In this episode of the B2B Marketing Methods podcast, host Terri Hoffman, CEO of Marketing Refresh, interviews Craig Baldwin, the Co-Founder and Partner at Upsourced. Terri and Craig discuss valuable tips and lessons learned to optimize your go-to-market strategy.
Gain insights into pipeline management, prospecting, deal generation, and learn about the crucial importance of pipeline hygiene. Discover how Craig’s diverse background in various industries has shaped his approach to driving revenue growth.
Topics Discussed:
- Importance of pipeline management and hygiene.
- Transitioning from accounting to sales/marketing.
- Systematic approach for lead generation and closing.
- Setting long-term goals and working backward.
- Maintaining accurate CRM data for decisions.
- Creating scalable, repeatable B2B sales processes.
- Emphasizing accountability in sales management.
To learn more about Craig Baldwin, connect with him on LinkedIn at: https://www.linkedin.com/in/craig-baldwin-aab37821/
To learn more about Terri, connect with her on LinkedIn at: https://www.linkedin.com/in/terrihartley/
To connect with Marketing Refresh, visit: MarketingRefresh.com
Full Episode Transcript
[00:00:00] Terri Hoffman: Welcome to B2B Marketing Methods. I’m your host, Terri Hoffman, and I’m the CEO of Marketing Refresh. Let’s face it, embracing digital marketing is daunting. This podcast was created to make it more approachable. Join me as we talk to CEOs, sales leaders, and revenue growth experts who will share lessons learned and tips from their own journeys.
[00:00:24] Terri Hoffman: Welcome to another episode of B2B Marketing Methods. Today I have a guest who’s named Craig Baldwin. Craig is the founder and, one of the partners in a firm called Upsourced Accounting.
[00:00:35] Terri Hoffman: You might be wondering, Terri, why do you have an accounting person on a marketing podcast? You’re going to find out. It’s going to be like a little twist and turns in the conversation. One of the reasons I wanted to have Craig on as a guest is because he has an amazingly unique perspective. I’m going to let him introduce his firm and tell you a little bit about his background, but some of the points we’re going to be talking about during the episode are pipeline management, pipeline hygiene.
[00:01:03] Terri Hoffman: We’re talking about sales pipelines here, nothing to do with your financial statements. Prospecting, we’re going to be talking about lead generation. We’re going to be talking about deal generation and he’s going to explain why he has a unique perspective on all those different topic areas. Once again, thanks for coming today to join me, Craig.
[00:01:20] Terri Hoffman: Welcome to the podcast.
[00:01:22] Craig Baldwin: Thank you, Terri. Yeah, I really appreciate it. It’s great to be with you. I have a accounting educational background, worked in public accounting for a couple of years, not a great fit for my personality, I would say.
[00:01:34] Craig Baldwin: And, just quit, terrible idea. I remember my mentor calling me at the time saying, hey, this is a bad idea. Are you sure you want to do this? And I said, yeah, I need a change. So I quit cold turkey went and worked in a restaurant for a little bit and was lucky enough that one of my old coworkers asked me to start Upsourced with him, and, and another partner.
[00:01:53] Craig Baldwin: And my motivation was to take on the sales and marketing aspect of Upsourced and not do the accounting. I just wanted to learn about sales and marketing. I wanted to do the work. I felt like maybe my personality is more geared towards whatever that meant. Didn’t really know at the time. And, ever since then, over 12 years ago, that’s what my career has focused on.
[00:02:13] Craig Baldwin: And so the organization Upsource has grown significantly since then. We’re about 35 employees now and close to 5 million a year in annual revenue. And I’ve also had lots of other jobs in the meantime, because, to be honest with you for years and years, Upsource just wasn’t large enough to support all the partners and, my family in particular, and we just kept reinvesting money.
[00:02:34] Craig Baldwin: Sort of to hire more staff, to, to earn more revenue ultimately. And so by making those sacrifices, I went out and worked full time jobs and ran a strategy on some client engagements at a WPP, marketing agency, innovation agency called Rockfish, which was an amazing experience. Actually, before that, started another software company and raised venture capital and boy, oh boy, was that a crazy experience that I hope to never go through again.
[00:03:00] Craig Baldwin: Also ran partnerships and sales at another tech startup for almost five years in the enterprise IOT space. Very much taking on, the AWS is in the Google clouds, or at least trying our best to do that. And for the last,
[00:03:14] Terri Hoffman: What was it?
[00:03:15] Craig Baldwin: That was an organization called Losant. It was a small, but mighty, IOT platform company
[00:03:23] Craig Baldwin: that’s still around in Cincinnati, Ohio, where I was at the time. Amazing founding team who knew how to grow, build great products and that’s really where I learned enterprise sales. How do you go out and close six figure, seven figure deals? How do you harvest relationships from nothing? How do you have 12 to 18 month long contract lead times, you know, that type of thing.
[00:03:43] Craig Baldwin: That was a totally different industry area focus that I was not familiar with, and I went out and got those skills. And fortunately, cause I was, were at a really small company, I was just kind of thrown into the fire. And so I had to learn on the go, that was a really great experience. And then I was recruited away from there to go run a consulting team at a very large BPO professional service company called Concentrics.
[00:04:05] Craig Baldwin: I ran their mobile app team. I managed the global Apple relationship and that looks much more like an agency, to be honest with you. I mean, we basically did digital work. We built and managed mobile applications for very large financial service companies primarily and the account and salespeople reported to me.
[00:04:21] Craig Baldwin: I looked after the PNL for a couple of years, and that was a whole other experience, again, very enterprise focused, but gave me a lot of respect for managing pipeline sales. PNLs in a publicly traded company, that, it was something that I had not done before and so, what I’m so fortunate to do now is all these years later, I’m back in Upsource full time, thank.
