Podcast

The Leadership Deficit: Why Startups Break at the Top

June 27, 2025 | 30:42

Season 4, Episode 6

Ever wondered why brilliant founders often struggle when it comes to actually leading teams?

Peter Ahn, Sales Performance Coach & Speaker, who’s worked with top companies like Google, Dropbox, Slack, and advised over 100 startups, joins Krissy to unpack why technical talent doesn’t always equal leadership success.

Peter breaks down why exceptional product minds can still miss the mark on leadership, the real myths founders believe, and why past success doesn’t guarantee future wins. From spotting leadership red flags early to recognizing the true currency of great leaders, this episode offers actionable, no-nonsense insights you won’t want to miss.

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Transcript Text

Krissy Manzano: Hi, and welcome to another episode of the Talent GTM podcast. I’m your host, Chrissy Manzano, and today our guest is Peter on. I’m so excited to talk with him about the leadership deficit, right? Why startups break at the top. And so just a little bit of background on Peter. He has over 16 years in enterprise sales experience at companies like Google, Dropbox, slack front.

Krissy Manzano: And Twin Gate. He has closed multimillion dollar deals for large Fortune 50 and 500 organizations and even early stage, and he’s helped over a hundred startups build sales from the ground up. And with all the experience, it’s no wonder that he is fully capable of advising everyone from first time founders to veteran sales leaders on authentic messaging pricing.

Krissy Manzano: Pitch prep, enterprise deal coaching and leadership development. Um, what a resume they always are for the folks that come on here. But welcome Peter. So glad to have you and definitely warranted for you to talk on this topic, right, about what’s going on with leaders at startups. Um, why are things breaking in this new, you know, era that we’re in?

Krissy Manzano: So glad to have you

Peter Ahn: totally. Thank you so much for having me on. It’s an honor, and I felt like over our first couple conversations we were on the same wavelength. So excited to dig in further on this topic.

Krissy Manzano: Yeah, no, I, me too. Um, I’ve, I’ve been looking forward to this and it’s something that I think as we talk about, it’s gonna resonate, but it, it also is a question that everyone asked, right?

Krissy Manzano: Why all of these founders. You know, they come from Ivy League, they’ve got high eq, very technical. So why is it that so many of them are brilliant and they struggle when it comes to actually leading a team and, and their go to market? Maybe even,

Peter Ahn: I mean, I think there’s a couple reasons. One is, yeah, like you said, a lot of these are young, brilliant founders who’ve never even managed a team before, right?

Peter Ahn: They might be. Brilliant coders and in the age of founder led sales, you know, a lot of these folks have credibility ’cause they can build the product directly, but that doesn’t necessarily translate to how you listen to your team, how you build empathy with individuals who are, you know, also jumping into the startup game for the first time.

Peter Ahn: I, I think there does take a little bit of experience and. Um, leadership experience specifically to, to get used to that. The other thing too is I think like a lot of founders also have natural instincts for leadership, but the mentorship isn’t really there. Right. A lot of the advice, especially in my world, comes from venture capital.

Peter Ahn: Mm-hmm. And a lot of the venture capital. How a lot of the, the firms have brilliant. Board members, brilliant partners. A lot of ’em are my friends. I get a lot of lead flow from them and business from them as well. Um, but first of all, they’re spread thin. And secondly, oftentimes they don’t have domain expertise in places like sales or [00:03:00] marketing, right?

Peter Ahn: Where a lot of these founders are looking for guidance on how to lead a sales motion for the first time, or a marketing motion for the first time. So I think there’s that combination of. Lack of experience. Um, and then also sometimes pressure that comes from where the capital is coming from, which is, you know, from these firms who are like, Hey, you need to grow fast.

Peter Ahn: Let me give you some advice. But you know, again, like a lot of these portfolios are, are one of hundreds, or, or a lot of these portfolio companies are one of hundreds. Yeah.

Krissy Manzano: Genuine question. Why is that acceptable in, in your view, that to know that there’s this gap, right? Mm-hmm. Of understanding how to be a leader and.

Krissy Manzano: Do you think the firms really recognize what they lack as far as the mentorship, or do you think No, they feel like they have it covered, so they’re okay investing millions into a very smart individual on paper who can build a product but doesn’t understand how to lead or it. And they think they have that, so it’s fine.

Krissy Manzano: Like where do you think Yeah, that that comes from, and maybe it’s not like a clear answer, but curious.

Peter Ahn: No, I mean, I think it’s a great question. I think it’s because a lot of companies have succeeded financially in spite of poor leadership, let’s be honest, right? Like we all know those founders who are not well respected within their employees, but somehow they still get 3, 4, 5, 10, $20 billion valuations, right?

