Transcription
[Music]
[Applause]
[Music]
[Applause]
[Music]
Good morning everybody and welcome to this episode of 30 minutes to president's Club. My name is Arman Fro, and I'm here with my co-host Nick Selski. And oh man, I was not on the round one recording of this one, but it is round two with Maddie Jackson. And I am bummed that I did not make the first one because she is an unbelievable rep who has made president's Club at Webflow. And this is not one of my, she's got some really, really powerful stuff as it relates to running extremely effective discovery calls by guiding your customer to problems, even if they're not aware of those problems. And then exploring both the hard metrics of impact as well as the soft metrics of impact. And then she talks about ways that you can keep your deal moving fast and moving on track. Stuff to make sure you don't get ghosted. Stuff to cold call into active opportunities to build groundswell. This is a can't miss episode.
All right, Maddie, welcome back. Back to the show. You may recall that we start every single episode with your top three actionable takeaways. So let's get your three.
Yeah, so the first one is to always set a backstop meeting. What that means is oftentimes when you're in a meeting and it's nearing the end, the following can happen. You're either on an early stage call or a demo, and it's unclear to the prospect who from their team needs to be on the next call and what their schedules are like. So they might say, "Hey, can I get back to you over email once I know XYZ schedule so that we can create a time that works for all?" Or on a late stage call, you might be in negotiations and the deal should be a matter of email confirmations or DocuSigns. While it can be very tempting to follow up with emails to get the meeting scheduled or assume that the rest of the deal can be handled via email or that you're just going to get that DocuSign back the next day, not often well, that always happens. So it's really good to create a backstop meeting. Suggest, "Hey, let's put a placeholder on maybe two days from now. If that doesn't work for everybody on your team for the next demonstration, we can always shift it around, but having that on the calendar really helps drive that sense of urgency."
The other version of a backstop meeting is when plan A did not work and you might not have something on the calendar. It's how can you revive that, um, rather than continuing to go down the email route or trying to call them. Sometimes I just throw on a calendar invite and I ask, "Does this time work?" While they don't always show up, it does always generate a response, even if it's just declining the calendar invite. That way, you have that line of communication going again.
What's number two?
Number two is about upleveling your impact questions. Once you're going through discovery, an average line of questioning is, "What are your biggest challenges? What's the impact of that challenge? What's your decision process?" But challenging yourself to go a lay deeper makes it a lot easier for the prospect to think about these things and answer them in a way that you can then use later on in the deal cycle. So a great line of questioning would be, "What challenge would you regret not solving six months from now? What are the ripple effects of that on the business? Why does that problem matter to the greater business?" And then, "What steps do we need to take as a partnership to make it a confident yes or no decision?"
Round us out, Maddie. What's number three?
The last one is a tactic I've been trying a lot this year, which is cold calling into active pipes. So traditional cold calling can often be seen as trying to break into a new account and reach out to the right people and say the right thing to pique their interest. But later on in the sales cycle, I found it really helps accelerate the deal cycle in several ways. One example is cold calling end users to build groundswell. So if you're worried about pushback, you can always ask for permission. Let's say I'm talking to, uh, a Chief Marketing Officer, Danielle. I could say, "Hey Danielle, when I'm working with large marketing teams, we often see the most successful implementations when the end users have been bought in on the rep platform from the early stages. Are you okay with me or my team, perhaps an SDR, BDR, reaching out to content marketers to get their feedback?" That helps you, of course, build the groundswell, build the business case. But it also helps with multi-threading, so that you have more people down the line to reach out to.
All righty folks, so we are going to come to that backstop meeting. But first, I want to talk about the discovery call. Everyone wants to be able to ask those juicy impact questions that get to business impact. What questions are you asking before you ask impact questions?
Good to start with situation and then process questions before you get to impact questions because you can craft your impact questions around what you've learned about the current process. Situation questions show that you've done your research on the account. So a situation question could be as simple as, "Hi Danielle, I saw that you're the Chief Marketing Officer and you've been with this company for two years. You were previously at this company. Is that correct?" "Yes." You could even say, "I saw that you guys are using our biggest competitor. How long have you've been using that for?" Now you're starting to get into some of the process questions. "Who today is involved in editing content and how does that process look?" Those are the things that you can start to ask before you then try to quantify the impact with them of the challenges in the current process.
