Topline · 30 Aug 2026 · From the week of 24 August
How To Make Your ARR 20% More Valuable To Investors | Keenan, CEO @ A Sales Growth Company
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Keenan, founder and CEO of A Sales Growth Company and author of Gap Selling, joins hosts Sam Jacobs, AJ Bruno and Asad Zaman to argue that two companies with identical revenue can be valued very differently depending on how that revenue was produced. He describes four sales org archetypes (heroic, random, peacock and compounding) and cites a paper estimating a 15 to 20% valuation discount on heroic revenue, with his own hedged figure. The episode covers the difference between a sales system (defined outputs) and structure (making everyone do the same thing), what he calls sales physics, and his view that sales enablement spend has risen sharply while quota attainment has fallen. The most important claim is that investors are buying a company's ability to repeat its revenue, not the revenue number itself.
For founders
- Keenan said investors value a company on its ability to reproduce revenue over time, and heroic growth undermines that trust even when the revenue number is the same.
- Keenan cited his paper Not All Revenue Is Created Equal, which he said could imply a 15 to 20% valuation discount for heroic revenue, and said he was not certain of the figure.
- Keenan said the buyer must come to see their current state as untenable and intolerable before a deal closes, and that a sales system's job is to help them realise that.
- AJ Bruno, QuotaPath's CEO, said he told his board he would hold 30 CFO conversations over three months, combining a road show, dinners and recorded listening sessions.
- Keenan said that for a brand-new company, awareness comes first, and he described focusing a launch on a single campus, with a hedged claim that prospects need several exposures before anything sticks.
For revenue leaders
- Keenan said a sales system defines the outputs the team must produce and stays agnostic about how each rep gets there, whereas structure means making everyone do the same thing.
- Keenan said that heroic deals can hide discounting, since the CRM records the closed amount and not the amount a deal started at, such as a $2 million close that began at $2.6 million.
- Keenan said that when he asks sales leaders for their MEDDIC definitions and how those are built into the CRM, most cannot show them, and he argued that training is over-invested relative to understanding the buyer.
- Keenan said hiring criteria need a vertical layer that maps the job to the specific selling environment, and that a gap in buyer-environment knowledge must be solved by hiring for it or training for it.
- Keenan cited figures, which he said vary depending on who you ask, that quota attainment fell from about 60% in 2012 to about 23% (or 16%), while spend rose about 7x, win rates fell 29% and sales cycles lengthened by 37 days.
What was said 23, most useful first
Keenan describes four sales org archetypes: heroic, random, peacock and compounding. Listen
Heroic organisations are the most common and get revenue through constant pushing and reaction at quarter end. Random and peacock organisations have many tools and programmes that do not connect, and Keenan said he had not yet seen a company operating as compounding, which is where he wants organisations to go. He noted that companies are usually a mix of these, and his firm offers a short assessment for it.
“we identified these four archetypes for sales organizations. And they are the heroic, which is most common for most.”
Listen to the episode Sales team, hiring & comp Link to this Report a problem
A paper he wrote suggests a valuation discount of 15 to 20% for revenue produced heroically. Listen
He said he was recalling the figure from memory and checking it while on the show. He added that measured against EBITDA the gap could be 1.5 to 2% versus 6 to 8%, which he described as three to four times lower. The paper is titled Not All Revenue Is Created Equal.
“the discount could be as much as 15 to 20 % discount on the valuation.”
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Heroic deals can hide discounting because the CRM records the closed amount, not the starting amount. Listen
Keenan said a CRM would show a closed $2 million deal without revealing that it started at $2.6 million. He presented this as the reason heroic revenue looks healthier than it is to an outside buyer.
“You don't go into a CRM and say, oh yeah, we closed a $2 million deal and nobody saw that that $2 million deal started at 2 .6.”
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Many organisations train MEDDIC but cannot define its elements or show how they are built into the CRM. Listen
He said he asks teams that say they run MEDDIC for the documented definition of each element as it relates to their product and customers, and then how it is built into the CRM. He said reps can tick different metrics and managers cannot say how those metrics drive a sale. He argued that training is over-weighted and the operating layers are under-built.
