🗺️ Failing to plan, is planning to fail
Anthony re-lives a rollercoaster ride of an enterprise deal.
Leveraging a custom account plan while dividing & conquering with his mighty SDR.
He created so much value that no competitor price-drop could touch (oh how they tried).
Hear how he did it!
Guest Feature
Anthony Natoli started as a BDR jumped to AE.
Then took another great opportunity starting back as an SDR.
And claimed his way to Mid-Market AE, Growth Director, Commercial AE, and Strategic AE.
Working at high-growth companies like DemandBase, Outreach, & Lattice.
He is currently the Business Development Manager at QA Wolf.
Deal details
What are you selling?
- Sales execution software
Where did the prospect come from?
- Prospect was on Anthony’s target account list
Company type
- Product Management SaaS company
Prospecting method
- Cold call based on buying trigger (new product/vertical roll out)
Barriers to Overcome
- The prospect ghosted towards the later stages fo the deal
- Had a competitor bid 3x less than Anthony
Buyer types
- VP of Sales
- Sales reps
Deal length
- 7 month sales cycle
Episode Highlights
Note: timestamps correlate with the full conversation
Objections: When the tech all looks the same…problem-solving > price dropping (24:60)
3 Tips for Account Executives
1. Get to the friction ASAP. Why would they say 'no'? Only hearing 'yes' = a red flag.
2. Hold micro-meetings with the prospect before deal milestones. Ensure you're on track.
3. Multi-thread internally as much as you do with your prospect. Loop teammates in.
Watch the full conversation
Full transcript
Taylor Dahlem
Welcome back to How I Deal, where we examine a single past close deal, how it played out that way, and provide some actionable sales tips right from the front lines that you can use in your deals today. My name is Taylor Dahlem, full cycle account executive, now content guy, and I'm joined as always by my cohost, Junior Lartey, the sales guru here at Pickle, June. What's up, man?
Junior Lartey
It's episode twenty two and I think sales guru is like the thing that everyone bashes on LinkedIn, so we'll remove that going forward. This is one week post-SaaSter. We've got some epic content lined up directly from SaaSter, think Street Interview, think Name That Pickle flavor and more. But for today, we're stoked for this episode.
Taylor Dahlem
Yes, post-SaaSter, it was a heck of a week. A ton of good content coming your way, including this pod. But if you have not tuned in before, a quick explainer for what is about to happen. Each conversation we chat through a single pass deal. We want to leave out all names, places, or at least keep them as fictionalized as possible, allowing us to dive deep from the first time a prospect was encountered, either through the CRM, a Target account list, LinkedIn, or wherever you find those individuals, all the way to getting that final signature through procurement and kicking off implementation.
Junior Lartey
Joining us today is Anthony Natoli. He started as a BDR, jumped to AE, took another great opportunity starting back as an SDR. He then steamrolled that into mid-market Ae growth director and commercial Ae roles and is now a strategic Ae with Lattice. Anthony, tell us about your role and what problems Lattice solves.
Anthony Natoli
Hey guys, pump to be here. Thanks for having me. But yeah. So I sell to enterprise companies that are looking to reduce regrettable attrition, create a people-first culture, increase employee productivity with the goal of retaining their top performers and growing them in their careers.
Taylor Dahlem
Fascinating. Anthony, we'd love to hear what deal you're walking us through today.
Anthony Natoli
Yeah, so I'm going to be walking through a deal that I actually closed last year. It's one that took way longer than I wanted it to. We're selling to a tech staff company and the product management software spits about seven hundred and fifty employees. We spoke to the VP of sales who reported to the CEO we had a nightmare procurement situation. There's about a six figure deal of one hundred seats, lots of up and downs, some ghosting here and there. We thought the deal was dead, potentially at one point. So really excited to walk through one of my proudest deals in my career.
