2400 - Driving B2B Success Through Sales Forecasting and Customer Understanding with Roadmap's Steve Whittington

29 Mar 2026 · 18 min · 8 chapters

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In short

How B2B professional service and manufacturing firms (revenue $5M–$75M) can drive predictable growth by replacing “hope casts” with mathematically modeled sales forecasting and deeper customer understanding, then turning that into measurable go-to-market activity scorecards.

Guest backgrounds

Steve Whittington, president of Roadmap Agency; 30+ years of alpinism/climbing, using risk management and focus as a metaphor for business execution.

Key claims

Many teams can’t forecast because they don’t model unit economics and account math; sales-cycle and conversion issues are symptoms of weak customer understanding and missing activity metrics. Use historical account averages, account tiering, and time-to-close/expand to compute the revenue “gap delta.”

Notable examples

“Boombright Media” takes 12 outreach touches to get a customer to the table; if $10M current revenue needs +$3M, tiered accounts and timing may require more than three accounts (e.g., six if revenue arrives mid-year). Guests/mentions: none besides Steve Whittington.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Getting to Know Steve Whittington

0:45 to 2:18

Steve shares his passion for climbing and its emotional benefits.

“Visit podverified.com if you'd like to be featured as a future guest.”

Overview of Roadmap Agency

2:18 to 4:46

Steve explains who Roadmap serves and the challenges they address.

“But what you're describing is that's, that's, that's next level.”

Tips for Effective Sales Forecasting

4:46 to 8:52

Steve provides actionable advice on creating accurate sales forecasts.

“Well, Steve, let's talk about Roadmap, your website, roadmapagency.com.”

Addressing Common Pain Points

8:52 to 12:43

Discussion on common sales challenges and how to overcome them.

“that will start to build the outcomes that you're looking for.”

Client Engagement and Support

12:43 to 14:01

Steve details the engagement process with new clients and ongoing support.

“Steve, when you are working with a new client, what does that typically look like?”

Exploring Roadmap's Resources for Business Growth

14:01 to 15:50

Learn about the Go-To-Market Readiness Index and Revenue Factory Toolkit.

“And then we have a roadmap, pun intended, about what we should be looking at.”

Conclusion and Call to Action

16:06 to 16:52

Wrap up with a reminder to subscribe and engage with podcast resources.

“Steve Whittington, again, president of Roadmap Agency.”

Conclusion and Call to Action

17:01 to 17:40

Wrap up with a reminder to subscribe and engage with podcast resources.

“These tools are built to help you get booked on better shows, deliver stronger interviews, and convert audience trust into revenue.”
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Transcript

Automatic transcript. May contain errors.

0:03Welcome to the Thoughtful Entrepreneur. If you're committed to growing your business by serving audiences with generosity and real expertise, you're in the right place. This is a daily 15-minute show featuring leaders who believe real impact comes from generosity, not hype, which means as a listener, you're going to get the good stuff. In fact, we created podverified.com to give thoughtful leaders like you free tools to show up better on podcast stages like this one. That includes your free podverified score, free podverified guest training, a free media kit builder, and so much more. It's the first ecosystem of its kind built by podcasters who genuinely want to help guests thrive and grow in podcasting.

0:46Visit podverified.com if you'd like to be featured as a future guest. I'm Josh Elledge. Let's get into it. With us right now, Steve Whittington. Steve, you are the president of Roadmap Agency. You're found on the web at roadmapagency.com. Steve, it's great to have you. Fantastic to be here. I've been looking forward to this. Yeah. Before we get going, I always love talking with our guests, high-level leaders and the things that they do for fun when they're not at work. and I understand you are a climber. Tell me more about that. Yeah, I've been climbing now for over 30 years because I'm an old climber, but that's how I recharge and reset.

