Ep.20- How to Hire Fast, Onboard Right, and Scale an SE Team Without Losing the Culture with Diana Cappello

All right. Hello, everybody. Welcome back to the pre-sales unplug the leadership playbook. I'm RV Karkanji.

I'm the founder of Elite Talent and I work with SaaS companies to hire top-tier pre-sales and post-sales talent. But today is not about me. As you guys know, this show is about the leaders building the pre-sales teams, the go-to-market teams, and literally the strategies that actually work in today's market in 2026. Okay, if this is your first time joining us, quick note before we jump in these conversations are live and intentionally unedited.

So everything that you hear here today is exactly how it happened. We stream it live, but we can also catch a replay on our podcast across Apple, YouTube, Spotify, or wherever your favorite platform it is that you listen. And my only ask is always that if you do get value from our conversation, make sure to follow, subscribe, or just simply leave us a review or comment. I personally read every single one of them.

And I also make sure to tag the guests afterward as well if you have any questions directly for them. With that being said, I'm so excited today, joined by Diana. She is the director of sales engineering over at Udly, um, someone with a very strong track record in the space. Um, I know that we've been connected for some time on LinkedIn, and I'm actually very excited to have you on here because you have a very different story uh from everybody else I've talked to.

And I can't wait to get you in and get you start asking questions and just delivering a ton of value. Oh, thank you. I feel like every SE has a very different story. That is true, and I think it's, I guess, the special part of being in pre-sales in general.

Everybody comes from such different backgrounds that I've I honestly think it's important because it's important to share the fact that there's no just like one-set path to get to where you are today. Exactly. With that being said, I'd love to hear your story and how you literally ended up in this wonderful world of pre-sales. Yeah.

Uh, so I was a film major at UC Santa Cruz and realized very quickly my options were limited if I stayed in the Bay Area to work in the industry. Uh, but I figured I really like short film and I would go into advertising. And so I started doing cold calling as an inbound salesperson at an online advertising company, thinking that would get me into the ad space and then maybe someday I could make an ad that plays at the Super Bowl. Uh fast forward, that didn't work out, but I was really good at cold calling.

So I went to go do that at a high-tech startup. And that's what got me into the AI space. They were actually pre-AI, they were in big data, is what we called it back then. They did web scraping without code.

I remember you could use that in all the AI stuff you're doing. So that got me into AI, and it also exposed me to systems. I was also the one and only marketing ops person. So I was a Salesforce admin.

And that led me into a career as a Salesforce admin, a business systems admin, which then one day I realized I was going to cap out with my pay range in that role. And I went to a friend who's in sales enablement. I said, What's that? And he goes, Oh, actually, SEs report to me.

I think you'd make a great SE. And I was like, No way. I am not technical. All the SCs I knew are super smart, like degrees in computer engineering.

He's like, No, no, no. You know how to build on Salesforce. We're built on Salesforce. That's all you need.

You've got the people skills, presentation skills, just try it. So took a leap of faith and never looked back. Loved it. Similarly, I was talking to my manager.

I'm like, gosh, but all this building stuff is just getting repetitive. It's not my favorite part of the job. He goes, Have you thought about management? I'm like, oh no, ew.

I don't want to be responsible for anybody else's well-being. Too many problems. And after a week or two, I thought about it again. I'm like, okay, you know what?

Let's give it a try. And so we did a trial run. It was supposed to be six months. It was like one month because I just loved it.

And he's like, Yeah, this is perfect. So never looked back again once I got into management. That's awesome. First of all, how unique that you basically came from like short film and like advertising to sales, which is, I feel like, well, they're not necessarily opposites, but it's not like the same thing.

And then just go into pre-sales. That's that's actually pretty unique. I don't think I've heard that before. Most of the people I've talked to so far, they've come from sales engineering through an engineering background of some sort.

So um, and I love that you're not from that because again, it just showcases the proof of like you don't have to be super technical to be in a C because every company is so different. Yes. And that's something I've carried with me. Like my mom is a CFO or was a CFO, she's retired now.

So for me, it was totally normal to have a woman in a C level position in a corporation. And as I got into the workforce, I realized how not normal that is and how lucky I was to have somebody so close to me as a role model and a resource. And I decided I wanted to be that for other women. And especially like with me, I didn't think of working in tech.

I never gave it a second second thought till I got it. And then it was like, oh, this is so much easier than I thought and natural and like not weird at all. And I think a lot of women in particular are intimidated by the tech industry. So I see it as my purpose to help women achieve family sustaining pay through tech jobs.

Yeah, I love that. And how cool that you had support also from your leaders to, you know, move you one first into SC without an experience previously, and then secondly into like management positions. Um, and that is something that I tell people all the time. Typically, if you're gonna do something like brand new that you probably haven't done before, is way easier to do it at either a company or somebody that knows you or at your current company to where it's an easier transition because they know your personality, they know how you work, versus like actually going and applying to you know SE jobs or management jobs without having that prior experience.

Yep, absolutely agree. Yeah, love that. What was it? Um, so you said at the beginning you when you heard the management word, you were like, oh yuck, like that's not for me.

And and then on that first month, you loved it. What was your impression of being like a manager? And then how was it in reality? Um, so reality is still evolving.

Um my impressions of being manager in the first couple of years are very different than my impressions of being a manager now. Um initially, I'd had so many management experiences that of managers that I liked and didn't like. And so I had no management training. I just sat down with myself and thought, okay, what did so-and-so do that I didn't like, and what does so-and-so do that I do like, and how do I want to show up?

And I read quite a few books. I love that. I had an hour plus commute and so audiobooks were my friend. Um so I took a lot of training from those.