So Maddie, what do you do on a call where, I think what's implied in some of what you've been talking about is they do have a problem that they really want to change in the next six months or there is a desire to fix an issue in their business. But that isn't always the case in sales. Sometimes we'll outbound somebody and we might say, "Hey, we know all of this about you. You're using our competitor." And they might be like, "Yeah, we are. We're on them." How do you get them to have some engagement in being willing to make a change or how do you start to poke holes in they use a competitor because you can't even get to impact if there's no issue that impact is is having around?
That's where I find it's really helpful to do some reference selling. Make sure that you've done your research on the account, similar clients who might be using your solution, who have done that same rep platform or switched over, and then have some ROI stats to share with them and and say, "Hey, I've worked with these companies and this is what they were running off. Happen to does this resonate?"
So let's say that someone says, "Yes, I'm using a competitor to Webflow, AKA I have my website hosted somewhere." Where do you take it from there?
Typically, I would then ask, "You're using this competitor, you have your website hosted in this place. With Webflow, we take on the hosting. We would be able to take on the onus of security. We'd be able to take on the onus of training. Who in your organization is managing those right now?" Trying to get more of an understanding into the process of who is impacted. Because if you're talking to someone and they don't have the personal pain, it might be being felt by someone else in the organization. And it's really helpful to get those names so that you can involve them in the sales cycle.
Let's just pretend that I'm feeling a bit of the pain, as well as two of my colleagues. How do you turn this situation into a problem?
I would work to get those colleagues on the line and then try to quantify with them what the pain is. Because it's really important that while there's pain, they also know what the impact of that pain is going to be if you're going to solve it. So let's say it's time savings. There's someone who might be in charge of managing the hosting of the website, and they're on call 24/7. There's someone, if the website goes down, it becomes their problem. Whereas with Webflow, for instance, a fully hosted solution, we've got a global team of engineers on 24/7. So it's time savings for that person, it's risk mitigation for that person, and it's what else could this person be doing at the company other than monitoring the website, where that could be outsourced to your service provider?
And how much of this is you trying to get them to say, "Yeah, my current solution doesn't take me a lot of time," versus you educating them on a problem that they might not even know that they have?
For the outbound, it's all about education. You have to be able to understand what the problem is and then make sure that it's not just known pain to yourself, but known pain to the end user or to the person who's feeling it, and that they know that you know the pain. So it's really important to reiterate once they have that "aha" moment and they start to buy into, "Oh yeah, you're right. Perhaps this person is spending a lot of their time on something that we don't have to handle internally." Then you just reiterate that and say, "Okay, so we've both agreed, we've come to consensus that this is something that could be taken off of your plate and that, let's say, Joe could be better repurposed working on the core platform versus the marketing website."
Let's assume that someone is currently on WordPress, which I imagine happens reasonably often, and they don't see that there's a big problem. How can you educate me that I might be losing time by not being on Webflow?
My guess is you're not just saying WordPress is slow. No, no. Because slow is something that they don't necessarily feel. It's what the day-to-day looks like on WordPress, where a marketing team would have to work with a developer who knows custom code in order to build out that website versus something like Webflow, where it's very easy to build and it's built for marketers because it's a visual editor. So it's trying to quantify more about the process at that point. You'd have to go back into the, the process and say, "What does it look like to build out a landing page today? Who's involved in that process?" And that's where you get them talking about, "Well, the design team builds the wireframes, and then they'll go to the engineering team, and they'll try to fit it into one of their two-week sprints." That's where you have the ability to say, "What happens if the engineering team can't fit it into their sprint? Has this ever happened?" Usually, it's always a yes. "This has happened. They have to deprioritize marketing initiatives in order to serve the core product."
This is really smart what you're doing. There's a million different things related to somebody's web hosting platform that you could ask about. But when you're asking about, like, their situation or their process or how they do something, you're asking specifically about some of the areas that you know there will be common pitfalls with where, you know, their current solution is weak. And when they start talking about it, it then sets you up to ask about, "Hey, you mentioned this. What happens if this point of failure happens or something breaks?" And so you're almost asking, like, a trap question for the competitor about something that you know they're weak with, which then opens the door for you to talk about how Webflow might be different. Is that right?
That is right, yes.
