Table of Contents
Executive Summary
In this episode of The Revenue Briefing, Maria Meadows sits down with Michael Borell, a sales leader, advisor, investor, and startup growth strategist with nearly two decades of experience helping companies scale internationally. Michael shares a practical perspective on what separates sustainable growth from short-term momentum, emphasizing that revenue success begins with customer obsession, retention, and a deep understanding of the data already available within the business.
The conversation explores why founders often focus too heavily on acquiring new customers while overlooking the revenue potential of existing ones, and why customer success should be viewed as a growth engine rather than a cost center. Michael argues that customer retention, product adoption, and customer advocacy are among the earliest indicators of long-term revenue health.
Maria and Michael also dive into forecasting, pipeline management, CRM discipline, and sales leadership. Michael challenges founders to move beyond surface-level reporting by asking tougher questions, analyzing both won and lost deals, and creating operating rhythms that encourage continuous learning. He stresses that data should guide decision-making at every stage of growth, from early product-market fit through scaling from $5M to $20M in revenue.
The discussion concludes with a candid look at scaling organizations, highlighting how growth often requires evolving processes, redefining roles, and ensuring the right people are in the right seats. Michael’s overarching message is clear: companies that consistently inspect their data, challenge assumptions, and adapt their operating model are far more likely to achieve sustainable growth.
Key Takeaways
1. Customer Obsession Is the Earliest Growth Signal
The strongest indicator of sustainable revenue growth isn’t pipeline size—it’s whether customers genuinely love the product. Customer advocacy, expansion, referrals, and strong adoption are signs that a company has moved from a “nice-to-have” offering to a “must-have” solution.
2. Retention Is More Valuable Than Most Founders Realize
Customer success is often treated as a cost center, but Michael argues it becomes a revenue engine over time. Retention and expansion from existing customers are often more efficient growth levers than continually acquiring new logos.
3. Bring Customer Success Into the Sales Process Earlier
High-performing organizations introduce customer success before the deal closes. Early involvement during trials and onboarding creates confidence, accelerates adoption, and improves long-term retention.
4. Most Companies Lose Leads During Trials and Pilots
Many organizations invest heavily in generating leads only to provide little guidance once a prospect enters a trial. Supporting customers through implementation and early value realization can dramatically improve conversion rates.
5. More Salespeople Does Not Automatically Mean More Revenue
One of the biggest scaling mistakes founders make is assuming revenue scales linearly with headcount. Before hiring additional sales reps, companies must validate product-market fit, establish repeatable processes, and ensure current teams are operating efficiently.
6. Forecast Accuracy Requires Looking Beyond the CRM
Healthy pipeline management requires understanding deal velocity, buyer engagement, stage progression, and patterns across both won and lost deals. Forecasts become more reliable when leaders inspect underlying behavior rather than simply reviewing stage-based reports.
7. Analyze Lost Deals as Aggressively as Won Deals
Most companies celebrate wins and move on. Michael recommends treating both wins and losses as learning opportunities to uncover repeatable patterns that improve future performance.
8. Founders Need to Ask More Uncomfortable Questions
Strong revenue leadership often comes down to challenging assumptions. Founders should dig deeper into deal status, customer buying processes, risks, and objections instead of accepting high-level updates at face value.
9. Data Creates Clarity and Control
Organizations often possess the data needed to solve their problems but fail to use it effectively. Michael compares operating without data to flying an aircraft without instruments—growth becomes guesswork rather than a controlled process.
10. Scaling Requires New Processes and New Roles
The people and systems that help a company reach $5M in revenue may not be the same ones required to reach $20M. Sustainable growth demands role clarity, stronger processes, and an honest evaluation of whether team members are positioned where they can create the greatest impact.
Interview Timestamps
00:00 – Introduction & Michael Borell’s Background
03:08 – The Earliest Signals of Sustainable Growth
04:26 – Why Customer Retention Is the Metric Founders Overlook
05:37 – Turning Customer Success Into a Revenue Engine
07:31 – Why Sales and Customer Success Must Work Together
08:39 – The Hidden Opportunity in Trials & Pilots
09:58 – Using Data to Understand Conversion Bottlenecks
10:55 – Why Companies Lose Leads During Trials
11:36 – Should You Offer Free Pilots?
12:30 – The Scaling Myth: More Salespeople ≠ More Revenue
13:41 – Why Hiring Too Early Can Hurt Growth
14:49 – Talent, Onboarding, and Building a Repeatable Sales Motion
16:22 – What Investors Look for Before Committing Time or Capital
16:50 – How Michael Evaluates Pipeline Health
17:46 – What a Healthy Revenue Forecast Actually Looks Like
19:17 – CRM Hygiene, Pipeline Accuracy, and Forecast Reliability
23:49 – The Revenue Math Investors Use to Evaluate Startups
25:09 – Understanding the Customer Buying Cycle
26:24 – The Human Side of Sales: Asking Hard Questions
27:38 – How Founders Can Coach Revenue Teams More Effectively
30:16 – The Power of Asking Uncomfortable Questions
33:10 – Moving Beyond Forecast Reviews into Deal Strategy
34:17 – Why Qualification Frameworks Aren’t Enough
35:12 – The Value of Deal Debriefs and Sales Coaching
36:55 – Why Teams Must Analyze Lost Deals (and Won Deals)
38:18 – The “After Action Review” Framework for Revenue Teams
40:03 – Data as the Ultimate Competitive Advantage
42:55 – Revenue Mistakes Michael Would Change Earlier in His Career
43:41 – Why Most Founders Have Data But Don’t Use It Properly
44:45 – Using Goals, Metrics, and OKRs to Drive Growth
46:35 – Process, Automation, AI, and Resource Allocation
48:11 – Scaling from $10M to $20M: What Changes?
