Outbound Sales is NOT Just Cold Calls. If You Hate Outbound, You're Doing it Wrong ft. Ross Nibur

Ross Nibur emphasizes the importance of objective, tangible milestones in the go-to-market process. He argues that subjective sales stages like 'proposal' or 'discovery' break down as a team scales from 5 to 500 reps. Instead, organizations must track concrete actions—like a quote sent or a contract signed—to maintain accountability and pipeline predictability. The conversation also dives into the realities of outbound sales, dispelling the myth that 'outbound is dead.' Ross points out that the real issue is a lack of effort and personalization, paired with wildly unrealistic conversion expectations. When reps rely on generic email cadences instead of offering real, upfront value, they fail to cut through the noise. Finally, Ross shares his fundamental tech stack for growing GTM teams: a reliable contracting/quoting tool, automated activity capture, and a data warehouse. By combining these tools with clear coaching and product-led value (like HubSpot's website grader), sales leaders can transition from constantly working in the business to strategically working on the business.

Discussed in this episode

• Why the tangibility of GTM processes allows for measurable cause-and-effect improvements.
• The danger of using subjective milestones like 'proposal' or 'discovery' in your pipeline.
• Why measuring objective actions like quotes sent and contracts signed is critical for scaling teams.
• Delivering upfront value to prospects before a contract is signed using tools like HubSpot's website grader.
• The difference between adding actual value and just slapping a generic ROI calculator on your website.
• Essential go-to-market tech stack priorities, including CPQ, activity capture, and a data warehouse.
• The reality of outbound sales conversion rates and why teams set themselves up for failure with unrealistic expectations.
• The necessity of personalization and deep account research in a modern outbound strategy.

Episode highlights

1. 0:00 — Outbound sales is hard, but it's not dead
2. 2:15 — Ross's background from line cook to GTM operations
3. 5:30 — The biggest mistake in scaling GTM motions
4. 9:45 — Why pipelines become black boxes at scale
5. 13:20 — Delivering value before the contract is signed
6. 17:00 — Top three technologies for a GTM tech stack
7. 22:15 — Why outbound is struggling with bad expectations
8. 26:40 — Working in the business vs on the business

Key takeaways

• Replace subjective pipeline stages with objective, measurable milestones.
• Build value-add tools for prospects instead of generic ROI calculators.
• Expecting 15% conversion on outbound is a recipe for leadership failure.
• Prioritize contracting tools, activity capture, and a data warehouse.
• Make outbound work by combining marketing awareness with personalized outreach.

Transcript

Um people think about it is bad because they suck at it. Right? Um outbounded is hard. Right?

It's extremely hard. And I think a lot of teams go in with first is unrealistic expectations. Welcome back to another episode of The Revenue Reimagine podcast. Today's a special one.

We get to go back in time, um to chat with one of the smartest go-to-mind markets that I know. Certainly someone that I consider a mentor who has given me more knowledge than I can share in 30 minutes. Uh, we have Ross Neiber, who is currently the director of onboarding operations at Toast, but that is like not I don't even feel like that does you justice, Ross, and we'll talk about this, but all of the roles you've held with Toast, outside of Toast in RevOps, Go to Market, head of sales. Like, I don't think there's anything in Go to Market you haven't done and you haven't touched and that you can't do or touch.

Um, so I'm stoked to have you here to talk a little bit about all things Go to Market. Yeah, Adam, thanks so much for having me. I'm super excited to uh, to join and chat with you. Um, the flattery might be a little bit too high, right?

I'll let your listeners decide from the end of this if I actually know what I'm talking about. Um, but that will be for them to decide, not me. Adam always hypes up all the guests, so don't feel that special. No, I'm just joking.

Well, and he said Go to Market to hype you up. He said Go to Market Minds, they said Go to Market. That Go to Go to Minds or something like that. I we'll have to we'll have to rewind in the in the beginning of that.

But um, going back to the Go to Market, Ross, um, what's your favorite part of the Go to Market process? Like you've done everything from sales to operations to onboarding. What's your favorite part of it? And why?

You know, Dale, I I think it's how tangible it is. Um, if you look far enough back in my experience, I cut my teeth in the restaurant and entertainment industries. Uh, working as, you know, whether back a house, I was a knife for hire for a long time. I did a lot of general manager and kitchen manager work and then did a lot in entertainment and nightlife.

You cooked? You were a cook? I I I I was a cook and I was a knife for hire for a long time. Ross can still cook.