Nick, it's very important to lead yourself down a road that you know you can be successful in. And if you're not going to be successful, know where you're going to pivot to next. This reminds me of something that I would often times do at Pave as well, where Pave was managing compensation cycles for companies. I would ask an HR leader, I would be like, "Okay, so you have this massive compensation spreadsheet. How do you get this big spreadsheet into the hands of every single manager in your company who needs to make comp decisions?" And I knew that that meant that they had to split it into a hundred spreadsheets and have version control and make sure that the comp was confidential between all the sheets. And so nine times out of ten, if I just asked that situational question, they would start complaining. The one time out of ten where they wouldn't, they just assumed that that was what had to do. And for the one out of ten, I would then educate them, like, "You don't have to do all of that stuff." But if you ask about a painful enough situation, whether it's updating a landing page or splitting a compensation spreadsheet into multiple small spreadsheets, that will naturally oftentimes get you to a problem. And then it's your job from there to turn that problem into a more meaty business impact.
The other thing I want to add that Maddie brought up and and you brought up here, Armand, is both of you knew what you were looking for. You did not just show up on that call thinking, "All right, I'm going to take this wherever I can and dig around and look for some problems that they might have." You knew the top four problems that a customer could experience because you were intentionally looking to go there. And my guess is, Maddie, you're doing the same thing, which is the top three to five places where there are breakdowns with your competitors, and you are intentionally taking the conversation there to get them talking about the problem that they have.
And now I want to ask you a bit about the impact because you said something earlier, which was problems don't really matter unless there is an impact or a sizing to them. And one of the things that I've been learning is we live with small problems all the time. There are small problems in everybody's life that we choose to live with. And if they're not big enough, we won't make a change. How do you now turn this into, "Oh, this is hurting the business"? How do you start to ask them about the impact here?
Yeah, I think that you just really hit the nail on the head because where I would go from then is starting to craft a business case. If they're not asking you directly for a business case, it's safe to assume that by the time you get to the CFO for sign-off, it's going to be too late and you're going to have to backtrack and use these impact questions to build out that business case. I found that more often, CFOs in need to see a business case to trust that the people who have done the research and gone through the evaluation with you are serious about the product and that they know the problems that they're going to solve. So it's really helpful to get ahead of that by starting to ask questions like, "Great, so you're telling me that your engineers have to get involved in building out a landing page." The first question I would go is, "How many hours does it take?" So that you can quantify that very valuable resource and how much time you could save the engineering team to repurpose on core product or somewhere else where their valuable time could be spent. And then the second is getting to that second-level impact, which is, "Let's say it is deprioritized. This marketing initiative, how would that impact the launch of this new product?" Then you're helping them think about the soft savings. Not just hard savings of time or leveraging a new technology, but you're you're helping them think about increasing revenue with a successful launch of a new product, which is where it becomes a little bit more difficult to quantify in dollars and cents, but what really matters to the success of the overall business.
Maddie, I'm hoping that you can help me solve this problem that I've run into in the past, which is I'll ask someone, "Okay, how are you going about splitting up these comp spreadsheets?" They'll say, "Oh, it's taking me so freaking long." And then the moment I start asking them to quantify how long it takes or trying to get them to put numbers behind it, they start to get really defensive. And I'm curious if you could give me some advice on that.
Yeah, I think the most important for me, and I've definitely run into that, Armand, and I still do most times that I'm building out a business case, is knowing who you're talking to. A good example at Webflow is if I'm talking to an engineering team, I will not say, "It takes the engineering team too long to build out a marketing website." You want to make sure that you're providing value or speaking to the persona that you're talking to. So for an engineer, for example, I would ask what they want to be working on based on that, rather than making it sort of a negative, "Hey, you're taking too long and marketing feels like they're not being prioritized." Spin it into positive for the business. "What would happen, engineering, if you were able to launch this new product faster?" Not even talking about the marketing campaign behind it, but let's say that we could build more product and ship quicker because you're not distracted with marketing initiatives.
