We got together with Jordan Wade, Product Marketing Manager at Workday, and took a deep dive into the world of win interviews. Jordan firstly explained how his journalism background has helped his product marketing career to date, particularly in relation to interviews, why he thinks win interviews are so important as a PMM, how he likes to conduct them, who he thinks should conduct them within an org and how many ought to be carried out, plus heaps more fascinating insights on the subject.

Full transcript:

Hi everyone, and welcome to the Product Marketing Life podcast brought to you by Product Marketing Alliance. My name's Emma Bilardi and I'm a content marketer here at PMA. This week, we're joined by Jordan Wade, and we'll be discussing win interviews. Jordan's a Product Marketing Manager at Workday, he's an experienced product marketer with expertise in taking HR tech products to market and he has a background in journalism.

Hi, Jordan, welcome to the show.

Jordan Wade 1:03

Hi, how's it going?

Emma Bilardi - PMA 1:04

Good, thank you. Could you tell us a little bit about yourself and your role at Workday?

Jordan Wade 1:09

Yeah, definitely. Thanks very much for having me. Very, very excited to chat today.

Emma Bilardi - PMA 1:14

So happy to have you. Thanks so much for joining us.

Jordan Wade 1:17

Yeah, of course. Yeah, so I'm a product marketing manager at Workday, I focus specifically on the employee experience, part of the product, Workday's obviously a very large enterprise with a pretty broad set of products, everything from HCM to finance to planning, but I get to focus specifically on the employee experience suite.

And one product in particular, which is Journeys, which is a pretty new and upcoming piece of functionality that I'm pretty excited about because it's still very much in the early days, hasn't been around very long. But it's a lot of fun getting to hone in specifically on where the employee experience market is going and it's rapidly changing. So it's been a lot of fun.

Emma Bilardi - PMA 2:05

Excellent. So you have a pretty interesting background in journalism, how's that helped your product marketing career do you think?

Jordan Wade 2:13

Yeah, so early on in university I focused specifically on journalism. And one of the areas, obviously, that I spent a lot of time on was just doing a lot of interviews, whether that was going and actually meeting with someone on the street, whether that's just doing a lot of phone calls, to try and get an understanding of a story.

What I spent a lot of time doing was just interviewing people. I really learned a lot about how to get inside someone's mind and try and understand their viewpoint, it was a lot of great experience, trying to build more empathy, whether you're talking to someone that was just in a car crash, or you're talking to a leader of a business, trying to better understand their strategy, what's going on in the market.

It was a lot of great experience, just learning how to talk to people, learning how to understand them, trying to get inside their mind and help them communicate their viewpoint, which is a skill that is pretty broad, and can be used in a lot of different vocations.

Emma Bilardi - PMA 3:29

Absolutely. So why is it so important to conduct win interviews?

Jordan Wade 3:33

I think that's a nice segway into doing win interviews as a product marketer, because with that background in journalism, I spent a lot of time trying to understand... whether it's a narrative, whether it's a viewpoint, and that has actually worked quite well as a product marketer, because one of the areas I'm most passionate about is that buying decision - what goes into it, what ultimately makes a prospect hand over that credit card and say, 'yes, we're picking you, we want to become a customer, let's do this'.

And I think trying to get inside their mind and understand that whole process from start to finish - where did you start the journey? Who were you initially looking to in terms of the competitive set? Why did you reach out to us? Or did we reach out to you? When did the lightbulb flick on? And when did you think this particular competitor is becoming my number one? All the way through to becoming a customer.

I think, as a product marketer, we need to be the champion of the buyer and understanding that secret sauce to why someone becomes a customer, if we really can understand that process, then we can hopefully replicate it over and over and over again and find more buyers, just like that initial person, what was it that worked for them?

Obviously, in a lot of different markets, you've got broad competitive sets so it becomes particularly valuable to understand why your buyers are picking you, in order to be able to not only use that language, whether it's a particular narrative that you're telling, or your product is really just differentiated, trying to really understand that and then become the microphone to amplify that message out into as many different channels as you can and replicate it over and over again, I think is incredibly valuable.

I think that's where product marketers can become to really be strategic in that they're focused on growth, they're focused on bringing in more of the right type of buyer, that's the right fit for your product. I think rather than just maybe getting down into the weeds and focusing on your website or your messaging, I think focusing on growth and how you can, you know, whether it's the sales team or the marketing team, find more people is where product marketers can really drive value.

Emma Bilardi - PMA 5:59

Absolutely. So in your opinion, who should conduct the win interviews?