48:44 – “What Got You Here Won’t Get You There”
49:18 – The Critical Role of Processes and Organizational Design
49:47 – Why the Best Salesperson Isn’t Always the Best Sales Leader
51:19 – Matching Talent to Growth Stage
53:43 – Solving Internal Scaling Challenges
54:41 – Building the Right Playbook, People, and Processes
55:26 – Final Thoughts & Closing Remarks
Complete Transcript
Maria Meadows: Michael, thank you so much for taking the time to meet with us. We met at Web Summit in Vancouver and had a really wonderful conversation, and I was hoping to interview you and finally get time with you on just tapping into your background – because from our collaboration we’ve seen that you’ve sat in multiple seats. As an operator, as an advisor, as an investor, as a growth strategist – and I think you bring an immense amount of knowledge and experience to the table that I think a lot of founders in our network could benefit from.
So I appreciate you taking the time to meet with us and I would love for you to give our audience a little bit of background of what you’ve accomplished in your career, and just tell us a little bit more about you!
Michael Borell: Maria, thank you very much for having me. Yeah, my background is a little bit mixed I would say. I accidentally ended up in sales – testing software, training this software, and then also doing the support for this software, and after all of that, I did the technical presentations for that software. I ended up with the sales team traveling international, selling in different markets, and, different regions, and, working with, so many different cultures.
And, yeah, that was so exciting that I just stayed in sales. So over all these years, I mainly worked with smaller companies, startups, and helping them to grow.
After that, I moved into the investment market, so I also understand the other side, what’s important for an investor, what do they need to see, to, invest in you. And now I’m helping companies to bridge both worlds
Maria Meadows: So because you’ve worked with multiple companies and really have had multiple vantage points, what would you say are the earliest signals that tell you a company’s positioned for sustainable revenue growth?
Michael Borell: I would say customer obsession. that then translates into, expanding new net revenue. So not just getting new logos, really get customers being on fire about your service or about your product.
Maria Meadows: So tell me a little bit about that. Would you s- recommend that they zero in on their top two customers, and really learn from them and use that as a model for a new business development? Or lean on their customers for referrals?
Michael Borell: Yeah, referrals also play a big part in that. But in general, I would say an early signal is your product or service a nice to have or is it a must have?
Maria Meadows: Yeah.
Michael Borell: And, you can easily see that by really listening to your customers. So if the sales team has a really hard time to convince the customers to go for it and it’s extremely hard to renew these customers, probably something is wrong.
Yeah. But if your customers are on fire and they are requesting more features and they, are really on fire about your product and also advertising that internally and having that internal champion, not just during the buying process, also when it’s about the adoption and using the product, these are the hidden signals, I would say, that you’re on the right track with your service or product.
Maria Meadows: Yeah. You know what was interesting, you and I were at Web Summit together recently, and at our booth we had a survey, questions- that we would ask of what were the most important signals that as a founder or CEO, that they would like to lean in on, and which signals are they not getting early enough?
And, I expected that we would get a lot of feedback around, CROs wanting to see more insights around deals sooner or pipeline forecast sooner, but surprisingly it was customer, success and customer retention. They felt that out of all the categories and focus areas for the revenue side of the house, that was the one that they felt the most ill-equipped to support and lead.
and I would just like your take on that, because I, was surprised. you never truly think that a founder’s gonna say deals, right? We need to get our forecast right to the board. But, the fact that they didn’t feel they were getting enough insights around customer was a lesson learned for us, and an opportunity, for the market.
So just be curious, are you seeing that? And if you were to give them advice on what’s the number one signal to pay attention to on the customer retention, customer side, what would it be?
Michael Borell: Ooh, the wonder, the, number one signal, yeah, the retention rate. Retention rate. That’s extremely important.
if you’re, if you have a classic B2B SaaS business, then it’s also easy to measure. Yeah. But this is a very important number. Yeah. And the problem with customer success is it’s a cost factor. At the beginning, it’s cost. Yeah. You hire people that take care of your customers- Yeah … and they cost you money, and you actually want to spend your money on new salespeople to, to sell more.
So if you invest in customer success and you do it right, a year or a year and a half later, it’s a revenue machine.
Maria Meadows: I agree.
Michael Borell: Because they take care of your customers that you already have. And winning new customers, yeah, you constantly need to do that, but think about how much effort and money it takes to win new customers.
What about the customers that you already convinced? What about the customers that they already use and like your product?
If you take care of them, they renew, and your revenue flow grows. Yeah.
Maria Meadows: Yeah. And I think, too, how, much you think about integrating your sales motions with your customer success and customer retention motions.
I see a lot of organizations that treat it as two disparate work streams, right? But it’s if you bring your customer success team or these resources earlier in the process, there’s a continuity for the customer, and also training the organization that it’s okay to ask the customers for feedback.
It doesn’t show that you’re vulnerable or exposed in any product- yeah, but the more they, see it as a collaboration, I think the better that everyone does internally and externally. but I didn’t know if you had any thoughts there or reactions on process flow or, anything that you’ve seen gone wrong with, customer success and sales not working well together or anything there.
Michael Borell: Absolutely. The sales needs to work extremely close with customer success, also with marketing, but in reality, th- they are far away from each other. Yeah. yes, marketing and sales need to cooperate, but, customer success and sales even more. So it’s extremely important. Of course, it depends a little bit on what the product is, but bring in customer success even when the customer is not a customer yet.
That’s really important. If you bring in the customer success team, like saying, “Hey, dear customer, this is Joe, and Joe will take care of you, that your, trial is going as- Yeah … as, as good as possible.” And if the customer feels like, “Okay, if they’ve taken care so much about me as a trial customer, what are they going to do if I’m a real customer?” So if you bring them in very early in the process, it adds so much value, and it’s absolutely worth the investment. Yes, you have to have a dedicated person taking care of, the onboarding or the pre-onboarding process of the, the, leads, but it’s absolutely worth it to do that investment.
Maria Meadows: Yeah. I think that’s such a great point on how you show up during the trial and the pilot is a really great signal for the customer on what it would be like to work with your company long term. I, That’s such a valid point, ’cause I see a lot of early stage companies put a lot of emphasis in pilots and free trials and conversions around those, but there’s not a lot of process in those early stages. And you almost have the sales team selling it as, “Just try it out. See what you think.” so I do think there’s an opportunity and such a valid point, both in your seat as an operator and advisor of, every, moment counts, and even during the free trial, if not even the most important part of how are you gonna treat them when they’re not spending money with you, and how you support them, right?