Peter Ahn: So I think it’s because. Um, the headlines and the success or ROI of the investment doesn’t always match up to strong leadership. Right. And, and I, so I do think people sometimes overlook that, but I also think those are the exception, not the norm. There’s also a lot of companies where if they had great leadership, um, folks who really, truly are looking for VPs and lieutenants who have empathy, humility, who actually like, invest in their.

Peter Ahn: Um, they’re young startup workers. Like if, if that were to happen, I think there would be a lot more success cases. But truth of the matter is, um, I think we sometimes gravitate towards the, the success cases where, um, it happens in spite of strong leadership. Yeah. Makes sense. So that, that’s my honest feeling.

Peter Ahn: Yeah.

Krissy Manzano: One more question on that, ’cause I know we have a lot more to cover.

Peter Ahn: Yeah.

Krissy Manzano: But. And I haven’t looked at this data wise. So you know, maybe, maybe this is here and this would help answer my question, but how you often hear from the investor standpoint, right, that there’s a small percentage that are successful, right?

Krissy Manzano: Yeah. Of the ones that they invest in. Yep. So if it’s a small percentage that are successful, I guess from that playbook, essentially, does this really work that well? And then I also say. How valuable is a valuation if it never comes to fruition? Because I think we all saw all of these valuations that were over inflated.

Krissy Manzano: Even, and I won’t say the company on here, but there’s one, they made a bunch of documentaries about it. Mm-hmm. And it literally never made any money. Yeah. [00:06:00] And the owners still got a massive payout. And so I, I struggle with a little bit of that. ’cause I’m, I wonder, do we, how are we defining success if the company is never profitable?

Krissy Manzano: Right. Yeah. But they have a. $5 billion valuation. That’s always interesting to me.

Peter Ahn: Yeah, sure. And like, I mean, there’s a recent example of like deal in rippling too, right? Mm-hmm. Like you heard that whole saga Yes. Like the corporate espionage situation. Right? Right. Like I’m sure they’ll make a TV show off of that.

Peter Ahn: Yeah. But I’m sure like the executives there aren’t hurting to your point. Right. And, and actually maybe the investment is a lot less from kind of like a VC standpoint, but, um. They, there’s, it’s like a kind of law of large numbers, right? That’s one situation and we almost kind of expect that to happen now, which I think is sad.

Krissy Manzano: Yeah,

Peter Ahn: sure. Where we kind of now, like we talk about it for a couple weeks and then there’s gonna be another founder who has kind of similar values and does similar things, but in the grand scheme of things, folks are still making a ton of money in tech. But I think what people, I think it’s shortsighted because what people don’t realize is.

Peter Ahn: Well within my generation and below, right? So people younger than me, there’s huge reputational risk that these firms and also companies are going to find out about. I think where folks know who the, you know, VC firms are, who are pushing these like old school VPs of sales who are not very good. Right.

Peter Ahn: And people know who the founders are, who aren’t really great at leadership, but happen to sell a product that flew off the shelves for a short period of time. And I think that it, there’s like a ton of costs in that, that people don’t realize because it’s not necessarily, doesn’t necessarily show up in the headlines, um, but will show up, you know, when that founder tries to hire again or hire great talent.

Krissy Manzano: Yeah. Right. So. Yeah. No, that makes sense. What do you think is the biggest myth founders believe about leadership?

Peter Ahn: Yeah, I think the biggest myth is that, um, folks who have really strong resumes are, um, responsible for the growth of companies. Like, I think, you know, it makes sense if you think about it, that one person is not.

Peter Ahn: Responsible for a company’s growth from zero to a hundred, but founder, a lot of founders, I still hear them say, oh, this guy or gal, she was there, um, from zero to a hundred and kind of grew the whole thing from nothing. And I always, like a part of me dies when I hear that because a lot of times people, you know, are at companies riding the wave, not building it.

Peter Ahn: Right. But I still think there’s this myth out there that resume. And experience trumps actually like skillset and acumen and you can never replace skillset and acumen. Um, and so I think that there’s like a myth around experience folks and what they can do because just because they did something from zero to 25, 50, a hundred million doesn’t mean they can replicate it.

Peter Ahn: Um, because they were probably part of the puzzle not building the, the entire ship.

Krissy Manzano: Yeah, I, I think that is so spot on and I think it’s, it’s, you know, there, there are a lot of cases where leaders are a part of that growth in riding the ship, right? And, and that’s not their fault. That just is what it is.

