Account Executive

May 26, 2022

Episode #02 Highlights: Maggie Blume

👋 No Follow Up…No Deal

How I Deal Episode #02 - Spotify & Apple

Maggie Blume takes Taylor & Junior through an epic inbound lead journey. Stretching over a year, but led to a solid closed-won deal. Utilizing her own platform, Mailshake, Maggie built personalized nurture sequences to keep the buyers engaged until the timing was perfect.

Have a deal in your pipeline with a distant targeted close date? Deploy Maggie's tips on the pod today to stay top of mind & unlock the deal next stage!

Guest Feature

Maggie Blume is an Account Executive @ Mailshake. She began her career as a staff accountant but made the switch to sales as an SDR.

After climbing the sales ladder at a previous company, she climbed about the Mailshake rocket ship as one of the original SDR hires and hasn’t looked back since!

Maggie Blume
Maggie Blume

What problem Does Mailshake Solve?

Helping B2B sales pros get in front of more qualified leads while prospecting. Leveraging Mailshake’s simple, yet powerful, platform, reps can automate mindless outbound tasks & help them generate higher-quality conversations.

Deal Details

Where did they come from?

  • Inbound lead via the website.

Company type

  • A growing insurance company.
  • 60 total employees. ~15 agents/reps (end-users).
  • Reps were a mix of brand new hires & very tenured pros.

Deal Length

  • Very long. Over a year.

Barriers to Overcome

  • Creating more urgency on a buyer’s timeline.
  • Staying top of mind throughout the process using a targeted drip campaign.

Buyer types

  • Users: agents who operate as full-cycle sellers.
  • Champion: a newer agent who spotted an issue with their prospecting email process.
  • Decision Maker: The champions manager

Episode Highlights

*Note: timestamps correlate with full conversation

Discovery: Inbound leads are not a given. Usually more competitive.

(8:05) “Nice! A demo just booked on our site. Quick demo time & send over the contract.”

While sometimes this is the case, it’s a terrible idea to start the first meeting this way.

Inbound leads can be like the Wild West. It feels predictable, you have no idea where they’re coming in their buyer’s journey.

They could have just read a couple blogs & wanted to learn more. Or they could be on their 10th demo with your competitor & just wanted to check out “one more alternative”.

Your inbound form probably won’t tell you this info.

Maggie approached her inbound lead with an open mind & ran a proper discovery conversation on their first meeting.

She learned the lead was an internal champion who was brand new to the company & to sales enablement software as well.

Here’s what she learned:

Follow Up: Sales timelines are never perfect. Follow-up holds it all together.

(11:25) In a perfect world, your sales cycle looks like this:

  • Find the prospect via LinkedIn (or they come inbound)
  • Hit ‘em with some personalized outreach, they love it & book time on the calendar.
  • You meet with the decision maker & dig up a lot of pain in initial discovery.
  • You run a pain-specific demo with every stakeholder.
  • They all agree this solution will solve their problems & they have the budget to buy it today.
  • The buyer signs the contract. You hit quota & can spend the rest of the quarter kicked back.

Sounds perfect! Well it’s a dream for a reason. Deals rarely go that smoothly. Things happen.

In Maggie’s case, the initial meeting with the champion in October 2020 went really well but the timing was off. The next meeting didn’t happen for another 7 MONTHS (June 2021).

What did Maggie do in all that time to stay top of mind? She created & maintained her own relevant follow-up drip campaign.

Here’s what happened:

Demos: No prospect is exactly the same. Why the hell are your demos?

(14:34) We have a saying around here at Pickle: “No pain, no demo.”

If there isn’t a defined pain or need for your solution (or at least a specific part of it), then it’s impossible to drive real value with a personalized demo.

It becomes a canned, feature-dump screen share that glazes the eyes of everyone involved.

Maggie even goes as far as feeling “uncomfortable” if she’s giving a feature-filled demo to a buyer that only needs to leverage one aspect of her platform.

Listen to how she describes giving three different demos during this deal:

3 Tips to Fellow Account Executives

1. You’re on your buyer's timeline.

While there are always ways to create urgency; ultimately the buyer decides what's next.

