The Ugly Truth About Pipeline (Real Talk for GTM Teams Running on Broken Systems)

Summary

GTM Live: The Ugly Truth About Pipeline (Real Talk for GTM Teams Running on Broken Systems) Release Date: May 22, 2025

Hosts: Carolyn Dilks & Trevor Gibson, Co-Founders of Passetto
Guest: Nick Flamini, Host of the Sales Architecture Podcast

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Introduction

In this candid episode of GTM Live, host Carolyn Dilks teams up with Nick Flamini from the Sales Architecture Podcast to delve deep into the systemic issues plaguing go-to-market (GTM) strategies within B2B SaaS companies. This conversation serves as a "go-to-market therapy session," where both experts openly discuss the often-ignored challenges such as bloated BDR organizations, fragmented data, and the pitfalls of operating with a broken pipeline system.

Understanding Go-To-Market Dysfunction

Carolyn introduces the core mission of Passetto—fixing GTM dysfunction by bridging the gap between sales and marketing through a technology-enabled approach. She explains how Passetto creates a department-agnostic data layer that ties GTM activities directly to financial outcomes and unit economics.

"[Passetto] strips away these department silos and helps executives understand what's working and what's not." (00:52)

Nick echoes the frustration of departmental silos, sharing his own experiences of sales teams blaming marketing for pipeline issues and the necessity of breaking down these barriers to drive meaningful pipeline growth.

The Importance of Unit Economics in GTM

A significant portion of the discussion focuses on the concept of unit economics and its critical role in measuring GTM efficiency.

Carolyn emphasizes that many revenue leaders lack financial acumen, leading to a disconnect between GTM efforts and overall business performance. She highlights how Passetto's solution unifies revenue, financial, and CRM data to provide a comprehensive view of GTM performance.

"Most companies are spending probably three, four, five times what they should to produce pipeline and new logos—and they kind of don't even know because they're only equipped to look at their program spend." (07:17)

Nick references David Spitz's work on GTM efficiency, reinforcing the idea that many organizations are still grappling with outdated "growth at all costs" mentalities that Passetto aims to rectify.

Cleaning Up CRM Data: A Critical Challenge

Nick brings up the perennial issue of CRM data accuracy, lamenting how messy and unreliable CRM systems can be. He questions how companies can make informed decisions when their CRM data is riddled with inaccuracies.

Carolyn responds by identifying data and process as the root problems rather than personnel. She explains that while marketing and sales teams are often talented, they lack the necessary data architecture to measure and communicate their impact effectively.

"Passetto is one of the only products or services in the market to be able to unify data by pulling together revenue data, financial data, and your CRM data to tell that story." (04:19)

The Problem with Overhiring BDRs and SDRs

A critical point of contention is the overhiring of BDRs and SDRs. Both Carolyn and Nick agree that merely increasing the number of business development representatives does not equate to better results. Instead, they argue for a data-driven approach to understand the actual productivity and effectiveness of these roles.

"Most people think that Cold outbound or like BDRs are what's driving revenue for the organization. Therefore, let's hire more of them and we'll get more as a result." (16:03)

Carolyn shares insights from Passetto's client work, revealing how numerous companies believe their large BDR teams are the primary revenue drivers, while in reality, the lack of structured data often masks diminishing returns.

The Impact of AI on Outbound Efforts

Nick introduces a forward-looking topic: the integration of AI in outbound sales. He expresses skepticism about AI's current capability to replace human connection in sales, predicting a future where over-reliance on AI could erode trust and effectiveness.

"The volume from AI is so substantial, and the lack of trust or willingness to respond is going to have a substantial effect long-term." (22:12)

Carolyn agrees, stating that while AI can enhance certain aspects of GTM, it cannot replace the human connection that is foundational to successful sales interactions.

"The best sales teams are the ones who build a human connection first." (19:25)

Bridging the Gap Between Marketing and Finance

A pivotal part of the conversation revolves around the alignment between marketing and finance. Both hosts highlight how siloed departments lead to misaligned KPIs and ineffective GTM strategies.

Nick stresses the importance of involving finance in GTM decision-making to ensure that all departments are working towards unified financial goals.

"Breaking down the barrier and creating alignment, what does finance need to do in order to unify these departments?" (26:40)

Carolyn concurs, suggesting that involving finance and possibly integrating third-party solutions like Passetto can serve as the "glue" to unify disparate teams and metrics.

The Role of Education and Cross-Departmental Understanding

Both Carolyn and Nick advocate for better education and understanding across departments. They argue that marketers often lack financial literacy, which hampers their ability to connect GTM activities to financial outcomes.

"The vast majority of marketers just are not revenue inclined or financially inclined to really understand like, how to connect the dots between the two things." (31:53)

Nick adds that integrating financial education into marketing training could foster better alignment and more informed decision-making.

Future Outlook and Passetto's Evolution

As the conversation wraps up, Carolyn shares Passetto's journey and future aspirations. Initially focused on advisory services, Passetto has evolved to offer robust data architecture solutions that enable companies to make data-driven GTM decisions.

"We help companies install a proper data architecture in their system to be able to actually get all of the data inputs we need." (38:24)

Nick inquires about Passetto's platform capabilities, confirming their support for major CRM systems like Salesforce and HubSpot, and hints at ongoing developments to enhance data integration and analysis.