Krissy Manzano: But at the same time, there are also people that have helped with that growth. But to your point, they can’t replicate it because. Just because you’re growing from, you know, 25 million to 50 million, the way that you do that at another company is not always the same. And I think people are too black and white on this experience of growth, of revenue is, is going, you know, if they don’t have that experience or not gonna understand, you know, what we need to do here.

Krissy Manzano: And I’m not saying that to some degree that doesn’t matter, but you  still have to assess if they have the right skills. So, and, and behaviors, because they could have at that other company. Right. We’ve all hired out of our network. Yes. And it wasn’t a good hire, even if they were super successful with us at previous orgs.

Krissy Manzano: Right. We all like, just think about that one person. Right. Um, or maybe it’s multiple, I don’t know. Yeah. This person was so good. They worked with me at all these places. They crushed it and they didn’t crush it here and it wasn’t ’cause they got bad all of a sudden it wasn’t. ’cause their successes weren’t real before and it was because this place required.

Krissy Manzano: Different skills. Yeah. That we, there’s no playbook that

Peter Ahn: works, right? Yes. Across every single industry. Exactly. And yeah, there’s not playbooks, there’s principles and approaches, I think, which is why I love, I love that, love to see how leaders like collaborate and communicate and take feedback during the interview process because especially in early stage, like that’s where I spend a lot of my time.

Peter Ahn: Yeah. Um, execution is, um, is king of above strategy. Right, because you’re probably gonna need to try 10 to 15 things before figuring out one or two that work. Yeah, and I think a lot of folks are stuck in this model of like, I did this at Google or Dropbox or Slack, and so I’m going to do the same thing here without really thinking from per first principles.

Peter Ahn: Right?

Krissy Manzano: Yeah, totally. No, I, great advice when a team starts breaking down, how can you tell if it’s a leadership issue versus a talent issue?

Peter Ahn: Yeah. So, and, and do you, do you mean from like leadership issue from the CEO or VP of sales or all levels? What are we talking like? Are we trying to figure out I would the sales leader’s not doing well.

Peter Ahn: Yeah.

Krissy Manzano: Well I would say start with like the who the team reports directly to, but maybe, you know, there’s also a second parallel of, you know, is it leadership above that person that they report to? Right?

Peter Ahn: Sure, sure. Yeah. So we could focus on VP of sales maybe first. Yeah. And yeah, I think one of the things that, I mean, he is very.

Peter Ahn: It seems obvious, but a lot of people, I don’t think, like look at this with the fine tooth comb and you just look at the person’s calendar. Right. And depending on the stage of company. For example, if I’m at a series A company and I’m at a VP of sales and I have barely any like enablement sessions or I’m not really on calls with my reps as probably a leadership problem, right?

Peter Ahn: Because I’ve seen time and time again, you know, VP of sales get hired from like a 10,000 person org and they’re used to being Mr. And Mrs. Dashboards. Then they join and the reps are taking calls and the reps don’t need dashboards. They actually need on the field help. Right? Yeah. Like positioning and messaging the product.

Peter Ahn: Yeah, so I think like looking at the calendar first, like where is this person’s time being spent based off of this stage of company is important. I. Right now, if you were at like a more mature company, maybe you do need to optimize more at a high level, right? And you still need to be enabling the field, but maybe there is a place for like optimizing dashboards and, and working more with rev ops.

Peter Ahn: But like looking at the mix of, um, time spent based off of their schedule, I think [00:13:00] is like really eye-opening. Um, and then the second thing I would say is how does the leader actually communicate with his or her peers? So much of startup sales especially is about how you actually educate other people, in my opinion.

Peter Ahn: Mm-hmm. And I’ve seen kind of VPs of sales or marketing leaders kind of go away into their silos. And so now like we like live in Slack in this remote era, it kind of boggles my mind sometimes when I like talk to A CEO who’s like. My VP of sales hasn’t actually provided an update in Slack in our sales channel in like since the time he’s been here.

Peter Ahn: And it’s like, that’s kind of crazy, right? Yeah. ’cause if you’re not doing that, how do other leaders know how they can best support you? And it doesn’t have to be that tactical like message. And so that’s not the point. The point is like, are you actually educating your CPO and CTO on what your team needs?

Peter Ahn: ’cause sales is a team sport and so I think hopefully that starts to get at your question. I think it’s really [00:14:00] like down to the tactical nuts and bolts. Like what are they actually doing day to day? And I feel like a lot of people over index on like. This person speaks really well at all hands, so they must have their shit together.

