Sales Hustle is now Sales Transformation
Jan. 19, 2022

#231 S2 Episode 100 - The Path Of SDR To CSM with Kelsey Calabro

In this episode of the Sales Transformation episode, Collin talks to Kelsey Calabro, Customer Success Manager at Dooly, and the solopreneur behind heretic : the agency. Kelsey talks about her journey into the sales world, and what sort of hoops she had to go through in order to land the role that she genuinely wanted.

For Kelsey, it was a winding journey that allowed her to acquire a lot of skills that she otherwise wouldn’t have gained through a linear sales path. Kelsey found success as an SDR and an AE, but found that the role of the Customer Success Manager fit her the best.

Kelsey also talks about the challenges she faced with starting her own writing agency, and advises people to just get on with it: you don’t have to have everything figured out.

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  • Entering sales via the support role 
  • Moving into a new state and acquiring a new SDR role
  • Job hunt tips: Build your own relationships with the company
  • Transition to CSM and enjoying the long game 
  • Try different paths in sales and see where you really fit 
  • Run into the water and figure it out
  • Starting a writing agency
  • You don't have to have everything figure out


Kelsey: "I wasn't the best cold caller. I'm not the best person that you meet on a call and 30 seconds I can pitch you and you see the value and you're like, yea, that was compelling enough. I had a lot of blind spots, a lot of weaknesses as an SDR. I'm definitely a better closer. And then for CS, that transition to Customer Success just really came down to, I like the adrenaline of sales, I'm just kind of tired of holding this heavy quota every month even though now I have churn and retention, and all these other things on my back, it's different."

Kelsey: "If you can, anywhere you're at, try to carve a path into different roles. AE if you're an SDR, don't be afraid to go backwards if you're an account executive and you want to try your hand in SDR work, that's great too."

Kelsey: "The vernacular of CS life is different. You have to learn a lot about advocacy and how you can champion and play into your customers. You're selling them constantly on the value, but you don't want to be a seller. So there's a fine line and a fine balance to walk there which was hard for me at first, as understanding the difference between demo and training and supporting and selling." 

Kelsey: "It is a role where you are given autonomy truthfully, and ownership. At the end of the day, if your accounts fail, it's the same as quota for sellers. Like if you don't hit quota, you got to look at your process. For CS it's the same thing. If your accounts aren't succeeding, you're gonna go back and keep tweaking your process and figure out how you can make it better."

Connect with Kelsey with the links below: 

Also, you can join our community by checking out If you're a sales professional looking to take your career to greater heights, please visit us at and set a call with Collin and Chris.

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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 very excited for today's guest. I've got Kelsey collabro. She is a CSM over at Dooley. She also is, uh, also Moonlight, uh, the owner of a Heredic the agency that she spends most of her days, helping customers sustain success. Kelsey, welcome to the show.

[00:00:45] How are you doing? Good. How are you doing? I'm doing good. I'm excited. I know I had to reschedule on you cause I had a crazy day. So I'm glad, uh, that we were able to get this rescheduled and make it happen. Yeah. You know, we're used to that CSM life everybody's rescheduled. So I got. Yeah. I can't remember how you came on my radar.

[00:01:04] I feel like it was Scott lace maybe. Yeah. I actually went back and looked like right before this podcast, you reach out because Scott posted about me on his LinkedIn. Yeah. I've had Scott on the show. Um, and, and yeah, sometimes it's always funny. You meet so many people. You're like, how did this, how did it, how did it start?

[00:01:24] It's also the dams. It's like, we'll just go look up the LinkedIn dams and see how this began. Yeah. Yeah. I've been saved by the LinkedIn DMS many times, like scrambling to get onto your call. And you're like, please tell me, we met on LinkedIn.

[00:01:42] Uh, all right. So give us, take us back a little bit. Where did your sales journey start? Or if you want to go back a little before. Yeah. Um, no, I, I started growing up in sales, just from my dad. He's always been in sales. Um, and it was one of those professions, like most people where you're kind of adverse to it for a long time.

