How SaaS Leaders Keep Deals Moving in Long, Complex Sales Cycles

Long deal cycles are not “hard” because of one big obstacle. They are hard because there are lots of small failure points. Data goes missing, stakeholders change, priorities shift, and a deal that looked healthy suddenly stops moving.

In this episode of the Revenue Revolution Podcast, Chris Muir shares how he has navigated mid-market SaaS deal cycles, what causes deals to stall, and how leaders can create a more reliable, less surprising pipeline.

Image idea: a simple “buying committee” diagram on a whiteboard, or a CRM dashboard screenshot style image (no real logos).

Why long SaaS deals stall when you only have one champion

Chris sees a common pattern in complex deals. A rep finds a champion and then over-indexes on that one relationship. The problem is not that a champion is bad. The problem is the deal becomes fragile.

When the deal depends on one person, any change can stall it:

• Internal re-orgs

• Priority shifts

• Budget changes

• A champion leaving the business

• A stakeholder who quietly disagrees

Chris’s view is that deals get stuck when the sales team is not connected to the prospect at more than one or two levels. In modern SaaS, the buying group keeps getting bigger and more cross-functional. If you are not multi-threaded, you do not really control momentum.

How CRM friction quietly breaks forecasting

Chris describes an issue many teams recognize but rarely fix properly. CRM only works if reps use it. When CRM becomes harder to update, reps do not stop working. They just move the real work somewhere else.

That creates two realities:

• The rep has the truth in notes, spreadsheets, and conversations

• Leadership has partial truth in the CRM

Once that gap appears, pipeline inspection becomes guesswork. The system that is supposed to be your single source of truth becomes a lagging indicator.

How hands-on leadership closes the “system of record” gap

Chris believes effective sales leaders stay hands-on, even at senior levels. A dashboard can tell you stages and dates. It cannot tell you what is actually happening inside the deal.

He recommends making time for consistent rep touchpoints because it surfaces:

• Where the buyer is hesitating

• Which stakeholders are not engaged yet

• What information is missing

• What is happening outside the deal that could derail it

One of the most useful insights here is that the goal is not micromanagement. The goal is staying close enough to spot risk early, before a slip becomes inevitable.

How call intelligence tools reduce admin without losing insight

Chris mentions tools like Gong as a way to pull information from calls and feed it into CRM with less rep admin.

This matters for two reasons:

• Leaders can verify what is happening without relying only on rep updates

• Reps do not feel like CRM is “extra work” that competes with selling

The point is not the tool. The point is reducing friction so the system reflects reality.

What “win strategising” changes in real deals

Chris built a framework at NetSuite that he calls “Win Strategising”. He describes it as a template that sits on top of a sales process, similar to account planning but applied to new business.

The intent is to answer one early question with honesty:
Can we win this deal?

If the team cannot align internally on whether the deal is winnable, then everything that follows becomes noise. Chris wants early agreement on how the team will win, and who will do what.

The template focuses on information, not format. It helps a team map:

• What they understand about the prospect’s business

• The strategy for discovery and demos

• How they will present value

• How implementation concerns will be handled

• Negotiation strategy

• Marketing strategy during the deal cycle

Chris makes a clear point that marketing does not stop once you engage a prospect. In his view, that is when marketing becomes more personal and more useful, because it can be tailored to specific stakeholders and gaps in the deal.

How stakeholder mapping improves demos and value messages

A key part of the framework is treating each stakeholder differently. Chris highlights something that sounds obvious, but is often missed in practice.

What a CEO needs to see in a demo is not what an operations leader needs to see. Value is not universal either:

• Value for a CEO can be directional and strategic

• Value for a finance leader can be risk, control, and measurable return

• Value for a functional owner can be workflow, usability, and day-to-day impact

When deals stall, it is often because value was presented, but not in the right language for the right person.

How to build multi-level alignment without losing control

Mick asks a practical question: how do you teach salespeople to release control and bring others into the deal?

Chris is candid about the default rep instinct.

"Salespeople naturally like to keep everything to themselves and tell us what's happening when they've won the deal."

His approach is to make multi-threading useful for the rep, not just for leadership. He gives an example from his own deals where a senior introduction might only be brief, but it creates an escalation path later.