Junior Lartey
The steel has got it all, or at least it sounds like it's got it all. Definitely one that in the sales career you probably reflect on quite a bit. And I mean, obviously it's the one you chose to talk about today. So tell us how you found out about this company that gave you a little bit of a nightmare sales cycle and then what research you conducted before reaching out?
Anthony Natoli
Yeah, so we had a Target account list like most AES do, and I was paired with a BDR and basically we divided and conquered that target account list together. For my top accounts, I created an account map, basically an account plan that has all the key stakeholders that we would typically find that having a meeting with them would be a win. And when I was working at outreach, one of the things that we looked at was to be a good fit of an account is the current tech stack. So knowing that they were on demand base and drift and using salesforce, all companies that outreach integrates with and partners really close with were a good sign for us to reach out. So this account was on our Target account list. It was probably on the lower end of our account list. So I kind of let my BDR have at it. But basically we prospected into the account. My BDR cold-called them and we were able to get a meeting. Our first discovery call with the VP of Sales who ended up being the main DM.
Junior Lartey
So you've got this account map, is it completely blank? And then you and the BDR go out and try to fill out some of these fields like you mentioned tech stack fields, like what are they using today? And then you have titles and now you got to go find the people that fit those titles. Are you doing that by yourself or is it like a tag team effort?
Anthony Natoli
Yeah, so we had a template which is basically like company information, what their tech stack was. And then we had an exercise where we would create a hypothesis for each account. Basically, why would this account ever be interested in what we have to offer? And basically that's how we prospected. Right, with that hypothesis. And we developed that hypothesis based on research we would do. So are there any key initiatives we found? Were they hiring? Was there something mentioned in like an article or ten K or something from LinkedIn that would give us a good idea of why we should be reaching out to this account? And then we would have a template of all the personas that we typically sell to. And then I would go out and every week create two new account plans based on the accounts that were in my target account list. I would share that with my BDR and that's how we would kind of divide and conquer the accounts.
Junior Lartey
A lot of transparency of information back and forth. I really like that aspect. Was the account plan something that outreach implemented across the team or is this just something that you did one off?
Anthony Natoli
Yeah, this was something that we implemented and it allowed us to share with our execs as well. So like on deal reviews with our VP. So it's like transparency of information across everyone in our company. Because the reality is we know to win an enterprise mid-market type deal, you've got a multi-thread on both ends, not just who you're reaching out to, but you need to be multi-threaded within your company. And what better way to do that is to set them up for success with all the information that you have. So not only were we using it to prospect, but we're using it when the deals were in flight as well.
Taylor Dahlem
Anthony, we dove into the prospecting here a little bit, or at least hinted at it curious, specifics, always better on this pod. What was kind of the exact messaging, maybe that caught the attention of this prospect and maybe what you mentioned some of the hypothesis and the triggers that you're looking for, but what was kind of the main problem that you pointed out that caught them?
Anthony Natoli
Yeah, so they were a company that helped companies create really great products. And so we noticed that they had an initiative where they were actually releasing new products to the market as well. There was a specific article that we read from their CEO and so that was like our BDR's message to them. It's like, hey, I saw that you have this initiative. Like, curious how you're going outbound with those new products to drive brand awareness. And it just so happened that they were actually thinking about that key initiative. How are they going to build top-of-funnel awareness for the new products that they were trying to sell to increase revenue as a fast growing organization?
Junior Lartey
I think that's really cool because you can't as like, a VP of sales of that company, you can't really refute an article from your own CEO at that point. It's like, oh man, I guess this is the initiative from the top down. So, yeah, I should probably take this meeting and try to understand the strategies here a little bit more. So props to this BDR, because it was a cold call that he made, was able to get some interest there and some initial pain. So now you've got to find, like, drive that pain home, really figure out what all of that means. So you hit the discovery phase at this point. What did you learn through this process?
