🏛 Socrates would’ve crushed Sales Discovery
Taylor takes us through a near-perfect SMB inbound deal.
From webinar to closed-won, Taylor discusses how she identified the opportunity.
Leveraging valuable content & building a solution-focused relationship quickly.
She overcame the barriers of working with an international company & a weary CEO.
How'd she do it? Give the episode a listen!
Guest Feature
Taylor started her sales career climbing the ranks at Message Desk.
From SDR to Account Executive & Community Manager in less than a year!
She then made the transition to QuotaPath & is crushing it there.
What problem does QuotaPath solve?
QuotaPath is a commission's forecasting and tracking software.
We help sales reps see and understand their commission and earnings attainment in real time.
Helping Sales, Revenue Operations, and Finance teams run commissions automatically.
Deal details
What are you selling?
- Commission forecasting & tracking software
Where did the prospect come from?
- An MQL inbound lead from a QuotaPath webinar.
Company type
- SMB SaaS company. 200 employees. 40-person Revenue Operations team.
Prospecting method
- Warmed up as an inbound lead. Taylor set the meeting via email.
Barriers to overcome
- Prospect CEO had been burned by software companies in the past. Had to build trust.
- International companies. So a lot of timezone & legal barriers.
Buyer type
- Decision Maker: Head of Revenue Operations
- End users: Revenue Operations team
Episode Highlights
Note: timestamps correlate with the full conversation
Discovery: Socratic Wheel of Discovery (12:05)
Demo: Finding the ‘Aha’ moment (17:17)
Negotiation: Navigating strategic discounting (24:07)
3 Tips for Account Executives
1. If your prospect is engaged, don't cut the conversation short.
If possible, go over time & answer every question.
2. Always be adding value.
Add 2-3 value touches to stay top-of-mind between meetings.
3. Don't be afraid to discount strategically.
Especially if it's the difference between closed-won & closed-lost (with approval of course).
Watch the full conversation
Full transcript
Taylor Dahlem
Welcome back to How I Deal! Where we discuss past close one and lost deals, how they played out that way, and provide some really actionable sales tips that you can use in your deals today, especially as we head to the end of the quarter. This is going to be a great one. My name is Taylor Dahlem, full cycle seller turn content guy, and I'm joined as always by my partner in crime, Junior Lartey, our sales brain here at Pickle. Jun, how's it going, man?
Junior Lartey
Good! It's episode ten, we've hit the double digits, which personally I think is amazing. Right? Like self taut for us. But in the past I mentioned that I love our intro song. Well, for all of you listening today, I just learned that our very own Taylor here put it together. He mixed it for us. So if he's not here for episode eleven, he'll probably be pursuing a full-time DJ career. But you did well, my friend.
Taylor Dahlem
Thank you. Yes, I've always said that's what I'm going to moonlight as if this doesn't work out, but the very least works well for pods. But yes, a quick refresher. Each conversation we chat through a past deal. All names, places, characters. We fictionalize, of course, but that's because we want to dive deep from the first time a seller saw a prospect, whether it's inbound outbound, in their CRM, on LinkedIn, anywhere, all the way to where a DocuSign is completed and that final yes is achieved.
Junior Lartey
So today we've got Taylor Shafer from QuotaPath. She climbed the ranks at message desk from SDR to Ae and community manager. All of this in less than a year, which is insane. In the past year, I suppose she's made that transition to QuotaPath. So Taylor, we're glad that you can make it.
Taylor Shaffer
Hi, Taylor and Junior. Thanks for having me.
Junior Lartey
So we've got two tailors. We'll try to make it easy to know who we're about to address. All right, Taylor, give us some insight into your role and what problems QuotaPath solves.
Taylor Shaffer
Yeah, so I am an accountant executive at QuotaPath, a commission forecasting and tracking software. We help reps see and understand their commission and commissionable earnings attainment in real-time and ultimately help an admin user such as revenue operations, sales operations, and finance run commissions automatically.
Taylor Dahlem
Well, as a former rep, I was always a hawk on commission, so this seems like it would have made my life a lot easier and probably would have made a little bit more on the finance side. But I guess what deal are you walking us through today, Taylor?
