Sean Lane 0:02
Today's episode is sponsored by the DevOps experts at full cast with me is their Head of Customer Success. Tyler Simon's Hey Tyler, revenue efficiency, sales productivity are everything today. How does full castes go to market planning platform help Reb ops teams achieve these types of goals.

Tyler Simons 0:19
Well forecast lets you build better territory so that the right resources are always focused on the right opportunities. When reps are motivated and zeroed in on their targets, they'll be more successful and bring in more revenue.

Sean Lane 0:32
That sounds great. I do a lot of that planning and spreadsheets today. And I'm pretty happy with my spreadsheets. How is full cast any better than that? You

Tyler Simons 0:41
must get rid of the spreadsheets because spreadsheets create lag and errors with forecasts planning and updating happen automatically, all in one place. Best of all, it automates all common headache inducing planning activities like territory rebalancing, account hierarchies, routing, and more. So when you're faced with those go to market plan changes which you know what they happen all the time forecast has your back.

Sean Lane 1:07
Alright, you got me convinced? Where do I learn more about forecast? Our

Tyler Simons 1:12
website forecast.io.

Sean Lane 1:28
Hey, everyone, welcome to operations at the show where we live under the hood of companies in hyper growth. My name is Sean lane. It's really quite refreshing when you see people being vulnerable about their own struggles in a professional environment. We all try to be so polished and put together all the time, especially as operators where our job is literally to have everything put together. So it caught my eye when an operator that I've admired from afar started a work advice column dedicated to navigating work relationships. That operator is Jackie Leahy, a fractional reserve ops advisor and founder of activate the magic. In the description of the column aptly titled dear Jackie. Jackie admits that workplace relationships is an area where she's struggled herself. And starting this column was her means of sharing the lessons that she's learned with others who might be in the same boat. Jackie approaches all of this from the core belief that you have to make room for different leadership styles and different working styles inside of a company. And while this conversation may feel different from some of our other episodes, that's kind of Jackie's point. In our conversation, we talked about pairing your skill set with the right environment. We're talking about the humbling experience that Jackie went through of becoming an SDR 10 years into her career. And why taking a Clifton Strengths Assessment was the turning point in her career. Let's start though with the motivation behind starting dear Jackie, and why interpersonal relationships at work is something that Jackie thanks so much about.

Jacki Leahy 3:06
For my whole life, I have been just obsessed with personality tests, and how kind of people relate to each other and systems. Like I remember, just in high school, I was like, what if there was a way that I could just know like, where I stand socially, figure it out. So like human dynamics and how people make decisions and how we learn and how we interface has just always been just an enormous passion of mine. And especially in my tech career, so I came to tech, at 33 Sort of like, starting over, I got to start over as a BDR. Which, so home like a huge slice of humble pie every single day. And it was so frustrating, and nothing made sense. And everyone was mean, and all the other PDRs hated me because I was old. Because I was like, I didn't fit in. They were all like, let's go out. I was like an adult. And it's just always been. Like, I've always tried to figure out, like, do you call it like, you know, politics, like inner politics or, like the social landscape. And, you know, as I develop from individual contributor to manager to, you know, managers, managers, then all of a sudden, it's not just my peers or like getting along with my manager who might think I'm a threat or things. Now I'm cross functionally, right. So leading my initiative heavily depends on on what marketing is doing, what product is doing, and how finance thinks it's me, right? So not only am I managing BDRs PRs, but also like, really needing to influence the AES really, really mean to like all of these disparate relationships that are so vital. And it's like, no matter what I did sometimes, like, I could not win. Like, I was making somebody mad, or stepping on somebody's toes. And it's like, Ah, my heart was in such the right place about just like, oh my gosh, like, just like Record scratch, like, like, clown honk noises. Like in my head, like, why am I like this? Yeah, and it's been like a journey. And, you know, I think a lot of, for me, especially, and I think this is common, like, we want to, like fit in and be appreciated and feel safe and valued and not be bullied. And a toxic environment is much more likely to change you, then you change the toxic environment. And it was really easy for me to think it was me, you know, and it's like, just in the wrong venue.

Sean Lane 6:01
While it would have been easy for Jackie to just try to conform to what she saw around her. Instead, what Jackie teams realized was that she hadn't found the right pairing of her skill set in the right context. Not every environment matches every skill set or personality. That's not a knock on you. It's just reality. And instead of trying to fit a square peg into a round hole, Jackie went in search for her match. Seeing what else was possible was a big unlock for her. And now she's trying to do the same for others in a way that only she can.

