Sales Hustle is now Sales Transformation
Nov. 12, 2021

#193 S2 Episode 62 - From College Graduate to Rock Star SDR Coach with Katherine Caldwell

This episode of the Sales Transformation Podcast with Collin Mitchell features Katherine Caldwell, Holistic Sales Coach at Katch Consulting. There is no silver bullet coaching manual. When it comes to sales, you have to play to the individual strengths of your team instead of rigidly following a playbook.

Katherine shares how she found her niche selling to VPs of sales. She uses LinkedIn as her main platform to develop her personal brand and become a thought leader to her ICP.

A winning strategy of hers includes using LinkedIn's video messaging feature as an opener and personalizing it. She shares that, due to the nature of her ICP, she can really customize her messages to the tone she thinks the receiver will resonate with.

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01:27 Using LinkedIn to sell to VPs of sales and training SDRs

04:19 Innovating sales and interview processes for clients 

07:01 Sales manager vs sales coach: Play to individual strengths with a vision board

11:03 Personal branding on LinkedIn: Use video and become a thought leader

15:48 Personalize LinkedIn videos: Do your research on your prospect

18:57 Creating a course and monthly on-demand access for clients

21:13 Connect with Katherine 


02:21 "I was selling to VPs of sales, which people say is the hardest persona to sell to. And so I was really having to figure out how can I break through the noise in this crazy time? So I started using LinkedIn like crazy."

07:23 "We can't have that management approach where everyone is doing ABC every single day. We have to have the coach mindset where we're able to easily pick out what people are good at and then get them doing that on repeat." 

09:25 "I don't think a lot of managers know that their new SDR wants a Mercedes next year or that someone's playing to buy a house or have another child coming soon. And so being able to create that vision board and have the holistic view of your salesperson will help you tap in as a coach in an insane way that no one else is doing."

13:12 "My golden nugget of advice is, after you've sent a video, they've heard your voice, he's seen your face, they've seen some follow-up, that's when you start cold calling. Because I just found so much gold in being able to call people."

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[00:00:00] In the world of sales, you either sink or swim or breakthrough to the next level. My name's Colin Mitchell, and this is sales transformation, a new kind of sales show designed to bring you through the epic life-changing moments of elite sellers. So you can experience your own sales transformation.

[00:00:24] All right. Welcome to another episode of sales transformation. I'm so excited today. I've got Catherine Cadwell on today. Uh, she is a young woman in sales. Uh, she started her own sales coaching consultancy. Former college cheerleader, auto immune disease advocate and all about work-life balance. Katherine, thanks for coming on the show.

[00:00:43] Thanks for having me. I'm super excited. It's been a long time coming. Yeah, I know we scheduled it and then I can't remember what happened and we had rescheduled, but we are here today making it happen. So I'm excited to learn a little bit more about your story and I'm sure we're going to pull lots of learning lessons and nuggets out of there for the listeners.

[00:01:01] So where did your sales journey start? Yeah. So my sales journey started in the midst of COVID. I graduated from university in may of 2020, and like a lot of people had no clue what I was going to do. I didn't know, fresh out of college, really what I was good at, but I did study entrepreneurship in college.

[00:01:20] So I knew eventually, probably in my thirties, uh, originally that I would start my own company. So I ended up reaching out to someone on LinkedIn that I found as a mentor. And she talked to. On zoom for about five minutes. This was right after I graduated. And she said, oh, you're a salesperson here. So you need to work for, uh, so she ended up directing me to a sales consultancy where I was the first and only ever SDR hire.

[00:01:47] And I actually started interviewing at a few different companies that were hiring for SDRs. And a lot of them were very like, you know, we've got a script and we know exactly what we want from you and you'll have 10 teammates, but what really interests me about. The one I was interviewing at was they were like, we don't have any scripts.

[00:02:05] We don't know really what our ICP is. And I was like, that sounds really hard. I'm going to do that one. So that's how I got my first SDR role. Um, I'm a super outgoing person. So I ended up going pretty well for me. And, um, I was selling two VPs of sales, which people say is the hardest persona to sell to.