So Maddie, you're in this place with the customer where you're having a conversation where you are exploring the impacts plural of this landing page example. And you talked about two types of impacts. One, hard metrics, and you used the example of number of hours that it would take the team to stand up any given page. I'm assuming you're able to then multiply that by number of pages they set up a year, big initiatives coming, what's going to come in terms of the hour impact based on their current tech stack. But then you're also saying, "Hey, I know engineering hours are limited, and there's going to be times that standing up a page gets deprioritized. I know you mentioned that you've got this launch coming up. What would that mean for your business if you had to delay that because the engineering team couldn't get to it because it's taking a lot of time?" And what you're doing there is you're getting them to talk about some of the softer stuff that you might not be able to quantify, but it has big meaning for the business and it still will matter on the business case. My question for you is, it seems like you've put a lot of thought into, you know, where you're going when you start talking about impact. My guess is there have been some false paths or distractions you've gone down when trying to talk about impact. And I'm wondering if you can tell me what those might be so I can look out for them when I get on my sales calls.
I think one pitfall that's easy to fall into is only going down the pain and impact to the person that you're talking to. So let's say you're working with the champion, and you're quantifying their pain and the impact to them. You build out this great business case, and then it becomes a "so what?" because the business case should not be for your champion. It should be from you and your champion to the business decision makers. What does the CMO care about? What does the CEO care about? And if you're not getting the right answers, then you're probably not talking to the right person. And that's where you need to uplevel and talk to someone who does understand the core business initiatives, what their OKRs are for the year, how you're going to plug into them. What this little landing page can do to really drive that up. To make it an inverse discovery triangle of what, what the business cares about at the end of the day. Because hopefully, the CEO is not falling asleep thinking about how many hours it takes to build a landing page, but hopefully they are thinking about how they're going to drive revenue in the future with new products that are brought to market in the right way, at a good speed.
So we've talked about finding situations that are painful, turning those into problems, turning those into quantifiable impacts, and even soft impacts, and now cross-departmental impact as well. That's a lot to do on a discovery call. Maddie, I'm curious, how much of that are you getting on the first discovery call versus in follow-up calls for the rest of the sales cycle?
Most of it is done in follow-up calls. I'd say on the first discovery call, you're earning the right to get those calls to get the answers. And that's where the first discovery call, like we've talked about, you have to show up having done your pre-call research. You have to know their situation. You have to guide them to pain because you need to earn their buy-in to this cycle. Once you've gone through the demonstration process and you've shown the value of your tool, then the turn, the tables turned, and it becomes, "How can I help you sell this internally?" When they've already bought into wanting it themselves.
What does it mean to earn the right on that discovery call? How do you know that you've earned the right to ask those questions?
I think the most important thing is to be able to walk away and know that you can have a conversation with your team, with your manager, do a deal review, and answer the question, the simple question, "Why would they buy Webflow now?" And if you can answer that question to yourself, and then you can answer it to the prospect, you've earned the right to have another call.
How much of earning the right for the next call is you getting problems from them versus you showing them places you can help?
Heavily weighted on the second. I think most people who take a call or come inbound, if you're lucky for one of those deals, they have one problem that they want to solve. But in order to make a business decision to switch over such a meaningful platform that powers, you know, their marketing website, it's one of their largest assets. You need to help them find five, six, seven areas of pain that don't only affect this one person who came, but that cross-functionally at at their organization affect everybody and can help improve for multiple different stakeholders in achieving their mission.
That's really interesting. So you'll get an inbound lead and someone will say to you, "Hey, I've got this big problem. We need to solve our landing pages take way too long to stand up. We need to be able to do that faster. I heard Webflow can help." And you know that if that's the only problem that you're solving for the org, probably not enough to get them to make this massive change. And so what you're doing then is you're saying, "Hey, if you have that problem, we probably have these ones also." And you're having to then create other problems. So even if they come inbound with one, you still have the responsibility of bringing up others. An example of that would be pivoting to the security or IT team and trying to understand what the process is today for any sort of bugs. Or let's say they're using WordPress, for example. There are a lot of plugins. Often, if a plugin gets updated, then things can break. And it's who has to handle that? Usually, it's IT. Sometimes it's a security vulnerability. So getting those folks involved and getting the names of those people so that you can help build out this business case so that it becomes beyond saving time with landing pages and more risk mitigation, you know, increasing revenue and innovation on the marketing team, and quantify savings across multiple different in the business so that you have a really strong business case at the sales cycle.
