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Sales and Marketing that's Scalable, with Peter Fillmore

Funnel Reboot · 2026-04-13 · 23 min

0:00--:--

Key moments - from our scoring

Substance score

57 / 100

Five dimensions, 20 points each

Insight Density12 / 20
Originality10 / 20
Guest Caliber13 / 20
Specificity & Evidence11 / 20
Conversational Craft11 / 20

Peter Fillmore, founder of the Ottawa Scaling Up Initiative and former startup founder, explains why incremental improvements to resources and tech stacks won't generate exponential revenue growth - companies need structural and cultural changes. Drawing on his experience scaling a startup from $1M to nearly $4M in six months, Fillmore emphasizes three core practices: creating visibility across the entire organization through shared funnel management (using physical whiteboards and weekly all-hands updates), rigorously qualifying customer intent before investing in proposals, and aligning sales on business, budget, and time drivers before proceeding. He argues that marketing must transition from one-to-many broadcast communication to segment-specific messaging, and that management must enforce weekly discipline rather than quarterly reporting cycles to maintain market fidelity. Fillmore also addresses pricing optimization, professional services bundling, and hiring for growth potential rather than mere experience. This conversation benefits B2B operators managing rapid scaling, particularly those in sales operations, marketing leadership, and executive roles where funnel discipline and cross-functional alignment directly impact cash flow and profitability.

Key takeaways

  • →Funnel visibility and customer qualification - breaking down buying decisions into business, budget, and time drivers - allows sales teams to say no to low-probability deals and redirect energy to higher-value activities.
  • →Weekly management meetings tied to daily metrics create accountability and prevent the 'drift' that occurs when quarterly board cycles obscure real market dynamics.
  • →Scaling requires cultural change and process discipline, not just larger numbers or faster execution; companies should test off-ramps (miniature studies, one-page summaries) before committing to full proposals.
  • →Pricing power emerges from quantified customer ROI; companies scaling successfully often raise prices 20% or add professional services fees once they demonstrate clear business value.
  • →Hire for growth potential and intrinsic motivation to learn new roles within the company, not just for years of specific experience, to build a pipeline of future managers from within.

Guests

Peter Fillmore

Topics in this episode

Funnel management and sales process designWeekly vs. quarterly accountability cyclesCustomer value proposition quantificationPricing optimization and professional services bundlingLead generation program planning timelinesHiring for growth potential and internal mobilityScaling Up by Vern HarnishOttawa Scaling Up Initiative

Questions this episode answers

How do you prevent salespeople from spinning their wheels on low-probability deals when scaling?

Break the customer decision process into three parts - business drivers, budget drivers/ROI, and time drivers - and conduct a miniature study or one-page business case summary before pursuing a proposal; if any of these signals are weak, take the off-ramp and reallocate effort to higher-value opportunities.

What meeting cadence should a scaling company use to stay aligned on growth goals?

The senior management team should meet weekly to track progress against the growth plan, with quarterly results aggregating that weekly discipline; this prevents the loss of market fidelity that happens when boards only check in quarterly.

How should marketing evolve its approach when a company targets new customer segments during scaling?

Marketing must update its messaging and positioning for each new segment rather than assuming the same communication will work; for example, messaging should shift to position the product as solving specific problems for a particular buyer type (e.g., tractors vs. trucks vs. cars).

What pricing strategies help solve cash flow problems during rapid growth?

Once sales teams quantify clear customer ROI (e.g., $300k benefit), companies can raise prices by 20% or add professional services fees for implementation, which customers will accept and which generates advance payments or improves margins.

When hiring for a growing company, what should you prioritize besides relevant experience?

