Your AI Hits Three Walls on Every Deal

Julia Nimchinski:

And we are live. Welcome back to AI Practice Sessions, and today we’ll be showcasing different elements of self-learning go-to-market. Recursive systems that don’t just execute workflows, but observe what happened, learn from it, and then change what they do next. And please don’t forget to just join the conversation on HSC Slack and ask Your hardest questions.

We have an amazing, session to open the day with Meredith Chandler, VP of Sales at Aligned. Meredith, welcome. Super excited to have you here. How have you been?

Meredith Chandler:

Good. Thanks so much for having me and us, Julia. We are so excited to join Hard Skill Exchange today. First time or longtime listener, first time caller. So thanks for having us.

Julia Nimchinski:

Our pleasure. Well, let’s get into it.

Meredith Chandler:

Amazing. I’m gonna go ahead and share my screen here. Here we go. Amazing. So, today we’re going to be talking about the three walls that your AI hits on every deal. And just a quick personal intro, I’m Meredith Chandler, as Julia has said, I’m VP Sales at Aligned. And we’re an AI deal workspace, formerly known as a deal room.

So, I want today to be as interactive and as productive for each and every one of you, so if you have any questions. Or comments, or just thoughts, please go ahead and throw it in the chat as we go along. Maybe we want to kick off the chat, because it’s, you know, the first session of the day anyways. Maybe you’ve had your coffee, maybe you haven’t had your coffee.

Maybe we want to judge each other for our coffee intake, so maybe just throw in the chat, I’m caffeinated, I’m ready to rock. Maybe you’re a quad kind of guy. Oh, Julia’s got hers, amazing. Maybe you’re a, you know, straight black kind of girl, maybe you’re Okay, she’s nodding. Julia’s a straight black. She takes it straight up.

But if you want to throw in the chat if you’re caffeinated or not, or any chat along the way is always welcome. So, with that, a little intro of myself. Again, Meredith Chandler, VP Sales at Aligned. And I have been in sales for about 15 years now. I’ve carried a bag. I have managed sellers who carry a bag. I’ve overseen CS teams. I have a BDR org right now that I oversee as well.

And I can say, and maybe some of you can relate, again, like, throw it in the chat if you can, or if I’m way off, but the deals that scar me, or have scarred me the most, are rarely the deals where we’re losing for product market fit, right? They’re actually the ones where we think we do everything right, and maybe we lob over a proposal, and we’re told, okay, I gotta take this internally.

And we never hear from them again. We either get the courtesy of, we’re going in a different direction, or oftentimes, you just get ghosted, or the deal slips indefinitely. So, that’s what Aligned aims to solve for, and we do that in a few different ways. So, aligned… has this theory that, excuse me, again, more than anything, deals are dying because your buying process is complex.

So if you think about it, we’ve got about 4 times the amount of stakeholders than ever before. There’s more budget scrutiny, more… or longer sales cycles. think about budget scrutiny, right? It’s not 2005 to 2000… sorry, 2015, it’s not 2015 to 2020, right? It’s not the golden era in SaaS and sales.

There’s not VC money, flying around anymore, so it’s really tight budgets, and not only that, but we hate to admit this, but only about 5%, so there’s studies by Pavilion. and by EBSTA that show Only 5% of the buying process happens when we’re in the room.

Now, I know that’s a harsh, harsh truth, and us as salespeople don’t always want to admit that, but if you think about selling, right, and especially in today’s day and age, when You know, I ordered DoorDash last night, right? You can order anything from your phone.

You can order a frickin’ Tesla to your phone, and the overwhelming amount of information on the internet is just so astounding that most people are doing a lot of their self-education before they come on these calls, right? They don’t always want to talk to a salesperson. I know, it hurts. I’m a salesperson, and it hurts. But we’ve got that, and then also think about once you’re in a sales cycle, right?

The decision Information is often lost in hundreds of email threads, links, files. Think about if you’ve ever been on the receiving end of a sales cycle, right? If you’ve ever received a follow-up email, or maybe you’ve received follow-up emails, and maybe you’re on a group thread, but then maybe you’re on a different buying committee thread, and then you’re on a proposal thread.

It is so difficult to keep track of all the correspondence. Certainly doesn’t help making buying any easier. And then when we do have a good call, we are so excited to just ram all that information down our champion’s throat that we’re giving them a 25 slide deck. And especially now with AI, you could just put a few prompts in and you get so many slides, right? So we’re overwhelming our buyers with information.