Carolyn remains optimistic about Passetto's role in addressing GTM dysfunction, anticipating increased adoption as more companies recognize and seek to solve these deep-seated issues.

"The future is going to be super bright for Passetto, and I can't wait to see what's in store for us." (41:12)

Conclusion

This episode of GTM Live provides a transparent and insightful exploration of the fundamental flaws in current GTM strategies. Carolyn and Nick shed light on the necessity of unified data, the pitfalls of departmental silos, and the critical role of financial alignment in driving sustainable growth. By advocating for data-driven decision-making and better cross-departmental education, they offer a blueprint for overcoming the "ugly truths" that hinder GTM success.

Key Takeaways:

• Data Integration: Unifying revenue, financial, and CRM data is essential for transparent and effective GTM strategies.
• Unit Economics: Understanding the complete cost and ROI of GTM activities beyond just program spend.
• BDR/SDR Efficiency: Moving away from overhiring towards data-driven optimization of sales roles.
• Human Connection vs. AI: Balancing the use of AI with the irreplaceable value of human relationships in sales.
• Cross-Departmental Alignment: Involving finance in GTM processes to ensure unified financial objectives and better decision-making.

For those struggling with a messy GTM setup, this episode offers valuable insights and actionable strategies to transform your pipeline from broken to robust.

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Listen to the full episode here.

Transcript

[Carolyn]

Hi everybody. Welcome back. In this episode, I joined Nick Flamini from the Sales Architecture podcast as a guest on his show. And honestly this conversation really felt more like a go to market therapy session than a typical interview. I was really open about a lot of the stuff that nobody likes talking about or saying out loud, like bloated BDR organizations, broken data, and just why so many teams are flying blind when it comes to pipeline and making data informed decisions. So if your go to market feels really messy under the hood, I think you'll learn a lot from this show and get a lot of value from it. Enjoy. You're listening to GTM Live, a podcast by Petto.

[Nick Flamini]

Carolyn, thanks for joining us for another episode of the Sales Architecture podcast. Give everyone a little explanation of who you are, what you're doing and what the future looks like and we'll go from there.

[Carolyn]

Thanks. Yeah, excited to be here. Thanks for inviting me on. My name is Carolyn. I am one of the co founders and managing partner at a company named Pesetto. Many people will recognize Chris Walker's name. He is our original founder and owner of the business. And we've been basically operating now for I think 14 or 15 months, just over a year. And what do we do? We are a technology enabled company. So part advisory, part tech and basically our objective is to fix what we call go to market dysfunction, which I think is a core problem that a lot of SaaS and tech organizations are seeing across the board, which is like just no alignment across sales and marketing teams, no clear understanding of what's driving ROI and potentially degrading their growth. And so what we do is with our product, we basically create a department agnostic data layer and attach data to financial outcomes of the business and unit economics to really understand, like stripping away sort of like these department silos and just understanding at a very high level how the go to market is performing, what their efficiency is and understanding and to be able to tell executives like, hey, here's what's working and here's what's not, here's what to do more of, here's what to do less of and so on and so forth. And so that's us. I feel really passionately about what we do. I come from the marketing world, I come from SaaS and for a long time I felt these pains, you know, departments competing for credit, blaming one another like sales sucks at their job or you know, marketing is giving us shitty leads. And honestly I really wanted to do something about it. Like I heard Chris talk about this problem over and over and over again. And he and I had built a little bit of a relationship through our businesses. And so I had said, like, I want to come work with you. I really fundamentally and philosophically align with the problem that you're trying to solve, and here I am.

[Nick Flamini]

Yeah, well, I appreciate what you're trying to accomplish because my background historically is not in marketing. I've become marketing obsessed the past two years. So I'm by no means what I would consider as like an elite level expert when it comes to marketing. But the reason that brought me into this world is because on the sales side of things, if you don't understand what's actually happening through the pipeline, you start to play the blame game. I've been the sales rep that blames marketing, and then I've also realized how to take control over that and overcome it. And so we can immediately find ways to break down that departmental silo, work together, and actually drive pipeline. And so when I started to follow Chris originally and I was listening to his content, I was like, he's really onto something. And then once Passetto came into existence of actually breaking down this data and figuring out ways to become more efficient, it really, for me, helped me understand where to just focus my time on marketing and how to understand it a little bit better for the sake of our business and what we do for clients. And I have to say that it's made a massive difference just following along, not even working directly with your team. And so I think that we're still on the precipice of making this the more the mainstream of how to think about things. And so one thing that you mentioned early, just jumping in here is speaking in terms of unit economics. I don't think a lot of people really even understand what we mean when we. We talk about that. Can you describe what you mean when you say learn how to speak in terms of unit economics as it relates to like, finance and go to market efficiency?

