Ep 206: Prospecting That Actually Feels Natural with Jenna Deyle

Natural Sales Skills And Simple System

0:01

Have you ever been incredibly jealous of people who just have that natural sales skill? Well, that can be you. Today, I'm talking to Jenna Deal, and we are talking all about how you can implement an easy sales system that's built into your everyday life. I'm Sarah Noel Block, and this is Tiny Marketing

Sarah Noel Block 0:25

hello. Can you introduce yourself to the audience?

Jenna Deyle 0:28

my name is Jenna Deyle. I spent a 15-year career in sales before going out on my own to start Level3 Sales Coaching, where I work with B2B sales teams to improve their capabilities

Sarah Noel Block 0:41

Sales happens to be my audience's favorite topic because everybody who listens to this show, they got forced into a sales role because, they were working in corporate or they work in marketing, and then they have to connect those dots. So you actually lived the life of sales. Yeah, everyone's gonna be jealous it comes so

Jenna Deyle 1:08

I don't know, I don't know if jealous is the word that most solopreneurs would use, but

Sarah Noel Block 1:14

No, honestly, if you can sell, you pretty much have everything else down. You probably had to sell to your one-year-old today on, like, putting on pants.

Jenna Deyle 1:27

That is an everyday sale for sure

Sarah Noel Block 1:29

yeah, I have kids. I get that. And they're constantly the worst prospects I've ever had. I have to really work a room for them.

Jenna Deyle 1:40

can see that

Sarah Noel Block 1:41

Yeah. Okay, so today we're gonna talk about the difference between marketing and sales and what that looks like when it comes to outreach. So let's first get into prospecting because a lot of people listening, they might have heard the phrase, but they don't exactly know what it is. So what is prospecting?

Prospecting Defined For Busy Founders

Sarah Noel Block 2:03

And then let's talk a little bit about like the workflow behind it

Jenna Deyle 2:07

Yeah. so essentially prospecting is you reaching out. It doesn't always have to be cold. Like, it could be someone that you have in your network. It could be a cold contact, which is a lot of what I do. or it could be, hey, you met someone a month ago at a networking event and you realize they could be a potential customer, how do you outreach to them?

Sarah Noel Block 2:28

Mm-hmm. Okay. So let's, before we get into cold outreach, let's dig into that a little bit. So what is your... You said you're doing mostly cold prospecting. What were

Jenna Deyle 2:44

I should have, I

Sarah Noel Block 2:45

is open.

Jenna Deyle 2:45

I mostly, I mostly teach cold prospects, much like I'm working with B2B sales teams. I do cold outreach myself as well. I'd say right now I'm probably like 50/50 cold outreach versus, "Hey, this person at least knows my name and is gonna take my phone call," type of situation

Sarah Noel Block 3:03

When it's cold, how do you approach them?

Cold LinkedIn Requests That Convert

Jenna Deyle 3:08

so I start with LinkedIn. I will just send a blind request. Like, statistics show people are more likely to accept your LinkedIn request if you don't put a message, if you don't already know them. and so I just send that and I start there. And I'll say, "Okay, here's my ideal customer. Go on LinkedIn. Here, try to find the correct job titles," which for me, the entry point is either, like, sales leadership or sometimes learning development. So I'll just send outreaches to, like, all of those people I can find. It might be two people, it might be, like, 15 people. I don't care. And when someone accepts, then I figure out how to engage them starting within the LinkedIn DMs. some people, I'd say it's probably 50/50 whether people will reply. I try to put something personal or relatable to kind of get them talking where I don't just jump right into like, "Hey, I'd love to sell you sales training," right? like one I just had a really great conversation with a sales manager. He's out of Nebraska. my husband is a Husker and it's football season, so, like, my opening was like, "Hey, my first question before anything else is, like, are you a Husker fan?" And we had a bunch back and forth about that. I have an upcoming sales call with him, right? So, like, just kind of finding a way in. if they don't reply on LinkedIn, it's finding the other outreach, like going to the website, see if you figure out the email, phone call, et cetera. And when it comes to, like, a sequence, I'm a big fan of, like, variety. Most of the time to a cold contact, it's gonna take seven touches for them to be willing to engage and meet with you, and a lot of that is just them building familiarity with your name and your company name. So, like, maybe it's, hey, they connect with me on LinkedIn and maybe now occasionally they see a post from me. I'm sending them an email. I'm calling and leaving a message with the receptionist, right? And, like, hopefully by touch seven, eight, nine, like, they're responding to me, I'm getting a meeting

Sarah Noel Block 5:05

So let's look at that workflow and then the warm outreach workflow. What does, one, is it fewer touches at that point? And two, does the workflow look any different?