Taylor Shaffer
Yeah, so we are talking about a deal with the company size of about two hundred. They were a super ICP company that I was working with, team size, I'm going to say around forty-ish. And I just really liked working with these people that I was working with. They happen to be rev ops personas, and they're just usually the people that are dealing with commission the most obviously depends on companies, but just really love working with Rev Ops.
Taylor Dahlem
Real quick, rev ups. I know we've got probably a lot of experience listeners here, but real quick, maybe one sentence liner about what is a Rev Opts team or what does a rev ops person do?
Taylor Shaffer
Yeah, so I would say a Rev Ops team or person usually sets up all of the like, the tech stack basically does a lot of data for the sales team, for the overall company, and then ultimately helps the growth team get to their goal.
Junior Lartey
Awesome.
Taylor Dahlem
Well, that tease us up nicely. We're learning that research isn't always a crystal ball scenario. These companies are out there, they're on lists, and they're probably already in your CRM. But how specifically with this deal did you find out about the company, the major players, and maybe what research did you conduct?
Taylor Shaffer
Yeah, so this particular deal happened to come in as an MQL from a webinar. So they attended a webinar that we hold with other people in software, just kind of learning about tips and tricks, best practices, all of that type of stuff. And they were under my name. And so I began doing research on the company and then ultimately did some outreach to a few different personas at the company. Like I mentioned before, with QuotaPath, we like to go for those revolts sales leaders and a little bit of finance here and there as well. But I found the person that I wanted to reach out to and kind of put them in my cadence, so they were a little bit warmed up by that webinar. So my outreach was a little bit different than it may be for a very cold prospect. And it was an email I sent and then a LinkedIn touch and then another email, and he finally replied, and we were talking back and forth, scheduled the demo, I think.
Junior Lartey
Okay, so there was a point that we were talking before this conversation. I just want to bring this back up because you're reaching out to sales leaders, you're reaching out to Rev Ops, but you also impact finance.
Taylor Shaffer
Yes.
Junior Lartey
And when we were talking before we start recording, you mentioned that you sometimes strategically leave out finance like you don't want to prospect. Tell us why first off, and then I'll add my two cents as well.
Taylor Shaffer
Yeah, so it's not that I don't want to prospect them. Love finance. People love people that can have finance. Got to have fun. But typically I find that maybe they aren't as concerned about the rep experience or enabling the reps as much as they are with their personal process. And then maybe here and there, they're worried about a few other product features that maybe I don't want to go down the rabbit hole on a first call, or we may not have it. What they're looking for?
Junior Lartey
To be truly honest, I think so. Anyone can really do this right when you're selling into a department, especially like yours, where maybe there's a bit of an outlier like your product impacts sales teams, but there is an aspect of finance that gets involved and there's products that are out there like that it's okay to strategically leave out certain departments or personas or people that don't respond well to cold outreach or at least understanding like what their role is in comparison. For instance, I also sell to salespeople, but I haven't had a lot of luck with sales enablement. Maybe that's just me. So I tend to reach out to the VP of sales instead and the revolves people instead and then they're like, yeah, we also got to loop in sales enablement. And I'm like, okay, great, well they haven't been responding, so now they have to but like strategically leave out the people that will just quickly say no or won't respond. And I think that's totally fine, but right. This is not a prospecting podcast, but we're finding that some serious gems on prospecting as we go. And you mentioned the way that you prospected this particular person was they came MQL an email on LinkedIn and an email which is really only three touches, right, that doesn't happen that often. Why do you think they booked so quick?
Taylor Shaffer
So they were obviously very warmed up by the email. But what I did find obviously when I had that first conversation with them is that they were really struggling with this process. So they were very much in need and we're probably looking for things already before I even had done a little research and reached out to them. So they're in the right time and right place and I just happened to slide into the inbox at the right time.
Junior Lartey
That's perfect. The timing aspect can help you a lot in your prospecting methods and what message you're trying to say. But it comes down to timing a lot of times. And the webinar aspect, I'm just now thinking about this, but it could have been a competitor webinar that they joined and maybe you joined those two just to see who else is in the room. But some ideas as we're moving along.