I like to joke, I got my MBA through Audible. Um and so I feel like sorry to interrupt, but like way better than at school, anyways. Because I took me a lot of courses. I wasn't gonna go get my MBA because I wanted to be in marketing, and then I realized how expensive it is, and the average pay rate for somebody with an MBA was lower than what I was making as an SE.

Which is crazy. Why do I need it? Yeah, yeah. Uh I might go back, but um, yeah, so so I learned on the fly, I learned by experience, I mimicked who I liked, I avoided what I didn't like, and I still do that today.

But I realized I was coaching and mentoring all these new hires already. And so a bunch of them, that's why he said you should be a manager. Um, so I got them as my employees now. And so then I I initially, before I was a manager, had this impression in my head that I am responsible for them succeeding or failing.

It is my job to make sure they succeed. And the best way I knew how to do that was to make them my little clones. Not a good manager. Don't do that.

That is a common mistake of a first-time manager. Yeah. Um, it's a lot harder to get somebody to be your clone, and it probably won't work and it'll take a long time. Um, now I figure out how to help them shine in their strengths and then where they're weak, get them to like the minimum viable product.

You know, like you don't have to be strong at everything. And you certainly don't have to be exactly like me because you're gonna do things totally differently that are probably better. Um, but initially it was okay, I could relate to these folks because they were fresh out of college and I like the structure of school. And I think corporate in my startup world lacks structure.

So initially I just focused on structure. How do I teach them about the job? And then how do I give it structure such that, like, here's your quarterly test, right? And so you you grow each quarter and you get better and better.

It worked, and I think they did appreciate it, but looking back, I was um unlimited in my feedback. So I'd be like, here's all my notes on your call. Here's everything you did wrong, everything I liked, unstructured. Here you go, figure it out, like take it.

And that could be very overwhelming. So now I give feedback very differently. Um, I do big rocks, small rocks. Hey, here's a few big things that you could do that would make a big impact.

Okay, here's three things you did that we need to address, and here's three things you did very well. And I do have detailed notes if you want them, but like let's just sit with those for now. Um but yeah, it was a totally different experience working for me in the first few years than it is now, I'm sure. Yeah, and and honestly, Dan, it's so interesting because it's in most, and including myself in this when I say most, most of us are like thrown into leadership without any prior experience, which again is okay because you're gonna have to learn at some point.

But the other part to it is like you don't always have support to figure out, you know, what is the best way to do that, you know, how to be a good leader. And like you said just recently, I mean, it's still an evolving job because you're working with human beings. I mean, there is no manual for how to treat like one person to the next one because everybody has different personalities, and it's even to this day, it's literally so hard to be a leader just because there's just so many different personalities.

Yeah, digital and and backgrounds, like leading a team of fresh college grads is very different than leading a team of people with more tenure than you. Right. That and that's such a great point, too, because in the beginning, you know, you're they're usually, I say usually because again, different, but they're usually more moldable, right? And then as you deal with people more tenured, they've already have their ways of doing things.

So it can be harder to change or give feedback, you know, so that it's perceived correctly. Um, I guess that's a really good point you brought up. Have you figured out a way or maybe tips on how to handle certain personalities that's like worked really well for you? No, everyone's different.

Um, I do love to see. Yeah, always start with what's in it for them. I think that's something I've learned along the way. I took training through Girls Club.

Um hashtag girls club, we are girlsclub.com. I think website. You might find other things for you, Google Girls Club.

But it's for women in sales that want to become leaders. And it was so similar to sales engineering, and we didn't have pre-sales collective back then. So that was my path. And um, I'd already been a manager, but I just was craving coaching.

And yeah, one of the things they talked about was uh this model of coaching for giving feedback specifically. It's coach N, it's an acronym, but in the I can't remember what all the acronyms are, but the at the very beginning it's about context. So you need to set the context. Why I'm having this conversation with you is I care about you and your success here, and I want to help you thrive.

And that's why I need to share with you now, blah blah blah blah, whether it's good or bad, or you know, so like never forget the start with why, Simon Senec. Um, yeah. To just to because there's so much anxiety when you're meeting with your manager, especially if it's feedback, yeah, or coaching. Uh, I know a lot of people skin crawl when it's that coaching word.

So reassuring them that you care about them and have their best interest, that's the best thing you can do. But even then, that's not enough sometimes. Yeah. Um, have you heard of the book Radical Candor?

Oh, yeah. Yeah. Yes, I oh, love it. I love that book.

And honestly, it really helped me understand like the different types of leaders that are out there and how you can differentiate. Because for me, um, I started off as like a really nice leader, like I didn't want to hurt anybody's feelings. And obviously, you know, you're trying to do the opposite, is you're really not helping them when you're not giving them any sort of feedback. And then I realized, okay, I can be, you know, radical and still give them candid, you know, information and feedback, but that doesn't mean I don't have to do it in in a way, in a nice way, or like, you know, I still care about them.

So I would that was definitely something really crucial for me personally to learn. And then honestly, I've worked for leaders that are on the other side of the chart, you know, where they're like narcissist and egoistic and all that crazy stuff. So that book was really helpful for anybody listening that you if you haven't read it, and um I love your feedback. I don't know if you read that in the beginning of your leadership journey or no, I think I'd been a manager for three or four years at that point.

Yeah, yeah. And I got the feedback from an employee, bless him of Israel. Thank you. We were in a one-on-one, he'd been reporting to me for a while, and he goes, Diana, I just wish we could have the kind of relationship um Quinn and Donna have.

And I'm like, What do you like? What? What? What are you talking about here?