Jenna Deyle 5:18

the warmer is gonna be yes should be fewer touch points. and depending on like how warm that person is, like in sales, getting to a no is a win, right? If someone like comes out and tells me, "Hey, I don't wanna work with you," or, "We don't need this service," or, "I'm not the right person," like that's a win so I can stop wasting my time. And I feel like you can get to that no thank you quicker with the warm. You know, like if they know-- you know, like they know you and they're willing to respond. So like it just kind of depends. And then as far as like the workflow or like the cadence of touches, my kind of rule of thumb is the higher someone is in a company, the more time I'm gonna put

Seven Touches And Smart Sequences

Jenna Deyle 5:58

between contacts. Like if someone's just, not to say just, but if someone's a sales manager and they manage 10 people and like that's their whole team, I might outreach them like once every 10 business days about is kind of how I look at it. if someone's like the chief sales officer for a big company, like I'm only gonna reach out to them like once every month. and then the other thing I kind of try to build into that workflow too is if I'm doing like an email or a LinkedIn outreach or whatever it is, is I'm not just reaching out and saying, "Hey, this is what I do. Can you meet with me?" I'm trying to find something of value or show that I'm thinking of what could bring them value. So I'm setting like-- I'll set, for a company that I like really wanna get into, I'll set Google News alerts so when that alert comes back of like, hey, they have a new president or they had this like stock offer or whatever, I can use that to like email them and say, "Hey, I saw this. Because of this thing you might be thinking about next year's plans. Can we ch-" like just trying to figure out a way to like make it personal versus like, "Can we have a meeting so I can tell you what I do?"

Sarah Noel Block 7:07

Yeah. Yeah. That, I wanna dig deeper into that, like ways that you can add value ahead of time. But that also made me think about, like Sales Navigator, how you can get a notification, or you can build a list based off of triggers. Like someone's new to the company to a specific role, so they most likely will be hiring for X. So what are... So we have Google News alerts. What are some other ways that we can find connection points before we get to that pitch?

Jenna Deyle 7:44

some of it's time of year depending on your industry. So I'm a big, like one of my favorite lines of questioning in sales is like, "What's your goal for next year? Do you have KPIs, key performance indicators, you're being asked to meet for next year?"

Warm Outreach Cadence And Value

Jenna Deyle 7:58

So I can figure out is there a way for me to help you meet those. So like, sometimes just like time of year. Like right now, getting close to Q4 is like the perfect time to be like, "What are you thinking for 2027? Let's talk." Like, "Do you need help with XYZ?" Right? so that's one of them. The news is one. Yeah, Sales Navigator, I don't pay for that right now just because, I've only been on my own three months, so I don't necessarily need that to have enough leads right now. but I had it when I was in corporate and like, yeah, the someone new in this role, that sort of stuff can be really good triggers. something, again, like something in the area, like if maybe you talked to them one time and like they're I'm in Kansas City, so like sports is everything here, okay? So like maybe it's just something really simple like, "Hey, last time we talked you, you, I know that you mentioned the Chiefs, and the Chiefs just won." So I'm gonna email you being like, "Did you watch the game yesterday?" Like, like things like that to make it personable

Sarah Noel Block 8:55

I just had sales call with someone in Kansas City yesterday. That's funny. And we did talk about sports.

Jenna Deyle 9:03

Like that's all, that's what everyone... Same with Nebraska, like everyone just wants to... When I moved, I covered Nebraska for my last corporate job and, when I married a Husker, like that was my way in for people of Nebraska. Like I would go into any meeting and be like, "Do you guys watch the Huskers?" And like, they were my best friend.

Sarah Noel Block 9:22

Oh, that does make it a little bit easier. So, okay, question. Because in your form you mentioned like prospecting versus cold outreach. So how would you differentiate those?