Anthony Natoli
Yeah, so I think when you lead with your prospecting with a hypothesis of a problem, you get the prospect to validate if they have that problem or not. And what that allows the Ae to do is come in with that point of view. Hey, so it sounds like you guys are really focused on building brand awareness for these new products that you're releasing. Why are you so focused on it? And then what that allows us to do as an Ae is really understand the meaning and the importance behind the initiative rather than going into and being like, oh, we can help you sequence all these people and you can look at all this data. I really needed to understand what they were trying to do and if we were going to be a good fit at all because there's a lot of tools out there that can accomplish what we do. So I needed to understand if it was there a big enough problem for us to solve. And what we found was that historically they were all inbound. They had reps that maybe weren't as savvy with prospecting as they would like and they needed technology to help them scale a new prospecting and outbound strategy for these new products that they were releasing. And this was going to be a main pipeline driver for them moving forward in two thousand and twenty-one. So this is like a critical initiative that they knew they couldn't continue with their current state to achieve like the pipeline goals that they had.
Junior Lartey
What's really cool about this too is outreach. While it impacts the sales team directly, the initiative of this company went just beyond we need to do better outreach. It was like touching. We've got this new product that we're trying to get to the market and it goes far beyond just like we want to send better emails, we need data on what the response rates look like. It's like way beyond just some of those face-level metrics that a VP of sales would find interesting, right?
Anthony Natoli
Yeah. And I think, listen, the reality is that goes for any company, right? If you're not talking about the prospect and what matters to them and the why behind what they're doing, you're not going to be able to stand out amongst the competition. The best-sellers are getting super clear on what the problem is, what the size of the problem is, what happens if they don't solve that problem. And they're talking less about what their product can do to help, but more about what problems can they actually solve. And sometimes they're not the best fit to solve those problems and they're willing to walk away. But in this case we found that like, hey, this is kind of our bread and butter, we do this all the time. So that made us feel really confident in the deal.
Junior Lartey
So you had mentioned multi-spreading towards the beginning at this stage was there any of that going on?
Anthony Natoli
Yeah, really good question. So they historically had been a really big salesforce shop. My VP came from Salesforce as well and so Salesforce obviously had some competing products and they could have really easily just did it internally, like they could have built it out internally with what they had with salesforce. And so I identified that as a potential risk really early on. And so what I did was I brought in my VP to the next call to kind of talk shop peer to peer of what the differences were why companies tend to work with our organization versus doing it manually. And that created like a really nice rapport between our VP and now that they've built that rapport, my VP could reach out maybe if things were going silent or whatever the case is, to kind of bring that peer-to-peer level of conversation to light. Had I not done that in the beginning, I could have very well run the risk of losing the deal to them doing nothing.
Taylor Dahlem
You might have mentioned this, but just to recap for the listeners, like, who are all the stakeholders involved in these initial conversations? And then obviously this will help us clue in along the way for the upcoming meetings too.
Anthony Natoli
Yeah, I think we're really fortunate to get the main DM on the first call where he didn't push us down, but essentially this was his baby, right? This was like him putting his mark on the map of like, we're taking this company to the next level and I'm going to spearhead this initiative. And so basically it was like a top-down approach where we talked to him and then he ended up bringing his team onto the demo, which was like, some sales managers and then some individual contributors that are actually going to use the product. That's one of the benefits of selling a product that impacts, like, a specific end user is that we can bring them on and kind of scope out what this may look like for them on a daily basis and then tailor it to them specifically.
Taylor Dahlem
Yeah, so like you said, starting at the top, VP of sales, working your way down. And it sounds like he's bringing everybody into the fold because he believes in finding a solution, maybe not necessarily yours at the time, but some solution. It has to be identified. I want everybody to have a consensus on this and that helps you a lot in the next stage here. Walk us through post discovery. You're finding this pain. You're understanding it's a historically inbound shop, but they're trying to move outbound. What did it look like when you actually had to have the rubber meet the road? You actually had to show products in that demo stage. What does that look like? Maybe from the top, all the way down perspective from each level? And how did you kind of personalize it to each of those individuals?