[00:02:28] And so I was really having to figure out. How can I break through the noise in this crazy time? So I started using LinkedIn like crazy. I was posting my own content. I was figuring out how to send videos to people, how to use the audio message in a time where I think a lot of people were just tapping into that.

[00:02:49] So I feel like I got a really strong grip on it, um, right off the bat. And then. That's actually how I started to form my LLC is I was reaching out to CRS, VPs of sales and head of sales all day long. And, you know, they would take a discovery call or maybe they wouldn't, but at some point there was one specific VP of sales I'm thinking about.

[00:03:11] And he said, Hey, we're actually not interested in any. Product from the company you're working at, but we're really interested in you coaching us and showing our STRs, this approach that you have so that we can emulate it. So I ended up doing that. I put together a six week program. I thought, you know, something repeatable that I can do over and over.

[00:03:31] And at the end of the program, the VP of sales reached out and said, I don't care like what you're doing right now, but you need to start an LLC. And like do this because you're passionate about it. You love doing it. And then also our SDRs are all setting meetings based off of what you taught us. So that is how I ended up quitting my day job and went full force into my sales consultant.

[00:03:55] Wow. All right. So let's, uh, let's back up for a second. I'm super curious to learn when you're interviewing, uh, you know, going to, you know, T T having teammates and having scripts and processes versus just kind of like the more challenging path, what was it that piqued your interest most about that opportunity?

[00:04:18] You know, I grew up the middle child of five kids. And so, um, you know, I've always known that to get what you want in life. You've got to be bossy and do it your own way. And so something about like being on a team with 10 other people my age and having a script, I just knew that wasn't for me, my, my life's never had a script and I've always been surrounded by.

[00:04:42] Um, you know, a lot of people, my age, I eat my siblings. And so I was like, I just don't like the idea of someone giving me a script and telling them what to say, because it's not how you stand out and get what you want. And so something about that interview process at the sales consultancy was just so interesting to me because they were just saying.

[00:05:02] We want you to figure this out and we want you to build this yourself. And I'm like, that's my language. That's what I do. I build. And I figure things out and I, I find loopholes and I go around the rules and I'm huge about, uh, the quote that's like, uh, don't ask for permission, ask for forgiveness. And that was something that the CEO had.

[00:05:24] Mentioned in the interview is he had said like, you're going to have to do things your way. And if I ever got an email from a prospect that. Like annoying the crap out of them. I'd be proud of you. Like you wouldn't be in trouble for that. And I'm like, all right, this is the place for me. Yeah. Yeah. If you're not, uh, if you're not pissing people off, you're probably not trying hard enough.

[00:05:48] Um, but okay. I love that. Um, wow. One of five, huh? Big family. Uh, I've got my fourth kid on the way. So people look at us like we're crazy with four. Cause I think like the average is two. Now anything more than two is a big family. Right. Yeah. No, our family is really crazy. Cause we've got four girls and one boy.

[00:06:08] So people always look at my brother with like sad eyes. Oh yeah. I'm going to have three girls and then I have one boy. Yeah. Um, all right, so you clearly like a challenge. I love that. Um, and I think that that's one thing that's missing in a lot of sales org is. Having things too, you know, too much like you, you need to have a process, but like not giving your SDRs, like the freedom to be creative and having the autonomy to like, just get the job done, how they best see fit, which is everybody has different skillsets.

[00:06:46] Some people are stronger on the phone. Some people are stronger on social. Some people are stronger on email, um, and having like the freedom and the autonomy and the creativity to be able to do that is something that lacks in a lot of sales. I love that you brought that up because I always ask the question, why did we have sales managers?

[00:07:05] We need sales coaches and that's, what's lacking in organizations, right? And a coach is someone who can look at an entire team and say, you are the quarterback, you know how to throw. And you're the linebacker because you're. I don't really know football that well, so I don't know why I use that analogy, but I always just think that, like, we can't have that management approach where everyone is doing ABC every single day.

