How AI and Automation Can Transform Your Post-Sale Strategy with James McKay

Welcome to the B2B Growth Blueprint podcast, where we talk with entrepreneurs, founders, and leaders at B2B services, tech, and SaaS companies to learn the systems and processes they've used to create success for their business. We'll also learn from marketing and sales experts to provide insights to help you grow your business. I'm your host, Mark Osborne, and the podcast is brought to you by Modern Revenue strategies and their 10x ROI B2B growth guarantee. Schedule a free diagnostic call to learn the fastest path to double your B2B revenues in just 90 days. Hello and welcome to another episode of the B2B Growth Blueprint podcast. I'm your host, Mark Osborne, and today I'm very excited to welcome James McKay. Now I'm going to read James's bio to make sure I get this right because he's got a lot of really exciting stuff going on. So James is the founder and CEO of Vin. Now Vin is a Toronto-based RevOps consulting firm. For those of you that aren't as familiar with RevOps, it's all of the sort of data and technology that fuels sales and marketing and really sort of growing for your business. We're gonna talk a lot about that today. So I hope that's something you're interested in. After its launch in early 2023, Vin expanded rapidly He now serves over 20 B2B SaaS and fintech clients across North America. So a lot of great experience and stories that James is gonna be sharing his insights from. Before Venn, James held executive roles at Clearco/Financial, TradeGecko, and 500px with a focus on sales and operational growth, driving cross-functional alignment across teams to promote smooth, consistent improvement in revenue. James is recognized as a LinkedIn Top Voice in sales, sales operation, and CRMs, and his career is marked by the dedication to helping startups and fellow founders thrive. So James, thanks so much for joining us today.

Thank you. I appreciate it and excited to be here.

Yeah, I'm super excited for our conversation. So tell us a little bit about your journey. So obviously it sounds like you, you know, worked for some other companies and helped them grow and then thought, well, I'd rather sort of take, instead of giving all this expertise to one company, I wanna help others. Tell us a little bit about your journey.

Yeah, for sure. It's, I think that most folks who found companies will tell you that it was like they had to, it was almost like a calling or they were really compelled to do it. But yeah, I think that I knew that eventually at some point I wanted to do something and I wasn't sure what it was. And I think when I came out of my, you know, 15-year career in In tech. I thought I want— I thought I wanted to build a different company, like a tech company. But everyone around me kept being like, okay, but just do RevOps. Why don't you do RevOps? You're the RevOps guy. And so without really much effort, I kind of came across my first contract and really just took it moonlighting while I was still in a full-time role. And it was Great. And so from there, I'm like, yeah, okay, I'll do RevOps.

Okay. So I'm curious and a lot of, you know, companies that we work with that are, you know, in this, you know, sort of growth phase. So, you know, they just as you described, they worked in an industry, they had an idea for a better mousetrap. And so they went out and founded a company to build that mousetrap and they knew enough folks and their Rolodex was thick enough that, you know, they could call on some potential customers. They knew what was wrong with the competition because they'd worked there. They knew what was right about their product because they'd built it. And so they, you know, they are able to close some deals and grow, but then they sort of reach the end of that and then they need to sort of scale to that next stage and build some systems. And that's where RevOps becomes really important for companies to do this. And One of the questions that, that we get all the time when we're working with folks is, well, when's the right time to bring in different pieces? And, and I'd love to hear, you know, sort of your thoughts about, you know, what are the most important pieces. And, and you and I chatted about this a little bit before, you know, whether it's data or technology and technology to organize data versus technology to execute against it. And, and, and what, what are those, you know, important building blocks. And then maybe we talk a little bit about, you know, what's the right stage to bring those in so the companies don't sort of overinvest. So they're spending all this money on, you know, sort of technology they aren't using or, you know, sort of overengineer so that they're spending too much time maintaining a system that isn't adding value to them versus underinvesting. And then, you know, they don't, they're not able to keep track of everything. They're missing opportunities because they're not doing a great job following up. They're, you know, missing opportunities because they're not identifying them fast enough. Talk to us a little bit about the progression that you see companies go through and the right tools at the right times.

Yeah, for sure. I mean, and there's the right progression and the wrong progression too. So I think maybe, maybe I'll focus on the right. I think by the wrong, I just mean doing things in the wrong order or doing things with the wrong emphasis. What I, so I'm a big fan of founder-led sales. I think founder-led sales is incredibly crucial and I think it's probably the best starting point for any kind of organization. And I think the most important element that a founder should be looking for is effectively figuring out a process.