Jenna Deyle 9:39

so the cold outreach, I think that's part of prospecting, but prospecting is just like having an active sales plan. Like again, it could be someone that you already know that you're outreaching. So for example, when I left corporate, I pulled-- I don't know if you know that you can do this. You can have, export all of your contacts and stuff from LinkedIn to an Excel. So I like pulled that. That was my very first prospecting list. Like I pulled that. I have like 1,000 contacts. I had Claude analyze it based on my ideal customer to kind of prioritize who I should be reaching out to, and like every week I reach out to like five people on that priority list.

Sarah Noel Block 10:18

Okay, let's pause there for one second because this episode is going to come out right after an interview I did this morning, with Annie Graziani, and that's how she launched her business too, is exporting, and she did it manually 'cause don't remember the reason, but she did not use Claude. but she did the exact same thing, and she got 87 warm intros from that, experience. And okay, I love that. I was gonna say a second thing and I don't remember what it was. Lost the train of thought.

Jenna Deyle 10:52

Well, and like already have it in my head of like, okay, once I do my first work through of this sheet, by that point it'll probably be like six, seven, eight months past when I first pulled it. Then I'm gonna basically pull it again. I'm gonna put it back into Claude and say, "Hey, can you highlight anyone whose job title or company changed since this first sheet?" Basically. I

Sarah Noel Block 11:13

Mm, smart

Jenna Deyle 11:14

the, kinda like the sales navigator trigger, right? Is now who in my network has changed jobs, and does that mean I should re-engage with them or see if they have this problem I can help them solve

Sarah Noel Block 11:26

Yes. Okay, I remember the second thing that I was gonna say. So, um- Jessica Lackey, um, sh- I just released her Ask Me Anything from the Solo Consultant Summit on the podcast. So anybody who's listening to this, go listen to that one right after this. Um, but she talks about how she creates these relationship rhythms, and that she starts with the list, but we didn't talk about this aspect of it, like this process. So combine them. If you're listening, combine these two things together.

Jenna Deyle 12:06

Well, and something I would add, so I call it like my cadence, my sales cadence. It's that same thing, that re- relationship rhythm's a great way to put it. Um, and then something when you're looking at like the B2B clients that I like as well is multithreading. So like you have that relationship rhythm, but then also for, like for me, I go in through sales leaders or learning development. So I might be working both of them, like, and I might be working together with both of them. I might be trying to get in through different ways, like kind of

Sarah Noel Block 12:37

Within the same org you're

Jenna Deyle 12:38

within the same org, yeah, because, and you've talked about this, like you have your champion, right? And like they both have different problems. Either one could end up being your champion, and like there may be, for me with sales manager, depending on the size of organization, like there could be 20 sales managers that maybe one of them is the way in for me. So I might be reach... And that's where I said I'll just send the cold ones, and if like I send 20 cold outreach to the same company and like two respond to me, fantastic. Like that's a way in. Yeah.

Sarah Noel Block 13:08

Smart. Okay, I love this. And I feel like anybody who's listening to this could also use it for, looking for a full-time job if they wanted. They can use it for finding leads. Like, there are lots of ways that you can use this particular workflow. How do you organize it though? 'Cause it's so many outreaches, how do you track?

Jenna Deyle 13:32

So I use Claude and Notion, um, and I use the free plan in Notion. I use the $20 a month plan in Claude. I had Claude build me a CRM essentially in Notion. I originally,