[00:07:28] Like we have to have the coach mindset where we're able to easily pick out what people are good at and then get them doing that on repeat. And then, you know, when something's not going well, okay. How do we coach to it more? What do we need to practice or try differently that we hadn't before? I just feel like that's so lacking in sales leadership today.

[00:07:47] That one-on-one approach versus the team approach. And it's just something that really needs to be brought to light. Yeah, I love that. So you heard it first right here. We're going to start doing away with sales manager, titles. Yeah, my, uh, my good friend, Andy Paul likes to call them sales bosses. You know, the typical dashboard jockey that likes to.

[00:08:12] Tell orders, uh, of things that they've, you know, have not done themselves for a long time or would not do on their own. Um, but anyway, I love that because different people have different strengths and a coach knows how to tap into that and motivate people and every, and also, you know, there's no silver bullet script, just like there's no silver bullet approach to like coaching people properly to tapping into whatever their super power is in their role.

[00:08:40] I love that you brought that up too. And it's funny, cause you're not even asking me questions, but I'm, I'm coming up with answers before you even get into the interview. But I love that you said, you know, figuring out what individually motivates a person and we all know motivation comes and goes. And so that's something that I actually do in my second session of.

[00:09:00] Is, we create a vision board together. I want to know, and this is a one-on-one approach too. It's not the group setting, but I want to know where someone sees themselves in 1, 5, 10 years. Right? Because when you're in a sales role, you may be making 20% salary. 80% commission or 50 50, or whatever the case is.

[00:09:20] And there has to be a reason that you want to make the extra money or close the deals. And I don't think a lot of managers know that, um, you know, their, their new SDR wants a Mercedes next year or that someone's playing to buy a house or have another child coming soon. And so being able to create that vision board and have the holistic view of your salesperson will help you tap in as a coach in an insane way that no one else has.

[00:09:46] Yeah. Yeah. And also, I mean, there's some people that do it in the beginning, but they don't do that. Like check-in to see like, Hey, has the, you know, has the plan changed or is this, you know, is this still the goalpost or has it moved or has it changed? Um, and I think for whatever reason, Sales managers are like, don't want to like cross that business personal line.

[00:10:12] Um, and actually it's what can really untap the potential of like leading your team to like next level success. Yeah. And even simple questions. Like how are you sleeping at. Who who's asking their salespeople that, but how important is that to know when your sales person wakes up every single day and they log into work for you, do you know how they slept at night and why they didn't sleep well and what you can do as their coach to help them rest?

[00:10:42] Um, just in instances of, you know, I'm looking to buy a car, buy a house or whatever the case may be from that vision board exercise. Then, if you can say, you know, how are you feeling about that goal? Is that goal keeping you up at night? So being able to tap into that is also huge. Yeah. Yeah. All right. So I want to fast forward a little bit here to, um, you know, the work that you're doing in that role.

[00:11:04] Right. So you've got, you took that role. You took the challenge, no script, no process. Let's go. Um, sounds like you had a lot of success in that role in using LinkedIn using social, using video. Talk me through like, you know, what you test, what you were testing and just kind of like finding your way and what was really working for you.

[00:11:24] I think I had an amazing opportunity in my first role to be selling to sales leaders. And at first, um, you know, I heard a lot of nos and I felt very discouraged by it because. I just thought, you know, VPs of sales are so mean and they're not listening and all that when it's really not the case. And once I broadened my view, I realized there was so much to actually learn from these people and every no was a little coaching tidbit.

[00:11:50] So, um, I think where I really started to see success was when my client. Was also aligning with the videos I was sending. So I was using my LinkedIn posts to position myself as a sales thought leader and I was selling to sales people. So really what I had to do through my content is create consultative advice, both for my ICP, who is a VP of sales, but also for their reps to gain interest and think I was smart because.

[00:12:23] When you're selling to, when you're selling to a VP of sales, you have to seem like a sales expert. Right? So if I was posting about my experience as an SDR and where I was seeing success, you may think like, well, how was that valuable to VP of sales? Well, it's creating coaching material, right? So I needed my content to be able to target both those audiences.