And then we expect them, like, okay, I just handed them so much information, they’re gonna go get this done now. Well, a lot of times, our champions don’t know how to buy. This is not their full-time job. We’re selling all day, every day, and so we have a very cookie-cutter process, but they don’t always.

And so, just expecting them to get things done, internally, if they’ve never bought anything, can be really lagging. And so, there’s a lot of stakeholders that maybe we’re not aware of that pop up at the final mile. And then lastly, a lot of this is untracked, right? So say you do everything right, think about those deals that scarred you. I know we all have some.

If you think about those deals, maybe you did everything right again, and somebody says, okay, give me that 25 slide deck, I think I have what it takes to get this done. Still don’t really know what happens, and so you’re forecasting a lot on gut instead of actual trackability. So, with that, I’m going to show you what Aligned aims to solve for through, some of our… AI deal workspaces.

So, through Aligned, you can very easily set up a template here. So think about if you’re running a sales team, maybe you… or a sales org, maybe you’ve got SMB, mid-market, strategic, enterprise, there are different cycles. You don’t want everybody in the same, cycle, same process, because it’s gonna be different. Maybe you even have different competitors.

So, for us at Aligned. we have completely different competitors, even within our SMB versus our mid-market segments.

So, the process is different, the way we sell is different, even our buying personas are different just in those segments, and so we have specialized templates where with just one or two clicks, you can spin up this buyer collaboration room that makes it so much easier for buyers to actually buy from you, because everything sits in one space.

You’re no longer chasing endless emails around, endless proposals, it’s all here. And you can put, you know, team introductions, you can put a process overview, you’ve got your 25-page slide deck here, you’ve got 25-page slide deck number 2, maybe you want to add some case studies or testimonials, whatever you think is helpful, you would just add to this room. And again, people aren’t chasing everything down this way.

So not only that, but when you share this room. We require an email address to enter it. So, say I’m selling to Julia, and Julia says, okay, I’m the champion, send me that 25-page slide deck. I’m gonna take this up the hill, and I’m gonna get this done for you.

But maybe Julia doesn’t, foreclose with us who she’s gonna share it with, but when she shares this room, it’s gonna require their email, and so we’re gonna see everybody that enters that room, and that way, it surfaces a lot of those hidden stakeholders. So not only that, but we’ll show you exactly when and when, when and where they’re spending time in your room.

So are they spending time in that 25 page slide deck, or are they spending time in those testimonials? Maybe it makes sense to proactively connect, one of your current customers with a prospective customer on a reference call. This actually, was really powerful for us. us just a few weeks, again, because we can show you exactly where people are spending time, how much time they’re spending there.

We had a call, or we had a deal that stalled in the proposal stage, and so, rightfully so, the rep is incessantly pinging me, hey Meredith, I think we need to shave 5%, 5% will get this done. Okay, well, what are they saying to the pricing we have right now? nothing, and that’s the problem. They’re not saying anything.

So we pulled up the deal workspace, and we found that they were actually spending time in the competitive analysis section. So we could have discounted 80%, and it wouldn’t have moved the needle. So, picked up the phone, walked them through the market analysis, and from there, we were able to unblock the deal.

So again, just having these insights behind the scenes, first row seat at who’s actually involved in your deal, really makes it easier for buyers and sellers to, collaborate here. Now, because we’re tracking all those emails, we can also make you a full-time stakeholder map.

So we know now that, thanks to Epstein Pavilion, that there’s 4 to 10 times the amount of stakeholders than ever, and oftentimes we don’t even know who half of them are, so we’ll connect with LinkedIn, enrich all of the data, do a bunch of scrapes, and put together this stakeholder map for you, and then we’ll show you with the seller agent here in just a few minutes. how we can craft, you know, if Julia takes us up the chain and I see Nick walked in, say, seller agent, what’s Nick’s role in all of this?

Craft me an email to introduce Nick, catch him up to speed, etc. So everything, lives in the deal this way, and so it’s all very focused on Again, buyer-seller collaboration. So… Through these aligned rooms, we’ve been able to, have 70,000, deals running through Aligned.

Almost a million buyers are entering these rooms each month, and 30% shorter sales cycles, just because it’s so much easier to keep everything in one space. But up until now, and everything you’ve seen so far is very, buyer-centric, right? It’s really aimed to make it easier for the buyer, and we just scratched the surface, right? We didn’t even touch on mutual action plans, business executive summaries, etc.

But as a seller, and anyone on this call, again, who’s sold, carried a bag, or managed people carrying a bag, you want them doing admin as… as in the least amount of time possible, right? You always want your sellers spending time with their most valuable asset, which is your customers, or your prospective customers. And so, up until this time, we’ve been completely focused on the buyer journey.