If a deal slows down, that earlier relationship lets you ask directly:

• What has changed?

• Are we doing everything we should be doing?

• Is there something blocking progress that we have not been told?

He also points out that technical alignment can unlock different conversations. Buyers often speak more openly to solution consultants because they do not feel like they are being “sold to” in the same way.

How mutual close plans prevent avoidable slip

When deals slip, teams often discover the cause too late. Chris uses close plans, mutual engagement plans, or project plans to stay aligned with the buyer’s reality.

He gives a simple example that happens more than anyone wants to admit. A deal slips because someone went on holiday and the team did not know. That is not a complex problem. It is a visibility problem.

Chris’s bigger framing is that buying and implementing software is a project. The project does not start when the vendor is chosen. It starts when the buyer decides they want to change something.

His suggestion is to position the plan as something the buyer should use with every vendor, not just yours. That removes the stigma of it being a sales trick and makes it feel like good project governance.

What leaders should look for when deals “go quiet”

Chris calls out a specific red flag he has seen repeatedly. A prospect is acquisitive and then suddenly becomes less responsive.

Often the reason is simple. They are working through an acquisition, and anyone who has lived through one knows it consumes attention across the business. The software project did not die, but it stopped being a priority.

This is why multi-threading matters. If you have multiple points of connection, you can confirm what is happening rather than guessing.

Why “healthy paranoia” improves forecast quality

Chris shares a view that stands out. One of the traits he values in strong salespeople is pessimism.

He does not mean negativity. He means healthy paranoia. The kind that drives:

• Better questions

• Better qualification

• Better risk spotting

• Fewer surprises late in the cycle

Chris connects this directly to curiosity. Curious reps learn more. The more they learn, the fewer surprises they face.

He used to write a mantra on his whiteboard:

"no surprises."

He admits this is impossible to fully achieve, but the goal is to reduce surprises. Fewer surprises leads to better forecasting and a higher chance of winning.

How leaders should use forecasting without pretending it is precise

Mick shares a controversial take. He does not believe reps should forecast their deals because incentives distort the number. He prefers looking at deal reality: complexity, red flags, and whether a deal can land in a fiscal period.

Chris partly agrees. He questions probability as a concept because a deal does not close 70%. It closes or it does not.

Where Chris still finds forecasting useful is accountability. It forces a rep to take ownership and make a call.

He also shares a practical way leaders can reduce noise: track historical forecast accuracy by rep, then adjust expectations based on the pattern.

If a rep consistently over-forecasts, the leader should reduce the forecast automatically rather than arguing about each deal.

What CRM indicators help separate “good” and “bad” deals

Chris lists a few pipeline signals he looks for when deciding if a deal is real.

He checks:

• When was the last activity?

• When was the last conversation?

• Is the opportunity stage consistent with the forecasted close date?

• Does the deal look stuck?

He gives an example that is a clear red flag. If a deal is forecasted for commit this month but it is still in discovery, something is off.

He also suggests CRM can do more of this automatically with dashboards and reminders, such as flagging deals that have not been touched recently but are expected to close soon.

Why forecast calls should be for team learning, not status reporting

Chris shares a strong point about forecast calls. A forecast call should not exist just to tell the leader the number. The leader should already know the number.

He sees forecast calls as a forum for reps to share what is happening so the team can:

• Learn from each other

• Spot common patterns

• Compare notes on buyer behaviour

• Identify risks earlier

That turns forecasting into an enablement motion, not just a reporting chore.

What one rule Chris would teach every seller

At the end, Chris is asked for one rule for successful sales. He chooses a cluster of behaviours rather than a gimmick:

• Be curious

• Be pessimistic in a healthy way

• Be open

• Actively listen to what is happening in the deal and in the environment

• Be honest with yourself about whether you can win

His closing point is blunt and useful. Do not chase deals you cannot win just to fill pipeline.

Conclusion: reduce surprises by building real deal visibility

This episode reinforces a simple idea. Forecasting gets easier when surprises go down. Surprises go down when you have:

• A CRM that reflects reality

• Leaders who stay close enough to spot risk early

• Multi-threaded relationships across the buying group

• A shared plan that keeps buyer and seller aligned

If your deals keep slipping, the answer is rarely “push harder”. It is usually “see more clearly”.