Taylor Shaffer
Yeah, that's a really good idea.
Taylor Dahlem
And real quick, as a marketing guy, I can't not glass over this, but anytime an MQL comes in for me, I'm always like where did this come from? Why did it go the way it did? And ultimately I always want to see the other side of the coin. How did sales follow up with that? So I am curious, like with either a quote of path webinar as Junior mention, even a competitor webinar, what type of information, what types of participants, when they do show up, what's the kind of information they get and then how do you leverage that in your outreach after the fact? I guess more specifically.
Taylor Shaffer
So I would obviously want to know what webinar was, what they were talking about, whether it had to do with keeping a sales team retained or maybe how to build a commission structure for a sales manager. So I definitely would get that information and then tailor my outreach towards the webinar. But then also, hey, would you like to know a little bit more of how we do it, this XYZ, instead of, can I have a meeting?
Junior Lartey
Yes. You got a little piece in the webinar. I'm sure it got you thinking, where that company? We can give you a little bit more, we can guide you a little bit more and help you find ultimately, like, solve the problem that you're becoming aware of. As you mentioned, they clearly have some problems.
Taylor Shaffer
Yeah.
Taylor Dahlem
And so the webinar being very it is top level, right, top of the funnel, but they're moving towards the middle, especially if it sounds like if the content is how to BX and it's specifically what your tool can solve. So that leads into the very specific prospecting play, but more importantly, leads into that first conversation, that discovery conversation, which also happens to not be the easiest. So maybe prospecting, you hit on a couple of points, but how did you dive deeper into the pain they're looking for or what are they looking to solve more specifically? And then how did you keep kind of that process organized, and ultimately, what did you learn?
Taylor Shaffer
So, in the discovery part, once we booked the meeting, I obviously ran it a little bit differently than I would have if they were straight cold. They already knew a few things about my company, QuotaPath, and then already kind of seemed to be resonating to some of the points that I made. So something that we do at QuotaPath is called the Socratic Wheel of Discovery, and it goes through the approach, results, challenges, ideal, impact, and objective. So really, what is their desired business outcome? And from the top of their company, what is really trickling down to where they need a potential software like this? Like I mentioned before, they were very ICP, which I found through my discovery. We're hitting all my points of how long is this taking you? Currently, they said it's taking me four to five days, two times a month to run commissions, and my sales reps don't see anything, and they're bothering me when I have to do other work. And what do they wish they had? So during the discovery, I kind of found out that they really wanted to automate the commissions and they kind of wanted a scalable process. They're adding a lot of new hires, and spreadsheets are ultimately not scalable anymore.
Junior Lartey
This sounds like an animal. First off, Socratic Wheel of Discovery. Approach, results, challenges, ideal, impact, objective. I had to write that down. Otherwise there's no way I could have remembered that that could be a podcast by itself, trying to understand how to sell to that type of methodology. So we're talking about like the aspect of your reps, having the reps not yours, obviously having no visibility into what is going on with their commission, with forecasting and how they're going to get paid, which is like the heart of all sales reps. Like we live for commission, we close deals, we have a salary, yes, but it is commission that keeps us going. And to not have that and to have a company growing with these spreadsheets, I can imagine the sales ops team is this has to be priority number one. It has to be. I see a lot of sales leaders posting on LinkedIn about how poor demo experience they have. And sometimes that stems from the fact that they come so prepared, they know it so well. And then reps are like, hey, I'm sorry, but I still have fifteen questions on my discovery doc that I have to ask, whereas it seems like that's not the type of conversation you are having and you roll into a demo. So what is that experience like for you and for that?
Taylor Shaffer
Yeah, definitely. So I always start going into a demo. I kind of give them a little thirty-second blurb of why quota, path, even as a company, what my CEO and co founder were dealing with at a previous company and why they wanted to build quoted pass. Usually this story resonates to certain points that the prospect has said during discovery. I always want to tie it back to things that they said in discovery to get them to connect the dots and already put them in the mindset like, oh, this might help me.