[00:04:42] Craig Baldwin: Thank God. And I can take all that experience and be really dangerous on behalf of our organization and inject that into our own sales and marketing team. And, hopefully over many years we continue to have success, but I’ve had a circuitous path, as I think some would say, and have learned a heck of a lot during that and have come out the other end with a lot of strong opinions, especially as it relates to the sales, but sales and marketing in general.
[00:05:05] Terri Hoffman: Okay. I cannot wait to dig into that. You do have a really crazy collision of a lot of different operational areas, but also types of pricing models and industries, right. That is really, really interesting. Even if you just focus on sales and marketing in your career, it’s not common that you would shift, and have to sell against one pricing model and then probably a different ROI that you’re helping to convey to the customer, going to a different one. So, that’s a pretty diverse background. That’s crazy.
[00:05:38] Craig Baldwin: I’ve always tried to find areas where I felt like I needed improvement or I wanted to learn, mostly with my own businesses or starting a new venture someday.
[00:05:48] Craig Baldwin: And I’ve always thought after every couple of years, where do I need to build up that expertise? What do I need to do that I haven’t done yet? And I’ve been very fortunate to have that flexibility. Very fortunate. My wife, God love her, has a great job, great corporate job and so that’s allowed me to take some risks that maybe the average person would not be able to.
[00:06:06] Craig Baldwin: Thankfully, when I left my job in public accounting, I had no family, no kids, no responsibilities. All I had to do was afford rent. So that was a great time to do that. But, yeah, I’ve always tried to focus on how do I build my skills for a future, which is unknown. I think for all of us and would lead to success in my own ventures or maybe a new venture that I haven’t even thought about yet.
[00:06:28] Terri Hoffman: Yeah. Oh my gosh. You definitely have that entrepreneurial spirit. There’s no question. So I want to dig into some of the topics we are going to cover later on. I’d really like to ask you about how you’ve taught yourself or where you’ve gotten some of your learning. Cause I think that’s something important for our audience even, but let’s start with pipelines. One thing that I think is always at the core of all the different topics we’re going to cover is CRM, There needs to be some system for accountability around all of these, concepts in a go-to-market strategy, whether it’s pipeline management hygiene, which I love that you mentioned pipeline hygiene, because no one talks about that enough.
[00:07:04] Terri Hoffman: That’s not discussed enough, right.
[00:07:06] Craig Baldwin: Yep.
[00:07:06] Terri Hoffman: How did you develop a framework or system to, view pipeline management? And do you think that’s important?
[00:07:14] Craig Baldwin: It’s incredibly important. I think it’s the single most important thing for any sales leader. That is to say if you’re managing a sales team or if you’re responsible for a large number too, a leadership team or an organization, because ultimately that’s the best way to drive performance overall.
[00:07:30] Craig Baldwin: Well, I’ll take a step back and say when I got into the world where I was managing deal by deal, and this is a little bit after we started Upsource. Cause when we first started Upsource, you know, we had a quote, unquote pipeline. I was taking coffees with people. I was just trying to find business. I didn’t even know what that meant. Anywhere I could find it, we would get it, or, maybe somebody filled out our website. So in that world, we were having sales conversations. We were closing deals, but, because we were starting from scratch, we didn’t really think about this ongoing business need and meeting a number.
[00:08:00] Craig Baldwin: We were happy to get any deal we could get.
[00:08:02] Terri Hoffman: Yeah.
[00:08:02] Craig Baldwin: When I moved further along in my career and I was managing partnerships at Losant and then for a short period of time sales before I left, I just noticed a lot of things. I noticed a lot of behavioral, things from our sales team, from myself, from my partnership team.
[00:08:17] Craig Baldwin: And because we were a venture backed startup, managing those deals, reporting on those deals in an accurate manner to our leadership team, staying consistent in that reporting and showing that performance to the best that I could, month over month, quarter over quarter.
[00:08:31] Craig Baldwin: That stuff is imperative, right? I mean, anybody who works in sales and marketing knows that nothing is given. Like we couldn’t say all day long that we know where the next deal will come from, or we know that we can drive leads on a website. Nobody knows that for certain. I always say when my team at Upsource even asked me, like, how likely is it that deal is going to close?
[00:08:50] Craig Baldwin: And I said, well, if I knew the answer to that, I wouldn’t have to work here, right. It doesn’t exist. And so because of that there are averages that occur over time, right? I know that I’m depending on an expected outcome, given my experience and so in order to have that expected outcome, though, I have to do a number of activities the wherewithal to be detailed enough or have enough rigor to know that I need to make this many calls or send this many emails or have this many meetings or send out this many proposals. And if I don’t do those basics, and this is strictly speaking in a sales context, I probably won’t get. That number that I need to get right.
[00:09:27] Craig Baldwin: And a lot of people overlook that. That is so remedial to many in sales, but to track that activity, to manage that activity, to optimize for it over time. If you do not have accurate and timely deal information in your pipeline, that is, that’s killer.
[00:09:43] Craig Baldwin: That’s a recipe for disaster because that moment that you show a couple quarters in a row, you can’t hit the number. You are falling short. You promised a deal was going to close and it never did. Nobody wants to work with that sales leader, right? And so I’m always fighting that outcome.
[00:10:01] Craig Baldwin: I’m trying to be the person that everyone can rely on. I’m trying to be the person who can meet the number and exceed it. In order to do that, you have to have the discipline, the rigor, not only for yourself as a sales leader, but that has to be expressed through us, the team. And they have to understand that and feel that and really feel that weight, that pressure, it’s an expectation I think for a sales team, and if you can instill that in your team, that gives you such a better foundation to operate from.
