Cybersecurity Sales Leadership In 2025 & More

The Security Revenue Live Show by the Cyber GTM Alliance gathered top sales leaders in cybersecurity for a candid discussion about the evolving landscape of sales leadership, pipeline generation, AI’s limits, and how to keep revenue growing in a crowded, competitive market. Hosted by Taylor, with panelists Jessica Crytzer (CRO, LimaCharlie), Colin Brissey (VP of Sales, Eclipsium), and Lucas Hathaway (CRO, Rivial Data Security), the conversation was packed with practical advice and fresh insights.

Here are the key takeaways and tactical strategies you can put into play.

1. Sales Leadership Philosophy: Human Connection Wins

One of the first questions posed was about how each leader’s sales approach has shifted in recent years. While AI and automation are hot topics, all panelists agreed that the core of sales—human connection—remains irreplaceable.

• Jessica Kreitzer highlighted the challenge of capturing buyer attention in an era of email/LinkedIn fatigue. Her team runs lean, forgoing SDRs in favor of full-cycle Account Executives (AEs). The focus: “Be laser focused on your ICP… Knowing where you win, not deviating, and making sure you serve customers you have a high probability of winning.”

• Colin Brissey doubled down on in-person relationship building: “My philosophy of being human and showing up… makes a difference for the buyer and makes you stand out.” The goal is to go past superficial outreach and show deeper understanding—something AI can’t replicate, especially on the creative and personal side.

• Lucas Hathaway noted that automation should clear space for creative selling. Today’s standout reps “think outside the box and use different touchpoints—whether it’s physical mail, unique events, or in-person meetups—to build trust and get noticed.”

Bottom Line: In an age of automation, the personal touch is still your best sales differentiator.

2. AI in Cybersecurity Sales: Helpful, But Not a Replacement

The panel was frank about where AI fits—and doesn’t—in the sales workflow.

• AI works well for research and automating tedious tasks, freeing up time for higher-level selling. But, as Jessica put it, “I don’t believe we’re in a space where AI can replace the SDR function, and I don’t know that we ever will be… It doesn’t create that human connection.”

• Lucas added that AI is useful for nurturing inbound leads and personalizing some follow-ups but “hasn’t cracked it for cold outbound yet.”

Takeaway: Use AI for efficiency and research, not for relationship-building or full SDR replacement.

3. Pipeline Generation: It Takes a Village—and the Right Event Strategy

When asked how to generate new pipeline in today’s market, the consensus was: there is no single silver bullet. Instead, results come from a balanced mix of channels and relentless focus on what actually works for your segment.

Colin described a “three-legged stool”—target for his team is 30% self-sourced pipeline, 70% from channel partners and marketing. He stressed the rising value of channel partners and deep OEM relationships.

Lucas has seen the highest ROI from highly targeted, niche conferences—not the big, flashy events. These small events give you repeated, quality touchpoints with your exact ICP: “In three days, you could get to four to six trust-building touchpoints that move the deal forward.”

Jessica emphasized coupling workshops and hands-on events with smaller-region conferences and her company’s free product trial—just beware of students and tinkerers in the funnel.

Key insights for events:

• Pre-conference engagement: Simple, personal invites to dinners or meetings yield the highest open and reply rates.

• At the conference: Lose the table—stand in the aisle to be approachable. Don’t just scan badges; focus on qualified, high-value conversations. Eat meals with attendees, never alone.

• Post-conference: Book meetings on the spot, not later via email.

Quote to remember: “So many people fail to maximize conferences… focus on qualified opportunities, not just badge scans.” –Jessica

4. Expansion & Retention: Keep the AE in the Loop

On retention and expansion, all panelists advocated for “ownership” across the full customer lifecycle, either by AEs or in close partnership with Customer Success.

• Colin is experimenting with a hybrid approach: a dotted-line CSM who acts on the AE’s guidance, ensuring clients never feel they’re being handed off to a stranger.

• Lucas and Jessica both like close collaboration between sales and post-sales/care functions, regularly holding check-ins to maintain customer health and feed customer feedback into product and marketing.

Lesson: Avoid the classic fumble of completely handing off a client after the sale—the relationship must continue.

5. Cross-Team Alignment: One Team, One Goal

Achieving revenue goals is a company-wide mission. Regular alignment between Sales, Marketing, Product, and even Engineering is critical. Each panelist advocated for transparent communication and shared goals as the path to:

• Ensuring messaging and product remain in market sync,

• Making data-driven marketing/content adjustments (“What are prospects actually asking about?”),

• Keeping everyone focused on solving customer problems.

Closing advice: “There’s one metric, one goal we’re all trying to achieve. Constant collaboration is key.” –Lucas

Final Thoughts

In cybersecurity sales, you can't automate your way to success. The world is more saturated, budgets are tighter, and buyers are more discerning. The real winners will be those who combine intelligent use of AI/automation with creative, relationship-driven selling—and who work relentlessly to make every touchpoint count, especially in person.

Above all, align your teams and keep the focus on the human side of the business.

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