[Carolyn]

Yeah, I think, honestly, if I can try and simplify this in the best way possible, I think most leaders in like revenue organizations, whether sales leaders or marketing leaders, like, they don't have a lot of financial acumen. And I'm not suggesting that it's their job to have that. But I think the problem is that ultimately everything that we're doing in go to market is meant to drive revenue for the business and improve the company's growth and enterprise value, et cetera, et cetera, and everything that we are spending money on in go to market to acquire new logos to Retain our customers, so on and so forth. Costs money to do that. And we're looking at ROI on what we are doing in a total silo. We're not actually connecting that back to like overall business performance. And a lot of companies have this like disconnect between finance and then in go to market when really like they should be attached at the hip, they should be able to understand like all of the things that we are doing in market to grow the business. How is that actually tying back to business performance? And like we are not attuned to be able to measure that. For one, I think posetto is probably one of the only products or services in the market to be able to like unify data by pulling together revenue data, financial data and your CRM data to be able to tell that story. Like most companies are out there trying to cobble together a story in an Excel spreadsheet and just can't. And the other reason to that too is like when you think about what you're spending money on in your go to market, it's not just programs which would be like you know, going to events, sponsoring events, paying for a media placement or paying for your paid social or your Google search or whatever. There are headcount costs, those are like your fixed and variable compensation. What are you spending on service providers? What are you spending on programs? What are you spending on technology? What are you spending on admin? What are you spending on travel? There's a shitload of costs that we're spending in go to market. And so when we're looking at like return on investment, like we're often only looking at like the return on the ad spend, which I think is not a great metric because what about all of the other costs that it took you to execute that ad? Not just like your in channel spend. And so when we're talking about sort of like tying it back to unit economics, it's really understanding like the whole story of how efficient you are as a go to market and understanding like what is it actually costing you at a very high level like with everything to acquire new logos or to retain your customers. And most companies just like don't know. Most companies are spending probably what I've seen like three, four, five times what they should to produce pipeline and new logos. And they kind of don't even know because they're only equipped to look at like their program spend. And so when you look at program spend it might look one way. When you look at everything, the story looks a whole lot different.

[Nick Flamini]

Yeah, well I Think you're right. I think one of the things that opened my eyes about it was looking at the Dropbox example when David Spitz was putting out some work around go to market efficiency. And I have the revenue architecture book on my desk and it explains some of that early on. And I feel like some of it's fueled from that growth at all cost error that still is kind of rolling over into the way people are still doing business. I'm pretty hopeful. I think that most organizations are starting to turn the curve. They just don't know how. And I feel like that's where what you're doing, what the company's doing, is hopefully going to be able to fill that void and make it a little bit more mainstream. You're talking about CRM data. I listened to your first episode yesterday. I know I talked about that before you jumped in. And one of the things you mentioned I would love to talk about, which is we almost never get into a CRM where the data is accurate. And that for me was it just hit home as a salesperson, being a part of various organizations, big and small, including our own. I think CRMs are always a nightmare. So what needs to be done here? How do we clean up CRM data? How do we fix this so everyone can understand? Because I think the first problem is that most people will find whatever narrative they want through how they're tracking attribution in almost every model. W shape, Y shape, burst, touch, it doesn't matter if you want to find. In my opinion, what I've seen is that if you want to find a way to support your narrative, you kind of can. And that's what makes it a little bit tough. And so what do we need to do to clean this up and have a more objective way of looking at it to actually get the results?

[Carolyn]

Yeah, really good question. And that's, I think, a problem that Passetto has become like super familiar with in the last year with all of the clients that we've worked with. So I think just start like when we talk about go to market being broken, we're trying to move away from the growth at all costs era and all of that. Honestly, I think it comes down to data and process. Oftentimes companies will be very quick to rip out a team and replace it. Let's get a new cmo, let's get a new marketing team, let's get a new head of sales. These people don't know what the fuck they're doing. Or let's just cut costs like our cac. Is too high. Let's just reduce the budget, give marketing less. And honestly, I don't think it's a people problem. I think there are so many talented marketers, salespeople, revenue leaders in organizations that know what to do and that know how to make smart decisions and know, you know, how to go to market. But unfortunately they don't have the data architecture to be able to one tell that story about impact. I have certainly been there. I would consider myself a really skilled marketer. Not to like toot my own horn, but I've been in that situation where I've done a lot of stuff that I think has been really impactful, but I just don't know how to communicate the impact. Right. Comes down to data architecture. And then I think there's this other camp which is you don't have the data architecture to tell you what's not working. Right. Like a lot of times we look at what is working. Oh, this campaign did this, this campaign did that. We're not really acknowledging like all the shit that didn't work, all the stuff we spent our money on that took us nowhere. And so ultimately that comes down to like how you are capturing all of your data in CRM, ideally, whether it's HubSpot or Salesforce or what have you, and then making sure that all of your different point solutions that you're using outside of CRM tie back into. So you're tracking everything. And I think one thing that most companies do really well is like you've got a sales cycle, right? Starts at stage one, opportunity creation, whatever, you know, your, your definitions might be for that. And then we track everything in the sales cycle, how it progresses through each stage. We know like roughly what the conversion rate is between each stage, what like actions a salesperson has. They track all their emails, they track all their calls, they track all their meetings. And so we have like total and complete visibility into the sales cycle. But like, that is one component of the revenue factory. We call it a revenue factory, One component of it. And you have the stage that happens before that, which is called prospecting, which is where your AES or SDRs or BDRs or whatever are calling on people and working them to become qualified opportunities or disqualifying them or whatever. That's like a black hole. Like we have seen that so many times at Passetto where you've got all of these companies that are doing shitload of BDR. They've got like BDR activity, they've got maybe 15 BDRs on their team. Or more.

