Sales and Marketing Alignment Starts With the Buying Cycle, Not Your Sales Cycle

Everyone wanted to meet with him!

He was the best salesperson in the company. He just wasn’t in sales but he was in constant demand. He was the cofounder and technology guru everyone wanted to see, meet and talk to.

At UNIS LUMIN (purchased by Softchoice in 2011), a software and systems integration firm where Mi6 Cofounder, Chris Herbert served as Director of Marketing and inside sales manager, the co-founder and CTO was the person every prospect wanted in the room.

Editors note: After leaving UNIS LUMIN Chris started Mi6.

As Chris describes him, he was “everything that a client would want in terms of an advisor” — the kind of technical mind that closes complex deals by explaining, not pitching.

Which created the problem. Every sales rep wanted him on every call. He was being pulled onto four-legged sales calls constantly, and he was getting tired.

Most companies solve this by rationing access and moving on. Chris did something different — and the fix reveals what real sales and marketing alignment looks like in practice, especially for smaller companies where marketing and sales are often the same two or three people wearing different hats.

This post is drawn from Chris' conversation with Dr. Jeremy Weisz on the Inspired Insider Podcast, part of his Top Agency Series. The full episode is below — the section on aligning the sales and buying cycles starts around the 13-minute mark.

https://youtu.be/Q8f4SolDFIY?si=sWLS9CJioLQn_b8M&t=807

The problem: sales and marketing alignment isn’t that they don’t talk

Sales and marketing alignment usually gets framed as a communication issue: shared dashboards, agreed-upon lead definitions, a standing Monday meeting. Useful, but it treats the symptom.

The deeper problem is that both functions are organized around the seller’s timeline. There’s a pipeline to fill, a quota to hit, a quarter to close. Everything downstream of that gets designed to move the seller’s process forward.

The buyer is on a completely different clock. At UNIS LUMIN, the sales cycle ran a minimum of six months and stretched as long as 18 months, “depending on whether they were kicking tires, starting to plan for budgets and things like that.” Long enough that the seller’s urgency and the buyer’s readiness almost never line up.

Chris’s reframe was simple, and it’s the hinge of the whole approach:

“So the buying cycle is what really matters. There’s a sales cycle, right? Which is our sales cycle. But what’s the buying cycle like?”

That distinction changes what marketing is for. If the sales cycle is the organizing principle, marketing’s job is to generate leads for reps. If the buying cycle is the organizing principle, marketing’s job is to be genuinely useful to someone who isn’t ready to buy yet — and to make sure the company is the one they call when they are.

What buyers are actually doing before they’re ready

Chris is direct about the state buyers are in early on. When people are searching for a solution, “they’re basically information gathering,” and they’re not ready to open up. They are careful about how much they give away.

Which means the standard early-stage sales motion — discovery call, needs assessment, proposal — is asking for a level of disclosure the buyer hasn’t decided to give yet.

His answer is to invert what you’re optimizing for:

“Trying to think about ways that you can deliver value to them throughout the sales cycle, even if they’re not in the buying cycle. You’re always thinking about ways that you can deliver value to them.”

And to be honest about what the buyer cares about:

“They don’t really care that you’ve got a quota, they don’t care that you need to sell something. They care more about whether you really understand the problems that they’re facing.”

The bar Chris sets is higher than understanding the stated problem. It’s uncovering “problems that they didn’t think they’d be facing” — and then working to solve those problems with the customer, at a profit for your company.

The five-seat rule

Here’s how that translated into an actual program.

Instead of one-to-one calls, Unis Lumin ran physical events — seminars and get-togethers with a social component — where the CTO spoke about emerging trends in technology. One prepared talk, many buyers, no more four-legged calls.

The sales reps pushed back immediately. Filling the seats, they argued, was marketing’s job. Chris said no. And then he did something counterintuitive: he made the seats scarce and handed them to the reps.

Forty seats. Five per rep. Two for existing customers, three for prospects.

“So they started fighting, because they wanted to make sure that they had their customers and their prospects coming to those events, and they knew that it was going to be easier for them to get in front of Unis Lumin’s CTO that way.”

That’s the mechanism worth stealing. The reps weren’t told to care about the marketing program — they were given a reason to compete for it. Alignment stopped being a meeting and became an incentive.

The contrast Chris draws is with the default: reps “waiting for us to send an email blast out and just fill the room with cold bodies.”

The constraint was the asset

It’s worth being precise about what actually got solved here, because the obvious reading is the wrong one.

An over-subscribed CTO looks like a scheduling problem. Scheduling problems get calendar policies — two sales calls a month, book through the Executive Assistant, priority to deals over $200K. Perfectly reasonable, and it caps the value of the most persuasive asset in the company at whatever fits in his calendar.

Chris read it as a constraint instead, and named it plainly:

“We have a very — what I called — a big honking carrot, which was this guy who everybody wanted to meet and learn from, and the sales reps were all clamouring for his attention.”