The best you can do:

  • Keep things simple by giving them one decision to make during each conversation.
  • Create more value around your solution or urgency on how much a problem is costing them.

But always follow their lead.

2. No follow-up, no deal.

We covered this above but to reiterate:

Outbound or inbound? Doesn't matter. Stay in touch consistently throughout the sales process.

Don’t just “any thoughts?” your prospect to death. Instead, always add more value.

3. Always have a Champion.

Of course, the decision-maker's needs are important; but strong relationships with the end-users are crucial.

The best buyers to work with are the ones that put faith in their lower-level employees to make informed recommendations about what to purchase that will make everyone's lives easier.

Identify those individuals who have that trust & build the relationship.

Watch the full conversation

Full transcript

Taylor Dahlem

Welcome to How I Deal! Where we discuss past closed-won and lost deals, how they played out that way, and the things that you could do and steal from us today to level up your sales game. My name is Taylor Dahlem, former full cycle account executive, turned content guy, and I'm joined by my partner-in-crime, Junior, our superstar seller here at Pickle.

Junior Lartey

Real excited for today. It's episode two. We're just getting the ball rolling. Each episode is going to be an absolute adventure.

Taylor Dahlem

Absolutely. Yeah. We'll see how it goes. But very excited for episode two. Just a reminder of how this works. Each conversation we chat through a past deal. All names, places will be fictionalized, of course, and we just really want to dive deep, take you from the first time you essentially saw that prospect on LinkedIn, all the way to completing that DocuSign. Today we're chatting with Maggie Bloom from Mail Shake. Maggie or Stoke that you're here.

Maggie Blume

Yeah. Thanks so much for having me on here. I'm super excited.

Taylor Dahlem

Awesome. Thanks again for joining us. I guess give us some real quick insight on your role at Mail Shake and maybe what problems you all solve today.

Maggie Blume

Yeah. So I started at Mailshake as an SDR turned account executive right now. So I do a lot of demos. I also help train the inbound sales team as well. And then I also work on revenue expansion. So talking with current customers, seeing how they can get more use out of Mail Shake. But the problem that Mailshake solves is we help other salespeople with outbound and just using simple and powerful software. So I use it myself. Probably pretty similar to what you two do, too.

Taylor Dahlem

Yes. We try to be our best users. Right. It sounds like you wear quite a few hats at the end of the day. Every aspect of Nail Shake probably falls into your depth at some point. So super cool to hear, I guess. Let's dive right in, Maggie, tell us what deal you want to talk about and what are we walking through today.

Maggie Blume

Yeah. So the deal we're talking about is an inbound deal. This was one I was pretty proud of, which I guess you'll hear about later. But it was an inbound deal. It was an insurance company. There was probably about sixty people that worked there. And I want to say out of the sixty people, they were probably like ten to fifteen agents. And I know I should know the exact number, but there's a reason why I don't and I'll get into that as well. But there was about ten to fifteen agents with salespeople on the team. And yes, there was a mixture, like some people were brand new to the agency, which they kind of have to start building their book of business and insurance, whereas there was like seasoned people, like principal agents on there. This deal in particular, it was long and there was a lot of people involved in it. So I always feel like those are interesting conversations because as sales reps, those always feel like the tricky ones where you're like solving a puzzle. There's all these different people to it, which we'll get into as well. But yeah, that's the one I picked there.

Junior Lartey

Awesome. Maggie, I love that you're bringing an inbound deal because inbound does not automatically win mean you're going to win. So there's a lot to be said there. Tell us about the research that you did to help you win this deal.