[Nick Flamini]

And.

[Carolyn]

And it's like, what are these people doing? We have no idea what their productivity looks like. You know, we make. We know they're making dials, but we don't know to who. We don't know why. We don't know how those people are ending up in CRM. Like, it's a black hole. Right? We call that a black hole all the time. And so that is like one component that most companies don't track. Passetto has a solution to work with companies to track that so that we understand basically, like, how efficient are you at prospecting? What are the reasons that you're prospecting a prospect to begin with, how many of those things lead to pipeline and revenue? And like, how much of that stuff that you're doing out there in the real world is it going nowhere? Like, that is what I think that data layer tells you, which is again, an important component of the revenue factory. And then of course, you have like, this whole stage of stuff that happens that marketing supports initially, like early on in the process, which is like engaging your prospects, having them become aware of your product or your service or whatever that's content. That's whether they're showing up for a webinar. You know, you're out there at an event meeting these people. But that's understanding all of the different signals and interactions that are happening earlier in the journey leading up to your prospecting efforts and then leading up to your sales cycle. And when we look at it and zoom out, a data architecture in CRM should capture all of those things. And unfortunately for most companies, it just doesn't.

[Nick Flamini]

Yeah, I'd agree. One of the things you mentioned, that's a big problem for us that we see is I think this is relevant to go to market blow. But when you say bdrs, we don't know how they're prospecting, what's efficient. I'm in the camp of we overhire SDRs and BDRs. This conversation, I think, is debatable. I think at the grand scheme of things, it is a smaller part of the budget when you look at other salaries, where spend is going. But as a sales organization, as a part of us trying to make teams become leaner and more efficient, I feel like there's still a big disconnect on how do we even measure on when and how to hire another sdr. There's not a great way of actually understanding this because we're not really sure how productive someone is, to your point. And that's something where we've Modeled a few things where I believe we're on the right track. But truthfully, it's still pretty difficult for us to navigate because how cold is a prospect? Where was the first time that they were even? How did they hear about us in the first place? Where does this all come into? How do we know to scale the sales team out? It's not really that straightforward. And so I'm curious on your thoughts. I think most companies are still overhiring VDRs and SDRs. I don't think that more typically leads to more revenue. And so what we're trying to figure out is how do we condense the sales team and drive the same amount of pipeline as people thinking, oh, if we hire five more people, we'll get five times the results.

[Carolyn]

Yeah, I think, like, go to market. Bloat overall is like a huge epidemic. And go to market. Like, I think most people think, like, if we hire more people, we're going to get better results. I don't think that's true. Again, I think the process and the data that you're working from are the problem, not the people. And so what I mean by that is when you're hiring more BDRs or you're inflating your team with more people, you have the assumption that more people means you're getting more return out of them. I don't think that's true. I think what you need is the data to tell you where to invest and the things to invest in in order to be able to make smart decisions. And I think what's causing this is that most companies want some way to like, understand how deals are getting in the pipeline. So they'll say, oh, you know, we'll just create a field on the opportunity record and call it like lead source or deal source or something like, where we'll find, like, one thing that happened leading up to the deal and say that that's the trigger that led to deal creation. And oftentimes what we see is that companies think that their SDRs or their BDRs or their sales team are like, out there, cold outbounding. And like, that is how they get deals. And when we install our way of looking at data in CRM, we can see that many times, like, pure cold outbound, like, doesn't actually go anywhere. Most people that you think are cold that you're reaching out to are actually pretty warm. And they got in the hands of your BDRs from something that happened potentially in marketing, whether they attended a webinar or, you know, downloaded some content from your website or something like that. And so when you actually have the data to tell the story, your data is actually going to give you a really different story than like what you might be able to see on the lead source field in your CRM. And so most companies I think, think that Cold outbound or like BDRs are what's driving revenue for the organization. Therefore let's hire more of them and we'll get more like as a result.

[Nick Flamini]

That's exactly the problem that we face when we're consulting a company. And I just think it couldn't be more wrong. I do think there's a level at which you need to have BDRs and SDRs. But yeah, this came from somewhere. They heard about the company somewhere. The contact only exists inside of the CRM for one reason and that's awareness. They've become aware at some level whether it was a piece of gated content or they attended a webinar or an event or who knows. But they're not necessarily cold. And so why are we over hiring and assuming that we're going to get better results? And the point that you made or one of them, and totally correct me if I'm wrong by the way, is that if you have a really shitty process, more people is not going to equate better results. We can improve the process with less people, decrease the overhead and drive more results 100%.

[Carolyn]

I could not agree more. There's one company that we're consulting with, they have like a 15 person BDR team or whatever and they have this belief that like 90% of their revenue is sourced from BDRs. I have a totally different perspective on that. I don't think that's true. But they just essentially like hammer the phones all day, every day. They call everybody that could be potential prospect. There's no really like rhyme or rhythm into like how they're calling people. They just think that this BDR team is just killing it and meanwhile it's costing them so much money and their new logo acquisition is stalling out. Like they're doing pretty good. Quarter over quarter. It's consistent but it's not growing.

[Nick Flamini]

Right.

