battle cards, but also calling campaigns against them. We'll go and call people who have them in their install base, and do marketing campaigns, paid ads, things like that to go after that competitor. We've seen those drive huge results from both a volume of opportunities, taking out a competitor, displacing them, but also from a conversion rate perspective.

Then we do monthly dashboards and quarterly readouts to inform corporate strategy, go-to-market strategy, and product roadmap. Those happen in different forums, but we make sure we hit all three of those audiences.

We present to product leadership, we present to sales leadership and marketing leadership, and then we also partner closely with the executive team and with strategic finance, who are more of our Corp Dev type people, to make sure that we're sharing what we're learning to inform product roadmap to inform what we're focusing on sales, but also investing as a company.

We shared the results widely

These are the ways we use it.


The results

I gave you that whole spiel about how Toast is growing so fast in the beginning and we've had great success. If you think about a growing sales team and growing your sales team over 100%, year over year, and onboarding hundreds of new reps, what usually happens to sales productivity when you onboard hundreds of new reps? It goes down.

As a company scales, usually, the expectation is sales productivity erodes a little bit, but it's okay because you make it up in volume because you're hiring lots of new reps.

We've actually seen sales productivity improve 30% year over year, as we've been scaling this fast, and part of it is because of the win-loss and sales enablement programs that are driven off of the back of it.

We've seen our win rate go up 66%, our productivity improves by 30%, and our op to deal conversion rate improve 60% since we've instituted win-loss and all the programs that go behind it supporting it.

It's been pretty cool to see that while the company is scaling at the rate it is. And part of it is because we're super focused on these metrics. We track these metrics, weekly, monthly, and quarterly, in metrics meetings and OKR meetings with our executive team.

So, we summarise in the monthly PMM dashboard, we deep dive with sales leadership, every single quarter, and cut all of this data by regional sales leader, by the district manager, by a competitor, by segment, and share that so an RVP who's having a great quarter on a win-loss against a certain competitor can share with the one who's last on the list.

So, we stack rank them, and we share that information so that they can all learn from each other. And it's also part of the sales leadership source of truth dashboard. For those that are looking at their metrics every day, they're seeing their competitive win rate and details about how we're running win-loss in that as well.  

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