“Do you know how many times I've seen people say we run MEDDIC and I'm like great run MEDDIC. My first question is could you send me or show me the definition?”
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Keenan's Gap method measures whether a rep produced a defined problem, not whether they performed a specific behaviour. Listen
He said that in his operating system the question is whether the rep got a defined problem, starting from the organisation's root causes. The definition covers how many root causes there are, how often each occurs, the downstream impact and whose impact it is, internal or external. He said the aim is to see the problem defined in the buyer's terms.
“we're looking for, did you get a defined problem?”
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Each product solves a small set of business problems, and new features should be mapped to root causes of existing ones. Listen
He said there are usually four, five or six business problems per product, such as low win rates, long cycles, discounting or low quota attainment, and each has root causes. He said a new feature usually addresses a new root cause of an existing problem, and a feature that solves a genuinely new business problem would prompt a question about whether the team needs a different buyer or different salespeople.
“What are the four or five or six? business problems you solve because there's never more than that for any product, period.”
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He is tired of the term go-to-market, which he sees as allocating resources rather than selling. Listen
He said go-to-market is about where a company points its resources, such as exposure, advertising or a particular university. He said the term has been co-opted by sales training and consulting firms, which he separated from go-to-market. Sam praised Keenan for simply calling his firm a sales training and consulting company.
“Go to market is basically Where am I pointing? Where am I pointing my resources?”
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Investors value a company on whether it can replicate its revenue, so heroic growth undermines trust in that repeatability. Listen
He said acquirers and investors are valuing potential, asking where the organisation is going and where its growth comes from. If growth comes from heroics, he argued, investors doubt the revenue can be reproduced if key people leave or the company is invested in. He said heroics rely on constant pushing and reaction, with no system producing steady, predictable results.
“if your growth is coming from a heroic environment, that undermines their trust that if you leave or they pluck you out or they invest in you and something happens, you can't replicate that revenue.”
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A system defines the outputs and stays agnostic about behaviour, while structure is making everyone do the same thing. Listen
Keenan said a system does not require every rep to do the same thing, and that the organisation should know what outputs it is looking for. Responding to Asad Zaman's point that the best salespeople make in-the-moment decisions a script cannot capture, he said making people do everything the same is structure, not a system. He said he never uses the word structure.
“Making people do everything the same is structure.”
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Keenan judges reps by whether they produce the outcome needed, not by how their behaviour looks. Listen
He illustrated this with golf, saying he focuses less on a golfer's swing and more on whether they can hit a draw when they need one. He said a system should recognise when a behaviour is not producing the target output and evaluate it quickly. He added that roughly 80% of behaviour can stay the same while leaving room for the 20% that differs.
“I focus less on what your swing looks like, and I'm asking myself, are you able to hit a draw when you need to hit a draw?”
Listen to the episode Sales team, hiring & comp Link to this Report a problem
Hiring fails when a leadership team has no shared definition of what a good seller looks like. Listen
He described a large software company whose VPs and directors listed traits on three whiteboards in a hiring workshop, with each person naming different attributes. He said none of the traits were wrong, but the group lacked a common language to evaluate candidates. Keenan agreed and went a layer further, asking whether anyone had analysed what the job actually requires.
“None of these are necessarily the wrong thing to look for. But none of you have said the same thing. You don't have a common language.”
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Keenan separates a general hiring trait, which applies everywhere, from the job-specific skills a role needs in its environment. Listen
He called general attributes such as attitude horizontal and said the vertical question is what the job specifically requires and how that was decided. He used the left tackle in an RPO offence versus one in a West Coast offence to show that the same base profile needs different skills in different systems.
“Yeah, you have to have attitude. But I need to understand the vertical.”
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If reps do not understand the buyer's world, Keenan says you must either hire for that knowledge or train for it. Listen
He described a client whose reps struggled with discovery because none understood the daily life of an IT manager in a security environment. He said the reps knew the root cause and the business problems, but not what sat between them, so they did not know what to ask. He concluded the company needed an IT environment training, since a method alone would not solve the gap.
