5 unconventional lessons from leaders who’ve sold, enabled, and earned trust in the toughest market
“You can’t just drop a good seller into cybersecurity and expect them to win. This isn’t SaaS. It’s something else entirely.”
— Lindsay Wolf, Head of Enablement, Torq
Cybersecurity sales isn’t like other B2B sales.
It’s more technical. More buyer-skeptical. Higher stakes. And more complex across every stage — from prospecting to procurement to post-sale trust.
It’s also full of sellers who are burning out or burning pipelines because they’re working from a broken enablement playbook — one built for horizontal SaaS, not cybersecurity.
To fix it, we went straight to the source:
Three leaders who’ve spent decades selling into the toughest rooms in B2B, and enabling teams to do the same.
- Ron Baden, Head of Sales at GTM Buddy — 25+ years, 100+ quarters, and zero tolerance for fluff
- Lindsay Wolff, Enablement leader at Torq — scaling high-trust sales at a fast-growing cyber startup
- Andrew Monahan, Cybersecurity sales coach — 103 quarters and deep scars to match
What they shared aren’t best practices. They’re earned insights — the kind you pick up over hundreds of quarters and thousands of calls.
Here are the five most important lessons they’ve learned about what actually works in cybersecurity sales enablement — and what doesn’t.
1. Experience doesn’t guarantee credibility. And credibility is everything in cybersecurity
“You can’t shortcut trust. Especially not with a CISO.”
— Andrew Monahan
The default instinct is to hire experienced SaaS sellers and drop them into a cyber org.
And on paper, that makes sense.
But in cybersecurity sales, your buyer is a deeply technical decision-maker whose job is to find flaws — in products, in claims, and in people.
A great deck and a polished pitch aren’t enough. If your rep can’t hold a thoughtful conversation about risks, architecture, and competing priorities — they’ll be dismissed quickly.
The lesson:
Hire for curiosity and resilience, not just a LinkedIn resume.
Lindsay put it clearly: “We’ve hired amazing sellers who stumbled because they didn’t know how to be a beginner again.”
What works in cybersecurity sales:
- Reps who aren’t afraid to say “I don’t know — but I’ll find out”
- Sellers who show up prepared, not performative
- Teams who obsess over buyer context, not just sales velocity
2. Don’t lead with the product. Teach reps to think like cybersecurity buyers
“If the first thing they learn is the demo, the only thing they’ll lead with is the demo.”
— Lindsay Wolf
Most onboarding programs kick off with a deep dive into product.
It’s fast. It’s familiar. And it creates the illusion of progress.
But in cybersecurity sales, product-first onboarding creates pitch-first reps. They default to features instead of empathy. Capabilities instead of credibility.
That’s why Lindsay rebuilt onboarding at Torq to start with the buyer:
- Who are they?
- What pressures are they under?
- How do they evaluate vendors?
- What’s at stake if they get it wrong?
The product demo doesn’t come until much later — and only after reps can explain the problem the product solves.
“Cybersecurity buyers don’t want you to sell to them. They want you to get them.”
— Ron Baden
The lesson:
Make your reps fluent in the buyer’s world before they touch the demo.
In cybersecurity sales, understanding the buyer’s environment is table stakes. Otherwise, every conversation becomes a product monologue — and those don’t win deals.
3. Role plays aren’t theater. They’re reps for high-stakes moments
“I don’t care if they’re uncomfortable. I care if they’re ready.”
— Lindsay
Let’s be honest: most role plays are awkward. They’re either too scripted to be helpful, or too vague to simulate anything real. And most of the time, they’re treated like tests — not tools.
But in cybersecurity sales, where discovery calls are surgical and credibility is fragile, role plays are essential. If you don’t rehearse the hard parts, your reps will learn in front of the buyer. That’s expensive.
At Torq, every new hire runs live role plays with their manager and AVP within the first two weeks. Real scenarios. Real personas. Real stakes.
Andrew takes it further. Drawing from his work with former Navy SEALs, he applies the same philosophy to sales training:
“SEALs don’t start with full missions. They practice opening the door. Then clearing the room. Then coordinating with the team. Sales should be no different.”
The lesson:
Break your sales process into high-impact moments — and drill them until they’re natural.
Don’t role play the entire call. Role play:
- The first 30 seconds with a skeptical CISO
- What to say when a buyer asks about competitors
- How to reframe risk without getting defensive
That’s what builds confidence in real cybersecurity sales conversations.
Want to make role plays more effective (and less awkward)? Try these AI-powered role-play scenarios for real-world sales training built for high-pressure selling environments.
4. AI won’t replace sellers. But it will show you who’s doing the work
“AI is not the coach. But it’s the mirror.”
— Ron Baden
We hear it everywhere: AI is transforming sales. But here’s the real story in cybersecurity sales enablement:
AI isn’t replacing reps — it’s exposing the gap between those who prepare and those who don’t.
Top-performing reps are using tools like GTM Buddy’s AI role play software to sharpen their messaging, test their reactions, and get smarter between calls. They’re not waiting for enablement to schedule a workshop. They’re self-correcting in real-time.
Meanwhile, underperformers are still hoping that product knowledge alone will carry the conversation.
“AI gives you a safe space to fail — and the feedback to improve fast.”
— Lindsay
And for leaders, it’s a gift. You can see:
- Who’s engaging with practice tools
- Where they’re struggling
- What content they actually use mid-opportunity
The lesson:
Use AI to create reps that scale — and insights that enablement can act on.
Cybersecurity sales is a high-context, high-risk domain. AI gives you a way to practice the nuance and surface the patterns — without slowing down the team.
5. In cybersecurity, you don’t just sell the story. You have to earn the right to tell it
“Salespeople don’t meet use cases. They meet people.”
— Andrew
There’s a lot of talk about storytelling in sales. And yes — stories work. But only when the buyer sees themselves in them.
In cybersecurity sales, storytelling isn’t a tactic. It’s a recognition mechanism.
A CISO won’t care that you improved some other customer’s workflow unless you can draw a straight line from their pain to that story’s outcome.
Lindsay’s approach? Capture real stories from the field — and help reps internalize them, not just recite them. Focus on what happened, who was involved, what challenges came up, and why the customer moved forward.
Ron summed it up best:
“If the buyer doesn’t feel seen, they won’t hear a word of your pitch.”
The lesson:
Great reps don’t just tell stories. They make buyers feel understood.
This is especially true in cybersecurity sales, where buyers are under constant scrutiny, juggling compliance, tooling gaps, and internal politics.
Reps who win are the ones who speak their language — and show they’ve done the work to understand their world.
Final thought: Enablement isn’t about making reps “ready.” It’s about making them credible
The big shift in cybersecurity enablement isn’t about tools.
It’s not even about training hours or onboarding timelines.
It’s about redefining the outcome. Enablement isn’t about knowledge transfer. It’s about creating credibility at scale.
That means:
- Hiring reps who are coachable, not just confident
- Training them on buyers, not just product
- Coaching them through pressure, not just process
- Giving them space to practice, and feedback that helps them evolve
- Using AI to support — not replace — human growth
In cybersecurity sales, the best reps don’t wing it.
They earn trust before they sell anything. And that kind of excellence starts with modern enablement.
Want to see how leading teams are doing it?
GTM Buddy is helping companies like Torq scale trust-building enablement for complex sales cycles. With AI-powered role plays, in-workflow content delivery, and insights that actually move the needle.
Selling into cybersecurity? The old playbook won’t cut it. Explore how GTM Buddy helps cybersecurity sales teams build trust and close complex deals with AI-powered enablement.