Because I was very like, what are your deals? What are your problems? Okay, we're done. And um, he was like, No, like I want you to know my girlfriend's name.

And I'm like, Oh, uh-uh. No, yeah, I'd been friends with people at work, and when you get in a fight, it goes bad. Right. I had put huge walls up, and especially with employees, I had this impression that I had to be separate from you, not intermingle like that, because then things get personal and messy and emotional.

It's very walled off. And so I took that to heart and I was like, okay, at the time, my VP Gordon, he was very interpersonal. He'd always start a conversation with how was your recon. I'm like, why?

Let's just get to work, man. Let's don't care. I don't care. Let's go.

Yeah. Um, so I started modeling him and I read Radical Candor and I was like, oh, now I get it. And I remember I meet another woman, she was a young manager, and she was in that initial phase of like, this is business. We only have so many hours in the day.

Let's get to business. Why do I need to know this personal stuff? And like me and the other women in that meeting were like, no, sweetie, like, just read this book. Um, that flipped me.

The book like explained the science behind it in a way. I know it's not science-based, but it was like, oh, you shouldn't just do this stuff. You should do it for a reason and you should really care. Like, it's not just okay, write down the girlfriend's name.

Like, let them know that you truly care. Um so now, yeah, totally, totally different. I have a time block at the beginning of every day called People First. It's 15 minutes, and I just go on Slack and I just say good morning.

And I think at first it creeps people out. So I let them know why I'm doing it now. I had a manager who never said good morning. He just came in and sat down and he never said goodbye when he left.

And I always felt very disconnected from the company's culture, even though it was a company with a good culture. Um, so now, especially with remote folks, I don't want them to feel like they're on an island. I want them to know I care. So I just check in as almost every day, like good morning.

I don't check in at night because I don't want them to feel bad about signing off, but I say good morning, like how was the weekend? How is your day? I try to start every team meeting with a people element. So tell me something good.

We go around the room, what was a win for the week, personally or at work? Yes, and one-on-ones, I always try to have that interpersonal conversation first, not at the end, which is what my personality type is normally, like, oh yeah, and how's your kids? Um, that's my normal operating mode. So I have to like retrain.

Um, I don't know if you've ever done disc personal personality. I have, yes, yes, yeah. So I'm like 99% one personality type, which is unheard of. And it's just like that type.

Yeah. So it is very unnatural for me to do this kind of personal things, and but I have really practiced, and I think it's so, so important to connect with your people. One, because you I do care, like I just don't say it out loud naturally. So I think as every manager, you find your personality type, you find your own way of communicating.

And for some, it's gonna be really hard to be blunt. For others, it's gonna be really hard to be nice. Yes. Yeah, yeah.

I guess we were on opposite ends uh on that end. I I always used to talk too much about personal. Um, and then I wouldn't say not enough about work, but like I it would take way too much time for me to talk about personal. So it's funny to see, like, obviously, even in leadership, how different personalities are, and you know, what are your strengths versus mine and others?

So that's pretty awesome. And right now, you're actually you're in a different position in the sense that like you're you're working for a startup at Udali and you guys are growing really fast. I think you told me offline that when you joined, you were at two people, and then in one quarter alone you grew to six. Did I remember that correctly?

Uh, we're growing two six. Oh, growing two. Two to six. I just hired two people.

One started today. Um, haven't had a chance to check in with her yet, right? No. And the other started last week.

And then I have um two more open head count. Love that. Which is it it doesn't maybe necessarily sound like a lot, but it is a lot in leadership, trying to get everybody through onboarding and making sure they're set up for success as you're still interviewing and hiring and you know, bringing in new people. Tell me a little bit about, I guess, what does that dynamic look like for you right now in terms of just managing everything in leadership?

And I believe you're also still doing some player coach positioning as well. So, how does Diana handle it all? Yeah. Um, well, it's not balanced, it goes by waves.

Yeah. Um, my initial onboarding for myself, I tend to be a process type person, and I knew hiring was the number one priority. And I crave structure and documentation. So I spent the majority of my first 30 days focused on that documenting what I was learning so that the next person behind me can come through and learn it.

And then also the hiring and what are the things that need fixing right now. I did not prioritize so much the getting involved in deals. And so now I'm like pulling up for air a little bit from the hiring. I'm going, oh shoot, I really need to get into deals because I have an employee who's going on the vacation of a lifetime, and I want to be able to fill in for him when he is not able to.

So we're we're getting there. I I feel confident. I told him before he goes, he has to document everything that's outside. Um, but um, yeah, we're we're in a good spot.

So now I can cover for him on these key accounts. He's in the enterprise team, so it's you know, these are big logos, and I don't want to mess it up. And I know I have my other team member to help me if I'm in a sticky spot, but um yeah, I I've had a goal of closing a deal in the first 90 days, and I really only have one opportunity in the pipeline that might hit that. So that's all it takes.

One one might be all I need. I don't know. Exactly. Yeah, but a good salesperson has a plan B and a C.

I don't, but the process of the people and the hiring and the onboarding, all that is in a really good spot. Yeah, that's awesome to hear. And one thing I wanted to ask you is obviously when again, when you're hiring for multiple people at the same time, you have to worry about team dynamics, you know, who are you bringing in, making sure that you have agreed to, you know, whatever the hiring committee is at the current company. What does good look like, you know, from one person to the next?

How did you guys handle that internally, you know, and what does the process look like, you know, versus like what is a must-have for this person versus how do you decide what's coachable? How did you guys do that internally? Yeah, that was the first thing that people wanted my input on was the hiring process. And um, so I I did.