Peter Ahn: Right, right. But that is like one snippet of the job. And so like, I think like looking at somebody’s calendar, how they’re spending time, and then how are you actually learning about sales If you’re an executive wondering, is there a leadership or team problem? I think that answers a lot.

Krissy Manzano: Totally. I, well, I think to your point, going to the calendar piece, to me, if I’m like summarizing that, it’s, do you understand your team?

Krissy Manzano: And that’s different than micromanaging, right?

Peter Ahn: Oh, totally. Yeah. And

Krissy Manzano: it, even if you have managers and you’re a VP of sales, right? Or you’re a CRO, do you understand your team and what’s going on? Have you taken the time to dig in or you, or do you consider yourself so busy that you don’t have the time to dig in?

Krissy Manzano: The most successful leaders I see will dig in, right in a non micro. Manager way. Right. And it’s just you, you brought up all hands and it reminds me a company I used to work at and they had just hired a new like CRO and at, you know, our all hands, he was supposed to share his fun fact. I kid you not. His fun fact was, I’ve never taken a day off of work.

Peter Ahn: Oh my gosh. In 23

Krissy Manzano: years. And everyone just in front of tons of people and we all just looked at each other like, is he joking? Is this Yeah, this is his, this is the joke. He was dead serious. Huge

Peter Ahn: lack of EQ there. Wow. Dead

Krissy Manzano: serious. Wow. Um, but he was brought in because he had that experience for growing at other companies and was a horrible culture fit.

Krissy Manzano: And of course he rode the wave that was already going. But you know, it wa it’s of course it’s was not able to go to where they, they fully wanted. So it was just when you said that was just interesting, but that he’s a perfect example of what you’re

Peter Ahn: describing. Yeah. It’s funny how like these behavioral things just kind of don’t, or, or like people ignore them during the interview process.

Peter Ahn: Mm-hmm. And just. Index on, oh yeah, this person was at Microsoft. We had a vp, another fun story who, um, at a prior company, previous company of mine, I won’t name which one, but he was self proclaimed top 100 VPs in Microsoft. And so I was like, how do you say that with a straight face? Like, oh, I’m top 100 VP of Microsoft.

Peter Ahn: Right, right. That was a red flag. And then he also, his fun fact was, oh, I, um, come from this startup. You might have heard of it, Microsoft. And I live in the same neighborhood, uh, as my friend Bill, bill Gates. Right. So, so talk about like, you know, trying to meet your team, right? Like, I think there’s like so much, so much of a gap of like connecting with people that is just Yeah.

Peter Ahn: Very basic human to human that a lot of these VPs miss because they’ve been kind of applauded their entire career.

Krissy Manzano: Yeah. Well, I think. What’s gonna be really interesting is as we transform into this new era of ai, right? There’s still a lot of bets out there. There’s, but we know it’s coming. Mm-hmm. It’s here.

Krissy Manzano: Mm-hmm. And we know what’s happening. We just don’t all know like what it will fully look like. Right. Sure. Everyone’s taking their guesses.

Peter Ahn: Yep.

Krissy Manzano: We’ve seen the model, the Silicon Valley model of spend at all cost hire at all cost. You need to become a unicorn. That’s the only way we’re identifying success.

Krissy Manzano: Mm-hmm. And we’ve seen how that worked out and it. There are companies that have exited. What we know is that there are fewer companies than ever that continues to go down, that actually become public mm-hmm. And become successful. Yep. We know that there are less successful exits. This whole trend is not, you know, actually increasing.

Krissy Manzano: We know that there are, there’s less success, um, and there’s more blowups, there’s more drama, corruption. Mm-hmm. All of these things are gonna be exposed. As we move into ai, one of the things that I think is gonna be so key, my prediction is that being a human

Peter Ahn: Yeah.

Krissy Manzano: And, and being able to connect and actually present something that AI will never fully be able to on a full human level.

Krissy Manzano: Right? Like you can’t completely

Peter Ahn: agree,

Krissy Manzano: meet you. Meeting with me in person is different than if you use a computer, even if it’s an avatar. Right. And I don’t know all the specifics, but I think there even. I was listening to Sam Altman talk about this, like, right. I just think there’s this inhuman experience that’s gonna be so valuable.

Krissy Manzano: And I think that’s where this model, ’cause you’re starting to see people wanna go fast again with ai, right? Mm-hmm. And we’re seeing like

Peter Ahn: mm-hmm.

Krissy Manzano: You know, another company that was in the news, right, that had. Said, we’re gonna replace this whole job. Um, and come to find out, uh,

Peter Ahn: you can, multiple

Krissy Manzano: companies came forward and said, I’ve never been a client of theirs.