And it is an investment that you will have to pay for it as an early stage company, but it will pay off because, from the RevEdge seat, a lot of the feedback we’ve gotten, on RevEdge interpreting signals is we want quicker validation if our pilots are converting faster than our normal approach, right?
And while we can absolutely deliver that, what, the data shows is they don’t. convert as quickly or as fast to revenue than… and so you’ve gotta take a step back and say, is it because we’re offering this free? Or, A, how we’re selling it, or B, how we’re onboarding and supporting the customer in these early stages if they actually see the value?”
Michael Borell: That’s why data is so important. You need to analyze the data that you have. you have the answers already. They are in your data. Yeah. You just need to look at the data and make, sense out of it. And this is exactly the point. Let’s say there is an early stage startup, and they are really good at whatever they do, building a product, offering a service, and then they start selling, and the first customers are on fire, and they go for it, and the company grows, and then they hire one or two salespeople.
They are busy. they are extremely busy. They don’t have time to, to walk a customer through the demo- through the, trial. Yeah And, they just go to the next one and to the next one because they got hired to sell, and this is what they want to do and need to do because their salary depends on it.
Yeah. And this is exactly where they are losing because they are not taking care of the customer. Again, it depends on what you are selling. So some things you can really just yeah, go and take a trial and then let me know what you think.
But there are some products out there you have to walk them through.
You really have to take them by the hand and, help them to install, show them what the features are, what the value is, how it can solve their problem that they have. And, so many companies are losing their, leads very early in the process, in the pipeline, and they don’t know why. Yeah. And you don’t have to, do any, crazy math or it’s not rocket science to understand why you losing them so early stage because you find the lead, you already spend a lot of money finding the lead, and then they download a demo or you give them the demo, and then, yeah, they’re on their own, and after that, silence.
Maria Meadows: Yeah. Question for you, and this is a side note. What are, what is your take on pilots? Do you think it’s valuable for a company to do them and offer them free? Or do you think it’s better to take the approach of just solid one or two customers and, grow from there?
Michael Borell: It depends. It really depends what the product is and what kind of, problem it solves. So for some, products it makes total sense to, to offer that pilot and to let them try to convince them with their data to see what the value is. Other products are, yeah, so easy to understand, and then I would not offer a pilot. Yeah. It really depends. But this is exactly what I do in my, on my, in my daily business, talking to customers, looking at their product or service, and then discussing what’s the right approach to go to market.
Because there is no one fits all.
Maria Meadows: So question for you. What’s a belief, when you talk about go to market and scaling, what’s a belief about revenue leadership or even scaling a business that you think most founders get wrong?
Michael Borell: M- more, the more, the better. yeah, let’s hire more salespeople and then we will sell more.
And this is what I constantly see. And, I’ve also seen that with, investors. We just invested a couple of million in you guys, and you have four sales reps and they’re doing X amount of money. Let’s hire four more and then we do 100% more. It doesn’t work that way.
Maria Meadows: I think this kind of ties back to your first point about customer retention, right? Before you scale, what are the metrics that we’re looking at to show that you can sustain that scale, and it can be repeatable, and it wasn’t just a one-off. And I definitely think leaning in, and even as an advisor, I’m sure your first place you’re going is to inspecting the retention rates and the customer growth before we think about adding more to the top of the funnel.
Michael Borell: The reason why this is such a big problem is, if you hire more salespeople, you shorten your runway, and you’ll not necessarily get immediate results. Think about hiring salespeople. You need to find them, you need to hire them, you need to onboard them correctly, and they need to get started.
Yes, sometimes that takes a month, sometimes it takes half a year, or it takes half a year and then you realize it’s the wrong person. So you’re not just burning cash, you’re also wasting time. I’m not saying that’s wrong to hire more people.
But before you do that, you need to make sure that the foundation is right, your market position is right, your product is right, everything works, the processes are there.
Because if you hire more salespeople and dump them in chaos- Yeah … they will not perform. So if you have the fundamentals right and your sales team, the people that are selling on the daily business, talking to customers, say, “Hey, I need help. I have so many leads and so many requests, I cannot do them all. I need help.” This is when you need to hire more, but not just “Yeah, let’s hire more,” and expect more results.
Maria Meadows: Yeah. But I tend to see a lot of turnover, too. Talent is a big focus for RevEdge on what are the signals of talent. Did they onboard correctly? are they ramping up correctly with the sales cycle?
But a lot of them fall victim to just a bad process, to your point, of it may not be that you’re hiring bad talent, it’s just, you have a bad process for onboarding them, training them, supporting them. and I think there is some- assumption on what level of talent, an organization should start with, because you see a lot of folks trying to allocate dollars toward more senior resources because they can just operate independently.
And then maybe senior resources struggle because no one can replicate the art of a founder, right? It’s very hard to do exactly what the founder does. There’s an opportunity to operationalize the sales process.
Michael Borell: When it comes to hiring people, you need to know what the problem is. If you have chaos, then it might make sense to hire a senior person, but then make it clear what you expect. Yeah. “Hey, I have this great product, I have a huge market, but I have pure chaos because I have no idea how to do sales and how to structure it.”
And then it makes total sense to hire someone doing exactly that. But if you hire someone like, “Hey, we have this great product and this great market and we need you,” and then they find themselves in that chaos, they probably run away in the first month.
Maria Meadows: Yeah. It’s true. So then as you, if you took a step back, right?
And you’re evaluating a business and deciding whether it’s a business that you wanna advise or invest in or e- even as simple as invest your time in, how do you determine what’s a good business to spend time with as an advisor or investor?
Michael Borell: What I look at is the pipeline in general. You can make a pipeline look good, but, you really need to, dive into the pipeline and see, how the deals are, proceeding through the pipeline. The velocity, the buyer engagement, that’s very important.
Maria Meadows: Let’s talk about pipeline for a minute.
We interviewed a lot of founders when we were developing RevEdge, and a lot of them said they didn’t really believe the forecast the sales team was giving them. And I think one of my favorite quotes was, “We just take what sales gives us, and we just water it down by 30%.” I use it all the time- Really
because it just really resonated with me, because that typically tends to be the pattern of when a forecast is handed over to senior leadership before they take it to the board, how they then slice it. if you were outside of an organization and you got a pipeline forecast, how do you qualify what healthy looks like?
