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⏳ How to Keep B2B Prospects Engaged Through Long Sales Cycles
Dragos' full-funnel strategy to sell multi-million dollar contracts with complex buying cycles
Capturing executive attention isn't the hardest part of enterprise sales. Not nearly.
It's maintaining that enthusiasm through months of demos, approvals, and technical reviews.
And you’re not just convincing one person. You’re battling buying committees, CFOs with cold feet, and decision-makers who move slower than molasses.
If your marketing strategy stops at lead gen, you’re toast!
We spoke to Jennifer Halsey, Director of Integrated Product Marketing at Dragos, to learn their strategy for keeping prospects engaged throughout their long sales cycle.
How to Keep B2B Prospects Engaged Through Long Sales Cycles
What is Dragos?
Dragos is a cybersecurity company that protects critical infrastructure from cyber threats.
With real-time threat detection, response, and intelligence, Dragos ensures industries like energy, manufacturing, and utilities can safeguard their most vital operations.
Top-of-Funnel: Building awareness with authority
Most B2B companies spam the world with content… praying that someone, somewhere, gives a damn.
Dragos would rather build trust in their quest to safeguard civilization than beg for attention.
Here’s how they go about it:
1. Educational content as the first touchpoint
Dragos knows the best way to catch attention is by offering something valuable upfront.
"We use a lot of educational content, partially because threat hunters literally every day hunt for adversaries coming against our critical infrastructure around the world. They understand these groups in a significant way. We currently track 23 different threat groups that are actively coming against critical infrastructure in different ways… A lot of our most popular content is their research, saying here’s what we’re seeing. Here’s how they’re operating. Here’s who they’re targeting, etc. And so when we come in through that top of the funnel, our job is to figure out how to get them on the journey, not just buying Dragos.”
Their team takes all that juicy frontline intel and turns it into threat intelligence bulletins, LinkedIn posts, and dedicated monthly newsletters.
2. Subject matter experts (SMEs) as the face of the brand
Jennifer explains that to build trust and win over new markets, you’ve gotta pick the right SMEs and match them to topics that resonate with prospects.
"We have a lot of different experts contributing to the conversation, and that's what we want. We want to hear from voices that are experienced and understand what our customers and prospects are facing.”
And get this: Dragos launched a new initiative to really take their thought leadership game to the next level...
"We recently started a Toastmasters club at Dragos to help some of our experts become more confident in their public speaking. Some of the most intelligent people might not be as comfortable getting up and sharing in front of people. We need that from a marketing perspective… because we'll have a bigger pool of experts that we can pull from, and there'll be more compelling when we put them in those scenarios.”
3. Industry groups
Marketers notoriously waste time convincing people they have a problem. Jennifer believes the smarter play is to find those who already know they do.
For Dragos, that means focusing on industry groups where leads are already engaged and primed to act.
"We’re pretty active in a lot of industry groups and that’s where we find some of our hottest leads are most likely to convert because they’re already engaging around the topics that we care about. Meeting them where they are is much easier than trying to convince them they have something to be concerned about. If they're already showing up to a security roundtable or something like that, then we know that they’re on the same page with us about needing to get on that journey.”
Authority gets you noticed, but engagement keeps you in the game. Here’s how Dragos turns awareness into real, ongoing conversations...
Mid-Funnel: Optimizing for engagement
Ask most marketers how to handle a long sales cycle, and you'll get the same tired advice: follow up, and stay top-of-mind. But Dragos’ team takes a sharper approach.
"We recently hired a new CMO and he's really passionate about engagement being the core metric rather than lead gen or pipeline or whatever. We of course want that to lead to the pipeline, but the engagement is super important with the sales cycle being as long as it is. And with a buying committee that often includes five to seven people, you need those levels of engagement across the personas to make that decision easier.”
Rather than targeting all leads, they group accounts into engagement bands and nurture them based on intent.
Jennifer shared how they optimize for engagement and better results:
1. Benchmarking guides
"So we have a benchmarking guide, and I think that benchmarking guide is really gonna prove to be a big converter for us. We just released it a couple of months ago, but it gives people a way to self-assess different critical controls and evaluate how well they're defending their assets and facilities. This helps them to see what's next on their journey.”
Dragos empowers prospects to spot their own problem, get frustrated for a second, and then be like, “Alright, time to bring in the pros.”
By helping them figure out the gravity of their problem, you’ll spark meaningful conversations about next steps and position yourself as a trusted partner for the long haul.
2. Field events and direct sales touchpoints
Jennifer mentions that Dragos aims to put the right people (CEO, sales reps, whoever) in front of prospects.
“We're able to come in with some nurturing, with maybe some field events, with some direct touches from our sales reps to hone right in on what they are missing and help them figure out how Dragos can get them to a better place over time.”
The goal is to have the kind of candid conversations that take those low-intent opportunities into the realm of enterprise-level, long-term partnerships.
3. The threat intelligence subscription
Multi-million dollar deals don’t happen overnight. So for Dragos, it's key to have a lower-ticket offering that keeps prospects engaged without scaring off their CFO.
“We have a product called Worldview, which is a subscription, and it's our threat intelligence subscription. We put out bulletins all the time that are like, this is what we're seeing, these are some of the tactics to watch for, here's a list of IP addresses that you want to be careful to avoid..."
Prospects get value, stay informed, and keep Dragos top of mind for when they’re finally ready to drop a serious investment on the full package. Smart, right?
If it sounds like a slow burn, that’s because it is. But for the B2B teams who play the long game right, the payoff is huge.
Time to play the long game
Selling complex products isn’t about a quick close. It’s about guiding prospects to see value for themselves.
Forget traditional lead gen. Shift your focus to trust, long-term nurturing, and those “aha!” moments where your solution becomes the obvious choice.
P.S. Are you a CMO or senior-level marketer at a B2B SaaS company? We’re looking to interview the best and brightest marketers in the game for the AskCMO newsletter. Fill out this form and we’ll be in touch.
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