Look for people with intrinsic motivation to learn new roles and move internally - someone willing to transition from administration to customer support to management - rather than hiring experienced people who will execute the same role with "eyes closed" and eventually become disengaged.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

12 / 20

The episode contains several useful frameworks (funnel management, three-part decision drivers: business/budget/time, pricing strategy, weekly cadence meetings) but spends considerable time on abstract concepts and throat-clearing without drilling into mechanics or data. The whiteboard/sales funnel example is concrete, but much of the discussion lacks specificity about *how* to implement these ideas or why they work beyond general principles.

break the decision down into these parts, and the parts may be a little different in different companies with different products and offers, but if you break it down into these parts, you give yourself the chance to take an off ramp
if the company wishes to grow continuously, there will be new discoveries constantly

Originality

10 / 20

The core ideas - breaking sales into repeatable processes, asking qualifying questions before proposals, aligning teams around goals - are well-established in B2B sales literature and scaling playbooks. The exponent metaphor opener is unusual but largely abandoned. Most frameworks echo Vern Harnish's 'Scaling Up' and other mainstream business literature without fresh angles or contrarian thinking.

What Got You Here. Won't Get You There
N to the power of five is equal to a hundred thousand, but N to the power of just seven is equal to 10 million

Guest Caliber

13 / 20

Peter Fillmore has relevant hands-on experience: he founded a product startup, led sales/marketing teams, and now teaches and runs the Ottawa Scaling Up initiative. However, the episode lacks evidence of *scale* - no mention of revenue achieved, growth rates reached, or companies managed through multiple inflection points. He appears credible but not exceptionally senior or battle-tested at major scale.

He then led sales and marketing teams for tech organizations until the late two thousands when he founded a product startup
He also teaches sales practices and scaling up to engineers at the University of Ottawa

Specificity & Evidence

11 / 20

The episode includes a few concrete examples (Texas/Toronto/Chicago company mentions, $50,000+ projects needing professional services, 20% price increase, 90-day lead generation planning), but most claims remain abstract. Few metrics, no financial data on actual outcomes, no named companies beyond generic references. The whiteboard funnel example is descriptive but lacks numbers on results it drove.

I worked in a company that was doing about a million a year and we drove it to close to 4 million a year over a period day, uh, six weeks of intensive work
when you get into. Projects that are over $50,000, the customer can certainly find a few extra thousand dollars

Conversational Craft

11 / 20

Glenn asks decent setup questions and references relevant sources (Marshall Goldsmith), but rarely pushes back or probes deep. He accepts Fillmore's answers at face value and moves on rather than asking 'how do you know that works?' or 'what failed?' The host allows some vagueness to stand (e.g., culture changes needed, but no specifics on *which* cultural changes). Overall, a polite conversation rather than substantive interrogation.

So let's talk about, we're at the million dollars and the CEO makes that pronouncement
Let's remember that if a company is scaling, the people who are here today will be in different roles 12, 24 months from now

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

marketing17sales13customer13scaling11million10different10customers9team9scale8better8management8process7funnel6product6ottawa6grow5

Episode notes

It goes without saying that the purpose of sales and marketing is to help a company grow. We create forecasts where revenue grows a hundred-thousand, a million, or 10 million dollars. But we expect to achieve that with incremental changes to our resources and tech-stacks. When Base 10 Math is used to express numbers that differ by orders of magnitude, we use exponents, noted with the letter N put in superscript (N stands for the Latin word numerus or number). N to the power of 5 is equal to a hundred-thousand, N to the power of 7 is equal to ten million. We don't have to raise N very much to see it balloon in size. Each increment it jumps by represents its value going up by a factor of ten. The question of how we reach scale then isn't how to change financial numbers by a basic percentage; it's how do we grow them by a factor of N? Our guest knows how sales and marketing can scale their organization without snapping them. *come with their own jargon like batch mode, local vs global maximums, and WIP bottlenecks. He graduated from the University of New Brunswick with an engineering degree and then went into technically heavy roles, working in IBM's semiconductor division.

Full transcript

23 min

Transcribed and scored by The B2B Podcast Index.

It goes without saying that the purpose of sales and marketing is to help a company grow. We create forecasts where revenue grows a hundred thousand, a million, or $10 million, but we expect to achieve that with incremental changes to our resources and tech stacks. When Base 10 Math is used to express numbers that differ by these orders of magnitude, we use exponents. Noted with the letter N .