[Carolyn]

And how do you expect to grow? At some point you're going to reach like diminishing returns on this like BDR machine that you have going. Right. And our data tells us you should have more structure and intentionality behind your strategy of like cold calling people. Meaning that you can call completely cold people that have never heard of you or you can call people that are Warmer have showed up to your, have visited your website, have shown up to your events, have engaged with you somehow and prioritize those. I'm not saying don't call these other people, but when you start to build a strategy around like who is more likely to close, who is more likely to become an opportunity, then you can actually optimize what you're doing versus just like hammering the phones all day long, hammering emails and hoping that somebody is going to book a demo and then go on to become a customer.

[Nick Flamini]

How do you think? I'm just curious your thoughts on this. I have a theory that could be wildly wrong. I've voiced this publicly before, so I'm just totally committed and I believe it. With AI being integrated into outbound, in my opinion, very poorly. I think there's a future there, but I think the use case for it is extremely limited. But right now with the use of AI overexploiting, the volume of calls and outreach, I feel like that the connection rates and the outbound efforts are going to decrease over time from a lack of trust. And so do you feel like AI is going to have an impact on decreasing the success of that cold outbound effort or what are your thoughts on it? I mean, that's just where I think it's going. I think there's going to be more regulation behind identifying who's a bot and who's not on LinkedIn and through other media outlets. But for now the increase in volume from AI is so substantial from what people can do and the more companies that leverage AI, I think the lack of either trust or willingness to even answer and reply thinking that it, it's not a person will have a substantial effect long term. I know right now everyone's getting short wins from it, but I just don't think it's there yet. This is just my opinion.

[Carolyn]

I, I don't know. Some people might disagree with my stance on this because I think AI has a place in go to market and can do a lot of great things. What I don't think it can replace is human connection. And I've had this belief like for years that the best sales teams are the ones who build a human connection first. Think of any thing that you've purchased. Why do you purchase it? Is it because somebody like spammed you and you know, got you into the funnel, or is it because you've established like a really meaningful human connection first? And so I think some of the best and strongest sales organizations are built with the people who share that value and Share that philosophy and I think you can build in productization into your sales tactics. But at the end of the day, it really comes down to, I think, human connection and how effective you are from that point of view. But again, that's my personal view on it. There's my have a different stance and that's okay.

[Nick Flamini]

I mean, I just think it's so unknown. That's why I don't want to backtrack. I've had people change my opinion on it a few times in regards to like the level in which I'm convicted of what's the future? I do think that it's really hard to tell. I just wholeheartedly believe that. First off, I agree with your point, is that human connection is the number one thing. And if we look at creativity, well, I think creativity is going to be one of the most employable skill sets in the future. And it's because of that. I think that a lot of the AI products, if you're using Perplexity ChatGPT, it looks creative, but that's not really how people are creative naturally. And so it's going to be hard to replace that empathetic touch. It's going to be hard to replace what people are able to do fundamentally versus how AI actually operates on the back end. So I do think creativity is going to be one of the most employable skill sets for people. But more so without that personal touch, I mean, we got connected. I didn't send out some bot to just spam a bunch of thought leaders to try to book a podcast. We see a lot of AI outreach. Businesses boast about 2% pickup rates while ours is 30. Why are we discussing the success of a 2% response rate while we can make it up in volume? And so I think that the. It seems like it's efficient. But if we look back at, let's just go back to the unit economics, are we even tracking the amount of time it takes to make a connection and the revenue tied to the time that's allocated to that task? And I think if we had a better way of viewing that through a system that can organize it, you would know very quickly that just cold calling or using AI to call 10 times faster is just going to get you 10 times the result, even if it's bad.

[Carolyn]

Yeah. I have two thoughts on this one. I think with like the rise of AI and these AI agents and all of this stuff, we're going to have to find different channels to capture like the eyeballs of the people that we're Trying to sell to like email now is so fucking saturated, it's crazy. So to be effective on email, its own, like can of worms, and then you've got cold calling, which is another. But direct mail, is that something we're going to be seeing more of? I don't know. I think you're competing now for attention and AI is making that competition that much greater. So there's that. But I think the other thing that we're trying to solve for is when you're looking at like how you're prospecting and what's working and what's not, and you're able to see, like, why did we call this person? Did it go anywhere? You're able to understand, like the dynamics with each of those different reasons that you're prospecting somebody. So maybe your AI tool that you're using to call people is giving you a little bit of a lift. But like, are you considering the days in which how long it's taking you from the moment you started working them to when they became qualified? Maybe it's like five times longer. Right. Like, there's other considerations that I think a lot of people, they don't look at the nuances in the data to understand the side effects of that, understand the other implications. Whereas if you have a warm prospect, you might qualify them in 10 days versus like the 350 days it took you with AI or something like that. That's a hypothetical situation, but I mean, that could be a reality.