I ran with what they had for a minute and was like, because I mean I went through it. How bad could that be? Like I hired, and then I was like, oh. Oh, now I see why you guys haven't hired anybody.

Um, I was like, how did I get through? But uh documentation. So I I have a side hustle on Etsy. I sell templates for SCs.

So I went into my template bank and I was like, Love that. What is my hiring process? Let's streamline here. And they were very similar, but there were just some tweaks.

Um, like taking some folks later in the process or not having them interview twice. Um then the assignment itself was a challenge. So I went back to my roots and I just remember um I loved how we hired at Clary, and we had our interview step or our demo step split into two parts. There was the demo, and then there was the tech exercise to see if you knew the functional tasks that needed to get done.

And how hard was it for you? Was the real key here. Some people could crack that nut and just breeze through, others struggled for hours, and it wasn't whether you could know it right away or if you struggled, it was how you got past the struggle. And so that's what I did.

I broke our demo into two things a demo and a tech exercise. And now I'm really looking at do you ask us questions? Do you ask for a dry run? Do you um reach out when you're stuck and admit that you're stuck?

Like I really want somebody who's gonna be capable of admitting they're stuck and getting help and giving help to others freely. Um so those are like the behind the scenes moments of that step in the in the hiring process. But then we had an issue where folks didn't agree on what was coachable or not coachable. And we had people from different teams coming in and going, Well, I don't really know what your bar is.

So here's my bar. And I was like, no, end of that. Grab my template for a scoring sheet. And I said, these are the things we're scoring on.

Here's a one, here's a two, here's a three, so that there's less bias in the process. And then I interview with my team, like, okay, two, two people. What do we all agree is coachable or not coachable? And for me, the tech skills are coachable.

Um, your how you handle pressure and like, can you admit you don't know and can you admit that you're wrong? Like, that is harder to coach. Right. Communication skills, a lot harder to coach, still coachable, but harder.

Um, so once we landed on that, it's okay if somebody's a one here because it's coachable, or hey, that that line item on the score sheet's got to be a three. Like, no ifs, ands, buts about it. So then I could tell my interview team, this is why we're making the decision we're making based off the scores that you gave and the notes that you gave. Uh, and we're also really big on transparency.

So I send the score sheet ahead of time to the candidates so they know what they're being scored on. And I think it helps them make judgment calls and how they demo, um, but also transparency. And then we're really big on feedback. So we go around the room and we give feedback live.

Like you should know when you leave that call where you hit and where you missed. Um, I won't say if you got the job or not on that call because sometimes we need to go about it, but you'll know how you scored basically. I actually love that, and it's something very unique because not a lot of teams do that, especially sharing the scorecard previously. Have you ever seen that backfire on you on any candidates?

No. Some people overthink it, it's a lot. You only have like a 15-minute demo, and you're like, there's 15 lines here. So yeah.

I I know if you get stressed out, that could stress you out. But if you get stressed out by that, you can't succeed here anyway. Yeah, that and that's so true. Because at the end of the day, it's not like you're giving them the answers to the test per se.

Like they still have to perform. And I agree with you. I think it'll probably point out the people that get too stressed and like can't handle pressure versus the one that are like, okay, I just need to make sure I have five points on mine. Here's how I'm gonna be able to present it.

And everybody still has a unique way of presenting on each of those points. So then then you guys see, you know, what does what fits in our team, what fits within our culture? Do we like the way he did that? Or, you know, is this coachable or not?

So um, I love that you do that. And I think that candidates nowadays don't always get a ton of feedback, especially in interview processes, uh, which sometimes to me is still bananas because it's it's hard for them to know. And and I mean, you've probably been the market yourself, but it is pretty brutal out there right now. Oh, I was in like final rounds, I think I'd done five or six interviews, did the demo, right?

Ghosted, yeah, which is insane. I get it if it was a recruiter screen, but uh not that step. Yeah, yeah, so crazy. Um, yeah, yeah.

I don't have anything to say to that. And then the only thing I usually have experience is like once it's somebody that goes through an interview process like that, like yourself, usually when they come in into the job itself, they make sure that the process is not the same for others, right? Like you know how it feels and you just try to change that to the best of your abilities. And we won't say, I mean, we're we're all human beings, mistakes will happen.

Maybe something fell through the cracks or somehow it was missed, but it's still, you know, you came in to change that process. So that's pretty awesome. I love that. Um, on the other side of this, I I want to talk about the onboarding because again, when you're scaling at a high level, you want to make sure that you don't miss on that onboarding because that will either set them up for success or set them up for failure.

And I know that currently you haven't just done the SC onboarding, but you're also helping build the AE and the SC programs too. What does a good onboarding look like for you? And maybe if there's anything that either you've done in the past or you've gone through other leaders that have done wrong in the past when they bring somebody new onto the team. Yep.

Uh, a good onboarding one is one that you have planned out. So there's no right or wrong answer there as long as there's a plan. If you don't have a plan, that's not good. Um leaving it too much up to the individual to learn it on their own, leaving it up to their buddy to teach them, you're gonna get inconsistent teachings.

Right. You, as a manager, really have to take charge of that, but you can't do everything and be everywhere at once. So, what I found is call-recorded trainings are really helpful. Folks can watch them on their own time at their own pace.

I'm a 2x person when I watch videos on the so we can get through it faster. Then a live interaction every day with either the manager or the buddy or both, where the learner asks questions about the content that they learn or proves that they internalize something. Yes. So um when I and I'm using Udly for Udly, which is really fun.

