Most salespeople are wired for now. The quota is now. The pipeline review is now. The pressure to close is always right now. And that urgency is exactly what gets in the way when you are sitting across from a prospect who tells you their contract runs for another 24 months.
The knee-jerk reaction is to disengage. Move on. Find someone ready to buy today. But that is how you hand your future deals to a competitor who was willing to play the long game.
I sat down with Harriet Mellor, founder of Your Sales Co, on the Sales Gravy Podcast, and the way she approaches long sales cycle pipeline nurturing reframed how I think about those “come back later” conversations. What sounds like a dead end is actually a head start, if you know how to work it.
The Mistake Salespeople Make in Long Sales Cycles
During our conversation, Harriet and I discussed how salespeople are so driven by an immediate number that they scramble for the next thing the moment a prospect says they are locked into a contract. That scrambling costs them.
The prospects who tell you they are two years out from a decision are still going to make a decision eventually. And when that moment comes, the question is whether you are the person they think of first, or whether another rep who stayed in touch has already earned that spot.
Long sales cycle pipeline nurturing is less about persistence and more about presence. There is a real difference between the two.
Step One: Block the Date and Work Backwards
The first thing Harriet does when a prospect tells her there are 24 months left on their contract is block the renewal date in her calendar immediately. Future her will be grateful for it.
That single action shifts your relationship with the timeline. It moves from abstract to concrete. You know when the window opens. Everything between now and then becomes purposeful instead of reactive.
From there, she works backwards. The goal is to stay recent and frequent in the prospect’s awareness, so that when the date arrives, she is already top of mind.
Step Two: Let LinkedIn Do the Passive Work
One of the most efficient things Harriet does in her long sales cycle pipeline nurturing strategy costs her almost no incremental effort: she connects with the prospect on LinkedIn and posts consistently.
The logic is simple. When you post regularly, your prospect sees your content in their feed without you ever having to reach out directly. It is a one-to-many approach that keeps you visible without putting pressure on the relationship. No awkward check-in calls. No “just following up” emails. You are simply there, showing up in their professional world, adding value through content.
For anyone managing hundreds of long-cycle prospects, this is the kind of infrastructure that makes the whole system scalable. You cannot personally nurture everyone every week. But consistent LinkedIn activity means you are present even when you are focused elsewhere.
Step Three: Set a 12-Week Touchpoint With a Real Reason
Every 12 weeks, Harriet sets a reminder to find a meaningful reason to reach out. The keyword is meaningful.
A check-in for the sake of checking in is a waste of both people’s time. What Harriet looks for is a genuine reason to reconnect: a new client win she can reference, an event coming up, a piece of content directly relevant to something the prospect mentioned, or an industry development worth flagging.
If she does not yet know enough about the prospect to manufacture a relevant reason, the reminder itself becomes a prompt to learn more. Over time, as she learns more about their business, their priorities, and what they care about, those 12-week touchpoints get sharper.
“The more I learn about them and the more I learn about what’s going on with my clients, the more value I can add over the two years.”
The touchpoints are low-frequency by design. Harriet is managing a pipeline with hundreds of prospects across multi-year timelines. The goal is to stay present, build the relationship, and let trust accumulate gradually. By the time the contract window opens, she is a familiar and trusted voice, and the prospect already knows what she brings to the table.
Step Four: Multi-Thread Across the Organization
Single-threading a long-cycle deal is a liability. Your one contact changes roles, leaves the company, or gets removed from the decision. If your entire relationship lives with one person, you may have to start from scratch.
Harriet addresses this by connecting with multiple stakeholders across the organization from the start. Decision-making authority for a technology purchase, for example, might sit with IT, but it might also come from finance, operations, or revenue leadership, depending on who is driving the initiative.
When multiple people across the org see your LinkedIn content and notice that you are already connected to someone they respect internally, something organic starts to happen. They get curious. They ask about you. They may even make the introduction themselves, because they want the credit for the connection.
Low-touch, high-presence, relationship-led.
Why This Approach Feels Authentic
One thing that came up in our conversation that I think gets overlooked in discussions about pipeline nurturing is the authenticity question. Does a structured system for staying in touch feel manufactured?
Harriet’s answer is that the system is a scaffold for human behavior, not a substitute for it. The goal is to stay engaged long enough that the relationship becomes genuinely natural. By the time you have been connected on LinkedIn for a year, exchanged a few relevant touchpoints, and shown up consistently, the relationship has its own momentum.
The system gets you to that point. It keeps you from dropping the ball when you have hundreds of prospects and one very human tendency to forget. But the warmth and the relevance in every touchpoint? That part still comes from you.
When I was in automotive sales, I would log personal details into the CRM because I knew a birthday message or a follow-up about a grandkid’s sports season would do more than any promotional email. The mechanics looked different, but the principle was identical: be the person who pays attention, and people will remember you when it matters.
The Payoff
The prospects who told you to come back in two years are still out there. Their contracts are ticking down right now. The question is whether you are already in their feed, already in their inbox every 12 weeks with something worth reading, already connected to three people in their organization who know your name.
Start today. Block the next renewal date you know about. Send the LinkedIn connection request. Set the 12-week reminder before you close this tab. The rep who builds the relationship now is the rep who wins the deal when the window opens. That rep should be you.
Want to learn more from Harriet Mellor? Check out her course, Handling a Discount Request, on Sales Gravy University.
Frequently Asked Questions
Every 12 weeks is a practical and sustainable cadence for direct outreach. Combined with consistent LinkedIn visibility, this keeps you present without overwhelming the prospect. The key is that each touchpoint should have a genuine reason behind it rather than a generic check-in.
The most efficient method is regular LinkedIn posting. When you connect with prospects and post consistently, they see your content without requiring direct contact. Pair that with a 12-week reminder system for value-driven touchpoints, and you have a low-effort, high-presence approach that scales across a large pipeline.
Start by blocking the renewal date immediately and working backwards from it. Connect on LinkedIn, engage multiple stakeholders across the organization, and set reminders to reach out every 12 weeks with something relevant to their business. By the time the contract window opens, you should already have a warm, trusted relationship in place.
Relying on a single contact in a long-cycle deal is a significant risk. People change roles, leave companies, or lose decision-making authority. Connecting with multiple stakeholders across the organization protects the relationship and creates organic introduction opportunities as those contacts interact with each other internally.