[Nick Flamini]

What I want to happen and what will happen is probably very different. I wish there was a way to just be human certified or to label everything as AI so someone knows that it's actually a person reaching out or not. Because I do think there's a large use case for AI in different areas. I just think for prospecting, it's still pretty limited in the way to leverage it. So I think it's here to stay. I just think that there's going to be a market for being able to prove that you're a person. We have a few strategic ways that we do go about doing that. Some of it involves direct mail, actually, and a lot of it is around events. Like if we go to an event, we're not going to sponsor an event, we are not going to go actually to the event. We are going to go to the area that the event is happening. We are going to go to the bars, we are going to go to where the what the real excuse is that people are leaving their house nowadays and we're going to Reach out ahead of time prior to going to the event and setting up meetings with people that are aware that we're going to be there rather than just aimlessly walking around and networking. If I knew you were going to be at the Saster event, we're going to reach out ahead of time. Hey, it looks like you're going to be attending this thing. We'd love to connect and we're going to meet them at 7pm at a cocktail hour. And so being more strategic with your time versus just aimlessly going to events or aimlessly blasting out these messages via email or with the AI bdr. This is like just my frustration. And maybe it's personal, maybe I'm totally wrong, but I just hate how all the intentionality and that personal touch that's being removed across the board. To me it just seems like a shiny object. So I think it's here to stay. I'm just not a fan. I need to be convinced otherwise.

[Carolyn]

Yeah, I feel the same. But I think like you said something that strikes a chord with me which is like doing things differently. And I think that comes down to like how we're actually measuring success across the go to market. Like we see it all the time in marketing. That marketing is measured on like how many leads they generate and kick over to sales. That is so flawed. I fucking hate that. I think it's so stupid. Pardon my language. But that's the problem is that when you're measuring a team on like lead volume, you're going to change what you do. You're going to go to instead of like trying to get 10 really like valuable meetings with a prospect around an event like you're suggesting, which is what I would suggest doing.

[Nick Flamini]

Yeah.

[Carolyn]

You're inclined to like spend 250k on like this big branded booth or experience or whatever you're doing to just like have a presence. And then you use like a, a lead scanner and get like 300 names and it's like woohoo. We hit our like quota for the 500 leads that we need to create. But they're just names. Like that's it, they're names. You're kicking them over to sales and then sales is saying these names are shit. And then of course you have now this divide between sales and marketing and everybody's pissed off. So I think it's comes down to the system and I think it's broken.

[Nick Flamini]

So this might be a little bit, I don't want to say elementary but maybe something that feels like beating a dead horse. You probably talk it a lot, but what you're talking about is going back to the departmental silos, finance being involved. Maybe we could talk about this just why finance needs to be involved. If the departments are siloed, typically we see the KPIs are and so marketing may be responsible for, let's say you have a CMO and they, they realize that what's happening is not the best of choices, but they want to keep their job. And so their job is to carry out the function of which the goals are set by either the CEO or maybe even the CFO in some cases. At this point they're just going to drive whatever metrics make that department's KPIs look successful, despite what the long term goal is for the company. And sales has their own set of KPIs. So then they're going to push back and do what they need to do. And so this breaking down the barrier and creating an alignment, what does finance need to do in order to unify these departments, get them to work together and to have KPIs that the end goal becomes the same thing. This way we're not just saying, oh yeah, we hit our MQL target. It's like, well what is an MQL again? And what's the value of that in the first place?

[Carolyn]

Yeah, you asked a few questions and no, I don't think this is an elementary question because I think so many companies are still doing it this way. Like measuring go to market by teams.

[Nick Flamini]

Which I, I hate then that's a better way to put it. I didn't explain it that way. Not, not to cut you off, but go to market by teams. Right, that's the core issue.

[Carolyn]

I think so, yeah. Because when you're doing it by teams, you're looking at like what team spent the money, what ROI did they get versus like when you look at it as a fact, like nobody's buying based on like how your team is structured. They're buying on a process of becoming aware about your brand, learning about it, engaging with it, talking to somebody and then getting into the sales cycle. And of course they're still having interactions throughout that process. So like if you think about it that way, you're literally looking at it like a process. And every team member is involved basically in every stage of that process. Like it shouldn't be like marketing over here, sourcing top of funnel leads, passing it to sales, sales works and passing it to the sales cycle and blah blah, blah, blah blah. Like that is broken. That's not how People buy, right? And so I think we need to start thinking about that differently. And that requires like a pretty big fundamental shift and of course alignment and that people need to all believe that and all get on board with it. And so oftentimes you have people like you've change makers in companies that want to do something different and unfortunately they can't get enough groundswell to actually do it. And so they're stuck otherwise they jeopardize their career or their future with that company. And so we see that all the time, right? There's just not enough momentum to actually create the change. And so teams stay stuck because it's a risk doing things differently. And so I think when that happens, my recommendation is rather than pushing to like try and change something that you probably can't change. People may not react well, but like take a leap of faith and try and find an organization that you are aligned with. Chris had the stance on a recent recording he did too. Which is sometimes it really comes down to alignment. And in some companies you'll have that, in some companies you won't. And so that is like point one. But you had asked a question about like where does finance sit? And I think from that point of view, like finance and the CEO, depending on the company size, like really needs to own and have involvement in go to market. Otherwise you're left with potentially like a CRO leading it. And then there's still this gap between like finance and go to market. And when you involve finance, at least with the Passetto way of doing things, you have the ability to look at like all of your go to market dollars and how that what kind of return that's generating for the business overall. Like most leaders don't have obviously aren't privy to like all financial information. Right. And so they are limited in some ways to really understanding performance against unit economics.