Anthony Natoli
Yeah, I think again, the reality is there's so much product that we have that I think a lot of reps, especially new reps, get lost in this demo that's so centered around like, shiny features and buttons and it doesn't tell the story of how it's actually going to help. It's just all about, here's what we do. We can help you send a ton of emails. It's like, no, you have to share the pain or the challenge or the future state and what the gap is, and then just show them how you can use your solution to close that gap and paint the future state together. Whenever I'm demoing, my approach is to tell a story around whoever the group is that I'm speaking with and how they're going to be able to solve their problems and their challenges with our solution and paint that future state. Because it's a scenario where once you show them what's possible, they don't want to go back after the call and start sending manual emails. They just realized that there was a better way to do things. And so we talked to the individual contributors prior to the demo and kind of scoped out their current workflows like what was the state that they were in, where do they want to go and then we were able to paint the picture of closing that gap. I even do that today at Lattice. We'll do like a demo prep call to make sure that the demo is really tailored and I'll frame it as hey listen, you're going to be bringing on these people to the call. They have no idea what we do to make sure the demo really hits the mark and makes you look really good. Let's get on a call to make sure we understand like fifteen to twenty minutes what's currently going on in your world so we could tailor it specifically to you all. So I think it's a really impactful step between discovery and demo that a lot of people miss is that prep work and so tailoring it to the individual contributors and then also telling the story to the managers that were on the call so that everyone feels like they're getting something out of it. You need to break out the sections of the demo to the specific groups that are on the call.
Junior Lartey
I want to touch on the demo aspect, but before I do that, I think you bring a really great point. An aspect of typically we look at the sales processor sales cycle as discovery, then demo proposal call, close or close loss. Whereas there are so many stages and steps in between that and you're talking about post-discovery, pre-demo prep call, something that I think a lot more people should likely consider for their own conversations. Really cool to hear the distinction and steps. There's a lot going on in between the big what would you call them? Like road stages, I guess road sign stages through this. So you had mentioned like a tell-show-tell. Can you just quickly give us a nice one to two-liner about what that looks like? Maybe it's like an outreach strategy but this was like the first time I maybe think I've heard about it.
Anthony Natoli
Yeah, it's really popular with solutions consultants but basically the method is you talk through, you have three main themes and those three main themes are the three main things that you want the prospect to take away and they're typically the three main value drivers of what they want to accomplish. So you go, hey, we want to do X number one. And then you show them in the demo. So you go from a slide, talking through the first point and then you transition to the demo to show them how you're going to do that. Then you go back and you recap it. Hey, so we just talked through number one. Next we're going to show number two, then you go to number two. So I showed you number one, I showed you number two. Now we're going to go to number three. Show number three, go back, I showed you number one, I showed you number two, I showed you number three. And basically you're just like beating a dead horse of those three main themes and obviously asking them to validate. Hey, based on what you just saw, how does this compare or how are you envisioning this helping with point one, right? And you're getting them to confirm that. Then at the end you bring that slide back up and then you ask, hey, what are the one or two things that stood out to you today as it relates to these three themes? And then you use that in your recap email and now you've got a very tailored personalized follow-up that is using their words about how this is going to help them with those three themes and that's what you anchor on in every single call moving forward. Right? So that's kind of the approach.
Junior Lartey
Hey, listeners, go back and listen to that two minutes and pick out the strategy because otherwise you can get lost when you demo. You had mentioned this before, Anthony, but in outreach there's a full side panel of so many things you could click on. It could get really overwhelming, but this type of strategic process really helps you stay specific to the problems, the two to three main problems that you're trying to solve without getting super carried away with the product post-demo stage before it actually closes. This is likely where a ton of stress in the deal happens. Talk about any roadblocks that came up that you faced that you eventually had to try and overcome.