1:34I like to put myself out on the edge. So it was like a week and a half ago, I was with one of my climbing partners and we went and we climbed Mount Merchinson, which was 280 meters, so just shy of a thousand feet of vertical ice. It was a 10 and a half hour day, long day uh reminded me that i'm still alive and uh yeah i get back to civilization and i uh i'm ready to go again after being inspired being out in the mountains when when you say climbing are you like climbing with like the picks and the special shoes client kind of climbing or are you on your feet and you've got the ice tools that are specific for ice tools you're putting ice crews into the ice like i do i don't i don't solo except uh when absolutely have to uh so try to protect the climbs but yeah you're you're going up and you're finding nice features like we actually belayed out of an ice cave uh you know 200 feet up that was one of our belay spots and then you then you rappel down you know wow my mind is blown so i did uh you know i've hiked mountains before i did pike's peak uh about two years ago and i'm really looking forward to doing it again.

2:42But what you're describing is that's, that's, that's next level. Any, any tips for someone? Well, let me ask it this way. What do you get out of that experience? Like, what does it do for you? Like emotionally? Cause I know even just hiking Pikes Peak for me, you know, I've done endurance, you know, marathons and that sort of thing. And there's, there's just something you get, you know, when the body starts giving out a little bit, you know, your, you know, kind of your brain starts like, oh man, this is really hard. But somehow it's like you have to dig a little bit deeper to get to something that, that I found that you can really only get through some of these endurance type things.

3:31I don't know what, what's been your experience with this? well with alpinism which is really what i'm talking about here you're combining endurance with mental mental ability to manage risk and so you know you have to understand when you're hanging off a tool and you're trying to put in protection with an ice screw and your arm is getting pumped out that you have the ability to say listen i'm just going to switch arms i'm going to shake this one out a little bit and I practice hanging off tools. So I know exactly how many seconds I have left before I get protection in. So it's like, listen, I still got 45 seconds.

4:10Keep going, Steve. And, and then you just, you just really have to be able to manage your emotional state to push through all those different physical limitations and fear that you might be up against. So it really does like, for me, you're so connected nowadays. You've got so much stuff. You get up have Wi-Fi, none of that stuff, you're dialed in, you're focusing literally on inches in front of your face. So it reminds me how to focus. It reminds me that I can do hard things. And it makes when I get back to civilization, as I call it, makes the challenges every day a lot easier. Yeah. Well, Steve, let's talk about Roadmap, your website, roadmapagency.com.

4:52Who do you serve? what are your superpowers? Well, specifically who we serve are B2B professional service firms, other professional service firms like engineering accountants. We have a few of those, but mostly it's manufacturers, people that sell to accounts. And there is a band, a revenue band, five to about$75 million because that's the size of company, a medium-sized enterprise that we really specialize in. And the superpower that we have, so to speak, is the pain point that a lot of those organizations are in is they can't really predict what their revenue will be, say, in the next quarter or what their next sales cycle will be.

5:37So we come in and put in a system that creates predictability. And so the pain point that we solve for these folks is that they have fewer surprises. Like, hey, it's like, I'm not surprised anymore. I have a pretty good idea of what it's going to be next quarter, right? I have, you know, less frustration with my sales team because I know what it's going to be next, next quarter. And so it also part of that becomes how you get more efficient. So you have less waste, leaner team, that sort of stuff. But it really comes down to building confidence in your go-to-market system. And that's the outcome that we produce.

6:08All right. How does one get there? So let's say we're going to give maybe two, three solid tips for our audience, to our friend that's listening to us right now. And they're like, all right, Steve, I'm getting ready to take some notes. Tell me what I, before maybe we have a chat about potentially working together, you know, help me get an image of maybe some things that I could be doing a little bit better, you know, with our organization. So the first thing I see a lot of these orgs doing, and we have this backed by research, We have a go-to-market readiness index. So we've researched this. So we've got a big data set that what I'm saying is actually backed by research.

6:49So we've got statistical relevance that this is what's occurring in the marketplace. So a lot of folks have what I would say they start with their first challenge is they actually have what's called a hope cast as opposed to a forecast. So they hope they're going to grow 30%. They hope they're going to get there. And they don't have that backed by any kind of mathematical modeling of unit economics and stuff like that. So it's like, how are you going to grow 30 % over, let's just pretend you're 10 million bucks and you want to get to 13 million bucks. How are you going to grow that$3 million delta, right?