N stands for the Latin word numerous, or number N to the power of five is equal to a hundred thousand, but N to the power of just seven is equal to 10 million. We don't have to raise N by very much. To see it balloon up to a hundred times in size. Each increment it jumps, takes us up by a factor of 10.

Hey Glenn here. Welcome to Funnel. Reboot the show for data-based marketers. The question of how we've reached scale isn't how to change financial numbers by a basic percentage.

It's how do we grow them by a factor of N. Our guest knows how sales and marketing can scale their organization without snapping. To do this gets us into topics that deal with batch modes, local and global maxima, and. WIP bottlenecks.

Our guest graduated from the University of New Brunswick with an engineering degree and went into technically heavy roles working in IBM's semiconductor division. He then led sales and marketing teams for tech organizations until the late two thousands when he founded a product startup with an app that helped salespeople gain visibility into their funnel. That's where I met him. Where I worked for him in his startup.

He also teaches sales practices and scaling up to engineers at the University of Ottawa. Join me now as I sit down in person with the head of Ottawa's scaling Up initiative, Peter Fill more. Welcome to Follow Reboot. Thank you, Glennn.

It's great to be here. Thanks. Uh, I'm reminded of a book, it's Marshall Goldsmith and the title of the book really arrested me. It's called What Got You Here.

Won't Get You There. If we're trying to scale a business, there are things that we've got to change. But you get along in a certain point, or you join a company, let's say, as a new marketer and you kind of fall into inertia. There's just a rhythm and you seem to slip into it.

But that's not the kind of thing that will. Cause that company to be a scaled up version of itself in the future, it'll just continue as it was. How does it look different inside of a company that is scaling up? How does it look different?

To actually scale up, if the company wants to go to go from a million to $5 million a year, let's say, or then from five to $20 million, there needs to be a very conscious effort to say. What are we gonna do along the way? Right? What kind of intermediate goals?

What is our strategy? And then I think really critically, what is our culture and are we using the right culture? And I've, I've talked to CEOs that have gone through this where they've said, we, we've discovered that to solve certain growth problems, we need to change the culture. So that means changing the words around believe in what our values are and those, those kind of things.

And how we behave with each other and within customers. So yes, things do change. It's a little different when you're going from the smaller to the middle than right from the middle to the larger stages. So let's talk about, we're at the million dollars and the CEO makes that pronouncement.

We want to be a $5 million company. Whether I'm in marketing or I'm in another part of it, What should the vision be so that I, as a person who works in marketing, let's say, can grab a hold of it and at least begin the process of thinking how in my own corner of things I can make changes that will eventually get us there. So, so Glenn, when you say grab a hold of it I want to just drill into that. I'm thinking of an example where I worked in a company that was doing about a million a year and we drove it to close to 4 million a year over a period day, uh, six months of intensive work.

And a lot of, uh, uh, what I was trying to do is to make mo both marketing and sales more visible to the rest of the company. Okay. And what we did is we put up a large magnetic whiteboard and we drew a sales funnel. So people knew that our range of products were being sold to a certain kind of industry.

And I brought that down to the detail to say we are now working with a company in Texas that does this. We're working with a company in Toronto that does that, working with a company in Chicago that, that does this other thing. And so here's the visibility on what's happening. And I talked regularly.

I'd have a once a week kind of a, anybody in the company wants to come. You look at this whiteboard, it's in the open area. Talk about the update, what is going on, and then there's marketing events where we'll say we're going to a trade in six weeks. Okay?

Or we've got a, a webinar, a thing that we're running in three weeks and let people know about that. What tended to happen was we got the whole team more focused on the things that we're customer centric and that worked very well. The last thing I'll say about this though is that we spent a lot of time working on what is the sales process design. So we didn't just say there's a salesman calling on that customer.

The internal people, I think it's the product which sells itself. And yet we, we stress the idea that we're working with customers on their business cases. We're working with customers on more precise definition of what problem we're solving for that customer. Right as opposed to another customer who gets the same product.