[Nick Flamini]

And so yeah, I do think there's a problem as well. If you look at how people learn marketing, even let's just walk through the traditional way. Somebody goes to get an undergrad, maybe they go and they get a post grad, then they get a job, maybe they're learning from other books and mentors. When has finance ever been taught to marketers on how to even interpret the information in the first place? And I think that that has to be in the very beginning of how and when you learn marketing, I think that people look at things the wrong way, they don't know how to interpret the numbers. And some CMOs could have probably identified the problem sooner. And Articulate it better to the CFO if they even understood how to calculate and read the information in the first place. And so we learned strategy and we learned the fundamentals of marketing, but nobody is teaching anyone how to read the information.

[Carolyn]

Yeah, it's a really good point. I certainly sort of like started my career not having understood that either. And like, I learned that obviously over. Over my experience and listening to Chris and seeking out information. But I would say the vast majority of marketers just are not revenue inclined or like financially inclined to really understand like, how to connect the dots between the two things.

[Nick Flamini]

I agree. And I, I just would like to see people learn this at an earlier stage. It's difficult once you start to understand it and then you go to hire internally. It's tough to see that somebody has a belief system, but no way to actually interpret what's working and not working because, yeah, it's very easy to learn philosophically how marketing can work and learn different rules and principles, but if you don't know how to read the information, it can be interpreted. And this goes back to some of the CRM stuff, right? If your CRM is messy and you're just compiling data, how do you even understand what's happening there? And that's why I really love what Passetto is trying to do with being able to organize it to have a more objective approach to reading that. But that's where I think that there's a big issue is just the, not necessarily the philosophy of marketing, marketing literacy from that standpoint. But marketing is so financially driven and understanding how things are effective or efficient and most people just don't know how to read the numbers. The only thing I ever hear is cact, ltv, cac payback. Okay, we get that. But it's way further and deeper than those things. And that does not. That just cracks a little bit open. There's so much more that goes behind it in for forecasting purposes. But that's something that I think if we can teach younger marketers this sooner, that's where the future gets bright for, for young companies.

[Carolyn]

I have like a interesting perspective on that. I used to have a very, like, not even that long ago, a couple months ago, I used to have this like, very strong stance that marketers need to have more financial acumen. And I've softened my belief on that because I don't necessarily think that marketing is the department or that a marketing leader is the person to like solve that problem. And not to say that like, I sort of straddle the fence on this one, because on the one hand I think that marketers should be like more financially savvy and have more sort of like financial acumen. But at the same time I also feel like it's not their responsibility to solve that problem for the company. Like it's. This goes beyond marketing. I think marketers feel the pain the most because they are the hardest department to track. But at the end of the day, like I think, I think you need a partner like Passetto or I think you need like a sophisticated rev ops function in house. I think that there are other people or roles to solve this problem and it shouldn't be marketing. Think of that like I guess the way that marketers were brought up and the education that they have. Many of them are creative, many of them are very strategic. Many of them like want to be doing the things in market to drive awareness, to drive demand, to create brand credibility. That is where marketers shine. And so I used to feel like as a marketer I gotta solve this problem. But I think now I've seen it so many times that I no longer believe that it's marketing that's going to fix this.

[Nick Flamini]

I think I can soften to that idea. And so part of that though goes back to why finance has to be involved. And so the other problem then is like if we reverse that, I'll be curious your thoughts on this because I think that's a really good perspective is who's teaching finance how marketing works. And that's the other side of the coin. And this is where maybe each department needs to just learn each other a little bit better. But having that third party objective way like you're saying, whether it's Passetto or someone else, I actually think that's the best option. And I think because again, we look for narratives and try to find the answers to what we want the outcome to be. And if you have somebody that is removed from your current internal operations, I think a third party is a great way to verify, hey, I know that this is how you're feeling about it, but this is exactly what we interpret. We're interpreting hundreds of other companies or hundreds of other data points. It's a lot easier to work with somebody that is not emotionally involved in the strategy. So I do like that. I like that from a sales point of view as well. But I'd be very curious to see how the cross, I don't want to say departmental function, but the education across departments can increase from both marketing to finance and finance to market. I do think that there's something there.

[Carolyn]

I think there just needs to be something to act as glue between the two teams. I don't know that they'll be able to solve it themselves without one bringing in like an objective third party person who's like, not roped into like internal politics or like bureaucracy or anything like that. Like you had said, emotionally tied to anything. So I think that's like one way of doing it. But I mean, we work with a lot of customers who, like our internal champion stakeholder at the organization is like Rev Ops or somebody in finance, the cfo. And it needs to be somebody who recognizes that, like, if growth is going down and like our acquisition cost is really high, like, it's got to be somebody to recognize that problem and want to do something about it.

[Nick Flamini]

It makes sense. I want to take a few minutes. I want to talk about a little bit more, just about Passetto, if you're open to that.

[Carolyn]

Yeah, of course.

[Nick Flamini]

It sounded like, and this was the case right when the company first launched, there was like an iterative process of where the focus was. And listening to the last episode that you guys put out, which I love, by the way, kind of like the new future of like your show. Everyone should go check out the Go to Market Live episode. We'll link that below as well. I think there's a bright future there. But can you describe what the future problems are that the company's trying to solve versus maybe what we thought we had to solve in the past? Because I think this iterative process is beginning to get more and more refined and it's exciting and I think people should know about it.