Jacki Leahy 6:37
So they're Upright Citizens Brigade, UCB. It's an improv theater in school. But like, long ago, it was a show on Comedy Central. It was like a sketch show. And there's this one sketch where it's like an ugly people support group. And there's one person is like, obnoxious, right? Like, like saying the comically the wrong thing. And it says to one person, you're not an ugly human. You're a beautiful monkey. That's like, no, no, no, like, don't be stuck in the offensiveness of not being, you know, a human like in your monkey, but like, You're a beautiful monkey. And, and so not just like, I think, go where you're celebrated. Sure. But like, no, no, you have you have greatness and brilliance and strengths. Unlimited, unlimited power, power, possibility, brilliance, genius that's already inside of you. And so like, what are you waiting for?

Sean Lane 7:52
And so, you know, you mentioned a lot of this came from your cross functional interactions. Ops is inherently cross functional, right? Like, you have to be good at making these cross functional connections. Otherwise, you're never getting anything done. Right? And so what's the right balance there between just like, Okay, I'm going to do things my way no matter what I'm going to embrace who I am and go versus trying to find that common ground? Like, what is the answer? Like, what is the advice that you give people who find themselves in a difficult internal partnership situation? Well,

Jacki Leahy 8:27
I think the trick is to be totally comfortable with your own brilliance to a point where you don't need to prove it. Like people who have generational wealth, don't have a logo, believe it, Tom versus like, I have a knockoff one with logos because like, you know, but being so confident and secure, with my own value, that I'm not seeking validation approval. Like, I'll call myself desperate for like, acceptance, validation, important significance, right certainty, looking outside myself, from others to pour into me, it's like, no matter when I have that, I can go in and fully listen and be present for what's happening around me who I'm with when my when I'm taking care of myself and my cup is full. And I'm not like, running on caffeine fumes. And I can actually like, deep dig in and like sink in with someone and be there for them like the gift of presence and listening. I think that's when you come and you can totally be yourself and just have so much space for the other people around around me. And when my focus is on my vision In er a shared vision, a shared goal. And I care more about that than my insecurities. All of a sudden feedback is information. And it's vital.

Sean Lane 10:12
The lesson from Jackie here is that if you're in a good place, personally, taking care of yourself, making sure your cup is full, you're gonna bring your best self to work and your internal partners, your company will all be the beneficiaries. But that assumes that you know, what fills your cup. And I think that's a pretty important prerequisite to Jackie's advice. And that's not something that's going to come to you overnight, I think you start to develop the answers as you go on in your career. So I wanted to know how Jackie figured out what filled her own cup, and what she's seeing with other operators struggling with this question today.

Jacki Leahy 10:50
I think the number one thing is to really sit with yourself in what are my core values, like what do I value. And there's like a online, very old website where it like, has 100 values, and you can pick them out and like whittle them down. And like one of my, this is just like comfort and joy and learning. Right? So. And I think this corresponds really well with if you've ever taken Clifton Strengths Assessment, I think it's like 100 bucks. So you can buy the book for like 115 bucks, and it comes with the assessment. This was truly life changing for me. I learned my top strengths. And it gives you like, Hey, this is a summary about you. In my life shifted when I read the first sentence, when do we start about me like that is what you're always asking, because my number one strength is activation. I'm an activator. And I realized I was currently at a startup who said they wanted all this growth and they wanted to drop, quit their very expensive paid lead dependency, like heroin, and they wanted to go cold outbound, and they said all these things, and they wanted to shift. And they brought me in to do that. And actually, they didn't write saying it in reality, and it's like, Oh, my God, no wonder I am like, a wet mop, in a Container Store, like no, like, get out of here, you do not belong here. Because I was an activator. And I'm learning and I want to move fast and go and but those weren't the values that wasn't what the culture of the startup actually was.

Sean Lane 12:38
And so like, how do you help people to I guess, figure that out when they're considering a new role or considering a company because, you know, it's never going to be one size fits? All right? You hopefully if that company is building in a thoughtful way, like you don't want, you know, everybody to be the same, right? You don't want this homogenous employee base inside of your company. And so how do you find that right balance of like, okay, this is the stuff I know is important to me, this is the dynamic or the mix that I see at this company, and like, how do I see myself fitting into that?

Jacki Leahy 13:13
Yeah, really knowing your own values, like what you've got what's, and not just like, what's important in general, but what's important during this chapter, right? So knowing that right now, like I remember, like, right now, what's most important to me is getting experience and working with a reporting to someone who is my God, like someone who I want to become, right. So I'm going to refactor my job search around that, and just being really clear about what it is that you're after. And there's like, so many ways, directions, we can go from there, but like being real about mapping, like, who I am, and like, who the company is, and what direction like, what's the bus route? Where is this bus headed? And what kind of terrain? And how is this bus going to get there? Is that a, I want to say match? It doesn't necessarily mean like, because sometimes, if there's a bunch of visionary people, and they needed someone to like, crack their goals, let's get like, I would be absolutely a hero in that situation.