So all of this is, was good and informative for the whole company. So if we're talking about it for sales and marketing, particularly sales, you seem to be teasing apart activity. So the activity could be, we have three salespeople and they are. Each running off like crazy people in their own direction to do their own thing.

And you said, that we're actively focusing on the process and maybe thinking about how the process is now and how it will be later. And I guess that's a crucial component of scaling up. That we're not just saying it's about just pumping out bigger numbers. There seems to be something about let's figure out how to do it better over time.

Yes. So, so, gosh, I, I don't know where to start the, uh. Doing it better over time involves things that I see as understanding what are the fundamentals that motivate customers to buy. And one of the tricky parts, and I'm sure you've in some companies offer, will offer say, can you give me a proposal?

The tricky thing is right, you have to buffer that. You, you need to say things like, yes, Mr. Kuman. I'm happy to do that.

And yet let's first of all clarify a couple of things about what's gonna drive the decision for your company. Came up with a formula and. The customer on what are the business drivers, what are the budget drivers or the ROI for them? And lastly, what are the time drivers?

Why would this be urgent? So I'll just deal with that for a second. That's one of these things that, that a team has to get better and better at, because otherwise, when you get busy, especially if you're ramping up a lot, you can kind of fall asleep with the switch and customers like your product so much, uh, you, there's a lot of demand out there. You just say, if I get the proposal, they buy something.

Yeah. You still need to go back to certain fundamentals. Like, do they need this next January 12 months from now? Or do they need it, uh, four months from now?

And why do they need it? What is it that's going on in their company? And my job as a salesperson has to be to develop that idea more clearly to motivate the customer. To create urgency.

I hope I answered your question. I think you did. And I think, uh, one myth that you blew up was that urgency should be something that we have just by default. And that scaling up is, it magically happens by just saying, do everything faster.

You gave an example right there of do something slower. Initially, so that it can go faster eventually. Let's not spin our wheels, right? Because we may be led into a false perception of progress by a number of proposals going out, but if we actually hold back and maybe not do as many of them, but do them when there is customer signal of intent.

Well, exactly. And so there's another thing that spins out of this, this funnel management philosophy I'm talking about, and that is that. If you break the decision down into these parts, and the parts may be a little different in different companies with different products and offers, but if you break it down into these parts, you give yourself the chance to take an off ramp. And the customer, and, and I believe you should talk to customers about this to say, you know what, if we do a little miniature study to come up with a one page summary of you are a business driver.

Yep. And it's not strong, I may decide not to pursue the proposal. And so companies which continue to grow through changes in the market are companies that, where I believe what they do is they take more off ramps and the sales team therefore becomes more productive, right? 'cause they can go spend their time on something else, right?

They've said no to things say no, Those cycles automatically get recouped. Now what can I do? What is a higher value activity? That's right.

Do you stare at your marketing analytics, but get stuck on what to do differently. You're not alone, and that's why I am hosting a free analytics clinic this June. I'm looking for up to three volunteers for a special live audit session. All of us will screen share our platforms playing cards, face up, and we'll dig into what the data is and isn't telling us.

Guests will get a personalized, real-time picture of how to make the measurement and marketing better. But this session won't just help these three guests. It'll be released as a public funnel reboot episode because there are many marketers who suffer in silence on their own their analytics, and they deserve to know how these problems can be fixed. Of course, any private details will be edited out.

You get to say what makes it to air. So if you wanna have an interactive marketing audit and do a public service to your peers this June, go to the Get in touch page at funnelreboot.com and scroll down for the form on the clinic episode. I'll be getting the applications in by May 20th, and then I will contact people between May 27th and June 4th to record the show.

Thanks very much. Let's get back to the show. Would you imagine that marketing can do that same thing where we don't need to go to that trade show anymore, or, we think that there could be a new way for people to indicate their interest and become fans of ours or become potential leads of ours compared to the way we've done it before? Do you think marketing should use that same strict ' what can we say no to' framework?

Marketing tends to be in a simple way, how do we communicate one on many as opposed to one-to-one. Yep. So the one on many communication. Often needs an update and, uh, it often needs a, a transition strategy.