Junior Lartey
No, I'm sorry, I'm just going to jump in real quick. So they say it's a four to five-day process. Every month when you're telling the story, you're saying something similar where our CEO, John He, actually found that it also took him four to five days to automate this. And you're kind of like helping them feel comfortable. Even though it seems like it's not a story about them. It really kind of is.
Taylor Shaffer
Exactly. And this isn't a made up story, this is a problem. So that's why it usually resonates with them. Spreadsheets are still something that everyone's using on a day-to-day basis for commissions and they want to get out of them.
Junior Lartey
I can imagine like, oh gosh, spreadsheets. Okay, so in the demo experience you're going through, I guess just quickly talk through like were there any ‘Aha’, moments that they kind of took a step back and were like, this is aside from we have a spreadsheet, this is exactly what we're looking for.
Taylor Shaffer
So I always go through the rep experience and then the admin experience. Obviously the admin is the one that's going to be using it the one who's reaching out to find a solution. But part of that problem was their reps not having any visibility. So I usually go in, I show the rep experience and what they're able to do. They're not bothering them anymore for, hey, what did I get on my commissions on that deal? Where am I at in my attainment? It's the end of the quarter, am I going to hit my quota? And usually in this process they are like, oh my God, thank God, my reps are going to stop bugging me. It's great, but obviously I need to go to the other part and show them how simple it is. Okay. Your commissions are already calculated, like I mentioned, automatically, and you basically have to press a few buttons to schedule it. You know, approve the deals and they're good. And instantly they're like, okay, where do I sign up?
Junior Lartey
If you can eliminate that huge aspect, this like four to five day period and the constant nagging, that really starts to add up. Well, what are you going to do when you eliminate all of that and you now have four to five days back every month? It's like, well, now I can manage their conversations, I can actually manage the team, I can get more MQLs going and start to spread the growth of where the time suck used to be. So I can see how appealing this would be on top of just like the product being really slick and being exactly where it needs to be.
Taylor Shaffer
Exactly. And you're really hitting on all the.
Taylor Dahlem
Points, junior that's what we do here. Taylor traditionally speaking, old school sales methodology when it comes to objection handling, and specifically whether it's in the sales conversation or even prospecting, you're always expecting some kind of pushback, whether it's the classic, it's too expensive, and then imagine like a flashcard. Most sales reps are trained on, like, here's exactly how you respond. But what we're learning, not that this is rocket science by any means, but throughout the podcast conversations we're having, when you're actually working a deal, an objection is not just a one-liner that you can just use and respond to and check a box. It's more of a real-life scenario where there's back and forth. It's really working through something. I think most importantly, it's working through it together. Almost like a partnership between here's the trust we've built, here's, the transparency, the objections that might overcome this deal or be a barrier to this deal. How can we get through this together? So, long-winded way of asking, what were the major barriers that might have come up? Maybe it wasn't straight line by any means, but how did you overcome them?
Taylor Shaffer
What do you mean? It's not always a one-call close.
Taylor Dahlem
The commissions would be awesome on that.
Taylor Shaffer
Right? Thank you for that question. There's definitely a ton of different places this could have gone. As I mentioned in the beginning, I really liked working with these two points of contact that I had at this one company. And something that you mentioned, Taylor, is that they were very transparent. They kind of were like, hey, we ultimately are not the budget holder here. We need approval. They had a budget that they really did not want to exceed. So that was a big problem there. Another big problem was that this was an international company. So with that obviously comes time zone issues and just even getting in contact with someone from another country. I did get very lucky that in the next two weeks, they were having a company off-site and they would all be together in the same area. Their VP was coming, they would be with them. And then I did have this next conversation with the VP, but another roadblock came up and I found out that ultimately the CEO needed full approval for everything. It seemed that he had been burned by software in the past and it was a little bit hard. And as I mentioned before, the budget was something that was big.
Junior Lartey
So you got this off-site where the whole team gets together. You're able to snag a time, and obviously the two people that you've been working with at this point, they're on board. In that little window, you finally get the VP to meet as well because he's in another country. Everyone's like, okay, great, this looks good. Oh, by the way, we have the CEO. So did you get in front of the CEO talk through that aspect?