Anthony Natoli
Yeah, I think roadblock is a theme of this deal. So it started in June, didn't end up closing until December. And so basically it felt like we had a really solid deal after the demo and then all of a sudden silence, right? And so that was like the first roadblock and sign of like, this is where being indifferent to any specific deal and having a lot of pipeline is so important because for me, I was like, damn, I'm on ramp. I thought this was going to be a deal like that big commission check and put my name on the map. Then all of a sudden they ghost and I'm like, I have two choices. You can either spiral out of control or I can do what's in my control, right? So what I did was I leaned on my manager, we game planned, we figured out what was the best path forward, how do we engage them thoughtfully to give them value, to get on a call with us and then go prospect to build more pipeline, right? That's the only thing I could really control. So that was one thing. I think we had a competitor come in at three X less than us, right? So that was a big roadblock. It's like, why wouldn't someone pay three X less for this? Right? So we had to really lean on those three themes and how we're actually solving business pain and driving outcomes for their business. We found that the competitor was solely leaning on price and feature functionality, and that's kind of what want us to deal with our approach to the partnership. And I think that the last one was procurement, right? So once we got the verbal that we were the vendor of choice, we had a procurement guy that was just really good at his job. So it was kind of a nightmare because what he was saying was a, listen, your competitors three X less, like, what are we doing here? And so we had to use our champions to kind of like, connect the dots for him because at the end of the day, he doesn't know outreach versus competitor, he doesn't understand the value. So we had to really paint the picture for him, and then eventually, obviously, we overcame that hurdle. So I think, just to sum it up again, it's getting ghosted. It's looking at a competitor that's maybe like, kind of chopping at your ankles with the pricing and then dealing with procurement. So those were the three main obstacles of the deal.
Junior Lartey
This is exactly how you beat the competition, though. Like, you go problem-centric, not product-centric, because three X is a bit ridiculous. And when the contract comes across the line, like you said, this procurement guy is like, is this really three X worth it? But when you know the problem and you've orchestrated it better than your competition, price at that point tends to matter a lot less.
Anthony Natoli
People justify their decisions based on logic and the logic of them being able to see that you can help them solve their problems. Right. As technology starts to look similar and more similar, as spaces get more crowded, you have to be problem-centric to drive distinction and how you're going to be able to help. Because the reality is, again, like I said in the beginning, a lot of people can help you send more emails or make more calls. It's about how are you going to uniquely help them solve their challenges and uncover those and talk about them in the conversations that you're having.
Taylor Dahlem
Yeah, price tends to work against you. I think once you're in a unique position where it seems like you have the meetings first, right? You built the gap, you built the value, you told the story, and then lo and behold, the competitor can always come in, drop their prints, cut price in half. But ultimately, I think that probably worked against them in the sense of, look, here's how much it actually costs you to solve this problem. Here's how much it's costing you to not solve it. Yeah, you can save some bucks throwing a band in on it, but ultimately it's still going to cost you this much in the end. So what does it matter to save some bucks now and learn the lesson a year from now when that contract is up or whatever it was going to look like? So I think if the competitor had come in before with a cheaper price before you all, it might have been even more of an uphill battle because you're like, oh, you're coming here three X more expensive. Why would we do this? But the way you got in first, and maybe that's a lesson to learn, is like, try to get in as early as you can to have those bigger conversations before a competitor gets just more of a reason to do that. And before we move to kind of this last section here, procurement, I'm always curious specifically, how did you arm your champions to maybe approach procurement to sell internally? Because ultimately it's not procurement's job to meet with you, right, for the most part, and to take a demo and do a whole discovery with you. That's not what they're there to do. They're there to get the best value for what they're buying and protect the budget. So maybe how did you balance that between trying to insert yourself in some of those conversations with the pre-agreement, but also how did you arm your champions specifically to sell it internally?