I love it. Um so I built a week-by-week onboarding plan. I think we're down to five or six weeks for an SC onboarding, and it's two to three weeks for an AE. But um, in there, we I'm a big fan of starting with the messaging.

You know, a lot of us techies want to just get into the product. We do on day one, you get into the product, but first you go through the messaging because you got to understand why someone wants this. Then, okay, what is this? So that's the product bit.

And then there's competitive, there's FAQs, there's setup, admin. Um, for AEs, there's slides and prospecting things for SEs, it's infosec and custom reports. Um, so we diverge at week three. But it's for me, you learn by doing, like that's how I learn, and I think a lot of folks do too.

And so that's where Udly is really valuable because it's a tutor as well as a role play. So it'll teach you a concept and you can discuss it with the AI and practice saying it out loud. Then you go to your role play, and that's kind of like your checkpoint. Did you pick up what you needed to pick up?

And can you have the call you need to have? But then every Friday there's a human checkpoint or gate. So the first Friday, it's just a check-in call with your manager and your buddy. And the way I described it to my newest employees, like, I just want to see how much you've internalized so that I know where to supplement the training next week.

It's not a judgment. Yeah, you're not being scored, it's not a pass fail, but like, where did we fail you in the learnings? That's what I'm looking for. So then I can put that into the week two plan for them.

And then at the end of week two, everybody has to stand and deliver a first call. So that's the pitch, discovery, demo, FAQs. I expect you to fail, but like a C should be a passing grade, right? You're not gonna nail it your first week.

Yeah, and then the end of your third week, you do it again. This time with our founder, Varen, and you should pass it. You should get like a B plus. And that's you're allowed to now go run calls solo.

So at the end of week two, you're allowed to run calls with a buddy, and week three, you're running calls solo. But it's all about how do I get you to value as quick as possible. So week one, AEs are prospecting on their LinkedIn in their networks. SCs are answering InfoSec questions or at least like granting permission to our InfoSec security docs and things.

So you're doing a task that's valuable to the company from day one. I I'm so happy you said all of that. First of all, uh, number one is the fact that you have interaction within the onboarding because sitting there and just watching videos all day, like their retention is going to be, I don't know, less than 50%. I haven't measured this.

I'm just like the learning loss curve or something, the forget the forgetting curve. It's 80% you will lose. Yeah, it's insane. So when you combine that with actually, hey, let's do some small little tasks here and there, it it's I I've been through onboardings when I worked at companies where it was just three weeks straight of videos and videos, and I'm like, I'm not retaining any of this.

I guess we're doing quizzes after the calls or you know, after the video, but I have no human interaction, and I'm just you know, here me in front of a computer trying to retain this information that I'm supposed to go to to know everything about the entire company like in three weeks. It's just impossible. I mean, it doesn't make sense. So I love that you guys have that interactive, first of all, and second of all, you know, you have human interaction and the other part of it you mentioned that it's not a pass or fail.

It's just like, okay, where did we fail you? And I think again, it just goes back to that retention. Like, no matter how much you try, you're just gonna retain whatever you mentioned, like 20 to 30 percent of what was said, and then the rest you're just gonna have to retain it through application. Um, that's pretty awesome.

I love that. Have you noticed anything um in terms of like failures when it comes to new onboardings or or maybe even early in the hiring process where it's mainly culture? Because like you said, I think that anything can be, of course, you know, culture. Some things are harder than others, but at the end of the day, if the culture fit is not there, it's just not gonna work out, no matter how skilled you are.

Is there anything that you do to identify like a cultural mismatch, whether it's on the hiring process, ideally is on the hiring process, but maybe you know, mistakes happen and you also identified it early and onboarding where it's kind of made you think. Yes, I have had some hiring mistakes. Um the way I'm looking for our culture fit, one, I make sure to mention our core values and bring it up in context of every question I ask in an interview. So I'm asking you this because winning together is a core value here.

I'm asking you this because act fast with judgment is a core value here, right? So that they really know that's not just on the walls. This is important, and here's how we live it. But then throughout the process, there's moments where I want culture to me is how you act.

And so I want to see how you act in these moments. So we will specifically not give you all the instructions for the tech exercise because we want to see how you act when you have to struggle. We will not give you a demo script because we want to see how you think and what you think is valuable and what order you would write your own demo in, because over here everything changes so fast, then there's no written documentation. I'm working on that, but like there is no one demo path.

So can you be successful in ambiguity? And are you like, I will draw a line in the sand, make a decision, and commit to it, kind of a person. Yeah. Um, and then the feedback.

Can you take feedback live in front of a group? Like, that's really hard. Um, are you self-aware enough to give yourself feedback and be accurate in front of the group? So that's why those moments are in our interview process.

I don't think it's perfect. Um, knock on wood, not here. I have not had a bad hire yet. I mean, yeah, one starting today, but I think she's fabulous.

Um, but I have in the past. And the thing that is in common is either I or somebody in the interview panel has said no. And we as a team went against that no and hired them anyway. Yeah.

Or somebody that I just had to spend a whole lot more time with than anyone else to get them to behave other folks. And it's not that I want a homogenous team, it absolutely is not. That is the furthest from the truth. It's that there are certain levels of expectations, like how responsive you are, yeah, or how coachable you are.

Like if you're always going to deliver your demo this way every time and that's not working, like you got to change. Yeah. One cool thing that I've learned throughout my experiences in terms of coachability, since you mentioned that, is as they're doing either some sort of demo or role play, you know, whatever that looks like, you give them that feedback live, just like you mentioned, and then you ask them to redo whether it's a portion of it or the whole thing, depending on timing.