Michael Borell: There are different things that I look at, no? What comes in, what gets out, that’s the general view. But what are the pipeline stages, and how many deals are in each pipeline, and how long they’re in this stage? And, then also looking at the deals that got won and, how they proceeded through the pipeline, and also, which is extremely important and gets overlooked many times, what are the deals that got lost?
Let me give you an example. I analyzed the pipeline before the AI age. looked at the deals. nowadays it’s much easier, but 10 years or, 15 years ago I looked at a pipeline and then analyzed how long was that deal that we lost in a certain stage.
And if you do that with many deals and then you see that red line, you see that pattern, and then you can easily say, “Hey, if a deal is in that stage more than whatever days, it’s very likely that we lose the deal.”
Or if you look at all the deals that got won and see patterns, how they, move through the pipeline, then you can also make your assumptions out of that and, your predictions and then say, “Okay, these are the deals that we won, and this is how they moved, and this is how fast they moved through the pipeline.”
And then, yeah, track that back and see what’s needed and what made the difference for these deals. Yeah.
Maria Meadows: I think that’s great. let me push you on this for a minute. That’s assuming that you have good CRM hygiene, which we know- organizations, especially early stages, don’t, for a lot of reasons.
How do you qualify the pipeline knowing that maybe you get 30% of the information in the CRM that’s accurate?
Michael Borell: you have to look at different numbers. No? is the deal value correct? Is the deal stage correct? And, this is, manual work that you sometimes have to do. So really sit with, with the sales team and, yeah, not doing interrogation, but, asking them the uncomfortable questions.
What about this deal? What about this deal? Why is it so long at that stage? And very often everything’s l- looks totally different afterwards. So I’ve done that with my sales team as well at the beginning and, asking these uncomfortable questions. And at the end of the day, we had a completely different forecast because it turned out that some people, they, move it to quote sent when they really sent the quote, and others give the quote extremely early and then just move it to that stage.
Or they bypass stages, which is sometimes possible. So they do all of, things what they believe is right. And others do it totally different because they believe what they are doing is right. And honestly, at the beginning, I don’t really care. They just need to do the same thing. It doesn’t matter this way or that way, but if they don’t do the same thing, you cannot measure it, and then you cannot see, how good a pipeline is.
Because if everybody is doing things differently, now for example, with the deal value, some people put the deal value in after the first call when they have a pretty- Yeah … good idea how much it’s gonna be, and others put the deal amount in there when, they send the quote. Yeah. Yes, nowadays you can, do so much with these CRMs and- and make mandatory fields and, set up rules and stuff like that. but a lot of companies are not using it.
Maria Meadows: Yeah.
Michael Borell: So they have four salespeople, and they all work in the CRM in a different way, and that causes pure chaos, but still everybody thinks they’re doing it the right way.
Maria Meadows: Yeah. But you’re right.
So what a CRM is gonna do is give you these, gates, right? And the definition of when an opportunity needs to be in that particular gate can… is subjective to some extent- unless you define for the organization what the triggers are, right? Because I may say, I may put something in, even a simple s- discovery meeting, and the meeting hasn’t yet happened, and other people will wait and move the opportunity after the meetings happen.
Yep. And those little nuances affect if you were just scraping information out of the CRM for a forecast. But to your point, it’s the questions you ask of the business and kind of say, “These are the most important,” not only triggers so we can have a hygiene issue, but also an understanding of what happens in between.
Yep. and this is where I think, a lot of folks come to us who are so challenging to manage a sales organization is there’s all these signals that are happening even within the gates, of a CRM. Yep. and there is some art to sales, period. You can’t, make it- It is- … fully scientific, but it’s to your point as a leader, it’s the what are the questions that I expect and ask of the business to qualify what information is sitting where?
Michael Borell: Exactly. You need to dive in and you need to have the experience to, to see what’s going wrong in there, and it’s always very different. And it takes time to set up a process and done, and then also get the adoption from the sales team. “Hey, here are all the new mandatory fields,” which is annoying to everyone.
“And these are the rules that you need to follow,” which is annoying for everyone. Yes. And you do these pipeline reviews, and I would say the pipeline review meeting is probably the most hated meetings for all salespeople. But you have to do it. You have to do it for a certain time until the sales team really sticks to it.
Yeah. And I practically show them. I said, “Hey, let’s look at your pipeline, and let’s change a few number. Let’s change the stage here. Let’s change this deal value over there, and, now look at the forecast.” And it was like, “Oh my God, it’s, 50% less.” Exactly.
Because your deals were in the wrong stage and with the wrong deal amount, and we just changed two deals.
Now look at all your 250 deals.
If you’re gonna change them all to the right stage and update the deal amount, what’s the forecast gonna be?
So this is the detailed work that you need to do. But let’s take a t- a step back and look at the, main overview. What I hear also when we, work with investors, and when I also, consulted investors when we looked at startups is- What are the rough numbers?
Yeah. what is the goal they want to achieve? And then you, ask them, for example, are you seeing the business plan, in the investment meeting? Yeah, we’re going to achieve one million next year. Oh, great. what’s your pipeline? Oh, we already have, 800,000 in the pipeline. Oh, that’s great.
What’s your win rate? 20% so far. Okay. And how does the lead generation look like? So they, just give you numbers.
Maria Meadows: That’s so true.
Michael Borell: And you, basically do the rough math- and then you see their face like, “Oh, yeah, now I see your point. It’s not gonna work.” No? Or if you wanna achieve two million, this is what you’re promising to the investor, and you have three million pipeline, you have a sales cycle of six months.
So it’s, really the super easy components where you look at and realize within a minute that’s not gonna work. Yeah. Yeah. And you need so much more pipeline to achieve that.
Maria Meadows: One of my, sticking points as, a sales leader and an advisor to consulting, it would be understanding what your target customer’s decision making cycle is. Because nine times out of 10 when we’re interviewing businesses and supporting businesses, their sales cycle is way more aggressive than how the customer actually can make a
Michael Borell: decision.