Maggie Blume

Yeah, that's such a good point, Junior, too, when I talk with some of my friends about inbound deals, they're like, oh, that means that they're just asking you a couple of questions before they sign up. And I'm like, absolutely not. You're up against competitors. And we're in a space where we have a decent amount of competitors in general in the software space. But yeah, there's actually work that goes into it instead of just what people think. Like, Maggie is just there answering phone calls, answering a question, they're signing up. But the research I did, I did research the person that originally booked the demo with me, which was going to be like the ultimate user. So kind of like the champion for me in this deal. And I did research. But just by going to their company, kind of like looking at how we approached other insurance deals in the past, too. So that helps because people who do work in insurance, it's a little bit different than if a software company was reaching out to me. Their sales teams are set up different. They have different busy seasons, things like that. So a lot of that research is for me, mostly done on LinkedIn, and then I took a look at their website as well. But that was kind of the extent of it. And also looking at some deals that we've closed in the past in insurance.

Junior Lartey

I really like that aspect, actually, of, hey, what deals have we won within this vertical? Because getting so caught up in this prospect and this customer. But there's a lot to be said about companies that play in the same space that you have one. And, you know, given the fact that it was inbound, you certainly did not like, take that for granted. I love it. I love that.

Maggie Blume

Yeah. You have to make sure that is there any reference that your team has, like from previously that could just help you because they might be pretty similar? You never know.

Taylor Dahlem

I guess. Maggie, there's always a hot debate and kind of prospecting approaches, but considering kind of like you were saying, this was an inbound. This is different than the traditional outbound approach and kind of what goes into it. But I'm curious, were there any additional outreach to other stakeholders? Did you say the meetings a day away? Did you do any kind of greasing the wheels, so to speak, with other stakeholders.

Maggie Blume

Yeah. I think later in the process because even though it's inbound and we have that initial deal come in and they book a meeting with you, sometimes you think sometimes it does go that way. Sometimes you get on that meeting and you have next steps already figured out. But sometimes they're like at the beginning of all their research with competitors, too. So it's not like I mean, that in itself has to almost turn back into outbound because you're still working that you're still trying to stay top of mind, you're still trying to figure out like after you did discovery is like, okay, they're looking at these five competitors alongside us. Where are we going to stick out here and how can I use that in my outreach in the follow up? So I definitely did reach out to stakeholders, but I'd say it was after the initial conversation got you.

Taylor Dahlem

Yeah. It's kind of always interesting. And Junior, I'm sure you've gone through this just with an inbound lead. You never know where in the funnel they're coming in. Right. Whether it's top level, where maybe they're at a funny blog. And I know Mayo Strike does a ton of good content. Maybe they caught something there and they're just checking it out or they reviewed twenty of every competitor and somehow they stumbled upon you and they're exhausted. But they're going to give one last look at another alternative and here you are. Right. And I don't know, Junior, is that something that kind of you've seen before, too?

Junior Lartey

Yeah. It's just don't sleep, don't sleep on your inbounds. Don't take them for granted. And I think Maggie is for sure going to show us a little bit later. As we talked about this deal beforehand, Maggie, talk to us about discovery. How did you actually get them to hold the calendar meeting one? Because also don't take that for granted. But what was that process like? And we're there anything in discovery that you uncovered that you really were like, okay, this will help us win the deal.

Maggie Blume

Yeah, for sure. Like you all talked about before, it's like the inbound process. Where are they at? Are they using another tool? And is there a huge problem that's coming from that that's going to help basically your discovery and this whole deal that you're going to figure out too. So for this discovery process, something we always do and is send like a pre demo email. Like you said, Junior, you don't really want to sleep on your inbound. Just because they book a meeting with you doesn't mean that they're going to show up. They actually probably have a pretty high no show rate sometimes compared to outbound. It's like almost surprising. You've probably both experienced it before. So I always send an email before. What was nice about this lead is they answered it because sometimes they don't answer it either. And that kind of gives you an in claim. Like, are they going to join this? Should I call them before? So you have to do all that. And for this one, yeah, it was just the champion on the first call with us. So I love having those conversations too, because it feels like very relaxed. You're like, okay, cool. This is someone who's going to use the tool. You feel like you can be comfortable with them because of course you want the decision maker there. But sometimes it is nice to just have like, that initial discovery with the champion who's going to be using it. And I feel like I had an all star champion who I was talking to during this. But what I uncovered was that they were sending tons and tons of manual emails and they didn't ever have a tool like MailChimp before sales engagement tool, which is always a fun conversation because you can almost like it's like mind blowing. I remember the first time I figured out about those different tools out there that you didn't even know existed as software. You just thought it was like, wow, I could save hours. So, yeah, the discovery, that's kind of how it went. And she was a newer person at this insurance company. So she was still building a book of business. And I remember it was like she was not having the same problems as people who had been there for longer. And so her and maybe a group of that's what I want to say. Like ten people were experiencing this. Like they were really hustling hard to build this book of business where there was like already principal people here who are seasoned reps, they get referrals, things like that. So the sales process for them is super easy. But yeah, that's where a lot of that came from. Discovery with her was great talking through that and really talking about her problems too, because super relevant never used the tool. And she was also in the middle of looking at different tools as well.