Jordan Wade 6:03

I've always been of the opinion that it should be solely owned by product marketing. And that's not to say that there shouldn't be maybe a broader group that jumps on to listen, I'm a big fan of that, whether it's maybe a sales leader, maybe someone in product management, they obviously do a lot of the user interviews, but I feel like when you're particularly trying to analyze the buyer and the buying decision that should really be driven by the product marketing team, as the champion of the buyer.

That analysis of, as I mentioned before, what happened from start to finish? Why did you ultimately pick us? What other competitors were you considering? What's the main value that we are providing you? I think those conversations really need to be driven by product marketing.

But again, I've always tried to take the community approach. So reaching out to different people, whether it's on the product management team to say, 'hey, we've got an interview scheduled with this buyer, who just recently joined as a customer, if you'd like to kind of join as a fly on the wall, or if I can share my recording afterward with you', I think again, that can drive and add a lot of value across the organization and more importantly share information that's really valuable.

Emma Bilardi - PMA 7:17

Okay, so a question we see quite a lot in the Slack community is, how many interviews should you realistically carry out?

Jordan Wade 7:25

That's a good one. And I think it's a time-consuming process where you're narrowing down this list of buyers, or potentially those that you lost out on, I think it's really important to analyze that by your ideal customer profile so that you're reaching out to the most important and impactful customers. But it's a time-consuming process, both the reaching out and trying to schedule and then also the actual interview, and then the transcription of all the notes and trying to distill those down into kind of the most valuable pieces. It's a lot of work.

So if you're doing that all by yourself, which I've done in the past, I've tried to do anywhere from one interview every couple of months, maybe a couple of quarter, I think it's really important to just keep your ear to the ground and be constantly listening for what's working in the market, what's not working, what competitive trends are going on, I think if you're every month listening and conducting those interviews and talking to buyers, you're going to be a far more effective product marketer. So that's what I shoot for but given our busy schedules, there's a lot on the typical product marketers’ plate, it doesn't always happen, but that's what I shoot for.

Emma Bilardi - PMA 8:39

So in your opinion, when should we start the win-loss process?

Jordan Wade 8:44

I think it's important to start as soon as possible for any organization, in terms of when in the process, I like to try and reach out as quickly as possible when the decision is still fresh. So, if a buyer just came on as a customer, I like to try and reach out within the first couple of weeks and just get that conversation going, try to get something scheduled. The same thing with a loss, if it's a big key deal you lost out on, the longer you wait, you lose out on those nuggets of information that potentially the prospect is going to forget.

I like to reach out as quickly as possible. And then just in terms of if this isn't a formal process built out in your organization, I think it needs to be built out this quickly as possible. Because again, I think you're intaking these pieces of information that can really drive strategy, can drive growth, and it needs to be started as quickly as possible.

Emma Bilardi - PMA 9:46

So as we were saying before, product marketers are always super pushed for time. So one option could be to outsource the whole process to a third party. Is this something you've done before? And if so, do you have any advice or recommendations?

Jordan Wade 10:03

Yeah, great question. So I've actually done a little bit of both. I've been in an organization where it was done completely in-house and I was running the vast majority of that process and also joined a larger organization not too long ago, where the vast majority of it was outsourced. So I've been able to see both the pros and cons there.

I think, when doing it internally, it's a very time-consuming process. So it was actually part of my sole focus as a product marketing manager was both win-loss and also competitive research. Which was, I thought a super valuable project to be spending all of my time on because win-loss bleeds so well into competitive research. So to kind of talk through what that process looked like I was doing not only the outreach to try and schedule interviews, I was working with people in sales and marketing and product management to look at what's our ideal customer profile so who should I be trying to reach out to?

Let's look at that list and make sure we're reaching out to the right, not only customers but prospects that we've recently lost out on. So outreach, unfortunately, takes a lot of time. But once you get those interviews scheduled, again, as I mentioned, you're sitting down for that interview, you're recording it, then you're trying to transcribe the notes, then from there, you're trying to distill that down into the most meaningful tidbits.

From there, I'd be trying to schedule whether it's a monthly or a quarterly win-loss, sync meeting across product, across sales, across marketing, again, to just talk through those trends. Let's talk through who are the main competitors were losing to, here are the main reasons we're winning here, the main reasons we're losing, trying to get those conversations going on a consistent basis so it can impact your strategy, it can impact your positioning, your messaging, your go-to-market, you can start seeing where in the sales process are things breaking down? And how can the product marketing team jump in and add value or vice versa?

This is the message that is continually working with the right buyer, let's try and amplify that out across all these different channels. So internally, again, it's a lot of time and energy. But I think the value there is that as you're getting these insights on the front line, you're keeping your ear to the ground, and you're the one talking to the buyer, you're the one talking to the prospects you've lost out on and I feel like that's incredibly valuable.