[00:02:03] So I spent a lot of my teenage years being like, no, it's never going to be me. I don't want to go into sales. I hate it. Um, he's traveling all the time. So that was like my first inlet to sales. But my first sales role when I kind of gave in, was in 2013. Um, and from there. So I was kind of living in Phoenix at the time.

[00:02:24] And it was when tech startups were really on the rise. It was like this cool office in downtown Phoenix and industrial warehouse. They'd built into a tech company. Um, and that's where I got my first, uh, sales. So I started out in 2013. I haven't looked that sense. All right. So I'm curious about a lot of things.

[00:02:45] Number one, what were you selling? So it was a PT, OT, like physical therapy, occupational therapy, um, CMR, basically. So for the health industry, so is a younger startup at the time. We were only a couple years old at that point. Um, but yeah, we're scaling out for CMR, for medical. Okay. And going from having that really natural, you know, uh, don't want to have anything to do with sales, to getting hooked and your first role, what happened?

[00:03:18] Tell me more about that. Yeah, so I mean, growing up, my dad was really good at what he did, so I was always curious. It seems fun. He gets to go travel. He gets to talk to people all the time. He's meeting people across the world. Um, he made good money, so it was intriguing, but it wasn't until that company, um, at the time where I got to actually meet and be more involved in tech and see what tech looks like in a really young.

[00:03:44] And I was like, this is everything that I want. Um, so I actually started out in customer support because that's really how you could get your in at the company was really tough to get into. And then after I stayed there for about 10 months, then I got promoted into the sales role, um, after going to a conference out in middle of nowhere, New York, um, with the director of sales at the time.

[00:04:05] So it was just meeting people and talking and just finding a connection to the product, which I think helped. Interesting. So you took a support role to get into the company. Was it a little bit more difficult to get into a sales role without sales experience? Oh yeah. A hundred percent, especially at that company at the time, it was a really hot market and it was one of.

[00:04:26] Big tech companies that was growing at the time and scaling. So a lot of people is just really competitive. Um, so that's really the only way that I could find my aunt at the moment. I think I applied probably four times and gotten rejected for sales roles or, or marketing role in then. It's like, you know what, I'm going to go into support and just see if it works out.

[00:04:45] And he did so. Wow. That was my next question. I was wondering if the getting the support role was a strategic move. Oh, it was very strategic. I was like, these people will not read my resume and take me seriously. The college. So I was like, no, maybe I to start really small fish and just go into sport, which not saying that's like an easy role by any means, but it was definitely the best in any way, because I ended up getting like all the technical experience for the product.

[00:05:11] So it worked out, but it was, it was tough. Yeah. What, how long did you spend in the support role and what did you learn in that support role that helped you get into sales? Yeah. I was in support for a little under 11 months at the time. So I stayed here for 11 months. It was honestly all product knowledge.

[00:05:32] It was amazing for me, like just being able to get in and really understand all the services we offer. Um, and, uh, really. Deep format. So being able to go in everyday and help solve customer issues, being able to speak to customers and take escalations down and just kind of like problem solve on the spot was really big in that role.

[00:05:51] And really, I think helped me catapult into sales, which looking back on it now, I wasn't thinking that then, but it definitely did help. Yeah, I've heard a lot of sales stores. This is the first time I've heard somebody that got into support and then went to S sales from there. So I was super intrigued, but I imagine, um, like you said, you know, learning, like dealing with customers, seeing what you guys were great at as a company, maybe even seeing what you're not so great at as a company.

[00:06:20] Like those are some, yeah, you must've built up just a great knowledge hub, uh, to be a pretty effective seller. Yeah. Well, I think to that field was unique for me at the time it's medical. So you're dealing with HIPAA, you're dealing with Medicare Medicaid. You're dealing with ICD 10 codes and like mapping.