Junior Lartey

So she's the big champion. Is she also in the end like our big decision maker here?

Maggie Blume

So no, yeah, actually the next call, which didn't take place until I talked with her originally in October of two thousand and twenty. And I know at that point it became kind of like a busy season at the end of the year and things like that, especially for their firm. So the next follow up that I had with them, which I'm not proud of, I wish I created a bit more urgency when I talked with her, but was in June of two thousand and twenty one when she got back in my pipeline where I had that decision maker on the call. But she helped a lot move this deal across, but she wasn't the ultimate decision maker.

Junior Lartey

Okay, so we've got discovery that was like really chummy with a great champion uncover some great things. And that happened in October of two thousand and twenty. And then it's not until June, two thousand and twenty one. So we're talking about a long period between discovery. What was that period? Was it just complete silence? We're there touch points between there talk to us about that.

Maggie Blume

Yeah. So luckily wasn't complete silence. I had followed up with her. She had told me in October, hey, follow up with me in a couple of weeks we have an event going on and I'm doing this, initial research, things like that. So I had a follow-up scheduled with her. It was just with her again regrets that I didn't bring the decision maker on but work in progress, I would have done that. Now this is two years ago or almost. And then I followed up with her and she said there's a lot of other priorities taking place right now. And then we touched base, I think again in January of twenty, twenty-one. I have my notes right here because I remember there was like just certain steps to this. And then she was like, hey, reach back out to me in March. And then I put her into and that was all like I was emailing her, calling her, this is someone I was like hunting in my CRM. And at a certain point if I do start getting ghosted and that's kind of like what started happening, I could tell I was starting to get ghosted. I put them into a nurture sequence using nail shake. So kind of like similar to Prospecting where you have like five to seven emails, you're doing nine to eleven touch points, things like that. I put her into a sequence like that of all. Kind of like relevant follow-up of what she was talking about. I tailored certain things to her and that's what kind of came in between then. And then one of the last emails of that sequence, she booked a meeting with me again and I was like, hell yeah. Finally there was like seven emails that I sent out to her. And so that's what got us on that other call of June of two thousand and twenty-one.

Junior Lartey

Okay, AEs, if you're listening, this was insane persistence. If you're like wondering what does this drip campaign look like or anything, reach out to Maggie after this.

Taylor Dahlem

Because quite honestly right.

Junior Lartey

This was an inbound that pushed and pushed and Maggie was like there every step of the way. Very cool.

Taylor Dahlem

So Maggie, let's kind of move to this next step, right? So we've got this elongated gap as you were discussing the persistence to get to the next step here. But eventually you have to show the product right? And more or less the demo stage. A necessary evil for sure. But the best demos are the ones that tailor the experience that or the pain you uncovered in those previous meetings with the champion, with other buyers. How did you kind of specify that for this buyer. And then essentially, how do you keep everyone engaged throughout that process?