“So either you hire for that, right? Or you have to train for that because you're not going to solve the problem with a method.”
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The sales job is to get a buyer to see their current state as untenable and intolerable. Listen
He called this sales physics and said nobody buys anything unless that condition holds. He argued that teams over-invest in training the behaviour of selling and under-invest in understanding what the customer experiences and what would drive them to switch. He said a good system helps the buyer recognise that state, which allows the deal to close.
“nobody buys anything unless their current state is untenable and intolerable.”
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In 2012 about 60% of reps made quota, and that the figure is now 23%. Listen
He said he was recalling the numbers from memory, and at one point gave 16%. He said spending on training and tools had risen about 7x over the period, and that the trend turned around 2017 or 2018. He used this to argue that current investment is not working.
“In 2012, depending who you ask, 60 % of reps made quota.”
Listen to the episode Metrics & finance Link to this Report a problem
Keenan cited a 29% decline in win rates and a 37-day lengthening of sales cycles alongside the quota decline. Listen
He said he would not accept the argument that quotas are simply unrealistic, given these two measures. His conclusion was that the sales investments being made were not working.
“But win rates declined by 29 %. Sales cycles extended by 37 days.”
This quote could not be matched to the transcript. Treat it as a paraphrase.
Listen to the episode Metrics & finance Link to this Report a problem
CROs are not given the time to rebuild a broken sales organisation while it is running. Listen
He compared a sales organisation to a boat with a hole in it, which must be fixed without being dry-docked. He said CROs are often given 18 to 24 months before being replaced, and that the pressure to hit the number pushes them toward heroics. He said his system is built to identify holes and fix them while the team keeps selling.
“I know the boat's got a hole in it. You got to fix it.”
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He planned 30 CFO conversations over three months as QuotaPath's CEO, as part of product discovery. Listen
He said he told his board in July that he would hold 30 CFO conversations in three months, using a road show, dinners and Q and A sessions with guests such as Pablo Dominguez and Kyle Norton. He said he would record the conversations with AI to find patterns afterwards. He said changing buyer behaviour made listening more important than before.
“I told the board in July's board meeting, I am going to have 30 CFO conversations over the next three months.”
Heroic revenue can be predictable for a while when the market provides a tailwind, but he argued this does not replace a system. Listen
He named AI leaders as examples of companies that may get revenue predictably because of market conditions for a time. He said individuals doing things differently does not mean an organisation lacks a system. On the example of a large asset manager, he said he did not want to touch it but would attribute it to brand.
“There are products and services and brands that can predictably get revenue because of the market. So they have a tailwind.”
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Asad Zaman compared sales organisations to venture firms, where individuals play the game differently but produce consistent outcomes. Listen
He said firms like Sequoia have partners who each work differently but who all bring investment memos to the partners meeting with shared information. He argued that a sales team could work the same way, giving people room to vary their approach while producing predictable results.
“They have a group of people that all do play the game very differently.”
Listen to the episode Leadership & culture Link to this Report a problem
For a brand-new company, Keenan said awareness comes first, and launch focus should be narrow. Listen
He described advising his daughter's AI-native company to focus its launch on a single campus. He said he told them to seek banners at fraternity parties, post on Yik Yak and put up flyers to build awareness. He said he had heard that prospects need about seven or eight exposures before anything sticks, but said he was unsure that was accurate.
“they say that nothing sticks for somebody that's new until after the seventh or eighth exposure”
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Sales teams try to create predictability by making people and process uniform, like a supply chain. Listen
He described the sales acceleration formula approach, which isolates each element that leads to a closed deal and seeks repeatability by giving the same kinds of people the same leads and process. AJ Bruno added that Roberge's approach also followed the customer lifecycle, and stressed the importance of one-to-one understanding.
“what the market values is predictability.”
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Teams that rely on scripted behaviour are the ones most exposed to automation, while creative judgment is harder to replace. Listen
He said it is hard to imagine AI automating away a firm like Founders Fund, with six different people playing the game differently. He said the sales teams that could be automated are those that run the same scripts. He framed this as his view of where the risk sits.
“that's the sales team that you can see getting automated away by some sort of, you know, AI technology”