Reuse Your Network With AI

Jenna Deyle 13:45

like, when I was planning my exit, I was, starting to get all this stuff set up, and I looked-- I probably tried out, like, a dozen, like, CRMs built for solo consultants or built for service and whatever, and, like, they all were missing something because I wanted to be able to track kind of not just, like, the potential clients, but also the network, right? Like, to the point of the relationship rhythm of, like, "Hey, this person..." For example, I have a great relationship with the head of learning development for, um, University of M- of Missouri, Kansas City. She's been a great connector for me, like, connecting me to all these different people around Kansas City. She's never gonna be the person that I sell to, but it's really important I maintain that relationship to my great network, right? And so I wanted to be able to have something to track both of those, so I just custom-built it with Claude, and I barely ever open Notion to be honest. when I do an outreach, and I use a lot of, like, voice-to-Claude stuff, I'll just say, "Hey, I outreached, Sarah Noel Block. I sent her an email." Or sometimes if I send an email or a LinkedIn, I might just even screen grab it and just drop it in Claude and say, "Log this in my Notion." and I'll put in there, like, "Hey, I I think I wanna reach out to her in about 10 days." And then that's all tracked in Notion as far as like what was my last outreach, what's the next outreach, what date should it be on. and then I have a scheduled task in Claude every Sunday evening. It runs, like... it pulls my calendar, my emails, all of the things together and gives me, like, a report for the week. And one of the things it'll pull is what's everything in Notion that has a due date within the next seven days, and it pulls it into my report. And then I also have-- This is getting a little complicated. I also have the Todoist app.

Sarah Noel Block 15:30

Yeah, I know that one

Jenna Deyle 15:31

version. It connects to Claude for f- free. and so when it pulls my Sunday night briefing, it'll say, "Hey, you have these six follow-ups from Notion. Do you want me to add it to your prospecting to-do list?" And so it goes and puts it o- on there, so then when I'm... It's great. And so it's one of those things I don't have to look in Notion, and then also I don't-- Like, 10 years ago, when I was in a sales, like, a sales role, I would've put, like, everything on my calendar. I would've had, like, 50 little things of, like, follow up with this person, follow up with that person,

Sarah Noel Block 16:04

Yeah, that's what my calendar looks like right now.

Jenna Deyle 16:06

then it-- Well, then if you don't get to it the day it's on there, it just is gone. It's gone. But if it's in my Todoist app, it's gonna stay there, and every night Todoist sends me an email being like, "You have four tasks overdue. What are you doing?" And it

Sarah Noel Block 16:19

Yeah. Get on it

Jenna Deyle 16:20

that momentum, yeah.

Sarah Noel Block 16:22

I love this workflow. I can't wait to hear, like, what listeners think of it. It's so good.

Jenna Deyle 16:29

And I do have a, a, a little I have a substack just under my name, and I recently did a series on my tech stack and what that flow looks like. So if they wanna see, like, pictures and stuff, I do have that, out there

Sarah Noel Block 16:45

Yeah, I was just scanning to see if you sent it to me. Sent... Would you shoot me an email with the URL?

Jenna Deyle 16:52

Yep

Sarah Noel Block 16:53

That's s- that's cool. I like that.

Jenna Deyle 16:57

And again, like I literally just pay for the $20 a month Claude. That's all I pay for. Right. Everything else connected, I use the free versions and it does just great

Sarah Noel Block 17:06

That's such a good workflow because that is the hardest thing is keeping up with those interactions. I use Boomerang for mine, and I'll even find myself like snooze again

Build A CRM With Claude

Jenna Deyle 17:20

Yeah. And it's so, especially when you start having client work, it can be so easy to forget. Like, if I follow up with you today and then all of a sudden I land, like, four things, and I'm like, "I don't... Like, I'm not gonna worry about this." And then I get to the end of, like, the two months worth of work and I'm like, "Oh, I never followed up with Sarah and it's been two months." Yeah. You kind of feel like a jerk. And, like, if you had momentum going, you lost that momentum, so yeah.

Sarah Noel Block 17:45

Yeah, you're just shrinking your pipeline when you don't keep up with those outreaches, and literally it probably takes two minutes to do

Jenna Deyle 17:52

Mm-hmm. Yep. Yeah. And

Sarah Noel Block 17:55

I dig that.

Jenna Deyle 17:56

other thing I'll add that I do as well is that's how I track, like, what's already in, my outreach, but I give myself rules for each week of how many out- Like, I, every week I try to do three to five outreaches for that warm LinkedIn network, and then I try to do, I try to send the cold, outreaches, like cold LinkedIn requests, I try to send to three companies once a week. And then I have a few things, like I have a few different networking groups I'm in, so then I also have a rule, like I send LinkedIn requests with introduction to like five people from those networking groups I'm already connected to. And I have those as reoccurring tasks in Todoist, so every Thursday it pops up, like you have this due. and that's how I keep making sure I'm adding new stuff into my pipeline so that I don't get behind because of that busyness of clients and the work and whatnot

Sarah Noel Block 18:51

Yeah, that I like that a lot. that would make it just so much easier, and then you're keeping your pipeline full. speaking of pipeline, so you're using Notion as a CRM. Does it also track your pipeline, like estimated revenue forecasting?