[00:06:39] For therapists into clients. So it was a lot of technical learning and a lot of medical terminology learning for me at the time, which I think getting into that sales role, it just gave me a leg up because I had a chance to already know all of that coming into that department. So it was the best decision for me at the time and it's how I got into sales, so.

[00:07:00] Okay. All right. So, and then how, how much time did you spend there at that company? And then walk us through kind of how your sales journey, um, advanced. Yeah, I was there for about three and a half years. So I stayed in that sales role for a long time. Um, and then we just started pivoting out side of we're growing a lot.

[00:07:18] And at that point I was dating somebody kind of in the middle of wanting to move outside of. Um, so I ended up taking a role at outreach was my next kind of pivot into a new part of the sales cycle. And I went into an SDR role at outreach. So I got to move to Seattle and just try something totally new, but it was just a need of wanting to branch out.

[00:07:40] Right. Uh, moving to a new place and then starting at a new company all at once. Was that a bit overwhelming? And so in a moment, yeah, it was a, well, Seattle's always been on my list of places I wanted to move. So it was like this far reaching goal. And then when I was looking at tech companies, like my thing was just reaching out to like top 50 tech companies that year and putting resumes and trying to get, um, sense with people on LinkedIn.

[00:08:07] So once I connected with outreach hiring manager was like, if they give me an offer, I'm going to have to go there and find a place pretty quickly. So that was stressful is like, they didn't offer. They're like, we need you here in two weeks. And you're like, oh shit, what am I going to do now? Yes. I think it was three weeks.

[00:08:24] They gave me three weeks and I was like, okay, I'll do it. That was the, tell me. All right. So after that first role getting some sales experience, right. Um, at that point, did you feel like, okay, sales is for me, this. Yeah, I think I still felt leaving my first sales job. Um, Difficult because I really liked that role and it was really tailored to me.

[00:08:47] And it was, it was so unique. I don't think I'll ever find anything like it again. Um, so going into the SDR role was totally different for me. I had no clue what it was when tailed SDR roles were really new at that point, that was like early 2016 or so. Um, so it was, it felt sold on sales, but I just didn't know about the.

[00:09:10] But I went into a try and be like, I'll just figure it out and see how it goes in. Yeah. So tell me a little bit about, uh, how you approached, cause I'm sure there's some people that are curious about how you approach getting that job. Right. So setting a goal of like, I want to work for a top 50 tech company.

[00:09:25] Um, how did you approach the job search of landing? You know, I guess a dream job and then kind of, uh, in a place that you also wanted to do. Yeah, it's kind of the same process for all of the jobs that I feel that I've gotten in the last 10 years. Trying to look up the list like top 50 tech companies in your area or an area you want to move and just we'll target them, um, with strategic messaging.

[00:09:51] So with outreach, I don't remember it as well. I know I pulled the list of top 50 and I was like outreach fits kind of all the molds of what I'm looking for. And I'm reaching out to people on LinkedIn and just trying to get understanding of like what their role entailed, what they thought about the company and just wanting to make connections.

[00:10:07] And I feel like some of that. If I remember correctly that I had connected with on LinkedIn, actually put my resume in to the hiring manager. And that's how I ended up meeting with them and having that and just like submitted on the other job board and believe, leave it up to them to reach out to you. I was like, no, follow-up no, not a no, wait, if you upset, I'm like hone in on something and I go for it.

[00:10:31] So, um, and then I flew up to Seattle for the interview and then it kind of landed. I so work your network, build some relationships with inside the organization. I would say if anybody's looking for like really unique creative things to do, that's kind of like a, I feel like an easy one for everybody to do, but I know in 2020 I was interviewing for this company called artsy at the time and their CEO does good morning.

[00:10:56] America sessions, like every couple of months, every few. And he actually did an episode on how to interview and what interview questions they ask in their interviews. So I pulled those and I answered them and sent him a LinkedIn video answering like three of the top questions he had posted about or talked about.