7:20Is that going to come from existing accounts? How many net new accounts that you have to add? That sort of stuff. They don't have that figured out with a mathematical model. That's the first issue. So if you do that first and actually mathematically model out and then you can have reasonableness based on what your growth goals are and you can see what it is that you need to do to get there. The second thing that you got to start with is, and this might seem counterintuitive, you should have started with this first, but then you do a deep dive into your customers. You really need to understand who your customers are and you tier your customers, like who are your strategic accounts?

7:56Who are your growth accounts? Who are your transactional accounts? Dial in on those growth and those strategic accounts, which are 80 % of your business. There's your ideal client profile. You don't need to do a bunch of research. You just need to look in your P &L and you'll see who your ideal client profile is. Get that understood. Get who the actual buyers are and then really understand what it is that you solve for them and dial in more on that. Then you can start to make the motions for how you go to market and how you actually bring that mathematical model, that gap delta, how you actually solve for it with various different motions of customer understanding.

8:30So that's the first things you do. First, actually create a real forecast with mathematical modeling of what you need to do with activities. Second, deeply understand your customers, who you have now, so that you can know who you serve best and understand what it is that you really do for them. And then when you understand your customers, you'll know how to reach them and you'll know how to actually have market message fit that will start to build the outcomes that you're looking for. Any tips on kind of getting to more realistic, accurate numbers instead of hopes and wishes and dreams? Yeah, I mean, the thing of it is, we have so much data at our disposal and we're not using some of these basics.

9:10So really it's pretty easy to take a three-year average of your accounts. And so you should have then a pretty good idea of what this is what my existing book of business. So again, using that$10 million analogy or example, let's pretend that's made out of 20 accounts. So you can say, well, geez, my average account is$500 ,000. Well, there's going to be variances in whether it's tier one, tier two, your tier one could be a million bucks and your tier two could be quarter million dollars. So then you know how many types of accounts you need to add if you want to get three million dollars. That could be three tier one accounts.

9:44So it's like, wow, I just have to land three tier one accounts to be able to get to what I want to get to. Now you got to back that up with some more math. How long does it take you to actually land an account? How long does it take to actually land and expand an account? So it could be that, you know, if you get an account, if your fiscal year runs calendar year, you get an account in June, we're only going to get half the revenue from that, right? So you don't just need three for the year, you might need six to get to your $3 million gap. So it is just math, and you have the historical numbers to back it up.

10:17And you've got to, you've got to think about like market conditions and stuff like that. But that is, that's where you start, you start with the numbers that you have, and you use that as a mathematical model to determine what it is that you need to go acquire. Is that part of the solution that you might provide to, again, just use data to get to an obvious answer? If the complaint or the pain point coming in could be something like, Steve, our conversion rate is just not what it was. Lead gen is just really sucking right now. Sales cycles are taking forever. People are just not spending money.

10:59Like, I'm sure you've heard it all, right? And again, no, no, those are three very distinct, different, you know, pain points or attributions of pain points. But where do you typically go when you hear complaints like that? So those are mostly symptoms of lack of customer understanding and lack of focus on a scorecard that has activities that you're trying to drive against. So if your sales cycles are taking too long, you probably don't have enough activity metrics as to how many times you reach out and how you reach out and what your market message fit is. Okay? And it's really apparent when you, again, start with your forecast, determine what it is that you need to target, and then what activities you need to do to get that to be figured out by deep customer understanding.

11:46Put it into scorecards. You have something to measure against. this is the savage truth is most times people aren't actually doing the activities they need to do in order to get the results that they want so they come up with our leads aren't converting we have too long of sales cycle or converting our close rate is too low all right have you have you reviewed game tape or what's your frequency of outreach how many touches are you doing i've heard lots of sales teams say well geez you know i've reached out to them two three times and nothing's happening. I'm like, well, you know, this company here, Boombright Media, another one that I own, it takes 12 touches to actually get the customer to the table.