But I think on on on the other side, on the other side of the coin, if you're outsourcing that entire process, I've seen the value there as well given that it takes one more thing off of your plate so you can focus more on other areas. So I've used in the past an agency where they were doing the outreach, they were doing the interviews, they were doing the distillation of the notes, and sending us as a product marketing team, both the quantitative and the qualitative.

So whether we're looking at our win rates and trying to analyze the top competitors we lose two, or we actually want to dig in and read all the notes for a particular interview, that was really valuable as well. And I think one thing to add to that - the value of having an agent external agency do that is that, particularly in the interviews, sometimes prospects feel more comfortable being a little bit more honest and upfront about what went well, and what went poorly versus speaking to someone in-house.

Sometimes they're maybe a little bit unwilling to give that unvarnished opinion. And so I've seen sometimes when you're reading notes from a third party, you're like, 'wow, luckily this buyer is being very honest with us'. Versus sometimes when I've conducted it, you can feel like they're maybe trying to just feed you the positive tidbits, 'okay, I don't want to be too negative here'.

But yeah, I've definitely seen the pros and cons of both sides, I think I really enjoy being on the front lines, conducting the interviews, really talking to as many buyers as I could, versus just being on the other end reading through a long-form document that was put together by someone else. But again, it just depends on your organization, size, the size of your product marketing team, and what your bandwidth looks like. So I've seen the value to both sides.

Emma Bilardi - PMA 14:33

So what's the best medium for conducting win interviews?

Jordan Wade 14:38

Yeah, in my experience, in the pre COVID world, when we were able to travel and talk to people in person, I actually hit the road and did some in-person win interviews and found that to be incredibly valuable. I don't think there's anything a product marketing manager could be doing that would provide more value and influence your strategy more than actually doing an on-site in-person win interview.

I actually reached out to a buyer of ours that recently joined as a customer, I had to make sure I worked with our customer success team to ensure that it was okay to do so - once I got the green light from them I reached out and then actually traveled out. It was fantastic because I got to actually meet with the whole buying committee. Not only our main buyer persona but also some of the other individuals that participated in the search so I was able to get their insight from top-down.

Not only the leader that was focused on price, focused on putting together the buying decision, but also the more functional roles who were looking into our product from a very particular and specific vantage point. So I was able to ask questions to this different audience and gauge their insights, which I feel like is really valuable for a product marketer to be able to say, 'okay, which messages work for which buyer persona, and what's gonna matter to this person versus what's gonna matter to this person?' was incredibly valuable.

So pre-COVID, I feel like doing it in person as often as you can, is incredibly valuable and meaningful. Now in this post COVID world, or excuse me, in the midst of the pandemic, I'm still trying to do it via Zoom, keep having those conversations, to put a face to a name, to try and establish a relationship there. But I think doing it in person is definitely incredibly meaningful.

Emma Bilardi - PMA 16:38

So once you've conducted the interviews, how do you analyze your results? And then most importantly, what do you do with that information?

Jordan Wade 16:45

That's a great question. I've always tried to approach it through a quantitative and qualitative viewpoint. So from a quantitative perspective, I think it's really important to pay close attention to win rates, to how effective is the sales team at closing deals? And trying to look at that from your ideal customer profile perspective. If it's 250 to 500 employees, how effective are we at closing those deals?

And then looking at in that scope who are the main competitors we're losing to? And then getting into the reasons we're losing or winning. Is it mainly product-focused? Is it sales focused? Is it that the sales process is taking too long? Is it that we're missing this one feature or piece of functionality that is continuously causing us to lose?

I feel like from a quantitative perspective, you really got to know those numbers, and be tracking them on hopefully a monthly basis, if possible. A lot of times, I haven't been able to get a dashboard built out so I've just built my own spreadsheets in Google Drive, or Google Sheets, or what have you just to be monitoring that and move those charts up the chain to say, 'Hey, we're taking a close look at this, we're tracking this, we know what's going on'.

And then from a qualitative perspective, I think it's really important to again, do those interviews, so you can understand the longer form stories and explanations. So, 'buyer, I know you told us that you didn't choose us because we were missing this piece of functionality. Can you explain in more detail why you need that? What's the main problem you're having? Talk to us more and explain in more detail, what's going on there?' I feel like is incredibly important. Doing those actually in-person or phone interviews is where you get more insight into the qualitative story there.

I like to compile that down and distill that down to again, the quantitative you're taking a look at your numbers and then you're also trying to distill down the main trends going on. So in this month, we're losing to this competitor, here are the top five reasons we're losing to that competitor, and trying to share those main pieces of information out so again, you're analyzing the product gaps, you're analyzing the competitive set, you're analyzing your positioning and messaging, if that's working or not. And then trying to share that out on a consistent basis, I feel like is very important. In the past, I've tried to schedule whether it's a monthly or quarterly product marketing or win-loss strategy session.