[00:10:27] Craig Baldwin: I saw many sales reps who would promise the next big deal that was going to close and they would do a quarter over quarter. And of course that deal never closed, but they held onto their job for a little bit longer. Right. And so there’s some people that just rely on the narrative to stick around,
[00:10:41] Craig Baldwin: and that, and that’s true in marketing as well. People can spin a lot of different stories from a marketing perspective without tying it to the actual ROI, right. I mean, I think we’ve all seen that type of behavior. What I want to do is say, look at the deals
[00:10:53] Craig Baldwin: we want, look at the revenue we’ve produced, look at the repeatable pipeline I produced over the last three, four, five, 10 years. That’s the type of person I want to be because that’s the type of people that my business partners want to rely on. And I rely on them to do the same thing in their own areas of the business that they focus on,
[00:11:09] Craig Baldwin: right. But for salespeople, not for the most professional, the most professional sales teams this is old hat I think for many of them, but there’s a lot of folks in small to medium-sized businesses who do not appreciate the amount of rigor it takes to manage a really great sales team and to produce the results that are expected of them and to do it day in and day out.
[00:11:30] Terri Hoffman: You said something really big there. Something that I really tried to use as like a piece of content or an angle is that you apply this type of rigor to almost every other part of your business, right? You produce a financial statement, or several financial statements every month.
[00:11:45] Terri Hoffman: You have people on your operational team look at time usage. How many wasted products did we have that we had to throw out or scrap?
[00:11:53] Terri Hoffman: How many days do we have inventory? How long does it take a client to pay us? Right. There’s all of these pieces of data that are tracked in a rigorous way.
[00:12:02] Terri Hoffman: Why aren’t you doing that or expecting that from your sales and marketing team. Your go-to-market team should be held accountable to the same type of metrics, and the only way that you can really track that effectively at scale is through some type of system. I love that you’re kind of reinforcing that mindset.
[00:12:19] Terri Hoffman: I think people really undervalue it. And, I see that particularly in B2B industrial businesses, because a lot of times you end up with that great relationship builder, who’s just been in the industry for a long time. And I am not knocking that person, that is a great person to have on your team, right?
[00:12:37] Terri Hoffman: But how do you scale that when that person retires or leaves, or, you’re trying to grow your business and one person can only bring in so much, right?
[00:12:45] Craig Baldwin: Yeah, and I think what you’re talking about is how do you build repeatability within your organization and specifically in the sales and marketing function, right?
[00:12:54] Craig Baldwin: I, I’ve seen this a lot in businesses that I’ve worked in, but also businesses I’ve consulted with. These are organizations who have just done things the same old way, and they have salespeople who manage everything, maybe they have a very small marketing team or no marketing team at all.
[00:13:07] Craig Baldwin: They have salespeople who’ve been in the industry for 20, 25 years. They pick up a bunch of business cards and that’s how they produce leads. And then they make calls and that leads to business and they just know everybody in the industry and somehow or another, that person, or maybe the team even meets that number.
[00:13:22] Craig Baldwin: Right. But when you ask the CEO or the leader of that business, well, how do you do it? They’ll say, Oh, I don’t know. Well, it’s just, we’ve got some folks have been doing it for a long time, right.
[00:13:31] Terri Hoffman: Right.
[00:13:32] Craig Baldwin: That’d make me really nervous as a business owner. Because I want to know precisely how we’re doing it.
[00:13:37] Craig Baldwin: I want to know precisely how we’re getting better at it. I want to know precisely what our plans to try new things and to get better in the future and to future proof our go-to-market methods, especially in the world that we live in today. And so I’m constantly trying to implement a playbook that is always evolving, always changing, always getting better to the extent that we can do that.
[00:13:59] Craig Baldwin: And I’m always placing bets, whether that’s an outbound sales or marketing activities or partnerships. I’m placing these bets and carefully watching their quote, unquote ROI, any given point in time. And then that’s indicating to me on a future looking basis, where do I need to invest my time, money, et cetera?
[00:14:14] Craig Baldwin: And that can shift month to month, year to year. The really important thing is to kind of have that scientific mindset, and deploy the scientific method when you’re doing this type of work. But again, this takes rigor. This takes really good data. This takes accountability from your team members.
[00:14:28] Craig Baldwin: And a lot of that that is just inconvenient to people, right? Like how many times after a long day, you’re like, I don’t want to step on the scale today. Like, I don’t know, I don’t want to know how much I weigh.
[00:14:36] Craig Baldwin: It’s those types of people or that mindset I should say that do not make good salespeople, right. Because no matter what you’ve done, you got to step on that scale and say, was it a good day or bad day? And what do I need to do differently tomorrow?
[00:14:49] Craig Baldwin: Those are the types of team members I want on my team from a sales and marketing perspective.
[00:14:54] Terri Hoffman: Right. Yeah. that kind of comes back to the systems for accountability too. Having a CRM, having an agreement in your company about how often it’s updated. What are the absolute critical pieces of information that you’ve got to be gathering that needs to be tracked.
[00:15:08] Terri Hoffman: Because you do start to learn over time, like, which things are going to indicate the highest probability of success. Cause I mean, you’re right. No one has a crystal ball.
[00:15:16] Terri Hoffman: And things change and they’re constantly evolving every day in decision making processes that are high six figure, seven figure decisions.
[00:15:24] Terri Hoffman: So a lot can change. And you can work a deal for eight months with someone and then that person, leaves and moves on to another company.
[00:15:31] Craig Baldwin: It, It happens all the time. I had one deal in particular
[00:15:34] Craig Baldwin: I did for a period of time that I had worked on for over a year. It was going to be a really massive partnership. When I worked at the IOT platform company, they were publicly traded company. And I thought, man, this would be game changing.
[00:15:44] Craig Baldwin: I’ve worked so hard developing the relationship. They’ve so bought into our product. We made multiple trips to the Bay Area to sit down with their product team and I just worked it to death. And this was a period of time where I just, I was still trying to get a grasp on enterprise sales. And I remember having a meeting and they asked us to come in and talk.
[00:16:02] Craig Baldwin: And they said, listen, we’ve got bad news, we’re getting acquired. We can no longer do the deal. And that was such a blow to me. And in my head, I was so reliant on the outcome, which was we’re going to sign a big strategic partnership. It’s going to drive a ton of revenue. I’ve put all this work into it. How can it not happen?