[00:11:16] And he wrote me right back and he's like, send me your resume. Submit it, and we got all the way to the end of like getting the offer letter and then it didn't come through, but I got that far. We got that far. Wow. When you found that video, it must have been like, oh, I can do something with this.

[00:11:35] Yeah. Okay. So, uh, fast forward a little bit to kind of, you know, what you're, what you're doing today. What was that transition like? And you know, uh, let's go, let's talk a little bit. Yeah, I think, uh, when I talk about a lot now is the, I felt like in sales, one thing that was kind of stifling me was the, the career path thing.

[00:11:55] Didn't feel synonymous with what I was looking for. So, you know, you see people going into SDR roles and then going to AA roles and then their senior year. It's very linear to me. I felt connected to that. So the CSM role has been on my radar for years. Um, it just wasn't until Julie came along, that I was like, this is the company it's going to be for.

[00:12:16] So it took me a while to figure out what that career path could look like. And it was really hard to get there. Um, but it ended up happening in 2021. So I got lucky. What is it specifically that attracted you to that? Yeah. And after being in like high pace tech, fast and fast tech, uh, for the last seven, eight years in sales roles and an STR role specifically, there was just a nature to it that I was over.

[00:12:45] Like I genuinely was just tapped out. I was burnt out. The best cold caller. I'm not the best person that you meet on a call in 30 seconds. I can pitch you and you see the value. And you're like, yeah, that was compelling enough. So I had a lot of blind spots, a lot of weaknesses as an STR. I'm definitely a better closer.

[00:13:03] Um, and then for CS, like wanting to make that transition into customer success really just came down to, I like the adrenaline of sales. I'm just kind of tired of holding this heavy quota every month, even though. Now I have churn and retention and all this other things on my back. It's different. Um, I like the longer strategic play of like diving into accounts and getting to know customers and championing for them and everything.

[00:13:27] So it was the right. Yeah. So what would you say for, for other sellers? Like if they're feeling that same, those same type of feelings of like, ah, just over like the activity quotas and like the stress and like the emotional up and down, like, this is, I don't even know if I should be in sales. Like how do they, what would you suggest they do to maybe, you know, Prepare for like a CSM role or start putting themselves out there for a CSM.

[00:13:56] Yeah. The best thing that I did honestly, was being able to try out different roles. Like I got very lucky and I really put my neck out on the line with every company that I was at to be like, okay, I want to try account executive role. So I would go work and get an, a job somewhere that I felt compelled towards or going for an STR role.

[00:14:14] Trying out different parts of the sales cycle helped a lot and figuring out where I really want it to be, even though I didn't have any CSM experience, I knew at the end of the day, after eight or nine years of being in sales, that that was going to be like a great role for me. Um, so I would say if you can, anywhere you were at like try to career path into different roles, a E if you're an STR, um, don't be afraid to go backwards.

[00:14:39] If you're an account executive, you want to try your hand at STR work. That's great too. Um, but ultimately like taking on side projects for me was a really key factor in knowing kind of that I wanted to step into something different outside of sales. I need a little bit more partnership, a little bit more management.

[00:14:58] I need a little bit more of the CS involvement, relationship building side of it. So I have a long time, but you'll get there. Yeah. What are some of the challenges that you've dealt with? Like transit. Um, um, challenges so many, I would say like the vernacular of CS life is different. Um, I mean, you have to learn a lot about advocacy and how you can really like champion and play into your customers.

[00:15:26] Like again, you're selling them constant. On the value, but you don't want to be a seller. Um, so there's a fine line and a find balance to walk there, which was hard for me at first, um, is understanding like difference between demo and training and supporting and selling so a little bit of time, but ultimately I got pretty lucky because I just got thrown into the fish at Dooley and I was like thrown into the water.

[00:15:51] We're good. We'll figure it out. So what is it you love most about being a CSM? So many things, it's hard. It's really challenging, but I. I love my team. Like my manager makes an amazing, and she's taught me so much, but I would say genuinely being able to reach out to accounts and look at usage and just like dive and get analytical with them.