Sean Lane 14:19
I also think, too, it's probably pretty healthy to have those questions or have those traits as things you can lean back on when things get hard, right? Because things are going to get hard. Regardless, you could have the best, most supportive environment that there is, and it's still likely going to be hard if you're in a high growth situation, right? And so, you know, being able to take a step back and say, Okay, this week sucked. But like my two or three core values that I asked myself if these things are still true, like, Yep, those things are still true. All right. I'm good. I'll see you next week. Right? Like, is that kind of the right way to think about the Balance of that to help manage the the ups and downs that comes with working companies like these. Oh

Jacki Leahy 15:05
my gosh, yes. And things change, like, slow, slow, slow, and then all at once sort of thing. There's like, kind of tipping points. And so how I fret this somewhere, I don't remember where. But it was like, if it's a bad two days, like it's up to two weeks, if something for two, yes. Two weeks is the threshold, right? And, gosh, I remember at my third startup, like, we, when I joined, I was hired number 10. First Lady hire, and I built the BDR. Team, I joined at 350k Arr. And a little short of two years later, we were at almost 9 million. And all of a sudden, I looked around, it was a very different situation, right? All of a sudden, it's like we had a C suite, vying for, I don't know, career growth and influence. And I found myself like, the I had all of like the tribal knowledge. And I wanted the company to succeed. But all of a sudden, there was like this new context of like, bureaucracy, right, like governance, bureaucracy, and it's like, all of a sudden, I wasn't a fit anymore. Figuring

Sean Lane 16:23
out your why, what fills your cup, the values you're looking for in a company? Let's face it, these aren't luxuries that everyone has. So if you can figure out your answers to those questions, and then relentlessly seek out environments where those boxes are checked, consider yourself amazingly fortunate. By the way, Jackie's reference to the two week rule comes from one of my favorite people to follow Molly Graham. Anything Molly writes, you should read it. Molly's two week rule says that you should observe any emotion or reaction that you're having to a change around you at work, acknowledge it, and then move on. Do that every day. And if the emotion is still the same after two weeks, then and only then should you consider doing something about it. We'll be right back. This episode is sponsored by fool cast a company that helps operators build better sales territories. Their platform focuses the right sellers on the right opportunities, making them unstoppable. And the cherry on top forecast automates common go to market activities like territory, rebalancing, account hierarchies, routing, and more. So the plan is always in sync with operations. With forecast say goodbye to go to market planning headaches, and hello to your own personal planning assistant. Learn more about full cast today by visiting full cast.io. Okay, let's get back to Jackie. Up until this point, Jackie has been talking a lot about her own experience and her own journey to figuring out her own strengths, what was important to her and finding the environments that she would thrive in. But she's also been a leader, helping people on her team to do the same. So I was curious, how has she built and managed her teams to incorporate all the personal learnings that she's had?

Jacki Leahy 18:15
What I really like to get across like, number one is i i care much more about you and your career and your happiness. And what you're doing for me here now, like my condolences, but you have me for life. I'm a lifelong fan of Sean lane. So whatever it is, please come to me if you're like, I'm not feeling this, or, you know, I'm thinking about a different job. Kind of thing. Like, please come to me because I care way more about you and your career and your trajectory than this job you happen to have right now.

Sean Lane 18:50
And this is probably a little bit of a tricky question, right? Because you're telling us that you know, every person is different, every person's cup is filled in a slightly different way. Is that the case with operators? Or have you found some consistencies across this group for what does fill their cups? Or what is the best way to manage them? Or is it truly unique?

Jacki Leahy 19:13
Yes.

Sean Lane 19:17
A bit of a Yeah, not a fair question.

Jacki Leahy 19:19
Yeah. Well, for Reb ops people, usually, it's two things, and like, just a passion to like, help, like serve, figure, like, let me fix that for you. I think nine out of 10 of us are accidental admins because we happen to be able to help people fix their bluetooth headphones, like classic classic. And then the other thing is just like a really intense curiosity. And just like that, like outrageous, just like to figure something out, like to get to the bottom of something because really, especially if that's If you've been on trailhead, right, like trying to figure things out in Salesforce, and like been trailhead, it like checks it for you, right? So it's like you can't just like, oh, let me guess it spins up a sandbox, and you have to configure it properly. If it's buggy, because it's third learning platform, like things are weird. And they have to go back over and over and over and over and over. And the only thing, at least for me, and a lot of people I've talked to that got me through to the other end, is just this insatiable hunger to figure it out. So like, when people ask me, Jackie, how did you schedule your studying to pass the certification? It's like, listen, like,

Sean Lane 20:47
how did I get anything else done besides the right question?