Maggie Blume

Yeah, that's a really good question. And so for this particular deal too, I had ended up doing three different demos. And the first call that we have on the Mailshake team and how we do things because again, we sell pretty simple software like Mailshake in general. So all of our calls are the first calls are discovery mixed in with demos, which some teams are different. I think it really just depends on the product that you're selling and the types of buyers that you have too. We mostly have been dealing with small to medium-sized businesses. So I had that initial demo with her and basically the whole focus of that call and I'll touch on three of them briefly. The three that I had, the purpose of that was really showing her like, hey, this is how much time you're going to save. You've been sending all these emails manually, you waste four hours. I think she had told me each day, like following up with people doing this. Most of her day was prospecting. She wasn't really getting anything across. So my main goal of that demo was like, let's just show this person how easy this could be, how she could do this in less than an hour. So that was the goal for that one and tailoring it for her. And then the next call was when her decision maker came on, who was also the person who did sales. But again, like I was talking about before, they're that principal rep, they get referrals their sales process. I don't want to say it's like easy, but sounds kind of easy. Sometimes they don't have to worry about prospecting at all. So the goal of that demo was like, I had to even ask them like, hey, what did my Champions say to you about Mailshake? What brought you on this call today? That demo was completely different. I think I shared my screen for probably ten or fifteen minutes and talked a little bit about I'm like, hey, this is what my champion had reached out to me before saying, and this is what's going to help save her time. Her big thing is time and really showing to that decision maker who is also her manager, but someone who is also selling like, hey, she's going to have so much more time to do something else than worry about following up here. And then the third demo was like other people from her team who are having the same types of issues too. So not having a lot of time to do outreach, spending a ton of time doing it. That was also like I had just kind of gone back and put my hat on when I talked with her before. It's like, let's just show all these reps how they're going to save a ton of time. Like doing outreach this way. So I think that's super important, too. And something reps don't take a lot of time to think about is like, I mean, know your buyer always, but you really have to tailor those demos. People's time is so precious. And this is such a cliche thing to say, but I would feel uncomfortable if I gave that decision maker, like, a full on demo or even get in any type of nitty-gritty unless he asked me. But I was like, okay, I'm going to try to share my screen for the least amount of time as possible today and get this guy off the phone so he can feel good about having some time back in the day. But I just rancid about that. But I think it's so important. Like, you can have multiple steps in this process and multiple demos, and you really just want to make sure that you're being efficient almost for people, too.

Taylor Dahlem

Yeah. And I think at the end of the day, like you said, the buyers only really want to see what they need to see. And it's really ultimately up to you to do the best job you can to make sure, hey, even if it's saving you ten minutes, let me cut myself off. It's bizarrely. A tough thing, especially I did that plenty of times when I was back in the full cycle selling days. And for me, that was a hard thing where it's like, I've got all these cool features. I want to make sure you see them all. Maybe this will help close the deal, or maybe this will. And it's just how do we take trying to catch a fish in an ocean to just catching the fish in the barrel? That's how you're doing it.

Maggie Blume

Yeah, for sure.

Junior Lartey

Through this whole sales process, we talked about one of the major roadblocks, like that timeline from October to June, and how you overcame that with a Mailshake specifically, which I think is really cool. It's not at all a shameless. Plug it's like there's real value here. Were there any other major barriers or objections that came up that you had to work through as well?

Maggie Blume

Yeah. So, I mean, luckily, it was just the timeline that was the major barrier, I think, trying to and part of that was on me. There's always calls, we listened back to his aides, and we're like, if we could have just done this, it would have changed it. And who knows? We always say that. And is it really the case? I'm not sure I can't go back in time. So, yeah, I'd say the major barrier in this one was just not getting the decision-making in there quick enough and also creating a bit more urgency in the beginning, too. Thinking back to it even before we had this conversation today, I'm like, man, I probably could have done something to get her on there quicker or like, get on another call with her. So luckily it was just that timeline of pushing things back and pushing things back was the major objection barrier.

Taylor Dahlem

Got you. Well, let's wrap this thing up, or at least kind of head towards that direction. But ultimately, at some point, this is either going to close or it's not really. You can't keep dragging this along. Yes, it's gone on quite a bit at this point, but at some point there has to be that closer that avoiding the beating around the Bush anymore. It's the direct ass. So maybe it was, hey, are you ready to buy? And there's an awkward silence or something like this, but ultimately, how did you close this thing up and maybe what happened there?