Yeah, right? Um, I'm still pretty, I think I'm still better at cooking than I am at Go to Market. Let's put it like that. Um, jokes aside, the the thing that I think gets me so excited about working with Go to Market teams is that you can really boil down what somebody's doing into a set of actionable steps and processes.

Right? This is stuff where you can really see cause and effect. Um, if you make processes like quoting or contracting, lead generation easier and faster for your team, you can measure it directly in output of revenue and impact to the business and the bottom line. Uh, that is very reminiscent of trying to structure a line in a restaurant or come up with the the load-in load-out schedule for an event.

There's a tangibility to what we do that is not as always always as clear for other teams or other departments that I've worked with and engaged with. And that tangibility, I think, particularly, um, when we talk about technology teams, is something that we should always come back to as leaders. Um, I've worked with a lot of of different groups who sometimes get disconnected from that what are people doing at their desk to drive revenue forward? What is the series of action and cause and effect?

But at the end of the day, if you go and talk to a seller, they can always tell you the things that are the hardest in their life or the most challenging in their systems and technology. And that that ability to just get back to Earth and get into reality, it's what keeps me doing this kind of work, um, at Toast and with other teams. Yeah. The hardest part of my day is dealing with Adam, so do you have a do you have a solution for that one?

Um, I'll send that to you in a text. I don't want that live on a podcast. Ross is the only person I know who curses more than me, by the way. Um, I I I do remember very vividly a a meeting, Ross, where we had a jar, I I think it was the DCNSSM, if I'm not mistaken, uh, where we had a jar that every time Ross dropped an F-bomb, Ross had to place money in said jar.

Um, Yes. So, the the I was Go ahead. Go ahead, Adam. The person who told basically taught me it's okay to curse.

Um, whether it is or not is a different story. Ross, you've you've been part of a good amount of scale, um, at many companies. And you've seen things go right, and conversely, I'm sure you've seen things go wrong. I'd love to talk about like the biggest mistakes that you see when people are trying to build/scale a go-to-market motion that are should be so obvious, but that aren't, that you're like, dude, like, how the how how the fuck did you do this or not do this?

Um, I think it really comes down to definitions. Right? In in where I see people blow things up in their face. And Adam, we've had a lot of conversations around this in the past, particularly about pipeline management and the milestones in your sales process.

The mistake I see teams make again and again is making those things subjective, aka open to interpretation by individuals, um, and really flexible across their growth, where they then add more and more and more into their process without thinking about how they take it away. And again, going back to changeability and trying to make this stuff as simple as possible. There are milestones that we can all measure about what's happening with our customers that are fixed, that will not change as we grow, that give us a very objective lens across different product lines or different markets into the behavior of our team. To give you guys an example, right?

We always know if we send a quote. We always know if we send a contract. We know if it was signed. Yeah.

Right? What I often see leaders doing is talking about milestones in between there that are again, more subjective. How often have you talked to a team where they've got a proposal phase? Right?

Where they've got a discovery phase, where what actually happens in those steps mean a lot of different things across the different product lines. And there's no specific action that will again, be repeatable and scalable that you are measuring to know if you hit those milestones. And this all ties back to then managing that funnel and the business as it continues to grow. Because the playbook is going to change.

Right? You might need to do discovery differently. Particularly as you move up market or down market or move different products in or out of your portfolio. But what won't change is how you're going to still send a customer a quote.

Right? And that gives you then very clean ways of measuring cycles and understanding behavior between these different business units. Because those behaviors, that's where go-to-market leadership needs to intervene, right? If you see that your, you know, I'm going to use quoting to contracting cycles as an example.

That might take four times as long for your mid-market enterprise team as your SMB team. And that's okay. But if then you're looking at individual reps and one person's doing it in 45 days and somebody else is doing it in 200 days, right? There's coaching that's available there.

And that transparency and objectivity of the milestone then lets us as leaders understand where we need to lean in and coach. Because that's what I think differentiates really great sales leadership. Do they understand their funnel in a way that lets them all have a shared understanding of reality? Do they then use that data to work on the things that are not objective, but totally subjective, right?

The way you talk to a prospect during discovery, the way you talk about a quote, the way you structure a proposal. Those are the things that then those leadership teams need to be in control over. Before I go into part of why I think this is so important for scaling teams in particular to think about, is that passing a sanity check from you two or do you want me to clarify anything that I was just talking about? Oh, look at you, you're still a true seller.