Krissy Manzano: Right. And so we’re seeing all of this stuff happen again.

Peter Ahn: Oh yeah, totally. Yeah. I know, I think I know which one you’re talking about. Yeah. I’m, I’m sure,

Krissy Manzano: um, it was only a few weeks, surprisingly, in the news, but yeah, you’re right. We’re seeing, we’re seeing all of these things happen and. I just think that AI might be, I thought we already hit the tipping point.

Krissy Manzano: I think AI might be the tipping point to take that to another level with leadership. Right. I co agree. What’s gonna be expected? Um, yeah. I think

Peter Ahn: what you’re talking about is like currency and leadership used to be based off of like a big exit. I. To your point. Mm-hmm. But now I think currency, like the value that you bring is going to be, um, I actually liked working with this person and learned something from this person and this person invested in my career.

Peter Ahn: I think those leaders longer term are going to be able to build strong teams. Yeah. Right. Because there’s so many leaders who a hundred percent hit the jack. Pot who I wouldn’t touch with a 10 foot pole. Right? Right. Like if they asked me to work for them and they were at the next a hundred billion dollar company, I’d be like, no, thank you.

Peter Ahn: Right. And that used to be the case, but now I think people don’t follow the, the valuations anymore ’cause they’re all very frothy or they were. Mm-hmm. Um,

Krissy Manzano: yep.

Peter Ahn: They’re following like repe repetition in leadership and um, folks who are empathetic and can actually provide value on a human level.

Krissy Manzano: Yep. I, I totally agree.

Krissy Manzano: I do think the currency changes, right? Um,

Peter Ahn: yeah, totally. And,

Krissy Manzano: and that might mean that the things that you’re not good at are actually going to matter a lot, um, when we come into this new world of how companies start and grow and what that looks like.

Peter Ahn: Yeah. Yeah.

Krissy Manzano: You’ve worked with a lot of founders, right?

Krissy Manzano: Mm-hmm. Mm-hmm. What separates the ones, let’s move into this, the ones who grow into actual leaders from the ones that don’t. We’ve touched on this a little bit, but would love to kind of hear your. You know, a view of that.

Peter Ahn: Yeah. So, so the run ones that grow into actual leaders, um, take the craft of learning something they don’t know very seriously.

Peter Ahn: And let me break that down for you. So I am oftentimes a deal coach for my founders, right? They’re trying to close their first five to 10 deals and they’re like, Peter, I’ve never done enterprise sales. How do I do this? There’s some founders who you could tell they’re listening, but they’re not absorbing.

Peter Ahn: And there’s other founders right after the coaching session, they’re slacking me being like, Hey Peter, is the wording on this email appropriate for an SVP? Right in it? Right. And, and the, and the folks who are like the most tactical and ask the most basic questions are the future leaders, if that makes sense.

Peter Ahn: Yeah, right. Um, the folks who aren’t future leaders, like, they’ll kind of paper over the, the frameworks and they’ll kind of do the thing, but they won’t ask you many questions. Yeah. Because they’re like, oh, I’ve heard this somewhere. Um, you know, like, I don’t really want to send Peter this call because, you know, maybe they’re embarrassed or they think the call went really well.

Peter Ahn: My best clients are like, Hey, I don’t know what the heck is going on. Can you like, pick apart every single dynamic of this deal? Right. Yeah. And, and so I think those are the most successful because they learn at a faster pace because they’re not afraid of, um, they’re not afraid of what they know. They’re afraid of what they don’t know, if that makes sense.

Krissy Manzano: Yeah.

Peter Ahn: And so they are constantly like trying to workshop and accelerate the learning of something like sales, because they know if they want to hire somebody, they need to know like what great looks like.

Krissy Manzano: Yeah.

Peter Ahn: And so those are like the clients that I love working with. There’s, you know, no surprise, very coachable, very moldable.

Krissy Manzano: Right.

Peter Ahn: And

Krissy Manzano: very curious in the,

Peter Ahn: yeah. In the beginning they’re like, Hey, like, I know this is a stupid question, but, and then I know that question is actually gonna be a great question because they’re literally trying to figure out the details and, um, I think these detail oriented clients do really, really well.

Peter Ahn: They don’t assume to know anything.

Krissy Manzano: Yeah. No, I love that. It’s, it’s such a simple thing at the end of the day that can be so hard to get. Folks to actually implement, right? Yes, yes. And just that whole, like there’s never a time where you should stop wanting to learn whether you’re a founder or not. The minute that you think, I have clout, I have experience.