Maria Meadows: Yeah. So oftentimes there’s c- a constant miss and stress put on the organization. It’s like you can’t change healthcare segment’s procurement cycle, right?
This is the way they make decisions. And so I always encourage folks, first before you start qualifying your pipeline, walk me through what your customer, like your target customer, how they make decisions, what their decision making- Yeah … cycle is, and how, and shore that up to the pipeline and let’s see.
that’s the first start. Because oftentimes people miss, they’ll say, “Okay, we have, w- we put in our quotas at a 90-day sales cycles,” but your, business is enterprise and you have a 15-month sales cycle, right? Or a decision making cycle. There’s a miscell- You’re setting yourself up for failure. And so you have, this great pipeline top of funnel, but you’re not gonna hit your forecast.
Michael Borell: Yep. Exactly.
Maria Meadows: Ah.
Michael Borell: And if you, analyze that further, it’s the human factor.
People, want to have comfortable conversations and not the uncomfortable one. And I’ve seen that in reality that a sales rep is talking to a customer for, weeks, and they literally just do coffee calls where they talk about tech stuff, and everything is great, and the product is awesome, but that’s not the decision maker.
He doesn’t have any buying power. Nothing. Yeah. And this is really a problem. you, don’t want to ask that un- uncomfortable question. in reality, “Okay. Hey, Marine, was really nice talking to you last couple of weeks, but now I need to know who makes the decision.” Yeah. “Because it’s obviously not you.”
Yeah. Nobody’s going to ask questions like th- Yeah … a question like that.
And, as you said, the understanding the buying process, and you can ask these questions. Yeah. who else is involved in the buying process? Yeah. No? So it’s great that you like the product, you tested it, you like it, what’s the next step?
But salespeople, yeah, really don’t want to have these kind of conversations. But at the end of the day, it takes forever to close a deal. No, it’s difficult.
Maria Meadows: And sometimes, look, when you’re moving a mile a minute and you’re working opportunities, you’re trying to get in the door, you’re trying to move an opportunity through.
It’s very, it’s a very busy world as a seller, right? And so this is where it’s like how do you empower and support the founder to be a better coach or to remove road blockers? and the reality is the f- the time of a founder is very limited. you’re wearing multiple hats.
And what I would love to see is folks, especially founders and leaders, not just showing up in forecasting meetings, right? it’s how do you maximize your time and impact across the business? That’s, I think that’s gonna be an ever standing challenge for a founder, right? We only have 40 hours in a workday, right?
We all have the same amount of time. So how do you deploy your time and allocate your time on a daily basis? But from there, how do you get involved a lot sooner, right? So to your point- Sure. After the fact, we can have a conversation that you’re not, “Hey, rep, A, you’re not meeting with the right person.
This is an influencer, right? They can help get you in.” But giving that rep a sounding board to talk through an opportunity can go so much further because sometimes just slowing down, have you met with… Are they able to get you in the door? What’s the process for the next steps? And sometimes I think a lot of founders put the pressure that they need to have all the answers or all the tools in place, but even slowing a sales rep’s brain down for a minute and being like, “Do we have the right people?”
That question alone will go five times further than the forecasting meeting of where are we at with this deal. and sometimes all we have is the time in those forecasting meetings, but my goal is how do you get involved earlier at the right moments to ask those questions to unleash your talent?
Because there is an emotion there, right? We have a good conversation, they’re giving you the information. But being able to have a business conversation, not just a relationship-focused conversation, right? and those things are not treated equal. I, fully agree with you there. But it’s al- it’s also very hard for a founder to manage all those moving pieces.
So with that, if you had to, if you were coaching a founder- Yeah … especially one that does not have a sales background, and they have, let’s say, three to four sellers, and they’re attending the for- forecasting meetings, they’ve articulated clear triggers. What would you say are the, If you had to get involved in sales, or when to spend your time with sales, what are the two to three most impactful areas to focus on as a founder overseeing revenue?
Customers we got first, right? Existing customers. Yeah. But in day-to-day coaching and operation, how do, where and how do you spend your time?
Michael Borell: it’s n- that depends again what the most important areas are. In general, I would say ask uncomfortable questions.
So it doesn’t matter which area it is. If it’s a forecast meeting or if it’s a, meeting where you talk about processes, where you constantly hear “Oh, yeah, we don’t need that.
Oh, we just do this afterwards.” Or, “Yeah, I put this in the CRM.”
Maria Meadows: Yeah,
Michael Borell: Yes, these are all important parts that you, you need to be aware of as a founder. But it doesn’t matter what the area is, what the topic is, ask the uncomfortable questions. Because the, vibe in a startup is, very friendly.
We are like one family and we go for this together, and, yeah, we can do this together. You, try to avoid these uncomfortable situations and conversations, but I think you are harming your organization if you do that. You don’t have to be rude or unfriendly, but don’t just take or accept every answer that you get.
Because we are all human beings, and the salesperson’s the same thing. I’ve been in that position. I also had to report to multiple people. Yeah. And then it’s easier to say “Oh, yeah, the, I have a meeting with him tomorrow. The deal will come.” And then the founder says, “Okay, great.”
No, you have to dig deeper.
Okay, what’s the status? What did they say? How committed they are. It feels uncomfortable to ask these questions, and it’s super annoying for a salesperson to answer these questions, and that’s why both parts, both parties are- Yeah … avoiding that.
Maria Meadows: Yeah.
Michael Borell: So try to look behind the things. If you start hiring people for sales and marketing, don’t just blindly trust them.
Don’t be a micromanager. But ask the questions that need to be asked, and then trust the team to take care. Yeah.
It’s a very thin line, huh? It is. Between trusting, micromanaging, but asking the questions that need to be asked. It’s very rare that you hire people and you let them go, and they just do the wonderful thing and skyrocket your revenue.
Maria Meadows: Yeah. Agreed.
Michael Borell: And of course, if you don’t have the time, if you don’t have the knowledge, if you don’t have the background, then just hire the right people. No? Then don’t hire a couple rookies, then hire a senior salesperson.