[00:16:16] Craig Baldwin: But I think as any sales professional who’s been around for a while knows you can’t count on anything until the ink is dry. And even then sometimes things come up, right?
[00:16:25] Craig Baldwin: And so I try to remain extremely humble. I set low expectations the best I can, but I’m very aggressive and, I’m not going to count any chickens before they’re hatched, because that just leads to bad habits and bad behavior and I don’t want to get sloppy. And I really, like I said, I try to instill that in my team.
[00:16:41] Craig Baldwin: And I think that’s the best way to be, from a mindset perspective.
[00:16:46] Terri Hoffman: I like that phrase, “don’t get sloppy” because I don’t really think it takes as much as people think. If you have a system and it’s very clear, and maybe have the right type of internal support, right?
[00:16:55] Terri Hoffman: Like looking at what does need to be done. How is this person’s time best spent? Could they be supported, in some other way that gets a little bit more into how to organize a go-to-market team, those things are factors and if you don’t take the time to analyze that and figure out how to use someone’s strengths.
[00:17:11] Terri Hoffman: You could actually be limiting the growth of your business.
[00:17:15] Craig Baldwin: Totally. And I think a lot of this starts with a good sales leadership. I mean, if I think about a lot of the bad behavior I’ve seen in sales teams, while they may exist at the individual level, they were enabled by the leader. it’s kind of like the principal office effect when you have to have that weekly or monthly meeting with your sales leader and say like, oh, you know, that deal fell through, we’re not going to get it or what I promised you was going to happen is not going to happen.
[00:17:36] Craig Baldwin: And a lot of people avoid, avoid, avoid, which is problematic in its own. Right. But poor sales leaders enable that behavior. They say, oh, that’s okay. Don’t worry about it. Or the inverse, which I’ve experienced as well, is they are belligerent. They are, constantly anxiety inducing and yelling at their staff and taking out every single problem.
[00:17:56] Craig Baldwin: I think good leaders are supposed to keep problems and challenges from going down below them. And the worst leader is actually push them down, right. And so it really starts with the leadership. I think really good leadership will say, hey, did we miss the number cause it’s something we did?
[00:18:10] Craig Baldwin: Or was it an external factor? If it was something we did, how can we evaluate the outcome and how can we improve for the next time? You know, I’m always fine with a mistake. I just don’t want to make the same mistake twice, right. So let’s learn from this experience. Let’s improve. And I know the next time you’ll do better.
[00:18:24] Craig Baldwin: And if you don’t, then we’re going to have a different conversation, but that’s for then not today, right. Those are the types of conversations I think sales leaders should be having with their sales team or their reps, but it starts at the top. I think like any organization, it starts at the top that sales leader has to set the tone.
[00:18:38] Craig Baldwin: And then you have to create an environment where sales reps and individual sales people know that they’re going to be held to account. Know the expectation is to have good and accurate data in the pipeline. but also know they’re going to be supported, to not act with fear and, that’s hard.
[00:18:53] Craig Baldwin: That’s hard in every environment. We all live in this world now where, our bosses, our leaders, our shareholders are demanding now, now, now more, more, more. The best part about business is when you can create an environment where you don’t have to think about those things and you’re still successful, I don’t want to have that type of energy in my organization. If we create the right culture and the right environment and treat people the right way, I never have to worry about that imminent threat from external forces or going out of business or losing business. I just have to continue to create this environment that everyone wants to thrive in and they feel comfortable in and they do their best work.
[00:19:29] Craig Baldwin: So again, it gets kind of amorphous. I know that this is you know, you get in the culture stuff, it’s different for everybody. But I’m constantly thinking about those things, even in my own organization today.
[00:19:39] Terri Hoffman: Yeah, I think that’s great. It’s really important. Not just, establishing a company culture, but you’re even talking about mindset and culture around going to market, right?
[00:19:48] Terri Hoffman: Like how am I leading the people who really carry a lot on their shoulders? Sales people are busy. It feels like you also kind of develop, a term that I’ve heard a lot with like head trash. I don’t know if you’ve heard that term before, but you have to deal with, a lot of, failure, you know, or what might feel like failure more than you do
[00:20:08] Terri Hoffman: experience feel like, yes, successes. And so you have to do a really good job of mentally separating that. And I think if you don’t have that good leader, And the good environment in place that is even harder.
[00:20:22] Craig Baldwin: It becomes toxic.
[00:20:23] Terri Hoffman: Yeah, it’s toxic and it’s building more head trash instead of helping to keep that trash out of the way
[00:20:29] Craig Baldwin: I love that point. You know, ultimately as salespeople, the key is to be productive, it’s all about productivity. When I’m spending my time, am I spending it on the right types of things that produce the best results? Yeah, at the end of the day, that’s what we’re all trying to do, right? I don’t even really care how you do it.
[00:20:43] Craig Baldwin: Somebody may be really good at making phone calls. Somebody may be really good at showing up door to door. Somebody may be really good at not doing any of those things. And they just meet some people at a conference every time and they keep meeting their numbers. Everyone stylistically has their own way of getting it done.
[00:20:56] Craig Baldwin: And I don’t want to interrupt that. However, I do need them to be productive or enable them to be productive because that’s what it’s all about. And if they’re good at what they do, I need to think about how can I enable them to outperform because it’s the outperformers that are really going to drive a lot of our success from a revenue perspective.
[00:21:13] Craig Baldwin: It’s the laggards that you kind of spend a lot of time managing and deciding, you know. Do they stay, do they go that type of thing. But, I agree with you a hundred percent. It’s about getting people to focus on the things that matter and to not focus on the things that don’t, but to your point in a world of sales and marketing, this is why the hygiene is so important.
[00:21:28] Terri Hoffman: Was just about to say you’re like bleeding right over to pipeline hygiene.