Krissy Manzano: Therefore, I don’t need to be digging in is the minute that things start to go downhill. It’s the reason why it trust me age by success, but it’s also the reason why. We see sometimes like an older generation struggle in getting a job because the reality is there are several that will say, I have all this experience, so I don’t need anything outside of like showing you this experience to have this job.

Krissy Manzano: Right? Yes. That is also reality on top of age bias being a reality. Yes. And don’t not understanding that you just, ’cause you’ve done this for 20 years. Doesn’t matter. Like you have to show that you’re curious and understand or willing to learn and continue diving in and you’re not done learning. So,

Peter Ahn: yeah.

Peter Ahn: Yeah. I mean, even me, I’m not done learning about sales, right? No. And I’m a sales coach, right.

Krissy Manzano: So. Right, right. Totally.

Peter Ahn: And, and um, you know, 16 years is nothing compared to somebody who’s been selling for 30 years. So there’s always something I need to learn. Right. And I’m learning from my clients too, by the way.

Peter Ahn: Right? Yeah, exactly. I think a lot of people, um, don’t necessarily take that mentality, but I try and self-select for that type of clientele, which is why I ask to see just one call first because how they receive the feedback says everything I need to know about whether or not I can impact them.

Krissy Manzano: Yeah.

Krissy Manzano: Yeah. No, that’s it. Well said. Right. It’s like you, you’ve never mastered anything. Yes. Yeah. Um, you can always continue. Um, trying

Peter Ahn: Exactly.

Krissy Manzano: La last question for you. Yeah. On this. If you could give one piece of advice to a first time founder, maybe they’ve just raised their seed round or they’ve gotten Series A right?

Krissy Manzano: And they, they have that product market fit mm-hmm. And they’re about to start hiring. What would it be?

Peter Ahn: Yeah, I think, um. My advice would be don’t be afraid to take bets on people who have non-traditional backgrounds, if you’re looking for like your first seller, right? So I’ve hired a lot of folks who are, you know, former lawyers or consultants.

Peter Ahn: I’m actually coaching a team right now where their entire go to market team is former consultants. Um, but the questions they ask are so refreshing because they’re coming at this from an outsider’s perspective and. From like a trust building perspective with their clients versus like, oh, I need to like map a sales framework.

Peter Ahn: So that’s my, uh, one advice for hiring ics. Don’t be afraid to take bats for heads of sales ’cause you are gonna need to hire heads of sales sometimes, right? As a series A founder. If you’re, if you’re wanting to build the team from the get go and there’s too many leads to handle, um, don’t be afraid to ask them to do very tactical things in the interview process.

Peter Ahn: Right. So I’ve heard founders say, Peter, like, I don’t want to offend this VP of sales and tell him to do a pitch deck on our company and present it to us like as if he’s an ae because he’s beyond that. He’s above that, or she’s above that. And I always tell the founders, you have to make them do it, because a lot of experienced people don’t know how to sell, believe it or not, right?

Peter Ahn: So if you don’t give them a prompt, if you don’t give them a writing exercise and you just trust their 30, 60, 90 day plan, you’re missing a big part of the pie because guess what? You know, they are supposed to be the chief account executive. And so when you hire four or five AEs and they realize their sales leader can’t sell, that’s gonna be a big issue for you.

Peter Ahn: Right. Yeah. So I think those are the two things, like don’t be afraid to take rest on up and comers. I’ve seen a lot of success there. Yeah. And then, um, for your head of sales, don’t be afraid to ask them to do very tactical on the ground things. ’cause that’s what your team is gonna need, you know, when they hire.

Krissy Manzano: Yeah. Yeah. I love that because even at the IC level, the amount of enterprise AE searches we’ve done where they bomb the presentation stage. Oh yeah. On it. Yeah. And at first we’re like our clients, our clients must be overcomplicating this. Right. There’s no way this many enterprise sellers with these backgrounds are bombing.

Krissy Manzano: There’s no way. Yeah. They crush it all the way through. Go in, have a conversation. They even show us the recording. Ooh. And what all, all the candidates that have all this selling experience did was pitch during a crazy basic discovery. And I, it’s really opened my eyes to how many, even when you prep ’em right.

Krissy Manzano: How we are in such a new era of selling. Yes. Where there has to be value like we have never seen before. And the buyers are more educated and you have to be curious. You have to, and you can’t be curious, I talk about this all the time without empathy. Mm-hmm. Empathy is not just about soft feelings for people, it’s about understanding and everyone, it’s a skill that I don’t, I don’t think I realize like we are lacking in our culture.