I wish we had had this interview years ago when I sold accounting, billing, time tracking software to law firms. Because what would happen is, we would have the billing team of a big law firm come inbound for us and they'd say, "Hey, our billing is a nightmare. We've got all these deductions and appeals and bill formats and they're a nightmare to keep track of. Can you help us?" And we could. And sometimes that would be enough for someone to make a move. Like, we weren't addressing the problems the attorneys had. And what I'm hearing is, "Oh, what I should have done was said, 'Yeah, we can help you with that. Let's explore that.' But then also, I needed to guide them towards the problem of, 'Hey, by the way, my guess is this is going on with the attorneys also.'" And what would have happened for me is I would have won over both of the big stakeholder groups at these law firms, while also accelerating the deal because the pain was that much bigger. So the learning for me here is, even if you have somebody come inbound with one pain for a persona, you still have to guide them to the other functions of the org that have problems in order to accelerate your deal and increase your win rate.
Okay, I want to ask you about that backstop piece, Maddie. So you have a great call with Armand. He's your customer. He's like, "Yep, we've got this problem. Security also has it too. Thanks for raising that for me. We're going to have to investigate this. I think our next call, I want to involve them and I've got to hunt them down and get calendars together. So why don't we coordinate times over email?" You talked about you're using a backstop to make sure things don't fall off the calendar. How do you voice that over to Armand at the end of the call to make sure that you get it on the books?
In this case, I would try to first ask, "Who in security do we need to involve?" Because once you have that name, then it gives you the ability to go directly to them. A way to frame it is, "Hi Nick, I know you're really busy," or "Armand, in this case, I know you're really busy. You mentioned that we need to get security bought in on this. We can't find a time where all schedules line up. Is it okay if I reach out to Nick in security and set up a time with them?" If the answer is not yes, it's a really good red flag because it's always good to understand if you're not having a qualified deal. And if they won't let you talk to the other folks who have pain and decision-making power, probably a lot more work for you to do on the qualification side.
It's also a red flag if Nick is the one who's running security. Nothing is secure in his hands. But actually, Maddie, what what you're doing is really important because you're not just asking them, "Hey, you mentioned that we can set up that next step with security. How's that going?" What you're doing is you're basically saying, "Hey, I might go do that thing. You better jump in front of the train tracks to stop me." And you will get a response from folks like that. And if they say, "No, no, no, don't reach out to Nick in security," then you know that you've got a problem on your hands because this person is a stakeholder. And then you have to go back to the drawing board and think, "How can I go to Nick with something valuable for him and sort of start a fresh, start a fresh sales cycle to security so you can then merge both of them once both teams are bought in?"
So let's pretend there's a world where Nick is not abysmal at running security and things end up going well and you're proceeding in the deal. You talked about another type of backstop, which was this almost throwing a dart at the calendar when you haven't been able to get a hold of the customer. What message are you including with that invite when you put it on the books?
Try to always make it relevant to them and include a piece of content or perhaps a new release that would be relevant to that person's job. So we're we're shipping quite often at Webflow. We ship something new almost every day. "Hey Nick, wanted to let you know that we've released this. Would love to tell you more about it and how it could impact you in security. Does 15 minutes work for us to catch up, talk about this, and do a touch base on where things stand in the deal cycle?"
So Maddie, one other situation came to mind the other day. I was consulting for a founder, and he was talking about this late-stage deal he had presented to his champion, and the champion said, "I'm going to go bring this to power." And he tried to get in front of power, and he could, but he trusted that his champion was going to go do the job. Problem is, champion goes dark for two weeks. He has no idea if the champion's actually in the process of proposing to power or if power just turned it down entirely. He was in this tricky situation because he didn't want to go over that champion's head because that could literally blow up the deal at the finish line. But at the same time, he's also not getting an answer and he can't just sit here and wait for two weeks for him to potentially lose the deal. So how would you coach someone in that situation?
Yeah, that's such a tough situation. I feel like it's one that every sales rep has run into, usually at the end of the quarter, and you're just devastated. What I've done in the past that has worked out is remove myself from the situation. Ghostwrite an email for an executive at my company to send to that executive. Because power will often at least open up an email from someone else in power. And if you have a succinct email that says the value, "Hey, we've been working with your team. I hear they're great to work with. This is why they're evaluating Webflow. This is the stage that I've been told that we're at. What can I do to help progress the deal along?" It's really important to know if someone isn't bought in at the leadership level on the evaluation. And if they're not able to get an email from someone at your company who's an executive, then you have a lot more work to do.