[00:12:44] And then once I found that niche, I was able to send way better videos. So I started using, um, The LinkedIn video feature and the video or the LinkedIn audio message feature. And I found they both worked equally well. So, you know, probably 50% of people are actually going to watch or listen to what you have to say.

[00:13:04] Um, and then literally just following up through LinkedIn, I have a cadence set up an outreach, and then that's when, uh, my golden nugget of advice is after you've set a video, they froze your voice. He Sr. They've seen some follow-up that's when you start cold calling, because I just found so much gold in being able to call people and like, you know, obviously they're not going to recognize your voice right off the bat, but you can say, oh yeah, I'm Katherine.

[00:13:31] Um, you've probably seen the video of me. And then it's almost like posing a question without really posing the question, but it's conversational, you know, you probably saw that video. I sent you on LinkedIn and immediately. I asked for a response of, no, I didn't see the video or no, I didn't have a chance to watch it, or like, what was it about?

[00:13:52] So that would be my golden nugget about, you know, using LinkedIn as an opener. And if you don't get that response there, you can move into your cold calls and start leveraging the work that you already did on LinkedIn to have an actual conversation. I hope. Oh for answer that. No, no, I think that that's great.

[00:14:11] Um, and I think that that's like a common misconception with a lot of say like newer STRs is they think that, that, that they're going to book a lot of meetings through just using social. Sending messages, sending calendar links and it just doesn't happen like that. Like it may happen occasionally maybe if you're like really crushing it on LinkedIn, you're putting out content that has significant value and you might get sort of more inbound people in you're sliding your DMS asking for your time.

[00:14:42] Um, but in a lot of cases, that is, you know, that's kind of the anomaly like that doesn't happen all the time and people are not just like, Hey, send me a calendar link and let's go, it happens occasionally. But, you know, maybe one out of every 10 and that the LinkedIn channel and the email channel is really to tee up those calls so that they're not as cold.

[00:15:03] So you're referencing those other channels, having more meaningful dialogue. They're a little bit warmed up. There's a little bit more familiarity with you when you make the call. And I think a lot of people get frustrated when they don't see those results on that channel, because they're expecting them to mostly happen on the channel.

[00:15:20] Yeah, exactly. And I think there's also a misconception too, with personalization at scale. So a lot of people think because they personalize something that they deserve a response of some sort. But when you really dig in, there are so many different means of personalizing and different, um, like levels of personalization.

[00:15:44] So some people think something might be personalized when it's. Um, so how personalized would you typically go on a video or not so much? Can you rephrase the question? Yeah. So if we're, since we're going down the, the personalization rabbit hole, um, I know there's people who sit, sit on different sides of the fence with this.

[00:16:06] Um, some people go hyper-personalized typically, those are, you know, your more enterprise sellers that have like named accounts and they need to go deep on those particular people to catch their attention. Um, then there's, you know, more people that are just kind of share more velocity activities, less personalized.

[00:16:22] Um, when you would be creating these videos, how personalized would they be or would they not be that personal? Yeah, I think it's important to know I was selling mostly into SMB companies. So I was, um, prospecting, mostly series a series B these companies had maybe recently just hired their first VP of sales.

[00:16:40] So I was typically only going after one person in each account. And, um, that helped me to be able to personalize quite a bit. So I often would try to find a podcast they've been in an article they've written and you'll find that people are both actually pretty interesting and also pretty nice. So when you listened to.

[00:17:00] Article they've written, you can hear their voice and you can see if they like jokes or if they're very serious. And so you can kind of play off that. So I typically would, I just, I remember one guy was really nice. He has a LinkedIn, he had some article about having four daughters. And so I, I messaged him and sent him a video.

[00:17:18] And then in the little comment I said something like. Girl, dad, question mark. Question mark. I have four sisters what's up something just really casual. Cause I could tell from his article writing about having four daughters. And so even just being playful. And I think something important to note is that I had that permission from my sales leadership to do whatever I wanted to do to book a meeting.