Taylor Shaffer
Yeah, so good question. I actually did not get in front of the CEO. We had basically a last meeting. Right after that meeting, I sent a full email with a proposal with everything we had talked about, basically laying out again, everything that I found in discovery that they really wanted. And everywhere that quoted pass was going to hit on everything that they wanted. And I think they literally sent a text message to the CEO that, hey, we're going with this. It's going to be fine. It's in the budget. And that was where I got the yes through the email reply from that proposal.
Junior Lartey
So at this point, like, you've built such a good relationship with your two point of contact and the VP of Sales that they felt comfortable texting the CEO and saying, this is our software of choice. This is slightly the project that you've allowed us to take on at this point. And then, I mean, obviously the CEO said yes, which means more automated commissions, not just for you, but for this other team. So they should thank you. They should be here to say thanks.
Taylor Shaffer
Right?
Junior Lartey
Okay, so I think we jumped the gun, but where did the ultimate yes come from?
Taylor Shaffer
The ultimate yes came from the email with the proposal. I did get an additional little discount for them to reach that budget. Had to ask my own VP, but if it meant that they told me, hey, if you can get it under this number, I will sign by the end of today. That's always what your VP wants to hear as well as their team.
Junior Lartey
Yeah. Assurances, like I'm getting an assurance from you that you're ready to move forward with this if I go and ask. I think that's the piece that a lot of people miss when talking about discounts. And that's probably the biggest problem is the rep here's the discount that they need, and then they take the discount back without being like, hey, I'm happy to go push for that, but if I push for that, can you move today? And so obviously you were able to navigate that really well and stay out of trouble. Stay out of the yes from you, but unknown from them. Some things to think about.
Taylor Shaffer
Yeah, definitely. I would always get a vouch. As you said, Taylor, you're working with them as a partnership. Hey, I want this to work for you, but I need something why would I go to my VP and waste my breath if you're not going to sign by specific date?
Taylor Dahlem
Perfect. Yeah. This is a nice way, I think, to lead into ultimately, what are everything you learned in this deal, everything that maybe you learned in past deals even. But what are three things any sales pro listening today can implement and ultimately try to get the deal closed before the end of the quarter here in a couple of days.
Taylor Shaffer
Yeah. So this first demo, like I mentioned before, was a discovery and a demo all in one. And it just so happened to go past the time that I usually allow for demos. And it wasn't because I was talking, it was because they were very engaged. They wanted to learn a lot. And I felt like what I was saying back to them was extremely valuable to them. They very much wanted to solve this problem. So I guess I would say don't be afraid to maybe go over time if you don't have a hard stop, if it's productive, obviously. If it's not, cut it off. Another thing was the two weeks that I had to wait for this meeting. I wanted to stay top of mind. I really wanted to get this deal done within that month and it was cutting it close. But you need to send them a value touch within those two weeks. And like I mentioned, I would say at least two weeks is pretty long time in the sales world. And so many things are happening. You don't want to get that email of, hey, we need to reschedule. This isn't a priority anymore because you weren't staying on top of them. And then the last thing I would just say, don't be afraid to ask your sales leader, your VP of finance, for the additional discount to get the deal over the line. They are a great partner with us. I think we even talked about them doing a case study so that additional discount will be worth it in the long run.
Junior Lartey
Taylor, it was really great to have you. For our listeners, if you tuned in today, go connect with Taylor Shaffer on LinkedIn. Thank your marketing team for the MQL. When people are engaged, keep them. And my personal favorite is ask for help. If you lose and you ask for help, you can't be blamed, but you're also more likely to win. So again, Taylor, thanks.
Taylor Shaffer
Thank you so much. I had a great time.
Taylor Dahlem
And just like that, another episode of How I Deal in the books. Please, if you enjoy the content we're pushing out, please like subscribe, leave a comment, maybe toss us a couple of stars here and there, but ultimately thanks for tuning in. We really enjoy this. Our tenth episode is a huge win and mile marker for this podcast. We're excited to crank out some more. We will see you next time.
