If you’re selling to small businesses, solo entrepreneurs, or low-ticket services, sales cycles can be short and forgiving. A customer might sign up in a day, a week, or even an hour. Then there is the world of long, complex sales.
I’m talking about $200k, $500k, six-figure, and seven-figure deals. Complex buying environments. Multiple stakeholders. Budget cycles. Internal reviews. Procurement. Legal. Risk committees.
If you’re new to that world, it can feel harsh
You land an incredible logo early on. A whale of a company. A big-name firm. A serious buyer. You get excited and think, this could change everything. Then reality kicks in. Evaluation stretches into months. Vendors are compared. Internal teams need to align. Suddenly, what felt like a Q1 close is drifting into Q3 or later.
That gap between early excitement and eventual reality is where a lot of founders lose their nerve.
The first shift you need to make is mindset. You have to be calm and realistic about long, complex sales cycles. You can shorten them, yes, but you cannot compress a ten-month buying process into weeks. It doesn’t work that way. I’ve been there, and once you see how budgeting, approvals, and risk are handled internally, it all makes sense.
Big investments are often planned annually. Miss the window, and you may be selling into next year’s budget. Smaller investments sometimes come from discretionary budgets, but even those are competed for and debated. None of this is personal. It’s structural.
Founders are busy. You can’t afford to spend all your time chasing one large deal, no matter how tempting it looks.
If you’re selling into complex, high-value deals, here are a few things to be aware of:
A. Map stakeholders early
Don’t assume one buyer. Identify who influences the decision, who signs it off, who will use the solution, and who carries the risk. Waiting for this to emerge naturally costs time.
B. Clarify how decisions are actually made
Ask early how decisions move internally. Budgets, approvals, committees, timing. Complex deals don’t stall randomly; they stall where the process isn’t understood.
C. Understand where each step fits
Demos, trials, technical reviews, legal checks, procurement, these are not obstacles; they’re stages. Know when they appear and what each one is meant to prove.
D. Manage the process, not just the relationship
Strong relationships matter, but they don’t replace structure. Deals move forward when the process is actively guided, not when everyone is simply “getting on well.”
A complex sales cycle can be shortened, but not through pressure, but through clarity.
Once you’ve shortened them and you have multiple deals in play, something changes. One large deal can be stressful. Two or three still feel overwhelming. But the more opportunities you have, the better you become. That’s when they become an asset. You start to understand probabilities. Revenue becomes less emotional and more measurable. Deals land instead of living in hope.
Finally, and this is where many teams make an unforced error, stop being afraid of trials.
Enterprises are willing to take risks, otherwise they wouldn’t be talking to you, but they don’t want to take all of it upfront. Paid trials or proofs of concept are how serious buyers manage risk internally. Yes, selling a $500k deal only to start with a $20k trial can feel frustrating. But if you get good at them, really good, they become a competitive advantage.
Clear goals. Tight timelines. Defined success criteria. Close trials properly, and the larger deal follows.
Free trials rarely work because free isn’t valued, and unvalued work doesn’t get internal attention or resources. If it matters, buyers will pay something.
Long sales cycles can drive you mad, or they can become your superpower. If you accept them, shorten them intelligently, get the right help, and build confidence around trials, they stop being a liability.
They become a system you know how to win at.
When you understand the buyer’s needs and can deliver them consistently.
Joe Dalton