The Cyber CMO Confidential is back, and we are starting with our favourite guest, Jennifer Leggio, Chief Strategy Officer at W2 Communications.

Jen’s back on the mic, taking us on her journey from cyber PR pro to CMO extraordinaire to brief, educational COO life. She understands why the brand isn’t just fluff but your secret growth engine. We break down how to talk about “the B-word” with a CFO who only wants more demo requests and explore why branding might just be your most powerful (and misunderstood) sales tool.

You’ll hear about the empathetic sale, how brand boosts pricing power, and why the buyer’s journey looks more like a bow tie than a funnel these days. If you care about brand, pipeline, or just surviving another board meeting, this one’s a must-listen.

Timestamps:

01:04 – Guest intro: Jennifer Leggio, CSO at W2 Communications

02:27 – Jen’s path to W2: From cyber PR to CMO to COO and back

04:17 – “Brand is the new demand gen”: What that means

05:40 – The empathetic sale: Qualify out as much as you qualify in

07:31 – Talking about brand with your CEO and CFO

09:00 – Real-life examples of brand influence (Carvana FTW)

11:15 – Demo requests ≠ demand strategy

13:09 – The bow tie journey: Reimagining the funnel

14:48 – Turning brand wins into sales enablement and retention tools

15:14 – Brand = pricing power: The Excedrin analogy

16:06 – Why does a brand build trust and support for go-to-market

17:14 – Brand’s impact on valuation and M&A (Sourcefire story!)

18:55 – Personal brand power and founder-led storytelling

20:53 – Budgeting for brand: “Brandman” and the peanut butter cup

23:02 – Using brand for customer retention and advocacy

25:26 – ABX + brand = targeted impact

About the guest:

Jennifer Leggio is the chief strategy officer at W2 Communications and has been a longtime force in cybersecurity marketing and operations. With nearly 25 years in the game, she’s held leadership roles across the spectrum, VP of Comms, CMO, COO, and built a reputation for driving bold, strategic growth. Known for her sharp storytelling, no-fluff approach, and deep operational chops, Jen has helped scale, rebuild, and position companies for high-impact outcomes.

She’s also a frequent speaker at top industry conferences like DEF CON, RSA, and CyberMarketingCon, and pens columns for SecurityWeek that spotlight the human side of cyber business. Whether building revenue engines or challenging the status quo, Jen brings clarity, candor, and an unwavering focus on what works.

Upcoming Events:

RSAC 2025 Marketers Party

On Sunday, April 27th, join the Cybersecurity Marketing Society for the best pre-RSAC bash. Drinks, Wagyu, and all your GTM besties. 🎟 Get tickets here

CyberMarketingCon 2025 – CFP Open!

📝 CFP closes April 15th!

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👉 Gianna Whitver

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