Jacki Leahy 20:52
Yeah, it's like, Jackie, how did you get yourself to eat all of those Cheetos? It's like, asking me that. It's like, these are so delicious.

Sean Lane 21:05
I think that's an interesting point, though, because I think every single one of these strengths that you're describing, right, or every single one of these traits that an operator might have or you found to be a pattern, like, could also be a weakness, right? Or could also be like a blind spot. And so how do you help people kind of be aware of that, or in the way that they you manage them? Or also in pointing that out to other people they might work with? Who might approach those problems totally differently, right, where, you know, like, the last thing they would ever want to do is go through the trailhead and spend time, you know, debugging the buggy thing, they just want it to work.

Jacki Leahy 21:47
Yeah. Yeah. We'll talk about a lot of fun things that I want to talk all about all the time right now. But I think a core question that I picked up on was, how do you like, manage? And coach in this strength, lead way? When their strength is kind of military sometimes? Yeah. And for me, like, one of my strengths is my humor. Right? I am hilarious. And, and have my eye am. But like, with that gift, my journey has really been responsible about my humor, and like, responsible about the impact of my humor. So it's like salt, if you're cooking of salt, if I'm not present, to the impact of who I'm being, and, you know, I can absolutely alienate. If I'm just focused on making people laugh, which is prep like, that is my currency, oh, my God, if I can make you laugh, like, good day. But if I'm only focused on that, then nobody can take me seriously. No, it doesn't work. It doesn't work, right. So I really get to be responsible about that. So when I'm managing people, it's like, okay, this is your strength. And this is your goal. This is your vision. Are you open to feedback? Yes, of course. Because this is actually, like, my ego can like, go chill in the backseat for 10 minutes while I take in this feedback, let it land. And, you know, iterate on that. So it's like, Jackie, the humor is absolutely your strength you crack. Absolutely. And your goal here is you want to become VP of revenue operations. Right? Yes. Okay. Great. Are you open to some feedback about how your strength is actually getting in your way? I'm not gonna like it, but absolutely, yes. Right. So leaders are in constant demand for feedback. And how the people are leading show up about feedback is my feedback. This

Sean Lane 24:17
idea of Jackie's strength lead management style is worth exploring some more. It's tempting for us to separate strengths into one pile and weaknesses in another. But as Jackie points out, sometimes our strengths can be liabilities when not utilized in a controlled way. For operators. She said that there's two things that she's found to be almost universally true. One we want to help. And two, we have an intense curiosity to find the answer. If all you do all day is reactively, say yes to every person who asks you a question. And you don't stop to consider whether that question is something that's even worth solving. You're going to be a very well liked and very ineffective operator teaching people how to maximize their strengths. Without those being the only traits they possess in a vacuum is what good leadership looks like. You have to know what that person's goals are, you have to know how they'll take in the information that you're about to share. And then you have to help them to quickly put your feedback into action. The other thing I took away from talking to Jackie is that throughout all of these different scenarios and factors, we as operators might just need to look at ourselves, look at the stage of a company, the makeup of our team and say, this role at this moment in time might not be right for me. And Jackie, to her credit, has developed the confidence and the knowledge of herself to say just that.

Jacki Leahy 25:44
Come back to your vision, what's your vision, like, if your vision is dead ass to be the VP of Reb? Ops? So XYZ of this role is crucial, then, yeah, right. Like this is a learning in, go into it with that, like, I'm about to get my ass kicked.

Sean Lane 26:07
And that's okay. And

Jacki Leahy 26:08
that's okay. And that's okay, right? It's not work life balance, it's work with choices. And different chapters look different for different people. Right. And just being clear, for me that difference make part is being clear and creating, like, standing as the uncontested author of my life of this chapter, and being clear about this chapter. Because like, not letting life happen to me, you know, like, obviously, like things happen and opportunities and organic, of course, but like being really in that authorship spot. And

Sean Lane 26:40
it sounds like you've been able to kind of, you know, extend the metaphor, turn that page yourself, like a couple times, all right, like so many of you became an SDR in your early 30s. Right? Then you're not necessary already more, right? Like you're then you moved into ops like, so was each of those evolutions, kind of the product of this like, kind of self assessment process that you're describing? Yeah,