I fucking love that. I love the checking. Never doubted, man. Dale, like, like we literally can package this up and like send it to um, so to me, it's it's it's I think it's so important.

I think it's something that's not talked about enough. Um, like especially when you're talking about proposal stage or discovery stage or whatever, like what what what are you doing in that stage? Like, great. Okay.

Like you're you're in proposal stage. They have a proposal. Now what? Um, Yep.

Like and does your do your sales stages align with your buyer's journey? And I've said for a long time, like a lot of people like to over-architect the sales funnel, right? Like we have a stage for everything. And if I were to ask Ross, my customer, where are you in your journey of purchasing this product?

Does what you say, not word for word, but map to what my my stage is in in one word. And nine times out of ten it's not because we've over-engineered this fucking sales process that has nothing to do with the buyer's journey. Well, and and this goes back to again, why does this matter so much for scaling organizations? Is because the leadership team is going to grow and change, and the responsibilities of leadership are going to grow and change.

Right? If you're VP of Sales with five sellers and you are their direct coach, you can be really close to what's happening in that proposal stage and working with every single one of them on it. Yeah. Once you've got 200 sellers, that's a pipe dream.

Right? That's never going to happen. And you need to then be able to measure the performance of your directors or your VPs or the people under you in a way that continues to be consistent and that you understand where they're delivering coaching or not. And again, this idea that if you keep moving those milestones around as you grow, it's much, much harder for you then to understand how performance is changing.

And as you introduce these new products and these new groups, that lack of definition and clarity becomes extremely painful. Right? And like Adam, I love what you're pointing to in the like, well, do we need a proposal stage, right? I think that I always want to kind of push on leaders to think about is the bookends of that process clear and clean?

Do we understand in a systematic way when it starts? Can we understand in a systematic way when it stops? Are those things going to not change, those milestones as we continue to grow? And that that's what makes a good stage in your go-to-market process.

If you can't answer those questions, probably not, right? It's not an accountable or actionable thing that you should be measuring, because again, as I you go from five sellers to 500 sellers, all of a sudden you're going to need to rework all of those processes and it's not going to go well. Additionally, for like the CEOs on the call that are listening to this and not just the sales leaders, right? You need that so you can change managers, go-to-market leadership comes in and out.

Right? Let's be candid here, guys. This is one of the highest turnover roles in any organization. 18 months, give or take.

Have you heard that? 18 months, right? 18 months, give or take. And so like, why should a leader?

What's the average tenure of a co-founder, Dale? How long how long how long am I going to be tenured here? Six more months you got. All right, fair enough.

All right, six more months. That's better than I thought, honestly. But um, but look, like that's why if you're your CEO, you should care about this. Because if those milestones are objective, then all of a sudden as that leadership changes, you can really compare.

Are the programs this new leader is putting in place to drive change effective? Or are we just moving the deck chairs around so that we're talking about this funnel in a different way that isn't actually changing the outcomes our customer is experiencing along the way. Or the things that are driving our revenue funnel in the first place, which is why we all care about this. Right?

You don't care about getting to a quote because a quote is the end of the journey. You care about how many quotes you send and how many contracts you send, because those milestones let you predict and forecast your revenue. Actually, there there's two paths I was going to go down, but the last part you just said, I'm going to go down this path. Um, because I think where sellers get this wrong all the time is that we're always worried about when the contract is signed, and the customers could give two fucks when the contract is signed.

The customer really wants to figure out when they're going to get value. And so, yeah. Not only should we be tracking specific milestones through the buying process. So we do a lot of this with mutual action plans, joint engagement plans, and get really concrete on each part of the journey because both the buyer and the seller have activities that need to be accountable and accounted for in that process.

But so many mindsets as sellers is I got to get to the contract. When I get the contract signed, and the customer really cares, like, when am I going to going to go live? When am I going to get value? When are when are my uh, the people going to use and and and see the product or service to value?

So, with that being said, what types of technologies have you seen being able to be leveraged in this process outside of like a typical CRM? Are there are there technologies like Gong or conversational AI or what are the AI technologies that can help leaders get better insight into helping them make these decisions? Because you're right, five sellers is great. 200 sellers, not so great.

How can you how can you bubble that up with that? Yeah. Yeah, really, really great question. And I I want to answer this in two ways, right?

Because there's two different things that you're pointing to that I think are both really interesting. The first is, how do we get value to our customers faster? And can you do that before they're even signing a contract? Mhm.