12:24So you got nine more touches. Get out of there. It's that simple. But if you don't have that to measure against and the data model in place, it's just a conversation that you can't have. So that's why you have to start with understanding those fundamentals, get that in place. And then you can have those conversations about the symptoms. Steve, when you are working with a new client, what does that typically look like? And like, where do you start? And what does engagement actually look like? Do you work with people long term or generally just kind of working more short term to kind of set the ship in a different direction?

13:02Well, we I always I always want to work myself out of a job, to be honest. So I like to come in and help them set up their foundations and set up their systems to the point where they potentially don't need roadmap anymore. However, as the organizations we work with get successful, there's always additional stuff that they seem to be coming back to us for. Generally, the engagements are a little heavier up front and then they scale down as they internalize all the different activities and they no longer need us as much. and as they're getting success they they continue to have needs for our services update crms updates to websites you know they want to launch this campaign that they don't have the internal capacity to deal with that sort of stuff we continue to support them however how it starts i say start with research take our go-to-market readiness index see where you actually are at and where the gaps are in your go-to-market system and then it gets benchmarked against your peers.

14:01And then we have a roadmap, pun intended, about what we should be looking at. And then we know what the symptoms are, and then we can diagnose with the appropriate cures. Your website is roadmapagency.com. I see under resources, you got a lot of good stuff here. You might share a few things that you'd recommend to our friend that's listening. Yeah. So we have the Go-To-Market Readiness Index, which is where you can participate in a long form survey with my researcher that will determine what your go-to-market readiness is. And you get an actual score to show where you're at and then you're benchmarked against other folks that have been in the study for months and months and months.

14:43We've been running this for about nine months now. And that's where we're starting folks out now because we used to do like, you know, discovering assessment, but we thought, you know what, let's put it into an index so everybody has access to this. So you start there. If you're further along, you can download. And by By the way, none of this is gated because I don't want to do that. I want you just to have access to it. You can download the Revenue Factory Toolkit. That's where you can figure out your cost of growth, your cost of retention, your tiering of your accounts, and then the efficiency of various different motions that you're running, like say trade show is a play, inbound is a play.

15:21You can do that. All the instructions are in there for you, which is some fundamental work that you can do to really dial in for a forecast. However, you can work with us to actually true it up and we'll give you coaching on how to actually do that. So you get those fundamental numbers and ratios in place to really understand where your business is at. So those are two places to start. And you can start with that independently and to educate yourself. But we're also here to support you through the process. Steve Whittington, president at Roadmap, your website, roadmapagency.com. To our friend that's listening, go to the website, hover over resources, take a look at the Revenue Factory Toolkit, the Go-To-Market Readiness Index.

16:06I'm a huge fan of just like you said, ungate it, give it away. Get people using your stuff. I absolutely love it, Steve. Thank you so much. Great conversation. Steve Whittington, again, president of Roadmap Agency. Thanks for joining us. Thanks so much.

16:24Thanks for listening to The Thoughtful Entrepreneur. If your goal is to grow your business, increase revenue, and build authority without gimmicks, this show is designed for you. Each episode gives you practical insight from leaders who have turned trust and credibility into real business results. If you value short, thoughtful conversations that respect your time, make sure you're subscribed. We publish daily 15-minute episodes focused on growth that actually compounds. And if you're interested in being a guest or you want to turn podcast appearances into measurable business growth, visit podverified.com.

17:00You can start for free with your Podverified score along with free podcast guest training and a free media kit builder. These tools are built to help you get booked on better shows, deliver stronger interviews, and convert audience trust into revenue. No more desperate sales. You truly can enjoy all the business you like by generously sharing your wisdom. Everything we offer is built by podcasters for guests with a focus on trust, organic growth, and long-term business success. Thanks again for spending your time with us. I'll see you next time. We'll be right back.

From the publisher
Scaling with Precision: Transforming B2B Revenue into a Predictable Engine with Steve Whittington

In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Steve Whittington, the President of Roadmap Agency Inc., to deconstruct the "hope-casting" trap that many medium-sized enterprises fall into. For businesses generating between $5 million and $75 million, growth often feels like an unpredictable roller coaster rather than a calculated ascent. Steve shares how his agency helps B2B firms and manufacturers move beyond guesswork by implementing data-driven mathematical models and customer-centric sales engines. This conversation is an essential guide for leaders who are ready to stop guessing at their sales forecasts and start building a scalable "revenue factory."