Yeah.

And I say that, and it might sound really obvious, but I say this because I'm a really, really big fan of manual work. Like, I actually think that manual work plays a really incredibly important, like, role in actually establishing a company's operations to be effective and scalable.

And you're saying manual versus Automating?

I think manual before automating is really what I'm driving at. So when you ask the question of like, when's it the right time to, you know, to bring in, say, a RevOps, or when's it the right time to scale, or when's it the right time to layer in technology, or when's it the right time to revisit my operations or whatever? I think that the answer is in like, what is the real sales process? What is like the real one that, that take all of your systems, all of your automations, all of the information out of the equation here and think about where your customer goes from just existing in the world to being somebody that might buy something that you do, to knowing about you, to being enticed by your product, to being part of the funnel, to buying it.

Yeah.

What's my role as a person or a company in that whole customer journey, right? That needs to be understood. When you, when you understand that, then all of a sudden it starts to make sense to be like, okay, well, this part is really laborious, or this part is very manual, or this part could be done a lot better with a tool. I think that's when you actually want to start having real conversations about bringing in process and automation and tooling, etc., etc.

That's such a great point. And so I'm oftentimes reminded of this. You, you're probably familiar with the MarTech conference and Scott Brinker and those folks. And, you know, they started putting out this landscape of all of the different marketing technology, ad tech solutions, and it includes RevOps stuff today, although that term didn't exist when they started publishing this list, probably, I think it's 2010, around 2014, something like that. When they first published it, it had 150. Different logos on there. There were 150 different, you know, across all stages. This year there's over 10,000. And so like there's so many places to get distracted, so many things that you could think about. And if you just go looking to buy a tool, it's gonna be a magic bullet. It just never happens. Whereas instead, if you do as you described, which is really sort of map out what the process looks like and we call it like a critical client flow. of like, what does that flow look like from an anonymous person that you don't have any relationship with to an identified target to you've got some relationship with them to, you know, you're working on an opportunity to they're your best client, whatever it might be. Just defining that then highlights where the opportunities exist to make the system better with the technology or data or whatever it might be. And the other oftentimes missed thing that we see is Like actually visualizing it, because something like 40% of the world is primarily visual in the way that they, you know, sort of interpret the world. I'm primarily auditory, so I like to write things down. My wife's primarily visual. But by just visualizing it, you stimulate so much more kind of critical and creative thinking to improve the process and sort of improve all of those things and come up with Oh, wow, we should go look for something that'll help us do this a little bit better.

Yeah, yeah, for sure. And I think if you don't actually— so the, the downsides of not doing that are so many, but there's a few that are really sticking out just in the context of what you said. If you don't have this mapped out, first of all, you're not— you don't know if who you're speaking to within the company is envisioning this the same way.

Right? Right.

And so there, there is a lot of opportunity for misalignment in the assumptions around how you versus like you as a sales lead maybe versus a marketing lead picture the customer journey and the sales process. So that's important. But the, the other thing is when you go start, like once your company has a level of success, Salespeople are going to start finding you and tools are going to start advertising to you. And we all know that one of the primary tactics and most effective tactics that folks use to sell is to sell the problem. And I think that if you're not super deliberate about what it is that you have in terms of a process and what it is you're trying to accomplish, It becomes like there are a bunch of things that are gonna try and pull your attention into other problem sets and other directions. And then all of a sudden you're gonna start buying and sourcing technology and software and tools that maybe you didn't need or don't actually solve a core problem for you because someone has taken your attention and convinced you that there's another problem here that you need to solve. And guess what? Their platform is the solution to it. Right.

What, what a surprise. Yeah, they, they happen to sell that, that Magic bullet.

Yeah, exactly. And so get it down, get it documented, get it understood, get it commercialized within your organization. Then all of a sudden you have something to anchor you as you're going to try and build operations and build process.

So let's assume that our founder has built some success. They've mapped out what the, that critical client flow that's working. Now they need to invest in some infrastructure or things to help them do better. What's the, you know, what's the first thing? What are the sort of must-haves, you know, for anybody kind of at any stage? And then, you know, how do they plus that up as they go?