Yes. And I think decisively, the answer is yes. The answer is yes, right? I will point to things like what Mark Roberge did over at the early days of HubSpot, the website grader.

Are you guys familiar with this playbook? Oh yeah, 100%. Absolutely. Okay, awesome.

For your listeners who aren't, right? HubSpot put out a basically lead generation tool, which was a website grader, where it would go through your website and basically say, how good is this, right? How optimized is it for SEO? Is it easy for customers to navigate?

How easy are the clicks? And give you a grade at the end for basically like, how ready are you for HubSpot? With a bunch of actual insights into things you could change about your website to make it better, whether you bought HubSpot or not. You are in a value conversation immediately when you answer the phone, right?

If you are calling that MQL, that is a better lead because they are in cuts with your product and they are getting value. And so, Dale, like, the one thing I want to like not push back on, but reframe a little bit, is that like we can work with our product teams to make sure that customers get value before they even signed a contract. And that will smooth out the road to getting to that signed contract because they both will better understand what your technology will deliver and they've already received value from your business well in advance of having to sign a check. But also, sorry.

No, I'm going to go on the paper because paper is one part of it. But I also think it's a a people thing as well because if you bring CS into the sales process, now you can like double click, they get product knowledge even before they go into the sales cycle. But if they're in the sales, in the middle of the sales cycle, when you're giving a proposal, bring your CS team in. So now you're like integrating the entire go-to-market.

And so now it's not only it's not only product, but it's also people. Go ahead, Adam. Yes, and yes, and yes. But a lot of people, and Ross, I'm curious your thoughts, think that by adding value is putting a shitty fucking ROI calculator on their website that says, if you use my product, you're going to save or make this much money.

That is maybe I'm wrong, that is not value. No, it is not. Right? Because listen, I want to juxtapose that with the website grader.

Right? If you put an ROI calculator that says, this is how much more money you'll make if you sign your contract with me, you have given me no value. If you give a grader that says, here are the things that are bad about your website, go change these seven things, oh by the way, you wanted to happen better and faster. Right, do it with me, don't do it with me, but go fuck and do this.

But go do this. You've added value, right? That's the difference between those two strategies. Right?

And listen, it's easy to get lost in the sauce because a lot of what we're talking about right now is product, right? And how is go-to-market leaders, we need to partner with our product teams so that they are building things that add value before a customer signs on. Right? And that's part of why I think that's so hard for a bunch of different leadership teams.

They have a go-to-market team that's talking about how do we add this value earlier, and all that they can do is put together a good spreadsheet that shows ROI. It takes partnership with people that can actually go and build those tools and create that innovation in order for you to really get there. And depending on the nature of your team and your partnership with product, that can be a really long road. I I think the best teams I've worked with, though, the product leadership and go-to-market leadership are tied at the hip, right?

They really understand one another and are getting consistent feedback on, why are we losing, why are we winning, how do we introduce value faster, how do we cut down on cycles, what are the blockers getting people into product? That partnership only becomes more and more important as you grow and you hit product market fit. But like, starting early, like, you know, HubSpot introduced the website grader very early in. Yeah.

And that was a huge channel for them to then grow and add value. And so like, I just want to point to like, there are reasons why teams do that approach, Adam, like, they build an ROI calculator because they can't quite figure out what else they can do with the resources that are at their disposal. People buy from people. That's why companies who invest in meaningful connections win.

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You want to talk? Go for it. I always want to talk. So, when you look at building and scaling, um, particularly in the economic climate that we went through, um, going from what was a very robust climate to COVID, and and COVID recovery, if you will, and work from home, not work from home, like where are you seeing the need for like critical adjustments and where where are people failing at this from a go-to-market perspective?

You know, that's I I want to actually hearken to some of what Dale was asking, which is the technology you should put in place along the journey to make sure that you have really good tools for a remote workforce. And tools that also drive efficiency and understanding of what's going on in your funnel. Because what to like paint a picture for a second. There's a lot of teams that I talk to where their pipeline is really a black box.

All they have are subjective measurements, the input of a sales rep that says this is going well or this is not going well. And none of the kind of automation of staging that's tied back to real cause and effect that lets them know what's really happening along the way in a way that's auditable and measurable. That's the same thing you should be thinking about of technology you put in place, right? Whether we're talking about activity capture and automation tools, the Salesloft, the Outreach.

io's, everyone that's in that space right now, so that you understand not just what your sales rep says they're doing against their pipeline, but the actual activities that are happening and the enforcement of best practice towards those activities. Tools like Chorus or Gong that help you interpret and understand call recordings and what's happening within them. Or knowledge access tools, right? Uh, I'll point to vendors like Glean or Intercom that let you provide both better information to your internal employees and access to knowledge, as well as potentially customer-facing spaces where if they have a question, they can go in and get information quickly and easily from an AI.