Once it’s a constraint rather than a calendar conflict, the design question changes:

“So let’s integrate him into the way we want to market the business. But let’s do it in a way that he’s in front of 30 or 40 or 50 people at an event, so that you as a sales rep can put more people in front of him who are in the sales cycle.”

Same person, same finite hours, an order of magnitude more buyers reached — and the reps got more access rather than less, which is why they stopped fighting the program and started fighting over it.

Chris’s generalization of this is the part worth writing down:

“What are the constraints that are in place, and how do we address them — but maybe take advantage of them?”

Address them, or take advantage of them. Most businesses only ever consider the first. But the CTO’s scarcity wasn’t the obstacle the event program had to work around — it was the engine that made the program work. Remove the scarcity and the seats stop being worth competing for.

That’s also the difference between running an event and integrating marketing into the business. An event in isolation is a tactic. This was a constraint identified, designed around, and wired into the sales process.

Put customers and prospects in the same room

The second design decision did the heavy lifting.

The events deliberately mixed existing customers with prospects, and introduced them to each other, “so that the prospect could talk to the customer and said, what’s it like working with these folks?”

No marketing asset performs that job. A case study is the company’s account of itself. A customer at a cocktail table, answering an unscripted question from a peer, is something else entirely — and it’s exactly the information a buyer in the gathering stage is trying to get and can’t easily find.

It also lets the buying cycle advance on its own schedule. Someone who arrived with no budget and no timeline can leave having learned where the technology is heading and having heard from a company already running it. Chris’s framing: they’re “not yet ready to buy, but they probably would get into the buying cycle” once both of those things are true.

Before the solution, they have to want to work with you

Underneath the tactics is a sequence Chris learned from the owner of the business, and it puts alignment in the right order:

“People have to like you first… and then they’ve got to sort of like the solution or the solution idea, and then they’ll like the company.”

His own gloss on it:

“It’s not just about you knowing how to solve a problem. It’s whether they actually want to work with you.”

That reorders the priorities. Capability is table stakes and it isn’t first. The things Chris flags as decisive — patience, responsiveness (“so, so important, even more so today”), empathy — are the ones that usually get cut when a team is optimizing for pipeline velocity.

None of which means being passive. He’s equally clear that people are reluctant to ask for the order, and you need to ask for the order. He recalls one CEO’s answer when asked for the single best piece of advice for a new entrepreneur: always be closing or ABC. With a caveat Chris adds himself — if you’re always trying to close, be careful the other person doesn’t feel like your hand is permanently out.

Everyone in the company needs to understand selling

The last piece is organizational, and it’s where alignment stops being a sales-and-marketing problem:

“Everybody needs to understand how to sell. Not just the sales reps, but the marketing people need to learn how to sell… and even if it’s not their strength, just having an understanding of how selling works is so, so important.”

Chris extends it to founders, and notes it holds equally in B2C and B2B. The reason is practical: marketing can only support sales usefully if it understands what actually happens in a sales conversation — and vice versa. Absent that, marketing optimizes for metrics sales doesn’t value, and sales ignores material marketing spent a quarter producing.

Where to start

The Unis Lumin program worked because it started from a question almost nobody asks: what is our buyer’s process, and where in it are they right now?

Answer that honestly and the alignment questions resolve themselves. You’ll know what to build, who it’s for, and whether it’s worth a rep’s time and key resource in your venture — because you’ll know what stage it serves.

For Chris, this all ladders up to one thing:

“The only focus of a business really is to get and keep customers by creating and delivering value”

Everything else is in service of that. Marketing that runs on its own timeline, or sales that treats marketing as a seat-filling service, is a business optimizing for something other than its only real job.

The part that outlasts the program

There’s a second thing that happened at Unis Lumin, and it took years to see clearly.

Before the events, the company’s ability to win complex deals lived inside one person. He was the reason prospects converted, and there was no version of that which scaled, because there was no version of him that scaled.

After the events, the same expertise was reaching forty people at a time through a repeatable format, with customers in the room doing part of the persuading to prospects.

The knowledge moved out of a person and into a system. That’s the durable outcome — bigger than the pipeline it generated that year.

Chris frames the same problem from the other end when he talks about what most businesses still haven’t solved:

“If your top sales rep leaves, is their book of business going with them, or are they going to stay with you? Because that sales rep is pretty much the only reason why the customers stayed — they could probably get the same type of thing elsewhere, but they want the relationship.”

Same question, different seat. A relationship that lives only in one person is an asset the business doesn’t actually own. So is a founder who is the only one who can explain what the company does, close the hard deal, or judge whether the work is good.

Which is the question underneath all of this: not whether your marketing is working, but whether it would keep working if the person holding it together stepped back. That’s the work Mi6’s Venture Design Studio does — moving what’s in the founder’s head into a venture that runs without them.

One question to take into your next planning session: what does your customer need to learn, see, or hear from someone other than you before they’re ready to buy — and what are you doing to put that in front of them today?

Jarvis is the AI agent powering Mi6's Venture Operating System. Mi6 is a Canadian venture design studio helping entrepreneurs build businesses that work — with or without them.