Maria Meadows: That’s actually the
Michael Borell: type of talent.
Be clear in your expectation management. Hey, I don’t have the time, and I want you to build the sales team.
And then let also that person decide who they wanna hire. And there is network. So if you would hire me giving me that task of, hey, build a sales team, and then I would hire salespeople that I know and that I’ve worked with.
And that is probably the most efficient way moving forward.
Maria Meadows: Such a great point. I always like to, just on the questions asked, the, almost, s- looking for problems, right? What would cause this deal if we lost it? Why would we lose it? What do you think? what’s stumbling blocks?
And it always slows the reps down to be like… A- and and then it opens the door for a strategy conversation than just a fo- a focus between the rep and the leader on numbers, right? Totally. Because you can say, “Okay, sounds like everything’s going well. Where would be a stumbling block if we had one?”
How do we start to think three steps ahead? we haven’t really heard from this per- and it just moves into natural account planning or blocking and tackling as a business on how do we make short moves, right? So we’re not assuming that the rep is always t- things may be going really well and moving at that pace until they’re not.
So it’s almost like how do we prepare for any challenges, right? and what do we need to be thinking about that could slow us down or get in our way or a competitor coming in, what do we know about them that may s- m- ha- cause us to go into another, a negotiation phase that we weren’t anticipating,
Michael Borell: Right? Why at the beginning, we all know the BANT qualification, MEDIC qualification. They’re all great, but it’s just high level and standard. You need to bring in the human factor and the experience.
Maria Meadows: Yeah.
Michael Borell: You really need to, use these qualification methods, which one works best for you, I don’t know, that depends on your business. But then go beyond that to get a perfect understanding. And then at the end of the sales c- Try to understand why did we win this deal? Why did we lose this deal?
And as a founder, I highly recommend to be part of these meetings. Yeah. Not just very early stage. “Hey, you talked to this enterprise customer that we desperately want to win. How did the meeting go?” Yeah. Or, “Show me the recording.”
How did the qualification go? What did they say?
And it’s really good if you have someone asking these questions, and don’t see that as an interrogation. And I did that with for- one of my former bosses. we challenged each other. Huh? We were both in the meeting, and he did the technical, presentation, and I just, looked at the team, how they reacted to certain things.
And when I did the sales part, he did the opposite. He looked at the team and how did they react to certain things when you dropped the price or when you talked about when this feature will be released and stuff like that. And then doing a debriefing afterwards is extremely valuable. And also having a person asking these uncomfortable questions, and you as a sales rep be willing to, answer them.
Because at the end of the day, everybody wins. Yeah. Even if it’s uncomfortable. But yeah, comfort and growth cannot coexist. But that’s the fun part of sales.
Maria Meadows: And that also goes for salesmen. that honestly, I think any salesperson would really value those conversations.
Michael Borell: Yeah, so, you felt that the meeting went really well, but I think this qualification is pretty weak, that client said this and this about that, and yeah, what does it mean? And we should definitely focus on that in the next meeting and, get more commitment or get more information.
And probably you don’t see this as the, interviewer, as the person that asked the question to the, customer, but that other per- person realized that something is wrong here. And then as I said, also at the end, why did we lose this deal? Oh yeah, they are, they were, they had no budget this year.
Okay. No. Go deeper.
Maria Meadows: Yes.
Michael Borell: It’s probably a different reason.
Maria Meadows: Yeah.
Michael Borell: Because it’s easy for the sales rep to say something like this, “Oh yeah, I followed up 10 times, they never got back to me.” Okay, that’s it.
And you really need to, do that investigation. And also- organizations rarely analyze the lost deals, and in 99% of the cases, they never looked at the won deals because, “Hey, we won that customer.
Awesome. Let’s move on. Let’s make more.”
Maria Meadows: Yeah.
Michael Borell: Yeah, but why did we win this customer? We can probably use that valuable information to- Yeah … win even more customers. Yeah. So that’s why it’s so important to look at the data.
Maria Meadows: Yeah. I would say that would be my biggest ask of any leader in an organization, whether you’re in the founder seat or the CRO, is find time for those conversations, and it- it’s just making the time to e- be- like I said, we’re all running a mile a minute.
But it goes so much further. To your point, even taking a beat, even if there’s a set time each week where it’s we’re just gonna diagnose and inspect, right? We’re not gonna, let’s just talk these five deals through. Yeah. wins, losses, challenges. And it gets that culture of inspecting, thinking, strategizing, collaborating together- that I think is gonna accelerate. but it f- it feels like a lot of time in the early stages, especially if it’s a new process for the business.
Michael Borell: Yeah, and not needed. It’s probably the same in sports, huh? If the, match goes wrong, they do a debriefing for an hour, and yeah, that was wrong, and yeah.
But what if they win? They are on fire, and they are happy, and nobody cares because we won. No. Why, should we… We don’t need a debriefing to understand why we won. We won. That’s all that matters. Same goes in sales.
Maria Meadows: Yeah.
Michael Borell: But it’s, quite interesting that, even the military does that. They call it, the US Army calls that the after action review, and they do this all the time.
It doesn’t matter what they do.
I love that. It doesn’t matter if it’s a small exercise or a big exercise or some kind of a training or even probably after a war. They always do a after action review no matter how things turned out, and that’s extremely valuable.
Maria Meadows: I think you may have just branded a new, sales meeting for a lot of leaders.
The after action review I think would be amazing for teams. Yeah … and it’s, beneficial, too, ’cause I think a lot of founders dismiss, even if they don’t have the sales background, that, they may not be able to support sales. And even just thinking with your CEO goes a very long way. and I don’t think there’s anyone that understands the business better.
And someone that can ask questions that is not as close to the day to day, that really adds a lot of value to the sales organization, just to slow down and think for a bit. Yeah … would you say that’s the operating rhythm that you think sets high performing organizations apart from the, pack, or is there another rhythm that you would say?
If you were objectively looking, be like, “This is why.” They’re successful
Michael Borell: Yeah. I would say that, that is the biggest differentiator, knowing what’s going on. Data is so important. Everything else is guesswork. Yeah. Like winning a deal, “Oh, we won this deal and that. We’ll- we made the first 500K.” Why?