All of those things give you a lot of signal information about what's going on through and without your funnel that you can then analyze to understand what's happening. But really critically, it lets you pick up any loose ends, right? Are reps effectively working their pipeline? Right?

What does effectively working your pipeline look like? How many activities does it take? When from those call recordings, you can get a tremendous amount about customer sentiment, right? Are calls going well?

Are customers happy? How often are they mentioning your competitors? What's the sentiment when they talk about your competitors? Right?

That is a gold mine of information as you continue to grow. And with this shift, Adam, to your point into this like climate where we need to be really focused on profitability, we need to be driving things forward effectively. Having that level of understanding is a competitive advantage. Right?

If you know with surgical precision, our SLA should be, we call you this many times before we close lost an opportunity, right? You will squeeze every drop of value out of your pipeline. Right? And also then be able to look at your team in the face and go back to the coaching, right?

Adam, I see that you called Dale twice and then you let it sit for four months, and then you called him once again and then closed loss date. You mean it shouldn't be subjective? It shouldn't be, oh, I think I should call them four times. I think I should call them three times.

Right? And also, I shouldn't have to take it on faith. I shouldn't have to ask you, did you follow up with Dale? Right?

I should be able to trust, but verify whether or not that actually occurred. And again, this is about creating visibility as you continue to grow. Right? Because let's go back to my example of going from five reps to 500 reps.

Right? It is so easy to manage that pipeline in a hands-on way when you have a small team. It's really easy to share knowledge about what those best practices are when you have a small team. True.

But if you don't put those things in place then, as you go to 20, 200, 2,000, all of a sudden, that is way harder to cascade down. And I feel like it's a soft spot for a lot of go-to-market leadership who get put in place because they're the best seller on their team. Right? What they're really good at is closing deals.

They understand. Oh, we we could have a whole show on this. Right? We we totally could, but it's why I'm pointing to this.

Right? This is the difference between showing up and being a sales leader and being the senior-most sales rep on the team. Right? And if you want to grow with your organization to that level of scale, you have to be thinking about how you're measuring these things and creating that completely objective understanding of what success looks like.

Dale, though, to to point to the answer your question, right? Those are the things the most important drum beats for a team to really have in place. Right? Along with any periphery tools that are uh, automating the actual quoting contracting process, right?

Like any team that doesn't have some version of CPQ or DocuSign at this point, like, what are you doing? Like don't have your team putting those things together by hand, that's just silly. But so so let's double-click on that a little bit because a lot of like startups or founders don't have unlimited budgets for like tons of tech. Like if you were if you were spinning up something right now, what are the top three things that you would have in your tech stack for your go-to-market team?

And let's let's focus on sales. I love that question. Oh, yeah, I like that question. Um, so like my my top three are going to be.

And forget about CRMs in there, like we have a CRM. Damn, I was about to say CRM. I was about to say CRM. Um, because you do need one.

Um, But which one? I have to ask. That's a whole separate again, a whole another show. They may not want to get into the conversation.

Who are we sponsored by? Just kidding. Um. I don't know who.

How do you guys feel about Speerow? Um, no, pulling pulling back out of the rabbit hole. Um, the I want to start with with contracting and quoting technology. Right?

Um, it's it's a cornerstone, it's table stakes, right? It's back to what I was saying of like you've got to be measuring cycles in a way that's subjective. If you don't have a tool like DocuSign that tells you with surgical precision when you send a contract, when you sign a contract, right? It's like non-negotiable.

You got to have that. You know, sure if you have less than ten customers and you're signing paper agreements, that's okay. But Ross, are you saying you're measuring that you should be measuring time from contract sent to contract signed? Uh, yes, and volume of contract signed, right?

Um, that's a milestone in everyone's process that we really need to measure and understand. I know it's not sexy or glamorous, right? And Dale, I'm sure you were hoping for a more glamorous answer than that. But um, it's back to kind of out-bounding in practice.

No judgment here. Dale's not a glamorous guy. No judgment here. Right?

But like I think we need to do the non-interesting stuff before we get to cool stuff, right? And and so that's why that's going to be number one on my list. Number two on my list is going to be anything to capture activity, right? Um, and listen, just to be clear, you don't need to go full boat and go buy Salesloft to get activity capture.