Anthony Natoli
Yeah, so I think once we got everyone's buy in from the team, like, all the individual contributors wanted outreach, all the sales managers wanted outreach. VP of sales wanted outreach. What I very quickly learned is that the procurement person can't say, no, they're not going to be able to tell the VP of sales, no, this isn't happening. So I needed to keep that in the back of my head and not let him dominate me in those conversations because I was confident that the team wanted it and we were going to get it done with their support. And so I armed my champion with kind of like a business case and an outline of like, here are your problems, here how we're going to solve it, here's your pipeline goals, here's how we're going to help you get there. And that really helps. I think the procurement guy used the competitor as a negotiating lever of like, hey, we're just going to go with your competitor. But in the back of my head, I knew that we're the vendor of choice. So I kind of was able to hold my ground and stay strong. Of like, well, you're going to disappoint your team if you don't go with the vendor that they want. And so we had to obviously find a common ground. We were both a little bit uncomfortable, but yeah, we ended up being able to use the champions to be like, hey, we got to get this done. We're anchored on a specific timeline of like, them releasing new products that they needed to get out to market and so that helped drive the urgency as well. And once we're all said and done, procurement guy was like, he got a win. So he was very appreciative. We got a win. So it ended up being just like a win-win. He ended up sending us like a really nice email afterwards, which is always funny.
Taylor Dahlem
That's awesome. That's awesome. I love how that worked out. Let's quickly recap this entire timeline, right? Like maybe just a high level. Walk us through how long this deal took and maybe how you managed it internally, how you kept yourself organized. You mentioned the account map, but if there was other functions that you deployed, let us know.
Anthony Natoli
Yeah, so it was a seventh-month deal from June to December. We had about fifteen meetings in between. I was on testing basis with my champion as the VP of Sales. We had a bunch of email threads going. We had a mutual action plan that we're working on together as well to keep us organized throughout the deal where all the resources were kept. It's like my favorite thing to do in deals like this and then obviously having the account map. But that's kind of like the high level of how I stay organized. Awesome.
Junior Lartey
Quickly tell us what a mutual action plan is. Just high level?
Anthony Natoli
Yeah, essentially it's a way to organize the steps from discovery to deal closure to hold you and the prospect accountable to those steps to get there. And it allows you to understand like, hey, is this deal really in? Are they bought into this plan? And it allows you to come off as a partner of like, hey, I understand your challenges, here's how we typically get there. Are you bought into this plan or not? And what would you change? Who do we need to loop in? And also here are all the resources that you could ever need right inside this plan as well. And then it just allows you to have a timeline to again hold both parties accountable to that timeline.
Junior Lartey
Awesome. Love that mutual action plan. If you haven't heard of it, check it out. It might help progress some of your deals. Keep everything organized. But Anthony hit us with the three tips you learned in this deal.
Anthony Natoli
Yeah. Number one, get to the friction as fast as possible. Meaning how and what are they going to tell you to say? No. So for me, I realized. That maybe there is a competitor that they could go with to do nothing like the salesforce scenario. So get to that friction as fast as possible, because if all you're hearing is yes, that's a red flag. Make sure that you have the micro meetings between calls. So the demo prep call is an example, right? So make sure that you're partnering with your champion in between the big milestones. And then number three, the importance of multi-threading not only with the prospect, but internally within your organization. So when the deal does go silent, you have other people other than yourself to be able to reach out.
Junior Lartey
This whole deal was friction. Get to the friction first. While the whole thing was friction. Awesome deal to walk through. Anthony, it was great chatting with you. For our listeners. Go connect with Anthony Natoli on LinkedIn. He's pushing out some great content. Again, thanks for joining the pod.
Anthony Natoli
Thanks, guys, appreciate you having me.
Taylor Dahlem
And just like that, another episode of How I Deal is in the books. Thanks again, everyone, for tuning in. Thank you, Anthony, for joining us, delivering some awesome insights on how to work through a pretty perilous deal that ultimately paid out in the end. Some awesome tips that you can implement today. We will finish up the cutting. Thanks again for tuning in and we will see you next time.