And you see if they applied any of that coachability or feedback or points that you gave them. It again, it's still it shows not only their retention lower, their listening skills as they're listening to you, but too, are they coachable? Are they willing to adapt to their, you know, their skill set, whether it's in, you know, just a 10-minute presentation or not. So yeah, um, that's something pretty cool that I've seen.

I I offer the step of would you like to do a dry run with us? And nobody's taking us up on that. I'm like, come on, that's crazy. But uh, you get bonus points if you do, but also if I coach you and you don't apply that coaching, it can hurt you.

So maybe that's why they don't do it. But one guy showed up in a t-shirt and I said, Don't don't wear a t-shirt for your interview. Um, wear a blazer over it or something, and he didn't. And I'm like, nope.

I told everyone in the room, I was like, No, I don't care. He didn't take the feedback, and that's a small thing, but it's a big thing. At that company, we sold to sales, and our VP wanted us to look like sales is the profession we take seriously. That's that's so crazy to me, honestly, in this, just in general, like when it's it's with I always talk to candidates and they're like, Oh, I'm not getting interviews, or I'm not getting through final stages, and they're like, Oh, I don't have this, I don't have that.

And every single person that we've gotten hired through our own, obviously, recruiting is people that did small consistent things throughout the interview process, you know, wearing a blazer, showing up prepared, sending the thank you notes, whether the hiring manager appreciates them or not. Some people will disqualify you for not sending one, some people don't really care, but it's something nice, just send it anyway. So it doesn't take you that long. Um, you know, just these little things that you think are unimportant, but as you do that throughout the entire interview process, that is literally what's gonna get you hired.

Plus, obviously the skill set and making sure it's a good fit, but that is how you differentiate yourself. And it's it's so hard to do that nowadays, but then yet again, the bar is so low, which is banana still. But I'm glad that you mentioned that because those are things that you guys are literally noticing on a day-to-day basis. And like you said, it comes down to the coachability.

If I'm giving you a very simple feedback and you're not willing to apply it, can you imagine if I gave you a big feedback or something that ruined a deal and cost the company, you know, X amount of dollars? It's yeah, it doesn't make sense. Nope. Love that.

Okay, awesome. I wanted to shift a little bit to um obviously your leadership and just being here currently. I know we touched on this a little bit earlier. I just wanted to see if we can dive a little bit deeper.

Obviously, you're hiring, you're onboarding, you're building, you're trying to also carry individual contributors uh responsibilities at the same time. Is there anything? And the best thing you said was that it's not a balance, it comes in waves, and I think that's literally the only way to do it. But is there any like tactical things that you do to know, okay, this is what's important for me right now, like in terms of prioritizing the three, um, you know, when to do what?

What does that look like for you? Yep. Um, so I calendar block, big fan of calendar blocking. I just started this new time block.

I haven't used it only once for fire drills. Okay. I time block a half hour for my lunch, and right afterwards I have fire drills. And it is meant for like, oh my gosh, this call came up, or I need you to do this, or an unplanned thing, because the unplanned things are what's gonna ruin your day.

That's so true. Um, so I have to be more disciplined about doing fire drills during fire drills. Yeah, we'll get there. Don't wait.

I also time block like strategic thinking because I operate very much in the practical tactical, and so I need to remind myself that I have to pull up and like look big picture. What are MBRs, monthly business reviews? Like, what did I commit to? How is the big picture going?

And where does that need attention? Um, but uh I want to use Claude more for this. So my old boss he uses Claude to send him regular reminders of like how he's doing to his OKRs and like what projects are related to which OKRs and all this stuff. So I'm gonna go pick his brain soon and like help me get better at this.

Yeah, I shouldn't just be remembering my MBR is like the week of the MBR meeting. Yeah. Um, I've got a sticky note with my quota right here on the computer. That's what I love.

Yeah. I I think um, I mean, obviously, I don't know what systems you guys use and stuff, but I've also gotten a lot more into Claude and it doesn't automate like my life, but it does automate this little thing set like, oh, I forgot I needed to do this, or like, oh, this is coming up in two weeks, just something to be aware of, you know, things like that. So um, and they've made so many what they call connectors and like agents within Clot. So um I I don't know how helpful I can be, but happy to share whatever I'm implementing so far on my end offline as well, if if that's helpful.

Yeah, I love it. Right now I've got a Friday afternoon email to myself that I could choose to send my manager with like a recap of the week. Um, I use it when he went out on PTO, and so I was like, oh, look what happened while you're out on PTO. Um and then I have a Sunday night slack to myself of like, here's all the open items.

Um, but again, that's practical tactical. So I need to get better at the pull up. I got you. Well, between me and your old boss, we'll we'll figure it out.

Yeah. Um, I wanted to ask in terms of like somebody that's listening to this, and maybe they're in an IC position right now and they want to move into leadership one day. Is there anything that most people underestimate when it comes to making that transition, maybe especially in a startup environment? Or on the other hand, um, anything that you would suggest about what could they do to get that leadership position if that's something that they want to right now?

Yep. So leadership is not for everyone. Um I remember in the beginning. Yeah.

In the beginning, one of pretty much the only interview question that my VP had for me before giving me the role was like, how would you feel about having to fire somebody? Um yeah, so I think a lot of people are afraid of that step. Um, I think hiring is the biggest scariest step because if you hire right, you won't have to fire. Yeah.

That's your one most important thing as a manager is hiring and coaching if you don't choose your hires. But um I think people are surprised to learn the pay isn't that much better. Sometimes it's less. If you've been a tenured seasoned A SC to go into management, you might get a pay cut.