If you look at the principles and if you're working with segment A and then you've got a bowling alley where you're gonna go to segments B and C marketing needs to be very clear on what your best guess is on the communication with segments. B and C. Right. You know, if you're selling something that is a piece of equipment that goes on vehicles.

You may start with tractors and then go to trucks, and then go to cars for some reason about whether your braking system or whatever is, is better for a particular system. Then it's going to expand. So yes, you have to keep updating the updating your sense of what the market is and who the buyers are gonna be. Yeah.

And I imagine you're going to be joined at the hip with sales and using feedback and information that they're plugging into their systems to advise Yes. Right. What you're doing there. You're a staunch advocate of having a process that.

companies have to follow. Let's remember that if a company is scaling, the people who are here today will be in different roles 12, 24 months from now. I've heard it described as a Frankenstein organization or an organization of strangers, when that kind of thing happens, it always seems like day one, everybody walks in and they're wondering, what is my job today? And they just feel disoriented.

What do you suggest we use as a process for helping make sure that there's accountability over time? Um, generally speaking, I don't think coming in on a Monday with a lark idea necessarily going to be, be good for the company. What, what are, what strikes me about this is that if the company wishes to grow continuously, there will be new discoveries constantly. One of the things that I I, I see happening is that very often rapid growth creates a cash flow problem, and so it's really beneficial to use the kind of funnel management I was talking about.

Yes. Where your salespeople are as a matter of discipline, not just to the den, they're looking to understand the customer value proposition. Which may give the company a chance to raise prices or to price differently. Go into a different tier or acquire advanced payments.

You know, some of the situations I've worked on, we decided to raise prices by 20% or to add a professional services fee so that the, the offer is not just the product, but the installation of your application. We make that recommendation and I say that of course because I know when you get into. Projects that are over $50,000, the customer can certainly find a few extra thousand dollars. The question is whether or not they like this, and if the sales team have quantified the typical benefit is gonna be $300,000.

Then you can solve one of the scaling up problems by changing the pricing model and making the professional services that are probably gonna be needed to get that person running. Okay? And the customers will accept that. So the self process ties into the ability to scale on multiple patients.

These things don't usually pop on a Monday morning. They pop up after months, weeks of, of work and yet you are making sure those good ideas surfacing that acted on. That's what I wanted to latch onto we have to make sure that we avoid drift. So drift to me is when the board wants to hear quarterly what's going on, but with a whole quarter to play with we lose fidelity with what's really happening in the market because maybe they're entering one thing, but another thing is happening.

How do you enforce the discipline that if we're gonna say all parts of the organization need to contribute together for us to grow, what's a good framework for carrying that out? How often do you need to meet? How often need to meet is a good question. And I'll start by saying I, there's a great, an excellent textbook I read called Scaling Up by Vern Harnish, which talks about.

A number of techniques. One of them is to have a, uh, regular weekly meeting of the management team to, uh, to discuss what, what's going on against the growth plan and against, basically. Not only what we wanna do with the year and quarter for the board presentation. And so, but that's typically broken down into once a month.

And we all know we've got enough business experience that to, to do something within a month, there's gotta be weekly progress. So you've gotta be able to say, you know what, by next week we should be there. And then week after that we should be there. And in a simple way, if it's something like lead generation, you might say, we, um, we don't have enough leads.

You gotta recognize that. And these are the marketing programs that we can run. And I can remember sitting in a meeting with, uh, with the president of the company years ago where he said, we wanna have new leads in certain markets in September, October timeframe. And my take was, Hey, you know what, it's the month of May right now.

It's gonna take 90 days, so may, June, July, August,. just to design the program, right? Even if you run it on September the 15th, you need to clarify how are we, what partners do we need to actually put on the lead generation program? Where is it gonna be?

Who are the, uh, the people that are gonna be involved in doing it? How do, how are, how do we get invitations out early enough and repeat those invitations so that people are aware we are there, we're in town, we're doing a right program to help add value and productivity into your company. Come and talk with us. Yeah.