Jacki Leahy 27:03
I think, yeah, me, my top strength is activation. I'm extraordinarily good at the pivot. On tick tock, the pivot is a big thing. Yeah, just being like, Okay, I'm bored. So how I got into tech was, I was a kindergarten teacher, and then real estate agent, and I had the best quarter in real estate as my whole life. I sold millions of dollars and condos here in Boston. And all of a sudden hit me, I was like, I can do whatever I want. Like, all of a sudden, the debt and the whatever, and the credit card and the data, data, data data. And I was like, you know, this isn't a chump, I, I figured it out. Right? I've, I've learned enough of this language to make friends and make people laugh onto the next language sort of thing. And just being very, like, now what's this adventure about, like, know what I want? And like, really stopping, assessing, pivoting? And, yeah, I think, release the shame of like, you know, when you're taking a walk, and you have to turn around at some point, and it's like, well, I don't want to see a lot of people see me like just like, randomly stop on this like, path and turn around and start walking in the other direction. Like, I look like an idiot. Embrace looking like an idiot, because you gotta get somewhere else.

Sean Lane 28:25
I don't know what the categories or the lists are on Clifton Strengths. But I would have to imagine that in addition to being an activator, there's something in there for you about being challenged. Right. There's something in there about like, having an opposite learner in front of you learner. Daigo learner, like just number two insatiable There you go. Yeah, and I think that that's probably true about a lot of operators as well. Like, I say this half jokingly when people ask me, but like, it's a massive overgeneralization. But the thing I have found to be the most true about ops people is that they like crossword puzzles. Right? Like, it is a massive overgeneralization, but I have yet to find it not to be true. Right. And like that's it, right. It's that challenge that curiosity to learn and like to, you know, literally fill in the blanks.

Jacki Leahy 29:21
Yeah. Yeah. Like, my brain is loud. It wants more.

Sean Lane 29:36
Before we go at the end of each show, we're going to ask each guest the same lightning round of questions. Ready. Here we go. Best book you've read in the last six months, Alex

Jacki Leahy 29:47
from Rosy 100 million dollar offers. It is absolutely blowing my whole universe in mind and it hardly makes To like, really huge realizations? Yeah. Yeah. Awesome.

Sean Lane 30:04
Awesome. Check that out has been hyped. Nice. Alright, favorite part about working in ops? Oh,

Jacki Leahy 30:10
making things magical for other people. Like truly like, Did you figure that like, I don't even need to know how but oh my god, thank you. When I get to like, really do that, like it's

Sean Lane 30:25
alright, Flipside least favorite part about working in

Jacki Leahy 30:29
documentation?

Sean Lane 30:32
Easy that was the fastest answer you've given the whole time we've been talking

Jacki Leahy 30:38
think I'm allergic

Sean Lane 30:43
not sexy but in boring we put in that category. I mean debatable. Alright, someone who impacted you get into the job you have today.

Jacki Leahy 30:55
Brad Smith, he's the CEO of sonar. He is the founder of wizards community. I was let go from winning by design in August. And I was just like, what that was my dream job. And I hopped onto a virtual Happy Hour on Friday afternoon. And I was just such a movie, little Gus coming on. And he's like, you're in the market. All right, I'm taking bets what's the over under on her landing? And so he's like, got the pivot going. And then Michael muse. He, at the end of that he was like, Jackie, why don't you go solo. And he shared with me, his business model and everything is like take it, copy, paste it. And he's just an incredible mentor and beautiful human. That's

Sean Lane 31:42
awesome. Brad's the best. All right, last one, one piece of advice for people who want to have your job someday.

Jacki Leahy 31:47
Enjoy the chapter you're in, and nothing's wasted.

Sean Lane 31:58
Thanks so much to Jackie for joining us on this week's episode of operations. If you want to learn more about Jackie and the work that she does, check out activate the magic.com. If you'd liked what you heard from our show today, make sure to subscribe so you get a new episode in your feed every other Friday. Also, if you learn something from Jackie or from any of our episodes, please leave us a review on Apple podcasts or wherever you get your podcasts. It really helps other folks to find the show six star reviews online. All right, that's gonna do it for me. Thanks so much for listening. We'll see you next time.

Today's episode is sponsored by fool cast your go to market planning platform. If you've ever spent hours or days building territory and quota plans only to have them be out of date. The second the reps hit the street, you need to check out full cast with full cast that you set intelligent rule based policies that automate all of the time consuming manual tasks that hit Reb ops teams throughout the year. with virtually no effort operations will always seamlessly align with your plan. Learn more about forecast today by visiting forecast.io