Engineering Growth: Moving from "Hope Casting" to Mathematical Certainty

The most significant barrier to scaling a professional service or manufacturing firm is often a reliance on "hope casts"—sales targets based on wishful thinking rather than empirical data. Steve Whittington explains that achieving predictable revenue requires a shift toward mathematical modeling, where a three-year historical average of existing accounts forms the baseline for all future projections. By breaking down growth goals into expansion revenue from current clients and acquisition revenue from new accounts, leaders can visualize exactly where their numbers will come from. This approach accounts for variables like sales cycle timing and churn, ensuring that if a new account closes mid-year, only the realistic, realized portion of that revenue is factored into the annual target.

Deep customer segmentation is the second pillar of a high-functioning revenue engine, moving the organization away from inefficient, one-size-fits-all messaging. Steve advocates for a rigorous tiering system that categorizes accounts into Strategic, Growth, and Transactional segments. By analyzing profit and loss statements to identify the most lucrative Ideal Client Profiles (ICP), businesses can align their marketing spend with the clients who offer the highest lifetime value. Understanding the specific "triggers" that cause these decision-makers to buy allows a sales team to move with surgical precision, addressing the exact pain points of their buyer personas rather than casting a wide, expensive net that yields low-quality leads.

Finally, the Roadmap approach emphasizes the "science" of sales activity management through the use of scorecards. Many companies suffer from long sales cycles simply because they underestimate the volume of outreach required to move a prospect through the funnel. Steve points out that while a salesperson might stop after three touches, data often shows it takes twelve or more interactions to secure a meaningful meeting. By tracking key activities—such as meetings booked, proposals sent, and conversion rates at each stage—leaders can diagnose exactly where their "revenue factory" is leaking. This level of measurement transforms sales from a mysterious art into a manageable process, allowing firms to eventually gain the self-sufficiency needed to run their own go-to-market strategies without permanent agency intervention.

About Steve Whittington

Steve Whittington is the President of Roadmap Agency Inc. and a seasoned expert in B2B go-to-market strategy. A passionate alpine and ice climber, Steve brings the same discipline, risk management, and focus required for the mountains into the boardroom. He specializes in helping $5M–$75M enterprises build sustainable revenue systems, drawing on years of leadership experience to help companies transition from chaotic sales efforts to predictable, data-backed growth.

About Roadmap Agency Inc.

Roadmap Agency Inc. is a strategic consultancy that empowers B2B companies to take control of their revenue growth. The agency focuses on building client self-sufficiency, implementing foundational systems like CRMs, scorecards, and segmentation frameworks. Through their "Revenue Factory" philosophy, Roadmap provides the tools and coaching necessary for manufacturers and professional service firms to execute high-performance go-to-market strategies that are measurable and scalable.

Links Mentioned in This Episode


Key Episode Highlights

  • The Alpinist's Business Strategy: How the endurance and calculated risk of ice climbing mirror the discipline needed for enterprise growth.
  • Mathematical Revenue Modeling: Why a three-year data average is superior to traditional "hope-based" sales forecasting.
  • The Revenue Factory Toolkit: A breakdown of how to calculate the true cost of growth and account retention.
  • Strategic Account Tiering: How to segment your customer base to ensure your sales team is focused on high-potential growth and strategic accounts.
  • The Twelve-Touch Rule: Why tracking sales activity via scorecards is the only way to shorten long sales cycles and improve conversion.

Conclusion

The conversation with Steve Whittington reinforces that predictable revenue is not a stroke of luck—it is the result of a disciplined, transparent system. By leveraging data-driven readiness indexes and aligning sales motions with your most profitable client segments, you can reach the summit of your growth goals with confidence.

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2400 - Driving B2B Success Through Sales Forecasting and Customer Understanding with Roadmap's Steve WhittingtonThe Thoughtful Entrepreneur · 18 min
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