And of course you link things like that in with your conferences or whatever events that are hosted by other people. We're getting into an age where each one of those activities means that systems are pumping our metrics and you know, we have a North star metric, let's say that the CEO is setting on. Do you have any thoughts on how to mesh the metrics that we might see on that daily or weekly with that very audacious goal that we're trying to hit. that's a matter of having the senior team sit down and say, uh, in order to get 10,000 customers for something, yeah, we need to get, uh, the next thousand lined up.

We to know where we're gonna get them, we have to go after the next hundred. It's, it's unique to every particular business. And of course after we're, we're, I assume we're talking about, uh, business to business. In business to business, I'll just go to what you said there.

You put it on management's shoulders to do it. Yeah. Too often, I'm sad to say I have seen those meetings break up and then the C-level person comes to the hapless team and says, you do it. Yeah, they may be able to figure out how in clumps of 10 or 20 they can get those leads together, but if they come out and they are just told by next quarter there must be several hundred, they're bewildered.

the thing that you want to point out is the detail and enough granularity, the tactics, right? Yeah. Uh, and I'll, I'm thinking of some examples where unfortunately I've seen seniors will try and resolve, uh, a growth problem. I did in that case that there was, um, an assumption that the growth was gonna come from the same kind of customers to get into new applications with.

And start going back to basics, building our value proposition for those new buyers, and from a marketing point of view, change the messaging so that the product was positioned as a good solution for factories who do this, as opposed to factories who do that. Yet again, management can't shirk their responsibility of understanding and having their finger firmly on the pulse of what the front line is seeing. Exactly. And they have to understand the dynamics of the market and be totally aware of, uh, the fact that the salespeople are, have to go after a different segment.

Yep. And therefore we'll need different support. Yep. It's a whole company effort.

And, and you can't like leave the quarterback. To throw another brilliant pass when the other team has sort of lined up to say, we're gonna block passes . That's it. We, we need to have a variety of ways that fit the situation.

If I were to prescribe how you can make this happen and do it well, it would be to make sure that the frontline, your entry level players possess traits that Suggest they could mature into managers and leaders. Why? The person who is being groomed from within. And not a manager who is parachuted in from without is intimately aware of how it's gonna fall on the ears of someone that has to actually do the work, the worker bee.

How do we always be thinking about developing people. How do we, do we dedicate resources in a scale up situation, knowing that we're gonna face, the need for managers, where right now we only have worker bees. Yeah. So, uh, a lot, some, a lot of that probably goes beyond my own experience.

However, what I'll, what I'll say, since I'm not an HR expert per se. You gotta have a vision for your hiring that says, I want people that are gonna be motivated to do a good job in what they're assigned to do and also have some of them that are gonna be growable into management ranks. And, uh, the other thing about hiring though and putting, filling the jobs is you don't wanna just say, I need somebody with five years experience as a sales member, five years as a customer support.

You need people who have want to come into your company as they're likely to be the A players than somebody who says, I've already done this, and I'm gonna come to your company and do the same thing and deal with my eyes closed, really. And it may be presented that way, and yet they'll get bored and they won't do a good job. See, so you are looking for people that are vicious and see the new, new position, even if it's a lower level position, I want to go out of administration into customer support, and eventually some others will say, I wanna go out of customer support into management.

So there's a mix that you need to pursue in terms of your, your all the talent team. It's clear to me you've got a passion for helping organizations scale up. Our listeners would like to learn more about what you're doing with the Ottawa Scale Up initiative? Okay.

So they can go to look at our website, Ottawa scaling up ca I can send people a background or a one page profile or whatever. I'm honored to be the founder of the Ottawa Scaling Up Initiative. I'm working with some really good partners, working with Invest Ottawa, with the Telfer School of Management with KNBA and uh, I'm always meeting other people who say, you know what, the skill sets involved are important, and it's good to have somebody trying to put up programs that will help companies improve those skills and scaling that.

Amazing. Thanks again for coming on the show. You're welcome. Thanks for having me in.

And as always, keep getting better insights into what you do so you can do it even better.

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