Jenna Deyle 19:09

Yeah, I have columns for all of that in there. I have like columns for like estimated revenue, committed revenue, that sort of... And like what stage I think they're at, whether it's cold or warm or whatever. I track all of that. And then I have like a full separate database for, So I have the database for like client outreach, I have a database for the networking side, and then I have a database for, um, speaking opportunities, 'cause I also do professional speaking, which is a different type and cadence of outreach. So I have a database for that. But again, like I'm not really looking at those once they're established. I'm just going to cl- Claude's just sending it to me Sunday night of like, "Hey, you have these three things from this, these three things from here, and these three things from here. Should we add them in?" Right?

Sarah Noel Block 19:55

Yeah. Yeah, so okay. So three different Notion databases tracking those different opportunities. I'm... We have like five minutes left, and I'm trying to anticipate what are my listeners going to ask, and I think that they will ask for the email addresses. Like when you said that if they weren't responding on LinkedIn, you'd look for their email addresses, how do you usually do that?

Jenna Deyle 20:24

Yeah. it really depends on the target. Like, some companies are gonna have it right out on their website depending on what it is, right? the other, like, secret, and I use this in my corporate career all the time, and it's not even a secret, it's kinda like duh,

Sarah Noel Block 20:38

An open secret?

Jenna Deyle 20:39

Open secret. My corporate email was jDeyle@company.com, right?

Sarah Noel Block 20:47

Mm-hmm

Jenna Deyle 20:47

Every single person in the company I worked for, it was their first initial, their last name @thecompany.com. So when you think about it that way, you don't necessarily have to go find Sarah's email. You could find anyone that works for Sarah's company's email and then just figure out... It's all, it's always, like, the same type of formatting, right? The only, like, sometimes there's like, if there's two J Deyles, like, one person might be J-E and one person might be J Deyle, right? Like, there's some intricacies with that, but if you figure out the format from anyone, then you can usually figure

Sarah Noel Block 21:21

Yeah And that's another thing you can ask Claude too. "Hey, find what the format is of their email addresses."

Jenna Deyle 21:26

Yes, 100%. And then the other tip I would give as well is... And look, I sold into manufacturing for 15 years, so it's a little bit different than a lot of places, right? Like, if I'm trying to get into a specific manufacturing facility, I can literally, like, walk in and go talk to the receptionist,

Sarah Noel Block 21:43

Yeah, they're usually pretty cool with that too.

Jenna Deyle 21:46

yes, it's a little bit different than if you're, like, calling the corporate of Coca-Cola or whatever, right? But if you can get to anyone, knowing someone's name is gonna make them more likely to help you. So for example, I would call a lot on, like, the safety manager. I might not know the safety manager, but before I would walk in those doors or make that phone call to the front desk, I would look up the person's name on LinkedIn, because if I would... could come in and say, "Hey, Sarah, I'm looking to talk to Mark today about his safety products," that goes over a lot better than like, "Hey, Sarah, I'm trying to get in front of your safety manager." Yeah

Sarah Noel Block 22:20

Yeah

Jenna Deyle 22:20

just thinking about, like, what information can you pull so that if you do have someone you can talk to, they're more likely to help you.

Sarah Noel Block 22:28

Yeah, that makes sense. Okay. I have one more question and I'm gonna go over on time, whatever. I think that people are probably going to want to know about your speaker workflow too.

Jenna Deyle 22:39

Yeah

Sarah Noel Block 22:40

Do-- what is, what does that one look like?