[00:21:31] Craig Baldwin: It’s so easy to feign production. It’s so easy to say, well, we’ve produced this many blog posts or hey, I made a thousand calls last month, it just hasn’t yielded yet.
[00:21:42] Craig Baldwin: Right. It’s very easy in our profession to point to the activity, but not the results. I want to do both. I want the result and then I want to go look at the activity and understand, what is driving the result. How do we do more of that? How do we get better at that? Should we try some other things to diversify our approach?
[00:21:58] Craig Baldwin: Right? A really compelling sales and marketing team those are the conversations they’re having. It’s not like, hey, we went to a bunch of events and, you know, we met a lot of people, no, no sales conversations, but it was great brand awareness. Well, okay, that’s great. But as a sales leader, I need more than that.
[00:22:13] Craig Baldwin: Right. So you always got to tow that line. Certainly understand from a marketing perspective, making those investments, sort of like the farming aspect of, of marketing as a part of that, you got to plant the seeds, but as sales professionals, you know, don’t come to me with your activity. Come to me with your results.
[00:22:29] Craig Baldwin: And then we can talk about what activity led to those results and how to get better at it.
[00:22:34] Terri Hoffman: Yeah. I mean, maybe you could just define what you mean by pipeline hygiene. That might not be a term some of my listeners are familiar with. Can you define that and maybe even explain your mindset on it?
[00:22:46] Craig Baldwin: So pipeline hygiene is, just a more direct way of keeping a clean and accurate pipeline. That is to say all the deals that I’m working currently are in there. They have the right information attached to them. They have the current notes from the most recent meetings attached to them. They are in the right stage, which is incredibly important, especially when you’re forecasting your pipeline out into your overall revenue forecast.
[00:23:10] Craig Baldwin: You’re not hiding anything in those stages. And by that, I mean, you’re not calling a deal qualified that’s not really qualified. So like we use the BANT method of qualification, which I think many folks use. Do you have budget authority need and timing, if you don’t have the answers, those questions can’t be qualified.
[00:23:25] Craig Baldwin: A lot of people will let deal sit in qualified and build up that number and say, well, look at, look at what could happen. I don’t like that. In fact, I ask my sales team to close deals. That is to say, whether they’re won or not, go ahead and move it to loss after a quarter. I don’t want to sit in qualified because you’re hiding something and I don’t want that to happen.
[00:23:44] Craig Baldwin: We need to move on. And be more productive in other areas. This is not a good use of our time. So I’m always trying to maintain a very accurate pipeline. I want the stages of those deals to be accurate and I want the dollar amounts to be accurate. This is a way of holding onto your job. This is a way of delaying the inevitable. That, that behavior is poison for a sales leader, because once you start to depend on that bad information, you’ve now misrepresented to your leadership team, to your owner, to your peers, whoever that may be, and you’re setting yourself up for missing a number quarter over quarter, year over year.
[00:24:21] Craig Baldwin: And most salespeople are not even going to get that long before they get asked to leave. So when I look at my pipeline, I need to know everything in there is accurate.
[00:24:30] Craig Baldwin: It has been updated in the last week. I don’t want anything updated, it’s got to be updated every week. Monday morning, you come in, update that pipeline.
[00:24:38] Craig Baldwin: If you don’t make sure it’s all ready to go by the following Monday, anything over that, we got to have a talk about why, you know, it’s kind of like time tracking or for an agency, you got to track your time. That’s just the basics.
[00:24:49] Craig Baldwin: I can’t overstate enough how important they are. And they’re so elementary. They’re so 101, but it’s the 101’s that keep sales teams from performing and bleed into the culture and lead to a culture who is missing that number and you start to miss that number for a couple of quarters.
[00:25:06] Craig Baldwin: Guess what? Now you really miss revenue targets and now that has carry on effects in the rest of the business, right? Now you can’t invest in much as marketing and marketing as you wanted to. And now to get the next deal is even harder, right? So there’s all these sort of chain reaction events that can happen if you don’t have a sales team you can depend on.
[00:25:26] Craig Baldwin: And at the end of the day, that’s my duty. That’s my job to the team members who work for us, to my partners, is they have to be able to depend on me before anything else happens. They got to know that I’m true to my word and I’m going to meet that number. If I can’t do that, the rest of the plan that we put in place for the year, we’re gonna have to change that plan.
[00:25:45] Craig Baldwin: We can’t do those things, right. And I don’t want to be the person that holds us back from that. So that level of responsibility, accountability, that trickles down to that pipeline hygiene. And if you can have that type of culture, we don’t even have to tell people to do that. You don’t have to ask them to update every week, man, you got a great team, right?
[00:26:01] Craig Baldwin: That’s something I can work with as a sales leader.
[00:26:03] Terri Hoffman: Well, I just, I can’t get over how, some of the things you’re talking about, like one example is that rule, have everything updated Monday morning, let’s say you have a sales meeting at 11 or 10, then, you should have an expectation that by nine, it’s going to be updated or something like that.
[00:26:19] Terri Hoffman: I don’t even think that there are standard practices out there, particularly in a lot of B2B industries where that would be known. I see happen from time to time is, either there’s no system in place, it’s not discussed, it’s not even really understood the importance of it.
[00:26:36] Terri Hoffman: And then there could be other times that they have the CRM in place. One department is trying to get data from it, the other department is like, we didn’t even know you were trying to get data from it. It’s not realistic to have a traveling person in a sales role going in every night after they’ve just been in meetings all day.
[00:26:53] Terri Hoffman: Right. So there’s a lot of friction and frustration that happens and then everyone says, we’ll just forget it.
[00:26:58] Craig Baldwin: Like,
[00:26:59] Terri Hoffman: Forget it. We won’t even do this. We’ll get rid of the system. Or they don’t ever resolve the issue in some way and come to some type of an agreement or, you know, compromise together. I see that happen all the time.
[00:27:11] Terri Hoffman: And unfortunately, then it’s like, eh, I don’t know, sales systems don’t work. CRM doesn’t work. Marketing doesn’t work. Well, maybe it does.