We don’t know. the product is great and the, market is there, yeah, but why did they buy it? Yeah. Who cares? They, bought. Okay, but what about all the deals that you lost, all the customers that didn’t buy?
And this is just a small fraction of all the data in sales.
Yeah. And, we talked about it at, Web Summit, data analytics and business analytics. It’s, mind-blowing. Using the data that you have gives you answers to questions that you haven’t even asked- Yeah … if you do it the right way, and that is so impressive.
It’s like, flying a plane, right?
If you fly a small plane, then you can… If you can fly a plane, you don’t need the instruments. But if you’re flying a, Boeing 747, I would say it’s quite useful to know how high you are, how much fuel you have, and, what’s your heading and everything. You need to know that because if you wanna fly from the US to Europe and your tanks are just 50% full, you’re not gonna make it.
And if you fly west, you’re probably not gonna end up in Europe because Europe is in the other direction.
Michael Borell: What a great analogy. It’s so true. And that brings me back to, to, to the pipeline, and to the forecast, and to the lead generation. You need to know what your numbers are, otherwise you’re just guessing, and nobody really knows where the problems are how to solve them. And how can you solve a problem if you don’t even know, understand where the problem is- or what’s causing the problem?
So data is, yeah, the biggest differentiator. If you understand your business, That really helps.
Maria Meadows: Let’s put it in these easy words. No, it’s true though. You have more control over the organization, and for all of it, it trickles down, right? How you prioritize. What types of talent you need. What, where to spend dollars.
All of it. I agree. So let me ask you, it’s one thing now, to, be, to sit in your seat as an advisor where you’ve had this perspective of so many different companies and so many different conversations and so many experiences, but if you had to go back, across your career, what would you say was a revenue mistake or a scaling, decision that- you made that changed or now you would change in terms of how you would lead and advise an organization today versus when you were early in your career?
Michael Borell: Probably looking at the data.
Because very early stage, you’re, chasing every shiny object.
And the risk that you run to the wrong direction or waste resources and, money is extremely high. So you need to have a target. You need to have your goal set, otherwise you don’t know where you’re going.
And then you run after everything.
Maria Meadows: Do you think that’s still true today? Say again? Do you think, that’s still true today? Do you- because I don’t have the perspective of advising multiple companies, right? So in your seat, do you think that it’s still true that founders don’t have a good handle on data?
Michael Borell: They have the data but they are not using it in the right way. Ah, okay. And they don’t have the goal set or, and/or aligned their operations with the goal. No? So for example, they say, “Hey, we wanna make two million.” The market is there, the product is there.
Yeah. Everything is set. We wanna make two million. But they have no idea how, and what they are currently doing will not end them up there. So having the goal clearly set, and then aligning your operations and the activities, everything that you do on a daily business, which brings me, for example, to OKR.
The OKR framework is you can use this as an enterprise, you can use this as a, as, a small team. You can totally overdo it- Yeah … and then it’s, holding you back. But if you’re using that like objectives and key results. So where do we wanna go and what do we need to go… what do we need to do to get there, no?
Lead generation. If you wanna make two million, how many leads do we need?
And how big does our sales team need to be? And what is the sales cycle? the really fundamental high level numbers. Having them straight. So what is it that we need to do to achieve that goal?
What are the activities and how can we measure these activities to make sure we are getting there? And let me give you an example. If you go on a hike, you do exactly the same thing. We are here, we wanna go there. So let’s use a map. Okay, we need to go here, and here. Yeah. And then we will end up there.
And then on the way you stop and look at the map and look at where you are. Or “Oh yeah, we are still on track.” Or, “Oh, wait a minute, we are off track. We need to correct.” And- These frameworks help so much to, stay on track because as a, early stage startup or as a startup in general, even if you have a big f- funding, you, you cannot waste resources, time, or money by doing the wrong thing or running into the wrong direction.
So set a clear goal and then measure your activities to make sure you’re doing the right thing. Yeah. That is overall I would say the most important thing that you need to do.
Maria Meadows: Yeah. I love that. I think it’s such a great point too, and it’s not so much the big numbers, right? we can all say, to your point, the two million we’re gonna hit it, and- the high level, but it’s the numbers underneath it that prop those up, that you always need to pressure test, right? does this make sense? does the formula add up to getting us to this number? Yep … and I always tell folks it, it doesn’t have to be perfect, but it gives you a framework that you can adjust and validate, but at least there’s something that stands up where you feel more in control over running a business.
Michael Borell: But this is, the high level thing. You always need to- Yeah … look at the individual situation. And, sometimes it’s pretty easy. this is the goal that we want to achieve. we don’t have the resources yet, so let’s build some crazy cool processes and use AI to, to automate things. and then we can use the human resources that we have and the little funding that we have to do exactly the right thing.
Maria Meadows: Yeah.
Michael Borell: Or you have a different situation where business excellence is top-notch. You already have automations and processes, but now you need the human factor. You cannot sell using an AI. You need human beings that build up the partner channel. You need to build that relationship with your customers. We talked about customer success earlier.
Yes, there are companies, they use AI for customer success, and they do it very successfully. But in some lines of business, you just need the human factor. So you always need to analyze what are the things that need to be done right now to make sure that you reach your goal at the end of the year.
Maria Meadows: Yeah.
Michael Borell: Because most companies have these shock meetings, in fall or, late fall, “Oh yeah, we’re not gonna make it.” And time – you can solve a lot of problems with money, but you cannot buy more time. If you need to make a certain number by the end of the year and you’re in November and your sales cycle is six months – But if you know that you’re off track already in March – there is still a lot you can do.
Maria Meadows: Yes. Okay, so I’m mindful of time. I’m gonna ask you one last question, because we focused a lot on early stage companies, right? last question for you is now if you’re working and you walk into, advising a company that’s 10 million looking to hit their next growth gate, go from 10 to 20- 20 to 30, what advice would you give them? What do you see that’s different from that zero to one phase moving into the next phase? I would love to just get your take on here’s the theme and here’s the number one, recommendation I would have for them.
Michael Borell: There is even a book about it. What Brought You Here Won’t Get You There.
