By Troy Harrison, sales navigator, speaker and author
Most people haven’t ever run a marathon. But many salespeople run them every day – the long sales cycle. Salespeople love the quick win – that satisfying moment when a prospect becomes a customer in a matter of days or weeks. Sometimes, it’s even the fabled “one call close.” But what about those industries, or even those times, where the sales cycle stretches into months or even years? How do companies keep their sales teams motivated, strategic, on-task and successful when the finish line seems so far away?
Long sales cycles present unique challenges. They test a salesperson’s patience, strategic thinking and ability to maintain momentum over extended periods. They also can tempt even the most disciplined sales professionals to neglect prospecting, as the gratification of a closed deal feels perpetually out of reach. But here’s the truth: mastering the long sales cycle is not just a skill – it’s an art form. And like any art, it requires dedication, practice and a specific set of techniques.
Let’s explore four key strategies that can help companies and their teams excel in the marathon of long-cycle sales.
1.Never Stop Prospecting
Imagine being a farmer (no, not the old, outdated “hunter/farmer” sales term). A farmer knows it takes months for crops to grow, but the farmer also knows that if they don’t plant seeds regularly, eventually they’ll have nothing to harvest. The same principle applies to long-cycle sales.
It’s easy to fall into the trap of thinking, “Why start new conversations when I won’t close them for years?”
But remember this: A salesperson can’t finish a sale unless they start one. Prospecting is the lifeblood of the sales pipeline, regardless of how long it takes to close a deal. A sales funnel that doesn’t consistently fill at the top will run dry at the bottom.
Make prospecting a non-negotiable part of the weekly routine. Set aside dedicated time each day to reach out to new potential clients. Use a mix of cold calls, emails, social media outreach and networking events to keep the pipeline full. Remember, the seeds a salesperson plants today are the deals they’ll close tomorrow – or next year.
The best prospecting cadence is to open with a phone call (yes, a genuine, pick up the phone, voice-to-voice call), and attempt to reach the target. If a salesperson doesn’t get an answer (80% to 90% of the time these days), leave a powerful voicemail message and switch to LinkedIn connections. Once connected, slowly play the connection using engagement techniques, then ask for the appointment two to three months after connecting.
2.Think Strategically, Act Consistently
Once a salesperson has initiated a conversation with a prospect, it’s time to shift into strategic mode. This is where the real art of long-cycle selling comes into play.
Start by estimating a realistic timeline for the deal. Is it six months? A year? Two years? This timeline becomes the salesperson’s roadmap, guiding interactions and helping set milestones along the way.
With each contact, the goal should be to move the Buyer’s Journey forward, even if it’s just by inches. This is particularly crucial when a salesperson is up against an incumbent vendor with an existing contract. The salesperson is playing the long game, so every interaction should add value and strengthen the position. Basically, it’s about positioning to be the vendor of choice at contract time.
But here’s the truth: mastering the long sales cycle is not just a skill – it’s an art form. And like any art, it requires dedication, practice and a specific set of techniques.
Maybe it’s sharing a relevant industry report, offering a fresh perspective on a challenge they’re facing or simply checking in to maintain the relationship – but offering some new piece of knowledge or expertise every time. The key is consistency. Regular, value-added touchpoints keep the salesperson top of mind and in a position as a trusted advisor, not just another vendor.
3.Keep Contacts Current
In the span of a long sales cycle, a lot can change. Decision-makers move on, new stakeholders emerge and organizational priorities shift. As a salesperson, the job is to stay on top of these changes and adapt strategy accordingly.
Make it a habit to regularly verify and update contact information. But don’t stop there – strive to expand the network within the organization. The more contacts a salesperson has, the more resilient the opportunity becomes to personnel changes. “High, wide and deep” should be their watchwords. Get as high on the corporate food chain. Get as many contacts (a wide base of influence) in the target company. And make sure that the company genuinely knows the value a salesperson brings. This approach not only provides a salesperson with a more comprehensive understanding of the organization but also helps safeguard opportunity if the main contact leaves.
4.Be Ready When the Stars Align
Here’s a fundamental truth about sales: a deal happens when need, solution and timing intersect, and the Buyer’s Journey completes. In a long sales cycle, the salesperson’s job is to be ready when that moment arrives.
Maybe the incumbent vendor slips up, the budget suddenly becomes available or a new initiative aligns perfectly with the offering. A consistent presence and value-added interactions have positioned the salesperson to capitalize on these moments.
Stay alert to industry trends, organizational changes and any shifts in a prospect’s business that might create an opening. When that window of opportunity opens, be ready to act swiftly and decisively.
Managing long sales cycles is not about passive waiting – it’s about active preparation. It’s about building relationships, demonstrating value and positioning the company as the obvious choice when the time is right. There are no shortcuts to anyplace worth going.
Winning in long-cycle sales requires a unique blend of patience, persistence and strategic thinking. It demands that a salesperson resist getting demoralized due to the lack of quick wins and instead focus on building lasting relationships and delivering consistent value. By maintaining a steady prospecting rhythm, thinking strategically, keeping contacts current and staying ready for opportunity, a salesperson can master the marathon of long sales cycles.
Troy Harrison is a sales navigator, a speaker and the author of “Sell Like You Mean It” and “The Pocket Sales Manager.” He has trained salespeople from 23 different countries who live on three continents and has spoken all over North America and Europe. He helps companies navigate the elements of sales on their journey to success. He offers a free 45-minute Sales Strategy Review.
More information: www.TroyHarrison.com/ssr