The other thing that I'm thinking, Armand, is your founder friend probably could have taken Maddie's other advice, which is set that backstop of, "Hey, awesome, great to hear you're going to be presenting to the the CFO. Why don't we put this backstop on the calendar so and I can catch up in terms of how things went? I'm sure there are going to be questions that emerge out of that, and this way I can get you some timely answers on things." The problem is is when you're that late in a deal and you have a relationship with somebody, it's so easy to just like you expect that it's going to be okay. Same with the DocuSign. Maddie, this is something I'm dealing with right now where I have a customer. We've been back and forth on contract negotiations. Things have been great. We agreed to a timeline for when they were going to get us red lines, and they haven't met that timeline, and I haven't gotten communication back in like a good 10 days. And I've reached out and reached out, and now I'm like, "Ah, every time I don't set that backstop, it ends up biting me." And it feels weird. I feel like bringing it up again and again and again with buyers, but I feel like it's one of the best ways to inoculate yourself against this issue.
Yeah, and I find it's helpful to be transparent with them and say, "Hey, quite often I'll send the DocuSign out, you say you'll sign it within 24 hours, but then there might be someone else who comes into the fold who needs to review it, and all of a sudden we're missing deadlines. Let me help you by, let's just set up this time to talk. And tomorrow or two days from now, if nothing's happened, you can get on the meeting and tell me, 'Hey, nothing's happening.'"
Maddie, this has been a phenomenal round two, and sadly, the clock is ticking down and we are running out of time. So I got to ask you our final question. And the final question is this: We've talked about a lot of really great things sales should be doing. Now I got to ask you about it shouldn't. And so the last question is, what is one bad habit that you see a lot of salespeople exhibiting that you think they need to break because it hurts them far more than it helps?
I'm going to go with the theme of what our episode has been about. I think that trusting your champion too deeply or trusting anyone too deeply without validating why that trust is in place. If you're trusting that someone's going to get back to you, if you're trusting that they're telling you business metrics that matter to the people who are making the business decision, that's great. Validate that trust. Otherwise, you might be, uh, going down the wrong path and you might end up in a situation where you have the wrong business case, your champion's not getting back to you, and you end up losing the deal.
Amazing. Maddie, thank you for joining us. All right, Nick, it is time for a two by two recap from this episode with MD Jackson.
Number one is when you're exploring impact with your prospect, there's two types of impact that you can talk about. Type one is hard metrics, stuff like hours spent, money lost, etc. The other type is soft impact. Maddie used the example of, "Hey, if your engineering hours get moved elsewhere and they can't get one of these landing pages up, what does that mean for your big marketing initiative where you need that landing page?" And that allows you to build a business case that's supported by both quantitative and qualitative impact.
Number two is when somebody comes to you with one type of pain. Often times prospects know, "Hey, we need to solve this thing over here for our marketing team." It's your responsibility to then also raise problems that other departments might be experiencing to help you accelerate your deal and multi-thread, which will impact your win rates, deal pacing, etc.
Number three, if you want to turn a situation into a problem, let's pretend someone is using WordPress as the competitor. You want to ask about a situation with that competitor that you know is painful. You might ask, "Hey, how do you go about updating a landing page?" If you know that that is something that is painful with that competitor, and that turns a situation into a problem.
And lastly, number four, if you are getting ghosted later in a deal cycle and you know who you need to get in front of as a next step, you can just email the person and you can say, "Hey, I know you mentioned we need to get in front of Nick and security. Would it be easier if I sent them an email?" And they will reply because they don't want you reaching out to other people on their team.
All righty, Nick, those are our four. How could people help us out?
So Armand, I love reading feedback from folks who listen to 30 minutes to president's club. And recently, when I'm procrastinating going to bed on time, I'll go look at our YouTube channel and I'll read comments that people write about our episodes. And folks, if you liked this one, I will read your comment. Go check out this episode on YouTube. Leave us a comment. Let me know what you thought of the episode. Say hello. Maybe I'll say hello back. Uh, and if not, we'll see you next week on 30 minutes to president's Club.
[Music]