Right? Baseline vendors like Zoom Phone or Dialpad or 59, anybody that you use as a telephony system will have an integration to your CRM and can do uh, click to initiate or CTI, which is any phone number in the CRM becomes clickable and dialable and it will log the activity and come. Oh, come on. Just call through your cell phone and your reps will log it.

Yeah. Yeah. Well, they're totally going to not do that, right? But like listen, like, you know, I hear that a lot, but they don't do it.

They don't or they or they bullshit. You're you're 100% right. Right? And so, well, like there's good, better, best in this space, right?

Like I would encourage teams to take a hard look at tools like Salesloft if they're at any level of scale and have the budget to afford it because the added features of sequencing automation, texting, emailing, compliance are just become more and more important. But like, at a baseline, like are you measuring the text messages, emails, and phone calls? And you can again do that with tools that are are very inexpensive or free or part of existing products that you already are buying to simply power IVR or your CRM. Right?

I'll use the other example like we're assuming that you have a CRM. Almost every CRM has a BCC function where if you add an email address to the email, it will automatically log it for you. And so like we don't have to boil the ocean to get this kind of stuff. Right?

The final thing, which is again going to be non-glamorous, is a data warehouse, right? Um, as much as I would love to be pinging like Chorus or Gong or one of those tools, the ability to analyze and interpret information um, is really critical. If you have an analytics function, um, being able to work with them in an effective way, get this information into a decen democratized space, um, is going to continue to be a competitive advantage. In particular, because I think to really understand our our customer and their journey, we don't just need information from the CRM.

Right? We need information from product. And that's why that data warehouse becomes so important. Right?

That becomes the space where you are bringing together the information on what's going on in my go-to-market, what's going on in my product, so you can create coherent analysis and understand. Interesting. The data warehouse was never something I thought about, but it's that's interesting because I always think we have enough of the data inside of the CRM, but that's not really true because it merges over through marketing and potentially customer success, so there's a lot of other data that's not getting captured potentially, so. Interesting one.

So. So much. Um, we're almost at time, but I want to I want to go a little over because I'm super curious your thoughts on something. Um, there's been a lot of changes related to outbound recently, right?

Um, and whether that be, you know, outbound in the field, whether that be specifically cold outbound, you know, BDRs or AEs that are, you know, in a tech-forward world, you know, cold calling, emailing, is it one sequence, you mentioned Salesloft and Cadences, like there's a lot going on with specifically cold email and cold calls. From like a go-to-market perspective, we'd just love your thoughts, like, is is cold outbound dead, or is there a right way to do cold outbound? And if so, what is the right way to do cold outbound? Yeah, uh, I'm going to be as direct as humanly possible on this one.

Um, people think about it is bad because they suck at it. Right? Um, outbounded is hard. Right?

It's extremely hard. And I think a lot of teams go in with first is unrealistic expectations on what an outbound funnel is really going to look like. Right? Like, back of the envelope, you're going to convert less than one percent of your accounts in an outbound motion.

Right? If you're like a god-tier outbound machine, it's like three percent. Right? But like, that is if you go and sit in the board room of a lot of these startup companies, they'll be looking at their MQL funnel converting 20 to 30% and be like, whoa, we'll probably get 15% on outbound.

And like, it's that their expectations are bad, right? It's not that it's not possible. It's that they are not grounded in how actually hard it is to execute. And then candidly, what makes a good outbound strategy is personalization.

Right? It is a lot of work. Right? This is not a set it and forget it machine, right?

I I see to your point, I get, I don't even know how many blanket email cadences where it's the same generic thing. All day, every day. All day, every day. My inbox is.

Hi Ross, I see you live in Vermont. That's not personalization. Right? And it's my title from three years ago, right?

It's not personalization. Um, outbound takes time. It takes effort. And so if you want to build a really successful outbound machine, right?

You need to be very tight list of target accounts, where your reps are spending the time and effort to understand this business, what are their needs, who are the people, crafting their messaging. If you work in an SMB space, going on site and trying to get time and attention with them, calling them, emailing them, sending them handwritten notes, who cares? But like, the thing that I feel like teams under index on is teaching their teams to personalize the experience that way and instead allowing them to just use generic cadences against lists of thousands and thousands of of potential customers that will never reach them the optimal performance. And again, just complete disconnection from the reality of what these conversion rates really look like.