Jenna Deyle 22:42

Well, so those are a lot more long-term, and I'm just starting to get into this. I've done some, like, conferences and stuff before when I was in my corporate career. a lot of times I may not know about something until it's, like, passed or it's past the due date, or maybe I see... Like, a big thing for, figuring out professional speaking is, like, if you can do a workshop, like if you, if they put out a call for speakers for, like, a workshop or a panel, that's probably not paid, okay? But the keynote is paid. The keynote's, like, almost always paid. And so I may not know something's an opportunity until it's at the call for speakers spa- time, where it's already, like, past the paid opportunity. So I'll put it in as like, okay, this conference happens every year in October. Hey Claude, put all this information in here for six months before, so that way I can start checking it out. If I know the contact for, like, who is the speaker per- like the manager for that thing or the event manager, like how do I figure this out? I'll put all that in there and then start engaging about six months, or if I know the flow. if like, if it's like, hey, it booked... They have this thing that comes out in November, I'm gonna put that ahead

Email Discovery And Gatekeeper Calls

Jenna Deyle 23:55

of time so, like, I'm not missing those opportunities, if that makes sense. So it's really kind of the same thing, it's just a lot longer of a cycle

Sarah Noel Block 24:04

Yeah. And you know the schedule, like the cycle of, of, that, so it's a little bit different in that too, because people can hire you at any time, but there's a specific cadence to what that is. With the speaking engagements, are you, like, networking and nurturing those relationships ahead of time or are you doing a straight pitch?

Jenna Deyle 24:30

it depends. So I'll just use an example. So I spoke at Association for Talent Development's national conference, like, as a workshop leader two years ago. and that was an... You know, they paid for, like, my flight and my food and, like, that, and the conference, and that was it, which was... It was great. and I know that the person that runs those programs from doing that free gig. So, like, I'm nurturing that as I go. The ones where, like, I don't have that in, I'm trying to figure out via LinkedIn. It's not as easy as like, like it's... Sometimes, e- especially for, like, sales stuff, like sometimes it's sales enablement, sometimes it's, like, the CSO. Like, it just is kind of all over the place, and so it just kind of takes some digging to, to figure that out. But sometimes for the things that for me are worth it to do for free, that's kind of like a good way in, where now I'm ready to pitch myself as the keynote for, like, the next time that they're gonna do it

Sarah Noel Block 25:25

Yeah, that, that makes sense. And those speaking, even the free speaking opportunities are great ways to... Like, I've gotten so much work from those, where people afterwards will come up and talk to me and be like, "Well, do you also teach workshops on this topic?"

Jenna Deyle 25:42

Yes. Well, yeah. so for me, like Association for Talent Development's a big one where, the conference ticket alone is like $2,500.

Sarah Noel Block 25:50

Bleh. That's a lot.

Jenna Deyle 25:52

But like, it literally, like the, their international one, they have like 8,000 people there that are in L&D. And so, like, and went in this last May as just a participant, and I went on, speaking, this is prospecting.

Speaking Pipeline Ideas And Final CTA

Jenna Deyle 26:05

Once I was signed up, you could go into a portal and see everyone's name, company, title, and so I went through that and found like potential clients. And when I went to ATD International in May, I had like 20 set up appointments with potential

Sarah Noel Block 26:20

That's the... I literally just talked about, like, trade shows and cons and how to do it right, and that was one of the things I talked about is, like, pre-schedule these meetings

Jenna Deyle 26:30

Yeah. So like if I, yeah, for the, for ATD, it's such a good, like, audience for me that, like if you wanna pay my $2,500 conference ticket and I do a session for 50 minutes, like that's worth me speaking for free, right?

Sarah Noel Block 26:44

Yeah. yeah. and all of those leads that you're prospecting will make up way more than the cost of that ticket

Jenna Deyle 26:52

Yeah. Yeah, for

Sarah Noel Block 26:54

Awesome. Okay. Thank you so much. I loved this conversation. And can you tell people how they can work with you and find you online?

Jenna Deyle 27:04

Yeah. So, Instagram and LinkedIn, just Jenna Deyle. my website is levelthreesalescoaching.com. I work with B2B sales teams, and I also work, with female solopreneurs. so I have some offerings on Instagram more for that audience, but primarily I work with, like, sales leadership. So just reach out on LinkedIn or Instagram.

Sarah Noel Block 27:24

B2Bs and solo foun-- female founders both listen to this show, so contact Jenna. Thank you

Jenna Deyle 27:33

work with anyone, it just has tended to be my network in Kansas City has been very, like, professional female networks prior to me leaving corporate, so that's just kind of what has happened, and it's been, it's been fun

Sarah Noel Block 27:44

Yeah. Okay. I'm