Which, you know, still leaves you after these stellar calls, you still have to make a mutual action plan. A lot of times, sellers are now going to call recordings. which are a great invention. In my day, you didn’t even have call recordings. You had to hop in a physical room with someone and hope that the client still showed up to your call and just take manual notes.

I know I’m dating myself, but maybe some of you can relate on how good sellers have it today. But oftentimes, today, they’re still reviewing those calls, right, and formulating a mutual action plan. Maybe they’re they’re putting together a business case or an executive summary. And so with everything else that we’ve been developing, we’re really focused on making it easier. for sellers to sell.

And we just wrapped up kind of conference season, right? So I don’t know if anyone here, feel free to like drop it in the chat. If you went to Dreamforce, there was also Unbound. GTM Pavilion, there were a few Vegas conferences. I’m jealous of you that got to go to Vegas.

I was back in San Francisco for the 10th time, but I hope everyone had fun. on the circuit, but essentially, and I don’t know if anyone else can relate, but the big buzz around town was, hey, I bought this AI tool, and it looked so snazzy, and it sounded great in theory, but I haven’t actually seen any results yet.

And so, again, I don’t know if anyone In the chat can relate, or anyone on the call can relate, but that’s kind of the biggest… biggest, egg we’re trying to crack right now in GTM. And so, at Aligned, we believe that it’s not showing up for 3 main pillars. So. Think about pillar number one. Maybe your AI, whatever you’re using, doesn’t know the deal in its entirety.

So. there was this mad dash to connect to your MCP, right? And that was really cool in theory, but even when you’re, you know, uploading those call transcripts, or asking it to. to study the deal, it doesn’t have the full context, right?

It might have one call, might have two calls, but Aligned syncs with your CRM, syncs with your playbook, syncs with your deal room activity, which is where your buyers are spending their time. It syncs with… I’m forgetting something here.

It syncs with everything that would touch your deal in a cycle, so when you ask it something, it has the full context, and it’s not sitting there trying to populate things for 20 minutes before popping something out. So, the main pillar, number one, why your AI isn’t showing up in your win rates, is because it doesn’t have the full historical context.

We like to think of our deal… AI deal seller as… or seller agent, sorry, as, like, a full-time VP of sales. Which is great for me, right? Like, I can actually go and work on strategic initiatives, and instead of the team spending 20 minutes catching me up to speed on a deal, it can just kind of ask the deal, hey, where are we at, and what would you recommend? Which we’ll show here in a second.

The second pillar of maybe why your AI isn’t showing up in your win rate yet. is because it can’t fully act, because it’s not really sitting where your deal actually sits, right? Yes, maybe you connect it to your CRM, or maybe you’re working out of Claude or ChatGPT, but again, it doesn’t have all of that context, so maybe it’s writing you an email. And that’s nice, but is that really acting on your behalf?

You know, to move a deal forward, it takes so much It takes so much more than that. It takes, you know, a mutual action plan, it takes an executive summary, it takes a competitive intel, and if you’re just kind of building emails from part of the deal, that’s also why it’s probably not showing up in your win rates. And then lastly. is it doesn’t necessarily stick.

So, AI has just come out in full throttle so quickly that it’s very much the Wild West still, right? If you think about all of the agents being built in your org, I know we had this problem initially. A lot of people were building the same bots, but with different prompts behind it.

It’s really hard to standardize all of this, and so You really want it in, one central repository where everything is kind of templated and standardized. So. With that, we are going to show you how we view that Aligned can actually increase your win rates and retention by having the AI sit inside your deal and not outside of it. So, gonna pop into a little live demo here.

Caught you up to speed with kind of the, just, deal workroom in general, but if we go to kind of the snazzy stuff, which is our new seller agent. So think back again to those deals that have really scarred you.

You didn’t really know what was going on, maybe you didn’t know what to do next. maybe your VP of sales or your direct manager is just in back-to-backs all day, so you don’t really have a ton of coaching, you don’t have a ton of resources.

Well, now with the seller agent, you have, again, all the context in the room, all your call recordings, all your CRM data, all of your. all of your… all of your anything you could possibly need. And so, we have all of that here, live in the deal, and so you can just ask your deal at any time, where does this deal stand?

And so you have kind of your seller agent. ride along here, and it’s gonna tell you everything that’s going on in your deal. So, right now, you saw that, 10 seconds, it’s in the final evaluation, we’re leaning towards a line, here are some next steps, here are the risks. Okay, well, let me ask… What are three things I should do to move this deal forward?