Because that's where all of a sudden you have all of this conversation around outbound is dead. Right? Because they teams either are not doing it well, or they're just going in with a really bad expectation. Is that what you guys are seeing as well or or are you feeling like it's a different root cause for for this whole outbound is dead conversation?

I mean, I 100% think it's because people fucking suck at it and aren't willing to put in the work to become good at it. And both on the personalization side and on the laziness of a tech stack side. Like if you're going to email from your primary domain and send out a thousand emails a day and like you're you're screwing yourself. Um, if you're going to get Dale on the phone and like, hey Dale, my name's Adam and am I catching you at a bad time?

Yeah, you are. Click, like it just doesn't work. I actually I actually think that this is a leadership problem. Um, I think it starts at the top and people are used to doing, you know, X number of activities equals Y number of, you know, calls, equals Y number of meetings.

Like that just doesn't like that doesn't convert in today's world. Like the unit economics isn't like it doesn't convert for me anymore. So, do the work in the front end, but that just is more of a long tail strategy for your outbound motion. And do investors and CEOs and heads of sales have the patience to go through that process.

And my gut is 95% is no. You know, and and Dale, I want to just point to something. It's not that you can't back into that kind of math. It's are you being grounded in realistic in your expectations?

Right? Like, you know, if an outbound rep makes 100 phone calls in a day and they book one meeting, that's a pretty good day. And that I think a lot of teams are expecting much, much higher velocity than that. And so it goes back to the need to be really smart about where you're putting those resources.

Right? If you are building an outbound model at a and have a terrible CAC to LTV, right? What are you doing? Right?

This is going to be really expensive. It's never going to pay itself back. It's going to be really hard, right? The good thing about outbound is it's in our control.

Right? We as a go-to-market team can just pick up the phone, we can go do more work, we can go evangelize. It's as much a marketing function as it is a sales function. Yeah.

And that's what I was going to say. Like you need marketing to like for outbound to be successful, you need awareness and marketing. And like a lot of people will pick one or the other. Like, oh, go do outbound.

And I always say, like if you have the sales team do outbound and you're expecting them to do the awareness, like it's going to take you 18 months. Wait, wait, wait, wait a minute. You can't just do cold outbound without any brand awareness and expect people to answer the phone and be falling over to talk to you? You don't say.

I'm shocked. Right? Look, I I think this is back to what we're talking about earlier in things like the website grader and adding value earlier in your funnel. Right?

What is your outbound team even armed with? Right? Because if the only thing they're asking for is, please, please, please sir, give me 30 minutes of your time so that I can give you my generic pitch and move on, people are not going to be excited, right? Give your outbound team things to offer, right?

Whether that's the kind of of tools that we're talking about, an event that you're hosting, an e-book that your team has written. Combine your strategies. Yep. Right?

Because the more that you can then say like, this is the toolbox that I've given to my outbound rep, where they're adding value in that first phone call, the higher those conversion rates are going to be. And again, they're going to be they're going to be bad, right? They're not going to be your inbound funnel conversion rates. But there will be conversion.

You we can find customers that way. It's about are you targeting the right customers? Are they going to be big enough to make it profitable? Are you setting the right expectations with your team on board on how hard and how expensive that process is really going to be?

Right? If you can be grounded in those things and and look at the math and say this looks right, go for it. Right? And then just keep measuring it to a lot of what I'm saying on this this conversation.

Right? If you then are measuring all those phone calls, all those emails, all those conversion rates, you know how your outbound funnel behaves differently than your inbound funnel, you can really predict and forecast it. Right? It still works, but you've got to be grounded.

So, what I've heard, like my number one takeaway today, and correct me if I'm wrong, predictability, process, leads to or excuse me, process leads to predictability, which is going to lead to repeatability. You cannot, no matter what the market is, no matter what the financial situation is, no matter what stage you're at, if you don't have the right tools, if you're not tracking the right things, you're not going to be able to grow and scale your business. Absolutely. And I will add one other thing though, Adam, which is this is your job as a VP of Sales.

Right? Where again, I think people get lost is because they're so busy in hypergrowth, worrying about the next contract they're negotiating. The the next board meeting that's coming up. They are not sitting down and doing this kind of operational work.

Yeah. And that if you plan it early, it only has to happen once and then you can grow it. Um, and then stay true to it. Yeah, it's it it Dale and I talk about this a lot.