[00:27:19] Craig Baldwin: How long until their business doesn’t work, right. I mean, that’s what I’d be thinking that you, what you just described is like one of the most anxiety inducing things I’ve ever heard, which is, well, we don’t know.
[00:27:28] Craig Baldwin: So how do you have any certainty over the future of your business if you’re not maintaining a pipeline with accurate information?
[00:27:34] Terri Hoffman: I agree with you. I just think that there are some products and services sold and they’ve been able to get away with it.
[00:27:42] Terri Hoffman: Right. And it’s been okay. Maybe even been okay for decades.
[00:27:46] Craig Baldwin: Yeah,
[00:27:46] Terri Hoffman: That time will run out eventually because their competitors are adapting. The market is changing the way those pain points are met. Maybe their product isn’t the superstar anymore, in the market. And so you’ve, you’ve got to really think ahead and kind of future proof
[00:28:01] Terri Hoffman: your business, like you said earlier, right?
[00:28:04] Craig Baldwin: Couldn’t agree more. Yeah. I mean, we all know what happens. People rest on their laurels or who get lazy or, I mean, it’s one thing to do that as an individual, it’s another thing to do that as a business leader or business owner. I would be a nervous wreck if I just said, well, I don’t know how it’s going to happen, but it’s always worked.
[00:28:18] Craig Baldwin: Jim always finds a deal at the end of the year. He has this one big account and they always buy a bunch from him. And that’s most of our business. Man, that would make me a nervous wreck.
[00:28:26] Craig Baldwin: Our job as sales leaders or people is risk mitigation. I put a deal into the pipeline. There’s risk associated with that deal. I need to knock that risk out of the deal each and every way, a step of the way. And that’s going to be reflected in the pipeline. So as it becomes qualified, as it goes to proposal, as we go ahead and win that deal, I’m trying to mitigate my risks through that process the entire time.
[00:28:48] Craig Baldwin: That mindset has been very helpful to me because if I haven’t done that, and I haven’t practiced pipeline hygiene, I’ve got a bunch of risk sitting in my pipeline. Which means as someone who started my career as an accountant, you have a bunch of risk sitting in your revenue forecast.
[00:29:05] Craig Baldwin: And if you have a bunch of risk in your revenue forecast, just imagine how much risk is going to be sitting in your P&L and subsequently your balance sheet and your cash flow statement in about a quarter or two. It just blows my mind how much owners, even in the agency space that we work with today, allow for that risk to occur day in and day out in their business, because they would never do that in other areas of their life.
[00:29:27] Craig Baldwin: They wouldn’t, right? But for whatever reason, because it’s learned behavior or they’re comfortable, or they just take it for granted, the fact that it always works. They don’t want to change their behavior, but there’s nothing that will change your behavior quicker than, a failing business and having to let some people go then having, to not have any salespeople anymore because you didn’t meet the numbers
[00:29:46] Craig Baldwin: you thought you were going to, that will change your behavior pretty quick.
[00:29:48] Terri Hoffman: I mean, I think another reason this kind of thing happens is because. there’s just a lack of awareness that it’s even important, right? And something I talked about at the beginning is I really would love to know how someone who started in accounting, how did you start to transition? As somebody who’s, you know, trying to figure out how to change that part of the way their business functions, where do you start? Right. It, I think it needs to start with like a bit of self education so that you realize like, why is this important? Why could this be something I’m missing?
[00:30:18] Terri Hoffman: How did you do that? How did you educate yourself and start to learn about something that was absolutely not part of your background.
[00:30:24] Craig Baldwin: My path is never conventional. Both my parents were public school teachers and
[00:30:30] Craig Baldwin: we lived in a very blue collar town, and
[00:30:32] Craig Baldwin: I’m the only person with a college degree in any part of my family that was not a high school teacher. They’ve all been high school teachers. So, and I love my parents dearly, but I always thought, and the one thing my dad always said to me is you got to go make more money than we did.
[00:30:48] Craig Baldwin: So the only, quote unquote wealthy people, which in my town meant like you lived in a home that was, you know, around 300, 000, that was like a huge mansion. Basically, I just thought like, man, if you live in the house that big, the people I knew that did that were accountants. And so,
[00:31:04] Craig Baldwin: being 15, 16, 17 years old, and then having to select a major and thinking, you know, I’m pretty good at math. Accounting made sense. Like that’s the way to make money and buy a 300,000 dollar home. I realized pretty quickly when I got into that career path after college that, man, I’m not made for this. My personality is not made for it. I want to interact with people. I want to get out from behind the desk. And I worked at an environment that just, I didn’t love and wanted to change some things about.
[00:31:28] Craig Baldwin: So fast forward to working with Upsourced, taking on sales and marketing, I actually tried very hard to find a marketing role at any number of companies at the time in Columbus, Ohio. I reach out to a ton of agencies. I interviewed for a ton of roles, a ton of internships. my biggest low point was sitting with an agency owner at a coffee shop in Grandview, Ohio, and telling him I will work for free for the next six months.
[00:31:54] Craig Baldwin: I just really want the experience. I want to learn, right? I want to learn what this marketing thing means. And he goes, listen, I really like you. I think you’re a great kid, but you have no experience in this and it’s just not worth it for me. I don’t even want you there. I mean, I think you can be successful, but I don’t want you.
[00:32:09] Craig Baldwin: That was like a real low point for me. Cause I’m thinking people won’t even take me on for free. Like, what do I do? Right. So the best thing for me to do is just create my own experience. And so when we started Upsource, I’m like, you know what? I don’t know what sales and marketing is, but I’m gonna go try to find a deal.
[00:32:23] Craig Baldwin: I’m gonna go try to sell my first deal. I’m gonna try to find my first customer. I’m gonna figure out how to price it. We’re gonna try to get them to sign on the dotted line and within a month we did. And I’m like, okay, well, I found that person online. I reached out to them on social media. I got the meeting and they signed with us.