And again, keep in mind, it has All of the historic data, so every call transcript. anything you could possibly need, and it’s already making suggestions. So I need to get so… I need to get Brian engaged. We need to sign off, we need to remove the commercial excuses. So it’s saying, you know, let’s make an executive summary. So, should we do that? Actually, I want to update the mutual action plan.

So that’s one of the great things about Aligned, is You can drive deals forward by a mutual action plan here, but I’m gonna say, let’s update the mutual… action plan first. So it’s gonna pull through all of the calls, everything that was mentioned, every player, our typical process, but also adhering to their process. And as you can see here, it’s going to. update the mutual action plan.

So, you know, it’s saying it’s got a December close, should I update it? And I’m saying, yes, please proceed. And… You can see here that it’s updated. Let’s see… It’s updated all of the mutual action plans in just a few seconds here, based on everything in the call. And so, with the seller agent, you can update mutual action plans, you can make competitive analysis, again, based on the calls, right?

You’re not going to spend time, inputting competitors that are in a different segment, they’re in a different market. You can update the mutual action plan here. You can say, let’s now make an executive summary. And it will spin up an executive summary. So, just a lot you can do in this… okay, it already exists, yep, let’s refresh the executive summary, right?

Maybe that’s from two calls ago, we got more information, we want to make it more current. Oh. So we’ll just give it a second there. Okay, let’s apply it. Okay, refresh… oh, boom, it just takes us straight to the executive summary.

So again, having the AI seller agent ride along in the space where your deals live, but also where your buyers live, is gonna be a huge lift in Win rates? close rates, sales cycles, because it has all of the historical data, and it has it all in one place. So, I know we’ve covered a lot, and I’m sure we have some caffeinated people on the call. I know Julia was showing her coffee. We’ve got some quarters.

I don’t want to overwhelm everyone right now. I want to encourage everyone who wants to continue the conversation to either add us on LinkedIn.

Meredith Chandler, VP Sales at Aligned, or we’ll drop some links in the chat to sign up for, we’re giving away free rooms for everybody on this webinar who wants to try it out, absolutely free for themselves, but also wanted to open it up for a quick Q&A in case anyone has A burning question based on anything they’ve seen today.

Julia Nimchinski:

Phenomenal presentation, thank you so much, Meredith. Yes, we do have a lot of questions here. So the first one, is how do you measure the shorter sales cycle? It seems hard to measure deals outside the system.

Meredith Chandler:

Yes, great question. So, our platform, Aligned, will actually help you generate reports, and it’s how we monitor on our CS org how successful the implementation is. So, we look at close rates before Aligned, and then we look at close rates for any deal that has an Aligned room attached to it. So, we can very much measure through CRM reporting.

And then also, you’ll be able to see a lot of engagement in your room, right? So you’ll be able to see when people are hopping in. When they’re not hopping in is just as valuable, right? Should I discard this potential opportunity earlier than later and save myself some time and spend time on deals that are actually showing interest?

Julia Nimchinski:

Another one, we are in construction tech. We have a lot of, small deals that are very unpredictable. Some deals, close from day one, others linger, even with good nurturing and pipeline management. How do you forecast in such a volatile industry and unpredictable market in any experience in construction sales cycles?

Meredith Chandler:

It’s a great question, and one of my personal favorite customers of ours, in fact, I was just on a call with him yesterday, just kind of workshopping some stuff, is in construction tech. And so, if you could add me on LinkedIn, I would be happy to connect you two, and you could just talk shop about the industry in general.

And, you know, he can talk about how he leverages Aligned, or if you want to leave Aligned out of it, happy to just make that introduction, because I think they’d be a perfect resource for you.

Julia Nimchinski:

Thank you, we’ll pass it along. And the next question here, do you do lots of scenario planning with AI tools with current and future risk context?

Meredith Chandler:

Do… sorry, can you repeat the first part, Julia?

Julia Nimchinski:

Yeah, basically the question is if you do scenario planning, testing future risk and current risk in that context.

Meredith Chandler:

Yes, so let me share my screen again.

A lot of what we do is based on… I don’t know if this room will show it. we’ll take a lot of those reports that I was talking about that will sync with the CRM based on the close rates for any deal that is connected to a CRM, but we also have insights and actions, which isn’t showing much for this, because it’s a test environment, I didn’t want to share customer data, but because we have and we track everything going on in the room. versus the calls.

We also provide a lot of insights and action. So, for example, it might be hard to see, but it’s flagging this, saying, you know, you need alignment. This is at risk because they’ve mentioned a competitor various times, but you haven’t progressed the deal, for example. So we also take these insights, A, to give you actions to actually progress the deal before it’s too late.