[Carolyn]

Thanks. Yeah, I would love to talk about that. So Passetto. I came in probably about six months after Passetto launched. And so at that time we were super heavy into like, advisory helping organizations optimize their go to market strategy. And we would do some data analysis to basically help companies like, isolate what their biggest problems or biggest levers are to like, improve growth. And so we did a lot of analysis and recommendations, but with every customer, we would reach this, like, point in time. Maybe like three, four months into our engagement, we'd hit a wall and we'd say, like, we want to make data informed decisions. We don't want to just like, make like educated decisions based on like our own experiences or what we know to be effective because every company is different. But we'd reach this point in time where we'd say, like, we need more data. Like, if we want to make like, decisions rooted in data, like, we need More of it. And so that's where we realized, like, a lot of companies, for example, had all kinds of opportunity data, but, like no contacts linked to it. So it's like, how are we supposed to know, like, how marketing is performing when like 60% of your opportunities don't have a contact?

[Nick Flamini]

Can I ask a question around that? Is that depending on. So you've got the opportunity level, but depending on who the contact is, could be why it's successful or not, whether we're contacting the right level of whether it's a C level executive, it has to start with somebody to work up the chain. That's what you're essentially referring to, right? Is like, who the contact is as it relates to the opportunity. So you could track who the right people are to reach out to.

[Carolyn]

Or that's one aspect of it. What kind of person are they? Like, what's their Persona? What's their job title? Understanding, like, who the ICP is. I think that's one part of it. But like, when you're marketing, you're marketing to people. People are having interactions with your brand, people are coming to your webinars, People are like, download content, people are visiting your website. And so if we want to understand the impact of the signals that people are giving to us, we need to be able to tie that back to something. Revenue. We're seeing revenue at the opportunity, at the company level. So we want to understand, like, what is the journey towards that happening? Like, what are the things that the people are doing? And so if you don't have people attached to the opportunity, how are you supposed to read that? That was my. One of my biggest challenges when I was in house is that we'd have all kinds of opportunity data. But I'm manually sifting through those opportunities to find the contacts and see what they did. And so that is one of the biggest problems there. That's one facet of some challenges we had around data. But ultimately we had realized that data is one of the biggest problems we need to solve for. We can interpret the data, we can tell a company what to do about it, but that's reliant on actually having the data. And so that's when we, like halfway through our journey. So that was sort of facilitated through a software product, which we still have and we still support. That's one sort of component of it. But then the other piece of it was trying to solve for the data architecture. And that's now what we do too. We sort of have like two components of Passetto. We have now where we help companies install a proper data architecture in their system to be able to actually get all of the data inputs we need. And then we have this other piece, which is the software and helping companies, like, make sense of the data and improve what they're doing in the market.

[Nick Flamini]

I love it. Yeah. And so thanks for clarifying on the other question. Now with what you're doing, are you. Is the company limited to what platforms that you can collect the data from? Are you working with? If somebody's interested in working with Passetto, if they're using HubSpot, Salesforce or. It could be a bunch of things, unfortunately, way too much. Usually I think the tech stacks are insane right now, but. But with that being said, can you pull data from everything? How are you guys doing that?

[Carolyn]

We primarily support Salesforce and HubSpot right now. Yeah. We don't really touch the other platforms at the moment.

[Nick Flamini]

Well, those are two of the big ones. So I think you're in the right spot, which is great. So we've got a couple more minutes here. I just want to wrap it up with, like, what's the future looking like for the company and what are some things that maybe are a little controversial that we're trying to tackle in the industry to get out there into the world?

[Carolyn]

I'm going to keep perpetuating and like, banging on the drum of Go to market is broken. And I know that we are going to get a lot more traction once people start to acknowledge and, like, want to do something about that. And so I feel pretty good about Passetto sort of like naming and claiming the industry and like, what we do. And I think most companies are going to like, default to Passetto to fix their problems and to help them optimize. I think now we're just sort of like creating momentum and getting more people on board with what we are doing. But I know it's a real problem because that is sort of reaffirmed in like the number of DMS I get on LinkedIn of people saying, like, I feel this, I feel this problem, you know, help me solve it, or like the number of inbound requests we get of people who want to come on to work with us. So the future is going to be super bright for Passetto and I can't wait to see what's in store for us.

[Nick Flamini]

Cool. Well, me as well. And so I think we're just right here at time, so I think this is a good place to stop. And I just wanted to thank you for taking the time to be on the show. I think this is valuable. I hope everyone else enjoyed it as much as I did. And thanks for being here.

[Carolyn]

Thank you. I loved you reaching out and asking me to join, so I appreciate the opportunity to. And I'm always down to do this kind of thing.

[Nick Flamini]

Awesome. Well, everyone, the links will be in the description below. Go check out the Go to Market Live. It's a weekly webinar you guys are doing. It's also in podcast form, correct?

[Carolyn]

Yeah, yeah. Weekly show, 1:00pm Eastern, every Tuesday. If people want to show up live, we'd love to have you.

[Nick Flamini]

Yeah, go attend. Go check it out. And Carolyn, thanks again for being here today.

[Carolyn]

Thank you. I appreciate it. Thank you.