Yeah, I think that I don't want to answer with it depends, but I think there are a few factors you need to consider here. So The complexity of your product is an important factor anywhere along these lines, but it becomes a really important factor if you are ready for the 0 to 1 level of scale, right? It's immediately a problem if you have a complex product. The other thing that you need to watch for, I think, is the sensitivity of the data that may come through a sales process. So if you're dealing with a financial services product or you're dealing with insurance, people's personal information, like actual sensitive personal information, I think that might change how you take your first steps.

Sure.

Because you're probably going to want something operationally in place to protect the data integrity of your business and of the people who are interacting with your business super early. However, I don't think that's the most common case. Like, I think that a founder who's established enough success and is confident that they can start scaling sales should be looking to sort of a people solution first. And there typically are 2 paths here that people take, which is the most wrong path, which is hire a VP of sales or a CRO. like right out of founder-led sales. That is a really dangerous path. I think that the folks who have been around a while are accustomed to a certain kind of budget or a certain layer of types of work that they do, and maybe haven't been in and been scrappy and been kind of hammering the phones And for a long time. And so the worst thing you can get as a founder is go hire somebody that's already maybe too expensive for your organization and they just show up and tell you the other 7 people they need to hire in order to run their process, right?

Not only the other 7 people, but also all the expensive software and data they expect you to license in order for them to do their job because that's what they're used to.

Yeah, exactly. And then the, I think the second most common path, I think it's the more right of the two, But I like a third, is get somebody young and hungry, maybe who's established themselves as a strong individual contributor who's looking toward management and put them in a position to succeed and come in and build their own function, but start like by continuing on being hungry and growing the company for you. I think the downside of going that direction is that you will get a lot of activity and a lot of effort, but you will you'll lose a lot of visibility because that's probably maybe potentially the worst person imaginable for documentation process, like keeping things straight. Like these people are customer-focused, hungry, and putting in a lot of activity. What I like, the third path, Yeah. which is all too convenient, but it is a part of the reason I'm building this business is I think that having hiring that person, but bringing in some level of expertise around RevOps is a really, really good launchpad.

Yeah.

So have somebody thinking through it operationally. And I don't think that this needs to be a full-time person. In fact, I don't think it should be a full-time person. I think there's really great fractionals and there's really great consultants in the RevOps world now. We are some of them, but there are others who I think can work with this like younger hungry person that's the right person to go out and get your message out there and start building something scalable alongside them as they're going out and hammering the phones and getting the conversations going.

Yeah, that makes tons of sense. And also it de-risks that investment so much. The other thing that we all, that I oftentimes see is instead of, you know, bringing in sort of like a fractional leader that's got expertise is they might kind of outsource it to an agency. That promises, oh, we're gonna generate all your leads for you. Then all you gotta do is call them. And then they hire that young hungry person to call those leads. But one of the— I think of agencies as they're kind of like power tools. Like they can help you accomplish a lot, but you gotta kind of be a professional at using them in order to get the most out of them. Otherwise you'll end up, you know, lopping a finger off. And so that can be a really dangerous path too.

And I think there are a lot of, like, I'll just call it like, I think there are a lot of bad actors in that space too. I don't think they're all bad actors, but this is such a pain point for organizations that it's not that hard of a sell. But you've got hucksters on there, like showing up on all social platforms, guaranteeing you 100 qualified calls a month. Like, sounds great. But it's, it's gonna be a mess for your organization. And so to your point, just like, that's like a really crappy power tool and you don't want your power saw falling apart in your hand and you not knowing what to do. So I think you also need to buy a good power tool.

That's right.

That's right.

So let's say they've chosen that path. They, so they bring in a, a RevOps leader like yourself. How do you help them, you know, sort of You know, pick those right solutions and, you know, what's your process that you use in working with businesses to sort of identify the right tools and to build that, you know, to build that vision for them?

It's an age-old process and it's a process that has kind of gotten political lately. People have started slapping names on it and selling it as like their special process that they invented. But really, To me, it's you set up 3 things and then you watch 3 things. So the 3 things you do is you map out this customer journey like we talked about. Hopefully the founder's done some of that, but it's really good to do this with a RevOps person. And this person in mapping this out should establish all of the stages that all the entities in the flow go through. The customer, like if you're using a CRM, what like a contact does, what the lifecycle of a deal or an opportunity is, what the lifecycle of a company Plot all that up. That's thing one. Number 2, define those stages in a way that is clear, memorable, and objective.

Yep.