Yeah. Um, but as you progress in management, your pay will exceed that of an individual eventually. So I know some people try to go to management because it's the next thing, or they think it puts them in the next pay bracket, but that's not always the case. The other thing that surprises folks is oftentimes when you're going from IC to management, you have to do both jobs.

And like your expectations of you of an IC do not change. You just get additional leadership stuff on top of it. So be fully prepared to be working two jobs for at least a year until you can transition off of your accounts and like make a little bit more space. Or if you're lucky enough to be at a company that realizes that dual jobs isn't a good idea and maybe you can ramp one down.

But you might not be doing as much management stuff as you like. You'll just be doing the not fun management stuff, like firing or having hard conversations or fixing fires, as opposed to like sitting down going, Oh, what should our comp plan be? That's my favorite. Or um let's plan our off-site now.

Like those are my favorite things. No, you don't get to do this. Those decisions are for somebody higher up than you. Um but especially as a startup, you got to wear many hats.

So I think we're all used to that. But I don't I don't think people realize how heavy it is and how important prioritization and setting boundaries is for yourself in those first years. Yeah, I am I'm so happy you mentioned that because I will say there's definitely some sort of expectation or internal, I should say, expectation that you become a leader and somehow you think you're just gonna quote unquote boss people around, you know, and be like, oh, you're gonna do this, you're gonna do that, and I'm just gonna sit here.

And especially, like you said, especially in that first year and in a startup, on top of that, it's like I wouldn't say the furthest from the truth, but you will, like you said, wear a lot more hats and it's probably not what you expected. So, um, and I agree, it's not for everybody. There's been some times people that have been promoted and they don't love it and they want to go back. By the way, nothing wrong with that, at least on my end, and I love your opinion on that end too.

But it's sometimes you just gotta try things and see if they end up working, and if not, great, you tried it, it wasn't for you. Now you know for sure what you don't want to do. Yeah, no, I've I've had that conversation and it was not fun. Um yeah, it wasn't because the person wasn't doing the job, they were they were excellent at being a manager, uh, but it was that they weren't finding joy in the management tasks that were at their level and that team that they were assigned, and the company that we were at.

It's not a great spot to be a manager at that company. Um, so the struggle's real. And I felt that he would be more valuable to the company and happy for himself as an individual again. And so I didn't tell him he had to, I just said, Do you want to?

Like, what makes you happy here? Pay's the same. Yeah, like what which way do you want to go? Um, I think that's important, not coming in and being like, not working and pull out the rug.

I think that's why a lot of people do these lead positions. I do not like them, not one bit. And that I think that was one of your questions for me later is like, what is a topic people are gonna disagree with you on? I do not agree with the concept of making a lead essay a title.

It is uh to me an interim moment, it is a test for both the employee and the company. Is this gonna work? I totally support the concept of a lead essay, but like to go put it out there as a separate job and like as your title and put it in the pay range, I disagree with because what if it doesn't work out? Now all of a sudden it's a demotion, right?

And there's a lot of like your pay changes, your title changes, it's very public failure. Um, there's also like an expectation that it should work out at a certain time. So I only have three months to prove myself or six months or a year, or I have to be in this position for a year. No, what if they're amazing?

Give them manager now. If they're not amazing, what if they hate it? Put them back in IC now. Don't draw it out.

So I am not a fan of the leads. Yeah, that that's actually a really good point of view. Um, obviously, I I hadn't thought about it in that sense, but it does make a lot of sense. It is a very public failure, quote unquote.

And I know it can be hard, even personally feeling like you failed at that certain position. So that's that's good. Um, before we jump onto my next question, we actually did get a question. I'm gonna pull it up here.

Uh, Norma said, uh Diana is an insight, which is awesome. In terms of KPIs, what metrics are you using for team performance aside from tech win demo, uh dry run demo reshoots, et cetera? Any AI-related KPIs? Oh, such a good question.

I have been dodging the KPIs. It is on my MBR studio. I didn't make it. I love how transparent you are.

Thank you so much, by the way. So I come from marketing, and marketing is all about the KPIs. I was the report person. I love a report in Salesforce.

It is so judgmental, like biased on how we are judged as an SC team. Like you could give somebody the same report and it could mean totally different things at totally different organizations. So I think this is hyper personal to every company. I've not cracked this nut yet.

What I am choosing to measure, and I just put this in front of all the managers last week, is attach rate. So I've never worked at a company before where SCs weren't needed to close. So I am curious as I'll get up about this. What is our current attach rate?

And then is that bad or is it good? I don't know yet. When are we being attached? And when we are attached, what is the average deal size and the average duration?

Those are the baselines I'm hyper curious about right now. And then I want to see if we can move some needles and figure out if that's right or wrong. Um, so that's for me. Now you might work at a company where an SC is on every deal, which is what I'm used to, and that makes it easier.

And then you don't need to worry about attach rate. But then you have to figure out well, how do I judge whether somebody is more effective than another? Or if an SC is even having an impact because you have no um, what do they call that? No, A B testing.

Yeah, you don't have A B testing. Um, so then I'm looking at um, I just started tracking in tickets. Did we do a POC or not? How long was the POC?

Did we get on the phone with someone from IT or security? How many times? Did we demo? We don't even demo over here.

Like I'm this is the first SC team where I'm like, you you guys don't demo? We do POCs. The AEs do the demo. So did you demo?

How many demos did you do? Um, and then we do professional services over here. So how many PS hours did you do? Um and then I'm you know I'm getting all these baselines, and then I'm gonna decide what's good and bad.