I think it's really important to get your product leader in there, a sales leader in there, somebody from marketing so that you're having those broader strategy discussions around what's working, how can we sort of pour more fuel on the fire there and amplify out what's working across all these different channels? And then also take a really close look at where are we going wrong? Where are we consistently tripping up? And why? So that as a product marketer, you can say, 'okay, we're losing to X competitor, let's build out some really in-depth training. Let's come up with some messaging points around how can we more effectively compete against this competitor?'

So you're enabling your sales team, and that's where if you've got somebody in sales enablement, that relationship is particularly important. I feel like it's really important to know your numbers, to be distilling these key pieces of information down on a monthly or quarterly basis, and then more important, your meeting with a broader team and I think it's important for the product marketer to be leading that strategy session or hopefully participating in it to be able to be saying, from a strategic perspective, here are the reasons we're winning and losing and let's make sure we're all on the same page here.

Emma Bilardi - PMA 20:38

So can you talk us through how you streamlined your company's win interview process?

Jordan Wade 20:43

Yeah, sure. So = in the past, I've approached it a number of different ways. When I was at a smaller organization, managing it myself. I, again, was doing a lot of the outreach. I was doing the interviews myself, and then I also try to work with our sales operations team to actually operationalize a survey. So as soon as a deal was marked lost, we would fire off a survey immediately that would just ask some really basic questions.

If you made a decision, which competitor did you choose and why? If you haven't made a decision, what's going on basically? Is it that you haven't been able to get approval throughout the organization? Is it because the decision has been pushed back a couple of quarters? Is it because you're leaning towards one competitor or another? Just trying to get more information there because I've seen in analyzing win-loss data in the past, a lot of it goes into this, the prospect didn't make a decision or the prospect went dark bucket.

That's where you really need to get in there and better understand, well, what's going on there? Is it that they can't make a decision? Are we not explaining our value proposition well enough that unfortunately, these decisions are just being held off, because not only were they not able to understand it, but transfer that up the food chain and make a decision. Being able to send out that survey immediately and collect those insights for again, if they chose a different competitor, or if they haven't made a decision yet to be able to understand the reasons why.

One little interesting tweak we added to that was if they actually say they're still interested, if they responded to the survey and said, 'Actually, you know what, I am still interested in your product', we would actually fire that back to the sales team to say, 'hey, this prospect reengaged, they're actually still interested, reach out'.

To be able to see those deals close, because we built out this process where initially, we just wanted to talk to people and understand what went wrong, but we also started finding this subset of people that just hadn't made a decision but were still very much interested, so we'd reengage those people. But just in terms of streamlining that process, we wanted to just start compiling data directly from the prospect because I've been in a lot of organizations where we have a lot of data from our sales team, that's win-loss related.

So we lost this deal because of this reason. And then sometimes I've reached out to that actual prospect and found that the story was very different. To be able to kind of compare those data sets, here's what our sales reps are telling us but here's what the prospects are actually telling us and from there, you can say, 'Okay, let's look if the data correlates, particularly from a competitive standpoint, our sales reps are telling us we lose to these five competitors but when we went out and surveyed prospects, it's these five'.

So I feel like that is able to really provide a lot of meaningful insights to the team. So I would very much recommend trying to operationalize a survey that goes directly to your prospects. We've tested out offering gift cards, whether it's 5-10 dollar Amazon gift cards, or what have you to try and incentivize prospects to respond. And then also asking if they're willing to jump on the phone for that broader loss conversation or win conversation is super important, as well.

I feel like it's just important every month to be trying to compile survey data, and also to be on the phone speaking with your prospects, speaking with your buyers, to be able to understand those insights. As we already discussed previously, the most important part of this is that strategic communications so that you're sitting down with people across your organization on a broader team, and sharing these insights, to be able to say, 'these are the reasons we're winning, these are the reasons we're losing. This is what the product marketing team thinks we should improve upon and here's why'.

That's really where I feel like product marketers can get strategic and can join those higher-level conversations to where are we taking our strategy? How can we find more of our ideal customer profile buyers? And how can we really drive growth in this organization? That's what I've seen work in the past. I'm always trying to tweak it and get better at it. But it's a lot of fun.

Emma Bilardi - PMA 25:08

Thank you so much for that, Jordan. I want to thank you for joining us today and sharing your insights. And that was a really great podcast. Thank you so much.

Jordan Wade 25:19

Thank you really enjoyed the conversation. Appreciate it.

Emma Bilardi - PMA 25:22

Excellent. Take care Jordan.