It's um, are you spending all your time working in the business, or are you spending time working on the business? And listen, we're we're guilty of it as well. We just talked yesterday how we need to block out time every week to work on the business because we're so busy in the business, which and just the spirit of being transparent with the listeners, like, no matter where you go and how high you go, like, you have to have this fundamental mindset and it has to be front of mind that you have to block out that time, or you are going to fall into the trap of the rat race. Yeah.

And look, it tells you who you need to hire, right? If you are a VP of sales that's spending every single day in pipeline reviews, you need managers and directors under you to help take that work away. Right? And when that work grows to the point where it's become your full-time job, it's pretty easy to go to your leadership team and say, I need to hire a head here and take this on so I can keep working on the business.

Right? But that again, it falls back to us as CROs, as VPs of sales, as leaders to create that time and that space and that understanding of what what our expectations are. And then look, again, I want to want to close on the it's also on us then to keep those rules of the road the same. Right?

It's so easy for us new leaders come in, new ideas come in, to add more and more and more complexity. And that there is a lot of power in keeping these things simple, right? It's why so many of the examples that I tried to give today are things that are fungible and non-movable, right? Tell me any sales team that's out there that doesn't have some equivalent of signing a contract.

Right? Tell me some sales team that doesn't have the equivalent of sending a quote. Yep. Right?

They they don't exist, right? They are these are are milestones. And again, like if you're a truly e-commerce team, like maybe those milestones are a little different, but there will be milestones that you can talk about that won't change as you continue to grow. And if you can tie yourself down to those and then hold yourself there, it's going to really help as you go through large incremental growth by creating that shared understanding of what is your funnel and how do we talk about success.

100%. I love it, man. Let's um, let's do some rapid fire. You down?

Yep, bring it on. All right, ten words or less. Early bird or night owl? Night owl.

What's the first app you check when you wake up in the morning? Uh, my email or Slack. Don't tell my wife. What's the one tech gadget you cannot live without other than your phone?

These headphones. They're basically glued to my head. What's one thing Is that is that is that why they're they're there's you have like you could see mine because I need a haircut, but like you you have the headphone badge? I I definitely have the headphone balding spot going across over here from the rub.

That's for damn sure. What's one thing you know about Adam that no one else knows since you worked with him for so long? Ooh, ooh, good one. You know, Adam's favorite bar in Boston is the Oak Room and uh, if you sit there with him long enough, you will drink an unreasonable number of Manhattans.

Or old fashions, depending on the day. Or old fashions. Yeah. I do I do like the Oak Room.

Ross, what's the one thing you do to unwind after a long day? I uh, I walk in the woods every day. Um, you know, I I live up in Vermont now, I used to live in Boston, um, but I take my dog uh, for about 30 minutes to an hour in the woods. I've been recently trying to actually do it without the headphones on so that I'm not listening to the news or podcasts and give my brain some time to just reset.

And enjoy the sounds of the woods. Yeah, enjoy the sounds of the woods, but that that time to unplug and give my brain a rest, um, I'm really really important. That's super interesting. I've been swimming every night just to get out of uh, out of it.

And I can't put the headphones in, so. Um, last one, let's uh, wrap this up. Dream vacation destination. Oh, Japan right now.

Um, I really would love to go to Japan. Yeah. Yeah, awesome. Some sushi, some ramen.

We uh, we were going to take Zachary, Ross, and we like gave him a little like project of like, if you were going to go, you need to like at least put something together of like why you want to go and what you want to do. Like it's an expensive trip. And I love my child to death. Everyone listening knows this.

So, when I say this, just forgive me. His lazy ass sent a text message that said, I want to go to Japan because they have great sushi and great ramen. We did not go to Japan. For the record.

That is a lot of why I want to go. Um, my my real uh, goal is uh, to bike pack the entire country, which takes about three weeks to start in the southern Japan Islands and then make your way all the way up to um, uh, the northern island. But it's uh, apparently a really beautiful ride, and there are dedicated bike paths that go across the whole country. And so, um, I feel like that would be a really great way to experience it.

That's pretty awesome. Um, outside of just shoveling ramen and sushi into my face, which will definitely be part of the experience. Absolutely. But then maybe I won't show up 400 pounds more than I am right now if I do some exercise along the way.

I love it. Ross, thank you so much for joining. Thank you so much for dropping so much knowledge. I feel like we could go on for several more hours, uh, but we're super grateful to have you here, man.

Always good to catch up. Guys. Yeah, so great having being here. Thank you so much for having me on.

Uh, this was a ton of fun. I really enjoyed the conversation. Appreciate it. Yeah, pleasure.