But then you can also incorporate these in your reporting for your planning. So for example, you might pull up the deal room and see there’s 10 open deals. But three of them have risk. So the ones that have risk, I’m actually gonna forecast only at about 15 to 20% versus the ones that have no flags, I’m going to keep at 35%.

Julia Nimchinski:

Amazing. And another question here is, do you, pertaining to this one still, do you do, role-playing based on the intel that you get from your customer? Any simulations?

Meredith Chandler:

Absolutely. In fact, after this call, I am headed into my team roleplay call, and so we do a few different things. So, every week, we. highlight each rep brings a must-win deal, and our C-suite actually joins us on those calls, and we dig, really far… we dig really deep into the details. And then the following day, we either all watch the same call based on the insights that are being surfaced to me as a manager.

I’ll pick one or two calls, and the whole team watches it. We provide feedback, and then we do additional one-on-one role play based on these scenarios, too.

Julia Nimchinski:

Thank you. Next question here is basically a compliment to your platform. They really love how it centralizes information. And the question is, isn’t this only for modern buyers in some industries? Some institutional buyers might want detailed information without accessing an external site.

Meredith Chandler:

Yeah, that’s a great question. You might be surprised, we have a ton of healthcare, banking, and cybersecurity teams that use Aligned. And if you think about it, think about, kind of, the analogy we like to use is think about when DocuSign first came out, right? Like, it’s technically an external source.

But it’s so easy to get started that you just send the DocuSign over, you input your email, and then you’ve got a signed contract. So, it might seem a little bit. Concerning at first, but buyers are so… Surprisingly receptive to it just because it makes their life so much easier, it really does.

Julia Nimchinski:

Thank you. Meredith, the topic of the overarching topic of today is Recursive Self-Improvement. So I just can’t help but ask you this. You mentioned that in order for AI ROI to show up, one of the first pillars is obviously capturing context. I’m just curious, based on all your customers, how do you approach, you know, the context, essentially the tribal knowledge that lives outside the system?

How do you motivate, you know, the teams actually? Capture it.

Meredith Chandler:

Yes, so… Luckily, again, there are call recorders, and so it comes down to getting the right information either live on a call and inputting that into the system. or getting that information. I don’t recommend this, it’s a lot harder, it’s a lot more limiting in written form, but you need to extract that information, because the AI is only as good as the information that we give it, right?

So that’s why it’s important to ingest your playbooks, your call recorders, your buyer activity. Maybe you take notes in Notion. Anything that helps you gather context, be as robust as possible up front. And then your prompts can be simpler because it has so much information to go off. So, I think that’s a great point, Julia.

The most disappointing outputs, I think we oversee, usually have the most disappointing inputs along with it. You really need that information so that it knows what to do.

Julia Nimchinski:

And just to finish it off on a positive note, can you share some ROI stories and just generally customer success stories, your favorite just results?

Meredith Chandler:

Oh, yes, I mean, we have a whole testimonial channel. It’s my favorite Slack channel. We have a whole, like, customer shout-out quote, channel. Anytime someone sends us a fun story, or anytime somebody. decreases their sales cycle. We actually had someone use the analytics in, kind of, the reverse.

So we talked about earlier, a proposal was stuck. we were gonna shave, we saw that they weren’t in the proposal, and we were able to unlock it via the competitive analysis. And somebody wrote us in and said, like, hey, I had a deal stuck in proposal, but I saw that they were actively signing in multiple times a day. They had looped in other stakeholders. And so I got to not be the pesky, pesky salesperson.

And I had the confidence to not nag them every day, every day and a half. And their customer actually told them, like, I really appreciated your sales cycle and your buying process, or sorry, sales process, was a big reason why I bought, is because you were not nagging me every day, and your competitor was. So, those analytics go both ways, and it was a six-figure deal.

So, huge deal for that company at the time, which was Series A still, so that’s one of my favorite stories.

Julia Nimchinski:

Amazing. Thank you so much again. And what’s the best next step? You’ve mentioned that you’re hosting a webinar tomorrow. So what’s the best way for our community to re-engage with you?

Meredith Chandler:

Yes, we will either send you some sign up links, or we’ll send the community, but you can find us on LinkedIn. I’m Meredith Chandler at Aligned, or we’re also going to send you to send the community some free rooms, so you can go ahead and check those out and play around with it. But if you want to continue the conversation or just talk shop, please find me, and I’m happy to connect. So thanks again for having us.

Julia Nimchinski:

Thank you.

Meredith Chandler:

everybody.