[00:32:39] Craig Baldwin: Let me do that again. Right.
[00:32:40] Terri Hoffman: Your accounting brain kicked in then. What were the steps I took?
[00:32:42] Craig Baldwin: Hundred percent. And then, then of course, pretty quickly you spreadsheet it out and you say, okay, well, if I, if I want to get this many deals, I probably need to do this many meetings and I need this many coffees or lunches, or I should meet this many people.
[00:32:56] Craig Baldwin: And then I applied the same thing to our website and trying to push traffic to the website and trying to get press releases and all these things. And then I did that subsequently at the tech company that we started, but I always had to make my own experience.
[00:33:07] Craig Baldwin: Cause nobody ever wanted me on their team. I’m not conventional. Salespeople have to deal with a lot of no’s. I will slam my head against the wall until there’s no tomorrow
[00:33:15] Craig Baldwin: Just to get it done. Like I’m a very stubborn person. I will work for a longer period of time, I will work really hard and I need a longer time horizon to be successful, but I know with a long enough time horizon, I will be more successful.
[00:33:28] Craig Baldwin: Like I give me a long time horizon. I like my odds, right. And that’s just because I’m going to get up and work every day. And over time I think I can find the answer. So that was the approach I took with sales and marketing and
[00:33:40] Craig Baldwin: now I’m 36 years old and I’m thinking like, I feel very confident in my ability to do these things and to make these decisions and judgments and to be in front of these people and to take these meetings, right. And so there’s this nice thing that happens in the middle of your career, I think for many people, which is,
[00:33:55] Craig Baldwin: That inner voice in their head that said, you don’t belong here. It kind of goes away. And now you get the, well, yeah, I do belong here and now I’m going to help a bunch of other people too, right. That combined with the experiences I’ve had and the work ethic I’ve developed, has helped me tremendously into being whatever sales or marketing professional I am today, but it helps to be really good with spreadsheets and to be very, I don’t want to say data driven, that terms used a lot, but I have observations. I certainly act with my instinct, but I tried to confirm what I’m seeing with the data so that I don’t make any wild guesses or do anything that’s out of the norm, right. So I’m always trying to blend the two of instinct and hard data. and I think that’s where most really successful professionals live because with enough experience, we can all make really good judgment calls.
[00:34:42] Craig Baldwin: We just want to make sure that from time to time, they’re not really bad judgment calls. Right. Yeah.
[00:34:46] Terri Hoffman: Well, I think this is how we know AI, can’t replace us right in any role, but it can help us.
[00:34:52] Craig Baldwin: It can help us.
[00:34:53] Terri Hoffman: You may not have meant to do this and I could be totally misinterpreting something you said, but when I think about prospecting, you kind of have to start with the end in mind and then work your way back, in terms of developing the rigor for your day in, day out or week in week out activities, it’s like when you described how you started the business, you were like, I want to get a deal.
[00:35:11] Terri Hoffman: I’m going to start doing these things and then it drove you to the deal and then you went backwards and figured out what.
[00:35:18] Craig Baldwin: I do that every time them now, we started Upsource in 2012. And then I went away from the business for a couple of years, I came back in a fairly large capacity, not until 2017.
[00:35:31] Craig Baldwin: And in 2017, Upsource was doing about half a million dollars a year in business. So we sell monthly contracts that are fixed fee. So it kind of looks like a SaaS company, but we always think about annual recurring revenue is kind of our metric we think about. At the time, $500,000 in annual recurring revenue.
[00:35:46] Craig Baldwin: We had a hundred clients. They were paying us about an average of 500 a month, give or take. It was hard. We were servicing clients all over the spectrum, bars, restaurants, mom and pop, freelancer, you name it and we were just kind of delivering them financial statements on the cheap. So when I came back in, one of my partners said like, this is, it’s just too much work.
[00:36:03] Craig Baldwin: Like we got to find a better way. And I said, okay, well, who do we like servicing? Who are the clients we like the most? And he said, well, I really like agencies. They’re great, like great people, creative, different than us, very clean businesses to manage from an accounting and finance perspective. And I said, great.
[00:36:17] Craig Baldwin: From now on, we only do agencies. I said, how many do we have? He’s like, we got like. 15. I said, great. So we’re going to shed this legacy business over the next couple of years. And we’re going to change our messaging, our positioning, our services, our strategy, just for agencies. So that was a very big strategic call that we made.
[00:36:33] Craig Baldwin: We had one team member who we had hired him at the software company, the startup, and we brought him to the accounting firm cause we loved him so much. And he had no accounting background, but he did a little bit of accounting work. And I said, okay, Jimmy, you’re done with the accounting.
[00:36:45] Craig Baldwin: You’re now a full time salesperson again. And I said, here’s the blueprint I want you to follow. I want you to send these emails at this cadence. I want you to use this prospecting tool to do email lookups. We’re going to get you on LinkedIn navigator, do all that stuff. I said, keep the messages short, but sweet.
[00:36:59] Craig Baldwin: And find the style that works for you. But the whole goal is we got to get on the phone with agencies who are in that phase of looking for a service provider. We’re not going to get all of them, but we’re going to get some of them. And then we got to get a proposal in front of them. We got to sign them.
[00:37:13] Craig Baldwin: Right. So that was in the end of 2017. Fast forward to today, we’re about four and a half million, and I’ve got a sales and marketing team who’s replicating those efforts. But I started with the end in mind.
[00:37:24] Craig Baldwin: I said, okay, this is where we’re at. How much revenue do I want to do in 2018? I wanted to add like another 300 grand. Well, how am I going to do that? How many deals do I need? How much are they worth? How can I push the average value up? So should we change our services? Which we did. So now the average dollar value of a client for us is about $3,000 a month
[00:37:40] Craig Baldwin: and we have just over a hundred clients. We’ve got about almost 120 right now. So the overall number of clients hasn’t changed, but the economics of our business has changed significantly, right. And that was a very strategic decision and to reinforce your point, like I’ve always started with the end in mind.