[00:17:41] And so just having that leverage and that confidence allowed me to set the tone based on how I was hearing my prospects. Um, yeah, so I love that because I think people tend to just like reference something like to check that personalization box, like, Hey, spend two minutes, 30 seconds, 90 seconds. Find something really quick, insert into the Tippet template, add message, send that out.

[00:18:07] And then the personalization box is checked. Um, but actually going a little bit deeper of like figuring. How to speak to that person, more casual, maybe a little more, you know, buttoned up business professional. I don't know. Um, I tend to just stick casual with most of my outreach and the way that I reach out to people.

[00:18:26] Cause that's just who I am and anybody who doesn't respond to that way, I typically just don't care. Um, but you know, in an SDR role, like, you know, you're trying to. You want to maybe adapt your messaging a little bit to just match, you know, what you're seeing in, you know, sort of that research. So I love that tip.

[00:18:44] Um, all right. So let's fast forward. Tell me a little bit, um, about like, so you were, you know, reaching out to somebody doing prospecting and then they basically said, Hey, we need you to help our team to do this type of work. Um, talk to me a little bit about the type of work that you do with the clients you work.

[00:19:01] So originally I had set up a six week course and I thought it was going to be such a gold mine. And I realized, uh, I've had about five different sales groups go through the six week course. And when it ends, I feel really distraught. And like, I feel like we built this relationship. And so, um, Typically, what happens after the course is we actually turn it into kind of a subscription.

[00:19:25] So they have a monthly, um, on demand access to me. So, um, the course is really like, you know, we start out writing content. We're finding our voice, we're building our brand. We're decipher, discipling. What kind of story you want to tell about her? Where we've been in our career and where we want to end up in our career and then figuring out how that can fit into LinkedIn content so that we can position ourselves as industry experts.

[00:19:52] And then once we've got that content going and we're starting to see some engagement on. We can start engaging with other people's content and then eventually reaching out to them. And then of course the art comes in, how are we going to reach out to this person? What tone of voice we're going to use?

[00:20:06] What are we going to say? Who are we going to leverage? Who are we asking for referral? And then how are we following up? So, um, it's been really fun getting to see. People I'm working with and the videos they create and how everyone does a little bit differently and then how we can tweak things to get responses.

[00:20:23] Um, and then, like I said, it typically turns into, okay, let's hire Katherine as an on-demand coach. So you pay a monthly fee and then it turns into. The rubs can message me at any time and say, Hey, what do you think of this post? I wrote, can you edit it? Can you change it? Or I had thought about this, or, um, you know, can you watch this video before I send it?

[00:20:42] And it turns into more on demand. Side-by-side one-on-one rather than the group. Wow. Okay. I love that, that on-demand piece. Cause I think that's pretty unique. I haven't seen that used a lot and I think that, uh, you know, a lot of trainings or courses or coaching could come in, you know, do a job and then they're gone and it's hard to kind of keep that going.

[00:21:04] And I think that that piece is, is sort of like the on-demand ongoing coach for like the things that you've gone through in that six weeks. Um, where can people find out more about this? Any kind of final thoughts and what are we going to include in the show notes for them? Yeah. Um, LinkedIn is the place to find me.

[00:21:23] So if you want to hear more or see a little bit more of my style of writing and how I coach people, you can find it all on LinkedIn to just Katherine Caldwell, Katherine with a K. And, um, you can also email me K a T C Um, but I think LinkedIn is really going to be the gold mine, where you can see what I'm up to and what I've been doing.

[00:21:50] And I respond to all my DMS except for, you know, obviously the really crazy ones. So, uh, reach out to me and you'll hear from me. And we. Awesome. We'll include that link in the show notes. If you enjoy today's episode, please write us a review, share the show with your friends. It really does help us out.

[00:22:08] And we're always listening for your feedback. You can go to sales transformation. Dot FM, go ahead and drop us a voice diem and we will get back to you. Hey, you stuck around that tells me you're serious about your own sales transformation. If you're tired of doing things the old way and want to get started in your journey with other people on the same path, head over to sales,, and crush your numbers on your loadable.

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