And I have a feeling we should be doing less PS hours. That's one of the jobs I'm hiring for, is somebody just to do PS. And then if we find that that improves how many hours are sold because the team doesn't feel like they're cannibalizing their SEs to sell PS hours, they might sell more. That's my theory.

Then we'll move that person and they'll become their own team and they'll report to customer success. Um, so yeah, that's that's what I'm measuring right now. It's very practical, tactical. Yeah.

Um, but I think we'll just iterate from there. Yeah. And I think what's important to recognize too is like not in kind of like you said, right? And in the past, in other companies, you've done it differently, you know, as SCs used to demo, etc.

And you can't just bring everything you did back there and implement it here. You have to adapt it to what the team is into right now. You know, what does success mean for our team here versus what it meant there? And you just are implementing everything just to see numbers.

Because I agree, I mean, it doesn't necessarily feel like, and correct me if I'm wrong, I feel like numbers should tell you a story, and there's a difference between um, you know, face numbers and numbers that actually drive revenue. You need the face numbers to know, okay, if numbers are not driving revenue, how what are our face numbers looking like, right? So that then we can see the full picture, but you don't want to just track every number under under the sun because you can't no.

There was a good book. Hold on, it's behind me. Um all right, I can't read it right. But there was one about sales metrics specifically, and I really liked that.

And I think my approach to it is you need early indicators and you need lagging indicators. And so as long as you have a balance of those um and measure what matters, great book. Um the rest of the stuff, it's noise, but if you don't measure it, then it won't matter and people won't follow it. So you have to be showing these reports regularly.

Like I'm showing them at our monthly manager meetings. I'm also gonna start showing them on the SC team calls each week and be like, here's where we are, here's where we are. How's everyone feel about that? Yeah, yeah, awesome.

All right, because of time, I'm gonna move us on to the next section because we're running a little bit behind because it's been such an awesome conversation. Um, this one I call the rapid fire, which you jumped the gun a little bit ahead. So I'll skip that question. But what is one tool that you can live without right now?

Oh, Claude Cowork. Yes, such a good same thing. That would be my answer right now, too. Um, what would be your biggest growth level or lever for SaaS in 2026?

Can you explain that question to me a little more? Yeah. So basically something that you're implementing right now that, or maybe you've thought about implementing that is really helping you guys um in terms of getting ahead in 2026. There's so many moving pieces and so many things that are changing right now.

Doesn't mean you got to do all of them in order to, you know, use it as a growth lever. Yep. Udly on Udly is our number one right now because of the ramp. And we're hiring a whole new mid-market team on sales that's gonna go through that.

So that's six or seven people, and then my team is gonna go through it. Um, so that's huge because I cannot have my team of two onboarding four people. Yeah. Um but but beyond, I really want to get consensus in um or something like it, that not demo automation, because the problem with the AI technology is really hard to automate a demo when it's supposed to be dynamic and live.

It's the demo delivery mechanism and capturing the wider audience and expanding their mind to new use cases and selling between meetings. Um, because we don't demo, I think that's where we can add value to the sales team by making these amazing demo vignettes that sales can then use to expand the deal. Yeah, you may or may not be blown up with DMs after podcasts on these tools that you can consider. So I love that.

And also I was gonna say there is probably no better testimony of like your product than using your own product for like the same thing in the sense that you're selling it for. Um, especially right now, I feel like we've seen, and you might have too, but I've also certainly seen companies that are selling their products, but they're don't they don't use it internally for the intended use? So love that. Um, and then I'll end with two hiring questions because I think that it's important.

I know we touched a little bit on this already. Uh, what are like your number two or number two, your the top two skill set that you look for in early hires? Coachability, thriving, and ambiguity. Love that.

And in your opinion, I guess expanding that a little bit further, what is what separates like a good SE from like an a player SE? A strategic thought leader, somebody who's not afraid to get in the trenches with the AE and run the deal, and somebody who's not afraid to get in the seat with customer and help them operate better. Yeah, I love that. And um, any last-minute questions or closing thought that you want to leave our audience with?

I'm hiring. I love that. Can they reach it? It's specifically in Seattle, but I'll take Bay Area or any West Coast time zone.

And you've got three plus years in enterprise. I'm sorry, we already did our junior hiring round. I need a senior person who's been there, done that, sold to the large name brands. Um, please hit me up.

And anybody who's done PS or PS work and like really likes it and maybe has the potential for building that team from scratch, no promises, uh, ideally in the West as well. Yes, then yeah, hit me up. And I know you mentioned you guys are also hiring within other departments as well, like sales, not just pre-sale. So I would encourage anybody listening to this, just go check out obviously connect with Diana on LinkedIn.

Um, but also check out your S's career page because there's so many roles. And of course, if you're good, Diana will make sure to present you or introduce you to the hiring manager for that department. Um awesome. Thank you so much for joining uh for being so transparent, by the way.

I feel like sometimes we we want to give the best answer, not the true answer. So I appreciate you giving the true answer, whatever that looked like. Um, and sharing your insight overall, so much notes to take from this episode. What for management, leading, hiring, onboarding, uh, which I feel like onboarding is one of the topics that usually we expect to have good as team members or somebody coming in, but it's usually the one that it doesn't always get nailed the most, especially in the startup environment.

We're just hoping and praying that somebody comes in and it's like, you know, perfect for us to jump in and start right away without much support, which is not always realistic. So I appreciate you breaking that down for us. Yep. Thanks for having me.

This is fun. Absolutely. Um, I'll see you guys all next time. For those watching live or catching the replay, again, feel free to connect with Diana on LinkedIn uh or or drop questions in the comments below.

I'll make sure to also link her LinkedIn as well so you guys can make it easy to find. Thank you.