And then number 3 is establish entry and exit criteria for all of these stages and all these places. Like in order, like you look on your map, you see I have a stage called Demo. I've just actually gotten into a public argument with somebody about demo. I got a stage called Demo. Okay, it, it is here in the visual process.

Yeah.

It is defined as this. This is what all the records are doing in the CRM. This is what is, what needs to be true in order for something to enter that stage, and this is what needs to be true for it to exit it. I've got a set of documents too that if anyone wants them, just send me a note. I'll, I'll give them to you. But To me, that is thing one.

Yeah.

Once you, once you have that, then you can measure the 3 most important things you always need to measure, which is the volume of your inputs, the speed of your inputs and the rate at which they convert through each one of these stages. Then you have a foundation.

Yeah. So simply said, but like so right to the core of it. And that's the thing that, you know, we always advise people is just as you said, define those stages, define the, you know, what's happening in those stages, and then the entry and exit criteria. Well, you've just described a lot of sort of data that needs to be captured and stored.

Yeah.

Okay. Well, now you need a solution to capture and store that data. And then, you know, that also sets up some key performance indicators of, well, we know what volume is coming in and what volume is coming out and where it's dropping at each stage and how long it's taking at each stage, which starts to define, you know, a lot of those things. The only thing that you didn't mention that I would add is not only the volume, speed, and, you know, sort of kind of rate, but also the quality because so often we see that folks will, you know, there's this obsession with more leads, more leads, more leads. I need more leads. And oftentimes that distracts them from really, you know, sort of attracting those tier 1 opportunities, those customers that have, or those prospects that have the potential to be your best. The, you know, 80% of revenues from 20% of your customers. If you just close, you know, 50% of your prospects, that means 10% of your prospects are gonna wind up, you know, being one of those tier 1 customers. And so being able to quickly identify Yes, they fit my, my tier 1 ideal customer profile. Yes, their need aligns to the type of customer that's a longstanding customer that's happy with my solution. Not they're gonna wind up churning out before they ever generate any profit. They're gonna wind up, you know, demanding price cuts for customization that I don't wanna do. If you just chase every lead evenly, then you don't put the resources on to win those really most important ones. And that's the, that's that quality piece that's so important.

I, so absolutely. And I think you can do that early. You can do that late. One, what I'm thinking of here, I love, love when the quality thing isn't established yet because what the way I have fun, like the sick pleasure I get in illustrating this to people.

Yeah.

Is, is one of my favorite things, like the, the whole more leads conversation. If you have your stages set up properly and you can, and, and you have your infrastructure set up properly to measure like the timing, you can very easily isolate how much of your sales force is spending time on some terrible set of leads in some early stage.

That's right.

And all of a sudden, then you, you can, I think I've effectively done this a few times, you can get people to stop saying more leads because all of a sudden they realize how inefficient they are being. Now, really sophisticated go-to-markets have really great scoring models and ways of prioritizing things. And yeah, I think that's, that's really good. But if you have your foundation right, you should at least be able to diagnose how bad of a problem it is when you don't have quality. Because it'll show up in the funnel and some funny lump or something that looks like an aberration. But no, it's true.

That's right. The other thing that we see and, you know, so often the focus in revenue and growth is just, you know, net new customers. But the net recurring revenue metric and the ability to get more referrals to get, you know, faster upsells, faster renewals, longer contract value, more testimonials, like that's so often so neglected in organizations, especially, you know, SaaS and, you know, technology companies that have long subscription models that just shining a little bit of light there can really be sort of transformational for companies. And the other thing too is for companies looking to sell, that's actually the fastest way to improve your, you know, sales price is by improving that, you know, net recurring revenue metric. Faster than, you know, sort of your pipeline velocity or other metrics that people obsess about all the time and they just sort of ignore what happens after that first contract.

Yeah. And I mean, I think it's worth adding that you also get a really good multiple on the price of your business if you have really slick, well-governed operations just in general. Like that's a huge de-risk and unlock for acquisition.

Yeah.

Targets. So just worth saying. But, but yeah, I think that the, the post-sale is the, that space is sort of the most underfunded, underconsidered space in the whole end-to-end customer journey. And it's upsetting and confounding because the, the cost of retaining a customer, especially if you have a high billing product, is so much less than acquiring it, so much less than acquiring it. And it just, and that's just on a CAC LTV, like—

That's right.