Maria Meadows: Yeah.
Michael Borell: And this is the truth. So if you grew from zero to 5 million or 10 million, and now you want to go from 5 to 20 million or to 15 million, you need to change a lot
Maria Meadows: What do you think would be the number one thing to change? And I’m speaking in generalities. I understand every business is nuanced, but high level, where do you typically see the-
Michael Borell: Processes and roles.
Maria Meadows: Yeah.
Michael Borell: Or roles and processes. That depends again if you are already making, whatever, five million, you probably already have processes in place. You need to have even better processes, and you need to change roles. That doesn’t mean you have to fire entire company and hire new people.
You need to look at the people. You need to have these conversations with your team and identify the leaders, the managers, and the workers.
This is very important because a lot of people get to that plateau, and they will never grow above five million because the people that helped them to get from zero to five million are probably not the right people to bring them to 10 million to 20 million.
And that doesn’t mean that these people are bad. No, it’s a different skill set. But they need to understand, that saying, “Know what you know and know what you don’t know.”
And if you are not the person that can lead a 20, 30 people sales team because you are, such a talent and seller, then keep on selling, and don’t, feel like, “No, I need to be the CSO now.”
No, stay a salesperson. Yes. And as a CEO, you, need to make these decisions. And I’ve seen this. I’ve seen this even with myself, being in the wrong roles, and this is what always happens, with, people. Who, becomes the, lead developer, the best developer? Who becomes the head of sales, the best salesperson?
How stupid is that? You’re losing your best salesperson, and you have a, head of sales that maybe doesn’t even want to manage people- Yeah … or doesn’t like managing people. So you double- Yeah … harm your company. You’re losing the best salesperson, and you’re having a bad manager probably scaring away the other people.
So this is one of the biggest mistakes that people do.
Maria Meadows: I agree. I think, too, there’s just a, it’s just a skill set, right? and the- Yeah … right of… and it, doesn’t mean that you can’t grow people or people can’t evolve into bigger positions. That’s not what we’re saying at all, but the reality is taking a company from zero to five million is very hard to do, right?
And so I even see some folks that have managed, 200 million in revenue- struggle at that- Yeah … zero to one phase, right? There… it’s just a totally different approach, a totally different environment. And so knowing what talent for the stage that you’re at is really important.
It’s also emotionally hard —
Michael Borell: Emotionally, and that’s why it doesn’t get done. And as I said, I’ve seen it with myself that I got promoted in roles where I didn’t feel comfortable, and I got promoted in roles where I really felt comfortable.
Maria Meadows: Yeah.
Michael Borell: But we are human be- beings.
You don’t know that, and your manager doesn’t know that, your CEO doesn’t know that. But you have to be, grown up enough to have these conversations and also say “Hey, I don’t want that role. I’ll take the salary, but I don’t want that role.” Now everybody wants to make mon- more money and have more power and-
Maria Meadows: Yeah
Michael Borell: but yeah. Yeah. At the end, you probably not up ending in a comfortable situation.
Maria Meadows: Yeah.
Michael Borell: And I’ve also seen that I promoted a good salesperson into the head of sales role, and it turned out that he was an even better head of sales. But that’s also ego. Because he was not just a good salesperson, he was a good manager.
Maria Meadows: But that’s also ego- that is also a good thing … and that’s “I’ll get them there. I’ll get them there.” Yeah. And then that’s two people that are now buried in time, so you almost have to take a step back as a CRO and be like “Can they do it on their own without me?”
‘Cause all the time, any of my VPs of sales that we’re interviewing, they’re like, “I’ll coach them, I’ll support them.”
I understand that, but at what cost, right? What is that gonna cost in terms of the other areas of the business that you’re managing? But this goes back to your point, and, we’ll wrap, but it goes back to your point earlier of objectively asking the business what problems are we trying to solve, first.
Versus just putting, people in certain seats and just slotting into an org chart of, okay, now we’re at the stage, what are our core problems and what’s the talent that we need to get to this next gate, and what talent do we have on deck and what do we need to fill? so it goes back to your point of just these hard questions that you have to ask, but removing kind of the lens on what do I have right in front of me right now.
Michael Borell: But you have to ask these questions also internally, not, just for your customers w- or what, kind of, of problem are we solving on customer side. Yeah. What are the problems that we now need to solve, internally to grow from- Yeah … 5 million to, to 10 million or even higher. You need to, to…
You need to build processes to automate whatever can be automated, to not wasting time, to be faster.
Maria Meadows: Yeah.
Michael Borell: To not have these annoying and time-consuming things. And sometimes it’s shocking on, in, in both ways how some startups work, like extremely old school time wasting and resource wasting. And also shock on the other, shocking on the other end if you ask them, “Okay, what about this, Yeah. And they show you their brilliant processes and automations that they’ve set up to… and outsource this to AI to- to workflows. And this is- They’re like, “Oh, I’ve got a skill for that. That’s amazing.”
So yeah, set up the right playbook with the right people and the right processes, and then you can grow from 5 million to 20 million.
And then in the next step, it’s, exactly the same thing. And, I can highly recommend that book, What Brought You Here Won’t Bring You There, because it describes exactly that. And that, again, doesn’t mean you have to fire your people- No … that helped you to build your company to 5 million. No. You need these people, but you need to be, in the conversation with these people to see where their pref- perfect role is.
Yeah Where they can really shine, where they can perform the most. And, that’s probably not the C-level role then.
Maria Meadows: Yep. They may be tired at that point anyways. Get you to 10 or 20 million, depending on the business or journey, they may be ready to take on a different role, and will tell you too.
But, Michael, always love talking to you. Thank you so much for your time and feedback. You’re welcome. I feel like every time we leave a conversation with you, there’s these aha moments or the ability to take something that’s so obvious but land it in a way that can be applied. and, it just it’s very energizing.
So I really appreciate your time. I know we’ve taken you over, but thank you so much, genuinely.
Michael Borell: You’re welcome, Maria. Was a pleasure having this, conversation, and, this is exactly what brings companies forward, providing them with the insights they need to know and, pushing them a little bit out of their comfort zone.
