The Long-Term Content Strategy Challenge
If your sales cycle is long, your content strategy can’t just chase clicks and conversions. It has to build trust, stay top-of-mind, and show up before the buying conversation even starts.
That’s exactly what Monday.com does—and their strategy offers a powerful blueprint for any B2B brand that needs to win the long game.
💡 This is a how-to guide.
Let’s break it down.
The Challenge: What to Do When Nobody's Ready to Buy
Monday.com’s platform helps teams plan, collaborate, and execute complex work. But here’s the challenge: most potential customers don’t wake up thinking, “I need a work OS.”
They feel the symptoms—missed deadlines, messy handoffs—but they’re not actively shopping for a solution. And when they do enter the market, the sales cycle can take 6 to 18 months.
That changes everything about how you do content.
👉 Takeaway for your business:
If your product has a long consideration window, your content must do more than convert—it must educate, engage, and earn attention early.
Principle 1: Split Your Strategy—Now vs. Not-Yet
Monday.com divides their content roughly 50/50:
- Half targets people actively looking for a tool like theirs
- Half reaches people who don’t know they need it yet
Why? Because long-term growth doesn’t just come from catching buyers mid-funnel—it comes from shaping demand before it exists.
👉 How you can apply it:
Audit your content mix. Are you only talking to people who are ready to buy? Start creating helpful, audience-first content for people earlier in the journey.
Ask:
- What problems do they have before they search for a solution?
- How can we show up with value at that stage?
Principle 2: Lead with Value, Not the Product
To connect with the “not-yet” crowd, Monday created The Monday Insights Series, a weekly newsletter designed to help people succeed at work—not to pitch software.
Popular topics include:
- How to admit you made a mistake
- How to support working parents
- How to navigate organizational change
It’s not about selling. It’s about being useful.
And it works:
🚀 3M+ subscribers
📈 50–70% open rates
🏆 Top-performing initiative
👉 How you can apply it:
Build a flagship content series that solves real problems for your audience. Publish consistently. Make it feel like a gift, not a tactic.
Ask:
- What would people read even if they weren’t buying anything?
- How can we create a “habit” around our content?
Principle 3: Make It Human, Not Robotic
A real writer leads the series. Topics come from real conversations—with managers, customers, and readers. The team asks:
“What are you dealing with right now?”
“What helped when your team went through a big change?”
The tone is practical, empathetic, and a little fun. Each edition includes trivia, curated links, and cartoons. The goal is simple: make the newsletter something people want to open.
👉 How you can apply it:
Start small. Interview customers. Ask frontline teams what people are struggling with. Use their actual language. Add voice and personality.
Ask:
- What makes this feel human?
- How can we bring joy or realness into the experience?
Principle 4: Re-Engage Cold Leads with Soft Value
When leads go cold, Monday doesn’t chase them with discount emails. Instead, they offer the Insights Series—a no-pressure, value-first re-entry point.
This transforms the relationship from “vendor trying to sell” into “brand I enjoy hearing from.”
💡 Cold leads who engage with quality content are 70% more likely to re-enter the sales process.
— Content Marketing Institute
👉 How you can apply it:
Build a softer re-engagement path. Instead of pushing product, offer content worth sticking around for. Use your newsletter or lead magnets to restart conversations, no strings attached.
Ask:
- What content would earn someone’s attention again?
- How do we reframe our email strategy for value, not volume?
Principle 5: Measure What Matters for Long-Term Success
Monday knows brand content isn’t about instant ROI. So they combine smart metrics with qualitative feedback to steer their strategy.
They ask:
- What % of our market is regularly engaging with this?
- Are we changing brand perception over time?
- What topics or formats resonate most?
They run surveys inside the newsletter, conduct reader interviews, and use opens/clicks as signals—not the whole story.
👉 How you can apply it:
Add feedback loops. Use surveys, interviews, and polls to gather insight. Track qualitative signals like sentiment, repeat opens, or social shares.
Ask:
- How does this content make people feel?
- What’s one way we can make next month’s version better?
TL;DR: Monday.com's Long-Game Content Strategy—In 5 Moves
- Split your strategy: Reach both in-market buyers and future ones
- Create a flagship series: Publish something useful, every week
- Make it human: Real voices, real problems, real personality
- Re-engage with value: Give cold leads a reason to come back
- Measure what matters: Use qualitative insight, not just clicks
Final Thoughts: Long Sales Cycles Need Long-Term Trust
The lesson here isn’t “do what Monday did.”
It’s this: Don’t wait until your buyer is ready. Build a relationship early. Show up with something genuinely helpful. Then keep showing up.
In a world full of noise, the brands that win are the ones that earn attention before they ask for it.
And that’s a strategy worth stealing.
Looking to Implement a Long-Term Content Strategy?
Need help creating content that builds relationships before the sale? Let’s talk about how your brand can earn trust and stay top-of-mind throughout long B2B sales cycles.