[00:16:14] Um, there's honestly nothing better than taking a look like. We just got like really big data overview for all accounts. So now I can kind of do deep dives and be like, there's drop here. These people need a little bit more turnkey leads where training needs to be involved. So going into every account with a different perspective and being able to really troubleshoot for them and come to the table with solutions.

[00:16:35] It's like one of my favorite things. Yeah. So just being able to like, be proactive and make decisions based on data and seeing who needs help, where, um, sounds like you really enjoy that part of the. Yeah, it's autonomous. It's something that you can really take ownership of. Um, one thing that I always say to people when they ask about like the pivot from SDR to CSM or out of selling and to see us, like it is a role where you are given autonomy, truthfully and ownership, and at the end of the day, If you, if your accounts fail, like you fail, it's the same with quota for sellers.

[00:17:07] Like you don't wanna hit your quota. You're going to look at your process. So for CS, same thing. If your accounts aren't succeeding, something, you gotta go back and keep tweaking your process and figuring out how you can make it that. Yeah. So tell me a little bit about your, your, your writing agency and the work you do there and when that started and all the good stuff.

[00:17:28] Yeah. Good question. I love talking about this. Um, so I started that in 2020 during COVID. So it really was just bred out of like being super exhausted of being in quarantine, by myself, in Phoenix for, uh, that amount of time. And I always wanting to start honing in on like what my passions are and what things I could optimize for the future.

[00:17:48] So two of those things for me, art and writing. So I started an art business called Curatorium it's on my LinkedIn, but I don't do much with it. It's just kind of something that if it trickles in, it's great, but I was trying to build it out and it just wasn't sticking, um, at the end of the day. So I pivoted and I turned that business into heretic, the agency, which is my writing business.

[00:18:10] And I just had somebody come out to me in 2020 that said they needed help with brand and writing for their website. So I took it on as a project and I got hooked on it and was like, this could be something great within B2B SAS. So I just ran with it incorporated and started getting clients through. Um, was it a little scary taken on the first client?

[00:18:31] Yeah, I was like, I do, you know, I don't do this professionally. Like I have no idea what I'm doing. Right. They're like, yeah, no, your guy trusts you. And I was like, okay, we'll just run with it. So it was scary. Yes. Because you had to do all of it on your own. Like truly solopreneur ship is counting, you know, retention, making sure they're happy and you're delivering.

[00:18:51] Yeah. Yeah. Cause I think, you know, people that are maybe thinking about starting something on the side or whatever, finding, uh, turning a passion into, you know, another revenue stream, uh, it can be a little scary, like taking on that first client. We were like, I don't even know if I can do this. Yeah, no, a hundred percent.

[00:19:07] I was like, I have no idea what I'm doing, but it took a while. I'll say like, it's been almost a little over a year and I'm still figuring it out, but I have great clients that have reached out so far. So it's just a learning. But I always caution, like everybody should try it at some point, if you're questioning it, like just dive in and I promise it'll work out.

[00:19:27] Yeah. Get into action. You don't have to have everything figured out. There's no such thing as a perfect plan. None at all. Well, awesome. Thank you so much for coming on. Where, how can people easily get into your. Yes. So, um, you can just hit me up on LinkedIn. So Kelsey collaborate on LinkedIn. I'm also on Twitter.

[00:19:47] Um, antisocial, Kells. I know the name is a little confusing, but yeah, you can find me on LinkedIn on Twitter. You'll find my heritage. The agency website is on my LinkedIn as well. So if anybody ever has questions about, um, ghost writing or book editing your content or their company, you can ask me. Awesome.

[00:20:08] We will drop all the links in there for free in the show notes for everyone. Uh, if you enjoyed today's episode, please write us a review, share the show with your friends, and then we're always listening for your feedback. You can go over to sales, and drop me a voice DM. I will get back to you.

[00:20:25] 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 page. Head over to sales, and crush your numbers on your leaderboard. Yeah. It's free sales

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