[00:37:56] Craig Baldwin: I just did a three year forecast the other day. Like I’m like, okay, well, we are where we are right now. I’m thinking in my head of somewhere in between 10 to 15 million. What’s the path? And I’m looking at that path all the time. And then I break those raw numbers down into my attribution channels.
[00:38:11] Craig Baldwin: Okay well, what am I going to get from my outbound team? What am I going to get from my marketing team? What am I going to get from the partnerships that we’ve signed? How reasonable is that? What do I do to invest in personnel and activities to make that happen? Are the economics making sense? These are the questions I’m asking myself all the time.
[00:38:27] Craig Baldwin: And what I found is the further I can look into the future and think about the future, the better things are going. When I’m thinking about, oh my God, we haven’t gotten a deal in six months. I need to find a deal. That is a place nobody wants to live.
[00:38:41] Craig Baldwin: That’s a hard place to live because it is so hard to perform when your back is against the wall, you don’t make your best decisions. That’s not a place I want to be. And so my whole mindset is always trying to avoid the moment where my back is against the wall.
[00:38:54] Craig Baldwin: And I just keep pushing further and further and further out to avoid that feeling, because by the way, I’ve had that feeling, I ran a software company. We raised venture capital. We hired a team and we shut it down and we didn’t give that money back. And we had to go find jobs for those people. And I never want that feeling to get in the rest of my life.
[00:39:11] Craig Baldwin: So was I shooting from the hip and willy nilly and thought I could do everything, absolutely. I thought I did. And then I was humbled and I realized you’re just like everybody else. You need to be diligent, rigorous, and roll that ball up the hill every single day. Just make more good decisions than bad, and you’ll get to the outcome that you want.
[00:39:26] Terri Hoffman: Yeah, another thing you said earlier in the conversation is it’s all about mitigating the risk.
[00:39:30] Terri Hoffman: And so almost every discussion point we had today, it ties back to that in one way or the other. Thinking about how to make things as predictable as humanly possible on this earth to make them predictable, but also mitigating the risk.
[00:39:42] Terri Hoffman: I mean, just really simple things like, hey, if we have not yet figured out if there is a near term need for this, And there’s a budget behind it. Why are we continuing to talk to this prospect. Put them in a nurture status, put something on the calendar for six months for now, if that’s what you need to do.
[00:39:59] Terri Hoffman: But I think developing that discipline so that you’re not overstating something in your pipeline and you’re mitigating any risk because, hey, the HR department could be thinking, wow, I need to recruit more people to work in the shop, or I need to get more welders because it looks like we have a lot of work coming in and,
[00:40:15] Craig Baldwin: And how dangerous is that, right?
[00:40:17] Craig Baldwin: How many times have you probably observed in your own clients where they overhire and then it doesn’t happen. And then, oh crap, we got to let those people go. No, I don’t want to be responsible for that outcome, right. I want to do the opposite. I want to say, hey, I’ve got some good stuff we’re working on.
[00:40:31] Craig Baldwin: I’m going to do my best to over deliver, on that. Now I’m not going to represent it to you that way, because I’m always going to set the bar low and I want to jump over it.
[00:40:40] Craig Baldwin: That’s every good salesperson should be that way. But I really put my business at risk when I’m constantly over representing my position, my deals, my sales. That is not good for anyone at my organization if I’m like that. And that’s why, good pipeline hygiene is really important.
[00:41:00] Terri Hoffman: Yeah, and that’s a good way to close.
[00:41:02] Craig Baldwin: Thank you so much.
[00:41:03] Terri Hoffman: We could really keep going, but I know
[00:41:04] Craig Baldwin: I love talking to you.
[00:41:05] Craig Baldwin: It’s so wonderful. And, I’m looking forward to having many conversations off camera and off microphone, because I just, I’m sure you see all of this all the time. And I can only imagine how much better we can make the world for sales and marketing teams.
[00:41:18] Terri Hoffman: I typically have some questions I ask at the end, but I’m sensitive to the time.
[00:41:23] Terri Hoffman: I want to ask you if somebody wants to take action and get in touch with you, please just do like a little commercial about your business and how someone could get in touch with you.
[00:41:34] Craig Baldwin: Sure. Absolutely. So you could go to upsourcedaccounting.com and find our website there and you could reach out. My email address is cbaldwin, B A L D W I N at, upsourcedaccounting.com. You can always reach me there. If you reach out on the website, I’ll see it eventually, but that’s the best way to learn about our organization, what we do, and the services we provide. But I’m also always happy to talk to people about sales and marketing in general. I work with a lot of businesses even today
[00:42:01] Craig Baldwin: that are not in the agency world, mostly tech companies about how they can improve their sales ops and, sales leadership. So, anybody who wants to check things out there, you can eventually get ahold of me. You can also find me on LinkedIn. and we’d love to talk to you.
[00:42:15] Terri Hoffman: Yeah. Well, I have a lot of friends in the marketing space and in the creative space who I know, listen to the podcast, get in touch with Craig, because
[00:42:22] Terri Hoffman: they do specialize in working with creative agencies and marketing agencies, and they have a pretty compelling, value prop that I think would be interesting. So, definitely check them out, but thank you, Craig. I really appreciate you coming on, sharing all the experiences and time with us.
[00:42:35] Terri Hoffman: And I hope you have a great rest of your day. Good luck picking up the kids.
[00:42:38] Craig Baldwin: Thank you so much.
[00:42:40] Terri Hoffman: No problem.
[00:42:40] Terri Hoffman: Thank you for listening to B2B marketing methods. Please be sure to follow us on your favorite podcast channel and leave us a review. We’d love to hear from you and connect. You can find me on LinkedIn or visit our company website at marketingrefresh.com.