Financial fundamentals, that doesn't even count for all of the things around referrals and reputational damage and everything that goes with not taking great care of a customer. So I think that that's, that if people don't have that locked down and so many companies don't, like that is such a huge opportunity to improve your business. Yeah.

So true. So true. So for, you know, companies that are out there, you know, sort of in there, they've identified these metrics and they're building, you know, there's a lot of buzz and conversation in the marketplace right now around, well, automate it, bring in AI to generate and do it for you. So let's assume that they have actually taken the time to really understand their process and define the KPIs and metrics. Are you seeing some tools in the automation or AI space that are really adding a lot of value to companies that, you know, I oftentimes feel like there's more hype than value in a lot of those things, but I'm curious which ones you're seeing that are actually like impacting and what's working out there today.

Yeah, I, so it's funny. I think there's like this reverse thing going on between where the attention is focused and where things are working. I think that the majority of the attention in terms of kind of new tooling and AI tooling is on top of funnel.

Yeah.

And I think that it's not even close to being solved and it's getting worse And not getting better at all. And I think there's not been nearly enough attention around closing, like the actual ushering a qualified deal to the point where it closes. And I actually think this is where AI and tooling are getting stronger and where there is a lot of actual opportunity for automation, like tools like Fluent, for example, are really good about keeping you organized around deals. Like RFP software is getting better. I think there's stuff coming out now with case study automation. I was looking into it recently. I can't recall any off the top of my head, but in that space, like folks just leave it to like sort of established account executives and don't actually think of that as a place for tooling. But then they'll go buy any dumb AI bot sort of thing at the top of funnel and start destroying their reputation and destroying their domain score by spamming the entire world with their low quality outreach. So that, that is something that I think is, is really confounding me. Now the tools that are, there's still some really good ones. Like I am a big fan of Clay. I think Clay is a really good way to get like to source, to validate, and to keep information up to date. I think it's a really good way for top of funnel folks to keep organized and have the best data. But I think by and large, a lot of the tooling there I'm seeing is just exacerbating this problem of people not answering as much as they used to.

So love all these conversations and we could talk all day, but I gotta be mindful of your time. What's something that's on the horizon that you're really excited about with Venn?

I think that with Venn, I think that people should stay tuned because I think I'm going to hone in a little bit on what it is that we do. So I'll just give you a little explanation of the business itself. We're largely undifferentiated, and I think a lot of kind of service providers in the RevOps space are right now. The differentiation has been that I've been doing RevOps for basically as long as it's been called something, and I— and as a result of like it being relatively new and the fastest growing role in America according to LinkedIn, is that there's a very low talent density at the top, like for people who've actually held, you know, VP executive level titles in RevOps. So that has largely been the company's differentiator. And so I think I'm gonna, I'm gonna, and that's what I've been using to win deals and it's been going really well, but I wanna scale this a little bit. So I think there's gonna be some information that comes out soon about how Ven's gonna bring a little bit of a different model and a little different approach and a little bit more segmented in who we are helping. And another thing that's just gonna come up on the topic of the staging and entry and exit criteria. I'm pushing out a free course sometime in the next week or so that folks can, can go to and, and do that work on the plotting out the stages, defining them, and getting the, the, the data validation written down and documented in visual.

That's great. So It'll probably be more than a week before this episode comes out. So we'll definitely get that from you and put it in the show notes so that you can get that. So that's super exciting. Well, James, it's been a great conversation. Obviously some really exciting things, you know, on the horizon for you. For folks who want to get in touch and learn more about how, you know, you and Vin can help them to build out some of these RevOps systems, how can they get in touch with you?

Find me on LinkedIn is the best way. James McKay, just my name. You'll have it linked. Reach out, DM me. But if not, you can, you can email me. Go, just go to my website. There's an email on there. My website's ven.studio, V-E-N dot studio. But yeah, LinkedIn is the fastest way. I'm there a lot.

That's awesome. James, thanks so much for joining us today. I loved the conversation. You've brought a lot of great insight for our audience. So thanks so much.

Yeah, appreciate it. Thanks so much, Marc.

Thank you for joining this episode of the B2B Growth Blueprint podcast. We hope you've gained insights to grow your business. If you enjoyed this discussion, please rate, comment, like on your favorite platform and share to others who will find it useful. Do you know a CEO, founder, or leader at an early stage B2B services, tech, or SaaS company who would like to be a guest and share their story, send us a note. Let's schedule a conversation.