Maggie Blume

Yeah. So the cool thing and that timeline like I talked about before, the initial demo is October, two thousand and twenty. I got on another call with her and the decision maker of June of two thousand and twenty-one. I think I said, yeah. And then it finally did close in August of two thousand and twenty-one. And that's in between. I had three demos, one with her, one was the decision maker and her, one with the team, and then a final wrap-up call with just her and the decision maker again. And I felt like that was helpful, like I didn't need the whole team on it. That other one in between was kind of like a little walkthrough, but really what helped me and I think this is so important about having those conversations with Champions, especially if you're maybe working with a bigger deal is like my champion kind of sealed the deal for me a little bit at the end. I mean, maybe I owe her Commission on this, too, because she's in sales, but she had been talking on those meetings about this is so important because we're letting people fall through the cracks. And Maggie put me into a sequence, probably using her tool, and it got me to book another demo of why we're all here today. And I remember she said that I was like, awesome. So that really is what sealed the deal. And I think her having that relationship with the decision maker as well because I didn't feel that pressure of the decision maker on it. He trusted her to recommend a really good software, and then that eventually closed it. So by the time that wrap up call came, it wasn't asking for the sale or what was your thoughts after that? It was really just, hey, here's my credit card. How can we get this signed up? So I want to say, yeah, the champion really did help me out of this kind of selling it for me there, too. And I think it's all those steps beforehand that are really important as opposed to I mean, obviously we do always have to ask for the sale or it comes up in some sort of way, but it kind of just naturally got to that place.

Taylor Dahlem

Yeah, it feels awesome, right? You're like, wow, I don't know how that worked out, but we just went through like, what, a year and a half worth of work that went into this. And yes, there always could be more urgency in any sale, but what made it so easy was all that work and that persistence that you put in. And clearly throughout this conversation was there. And I know last week, Jr, we talked about a little bit, but don't never overlook the champion or the person that doesn't ultimately sign they play such a crucial role. And there's a reason us and sales have coined in the champion. They can do a lot of work for you and a lot of help there. And ultimately, it sounds like that's kind of what led to this. Anything else for you, June, in terms of the close?

Junior Lartey

No, Maggie just hit us. Like, what are three things that any account executive can do today to inch closer to the close one on some of the deals they currently have?

Maggie Blume

Yeah. And kind of just wrapping up from the story and the deal that I walked through, too, it had some craziness in it with the timeline. But really, at the end of the day, you are on your buyers timeline like we talked about with urgency. There's always urgency you can create. But if you maybe slipped up on doing a good job with it or coming out of it or you did a really good job creating urgency, at the end of the day, you're still on your buyer's timeline. As much as you can create urgency in a call, they're not buying until that actually takes place. It's naturally the way that it works. And of course, we can always do a better job of doing that. So that's one thing I'd say is patience and persistence with that for sure. The second thing I'd say, too, is following up is definitely key, especially with outbound. And I know this is a Mailshake plug, but that deal did close and it wasn't something like I was persistent and I followed up with her manually after that. Like, I did it on my own, but I eventually put her into a sequence and kind of let the work do it for me. But following up is really important because you want to stay top of mind. And it's not just pushing people, hey, following up on our conversation, but it's really like, how can you win them over while they're still in this process? Like in this inbound process where I've already talked with them before. So, yeah, you're on your buyer's timeline, following up is key. And then the third thing I'd say is, like, we talked about getting the champion to sell for you. I think people get really fixated on the decision maker, and obviously the decision maker is really important. But yeah, that person can play such a vital role and most of the time the decision maker is their manager. Their managers hopefully trust them to make a really good decision and recommend that decision to them so never look past them either.

Junior Lartey

Awesome. I think that's a really good wrap-up to the deal. And for sure, those three things we can see in this deal that helps you win. Thanks for being here, Maggie. Walking us through this for all of you listening, be sure to connect with Maggie on LinkedIn. She's fantastic. She's got a great presence there. And make sure to take some of the advice you heard today and try to plug it into the deals you're currently working on.

Taylor Dahlem

Yes. Thanks again, Maggie. And just like that, it's another episode of how ideal in the books. Thanks for tuning in. We'll catch you next week.

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