Krissy Manzano: Oh, totally. Yes. And it’s actually impacting. Current jobs even before AI comes in and might be able to do that even better. Right. And so it resonates even with the leadership one, but just in seeing that, um, where we’ve transitioned, it’s, it’s been powerful to experience firsthand and go. Oh my gosh. Yeah, of course.

Krissy Manzano: You, you’ve moved on from them. ’cause they’re not able to follow something as simple as just asking questions. Yeah. And not their number one thing is don’t pitch. That’s all they did.

Peter Ahn: It is pretty crazy how that’s happening. Right. And it’s, it’s, um, a lot of bad behavior has been okay to

Krissy Manzano: Yeah.

Peter Ahn: Kind of go through because we’ve had so many products just sell and fly off the shelves.

Peter Ahn: Yeah. Right. Yeah. So you have AEs of hit 200% quota who maybe haven’t really gotten call coaching before. Yeah. Right. And em, you mentioned empathy. I do think, like, especially in enterprise sales, the job is to make your buyer feel inspired and to trust you. Yeah. And so feelings and emotions are a crucial part of the sales process.

Peter Ahn: I. And so if you don’t feel that from a candidate in a mock scenario, like good luck with your prospects feeling it too. Right, right, right. And the other thing, sorry, one more thing. Um, time just flew, by the way. This is fun. I know. But, um, a lot of founders are like, well, maybe this is just sales, right? Like, maybe I don’t need to, like, how many times have you heard this, right?

Peter Ahn: Yeah. Maybe I don’t need to, like my VP of sales, like that’s kind of what I’m, sometimes people convince themselves and they’re like, that’s what I’m looking for actually. I don’t want people to like this guy. I just want him to hit numbers. Yeah, but that’s like the wrong attitude, right? Hundred. Like your clients have to like this guy that’s like half the sale.

Krissy Manzano: So Yes. Yeah. As does your team who is doing the selling Exactly, exactly. That, that, that gets you the revenue.

Peter Ahn: Yeah.

Krissy Manzano: So, well, I know we’re at the end, um, could talk about this for a long time, Peter, where can people find you if they wanna reach out?

Peter Ahn: So yeah, I’m very active on LinkedIn and then a pet project of mine that is becoming a priority now is, um, I’m heavily investing in my YouTube channel, so it’s at Peter on sales.

Peter Ahn: I just love the content creation process, so would appreciate if anybody listening to this could check it out And

Krissy Manzano: yeah, and see

Peter Ahn: some of my videos there

Krissy Manzano: and Peter on is. A HN, not on Yes. A HN. That’s

Peter Ahn: right. Yep, yep, yep. Maybe I should change it to ON to make it easier, but

Krissy Manzano: like No, I love it. Well, thanks for being with us today, for, you know, more hiring insights.

Krissy Manzano: You can find that with other leaders on our talent, GTM Podcast and other episodes. If today’s conversation piques your interest, subscribe to our podcast. On Spotify, apple Podcast or our website@blueprintexpansion.com, and never miss an episode. Until next time, we’ll see you. Thank you, Peter, so much for being here.

Krissy Manzano: This has been great.

Peter Ahn: Thank you, Chrissy. Appreciate it.

Krissy Manzano: Thanks. Bye.

 

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Frequently Asked Questions

Hiring Companies

How do you charge for your services?

We offer multiple services, depending on the needs of our clients. Please reach out to us for more information, and see our GTM recruiting services page for more details.

Do you recruit outside of the US and Canada?
Our focus is currently North America, but we’ve also worked with tremendous people in APAC, LATAM, and EMEA. If you have needs in these regions (whether you are based in North America or elsewhere), we want to hear from you!
What roles do you recruit?
Our team superbly recruits for any roles within go-to-market (GTM) functions, including:

  • Customer Success: Standard, Senior, and Principal Customer Success Managers, Onboarding Specialists, Implementation Managers, Community, Customer Support, & Solutions Architects
  • Marketing: Growth & Demand Generation Marketing, ABM, Events, and Content / SEO Marketing
  • Sales: Sales Development, SMB, Commercial, Mid-Market, Enterprise, and Strategic Account Executives
  • Account Management
  • Revenue Operations and Enablement: Marketing, CS, and Sales Operations
  • Solutions Engineering and Post-Sales Solutions Architects
  • GTM Leadership: Front-line, second-line, VP, and SVP / C Level placements (CRO, CMO, COO)
I've worked with so many headhunters and recruiting firms. What makes you different?

Put simply, we aspire to be as proficient in articulating your business value prop as your internal employees. Exceptional talent does not want to speak with “head-hunters;” instead, they want to connect with educated ambassadors of your business and your brand about meaningful career opportunities.

We go deep on your business and into talent markets to foster connections that other recruiting firms tend to miss. And we work with our hiring clients to ensure excellence in their hiring process. Please reach out to us for more information!

Is SaaS experience important when hiring?

Hmm, what does this mean anyhow?! We recommend defining the skills and behaviors sought before running a search rather than using buzzwords or phrases from other people’s job descriptions. We help employees go beyond acronyms to ensure they develop robust job descriptions that tie to specific candidate profiles for targeting in the market. Need help? Let us know!

Job Seekers

I don’t see any roles for me. What Should I do?

Blueprint runs a monthly Transferable Skills Workshop to help early talent and career switchers find opportunity in the market and prepare to interview. It’s currently offered at no cost. Interested? Please reach out to us.

How do I negotiate fair compensation ?

The Blueprint team always shares compensation range information with candidates before initial screening calls. Beyond this, we encourage you to consult with review sites and other data sources to educate on the market for the roles you’ve held. Want to discuss? Reach out to us.

Is it still important to send 'Thank You' notes?

Interviewing should always be treated as a two-way street, and a candidate should never feel obligated to show gratitude and follow up first.

That said, if you believe a given opportunity aligns to your role and company interests, we recommend sending interviewers a follow-up email after every step in the process. This gives you a chance to recap your learnings & enthusiasms briefly and authentically. It also helps you stay top of mind with interviewing companies.

Check out the roundtable discussion our leadership team recently held on the topic of post-interview thank-you notes.

What are some additional basic tips for candidates?

Make sure you prep before every interview, particularly by reviewing the company website, recent new articles, and the LinkedIn profiles of relevant interviewers and company leaders.

Consider business casual attire - ask your recruiter for any additional guidance. Try to make sure that you are able to sit front and center facing your camera - test it with friends prior to running an interview. If you need to take a call by phone, it’s best to let your recruiter or the hiring manager know in advance, and offer them an option to reschedule if they prefer.

Lastly, prepare some questions in advance based on your research, but do everything you can to stay in the conversation. The more you can listen and be in the moment, the better you’ll execute and be able to vet the opportunity for yourself.

Have more questions? Contact us!

Why did you launch Blueprint?

Despite so much innovation in HR tech and recruiting, hiring remains broken. As former operators with decades of experience hiring GTM talent, we wanted to start our own business dedicated to helping B2B tech companies across a range of industries do a better job at attracting and sourcing tremendous (and diverse) talent.

How do you charge for your services?

We have multiple services packages, depending on the needs of our clients. Please reach out to us for more information, and see our sales recruitment services page for a breakdown of our packages.

Do you recruit outside of the US and Canada?
Our focus is currently North America, but we’ve also worked with tremendous people in APAC, LATAM, and EMEA. If you have needs in these regions (whether you are based in North America or elsewhere), we want to hear from you!
What roles do you recruit?
Our team superbly recruits for any roles within go-to-market (GTM) functions, including:

  • Customer Success: Standard, Senior, and Principal Customer Success Managers, Onboarding Specialists, Implementation Managers, Community, Customer Support, & Solutions Architects
  • Marketing: Growth & Demand Generation Marketing, ABM, Events, and Content / SEO Marketing
  • Sales: Sales Development, SMB, Commercial, Mid-Market, Enterprise, and Strategic Account Executives
  • Account Management
  • Revenue Operations and Enablement: Marketing, CS, and Sales Operations
  • Solutions Engineering and Post-Sales Solutions Architects
  • GTM Leadership: Front-line, second-line, VP, and SVP / C Level placements (CRO, CMO, COO)
I've worked with so many headhunters and recruiting firms. What makes you different?

Put simply, we aspire to be as proficient in articulating your business value prop as your internal employees. Exceptional talent does not want to speak with “head-hunters;” instead, they want to connect with educated ambassadors of your business and your brand about meaningful career opportunities.

We go deep on your business and into talent markets to foster connections that other recruiting firms tend to miss. And we work with our hiring clients to ensure excellence in their hiring process. Please reach out to us for more information!

Is SaaS experience important when hiring?

Hmm, what does this mean anyhow?! We recommend defining the skills and behaviors sought before running a search rather than using buzzwords or phrases from other people’s job descriptions. We help employees go beyond acronyms to ensure they develop robust job descriptions that tie to specific candidate profiles for targeting in the market. Need help? Let us know!