211: Rachel Roberts President of Sales, Check Point Software

In this episode of Sales Is King, host Dan Sixsmith sits down in the New York City studio with Rachel “Rae” Roberts, President of Americas Sales at Check Point Software, a leading cybersecurity company. Rachel shares why she joined Check Point to help lead enterprise AI security, how the company has radically restructured its go‑to‑market model, and what today’s best sales organizations are doing to win and retain customers in a risk‑filled, AI‑driven world.​ Rae explains why AI has fundamentally changed cybersecurity economics, with attackers already monetizing AI to accelerate phishing and compromise corporate networks in under an hour. You’ll also hear a deep dive on the evolving role of customer success, the rise of revenue‑oriented CCOs, how buyer groups have exploded from 4 to as many as 17 stakeholders, and what it now takes to earn and keep C‑level attention. Rachel closes by sharing her personal journey from marketing and business development into enterprise sales leadership, the traits she looks for in top sellers, and her definition of success as she drives double‑digit growth at Check Point.​ Why AI is different from prior tech waves—and why “the bad guys” are already winning with it in cybersecurity​ How AI‑generated phishing has exploded: higher click rates, more credentials surrendered, and attackers moving from nine weeks to under an hour to do damage once inside a network​ The major go‑to‑market restructuring at Check Point: hunters, ranchers, specialists, renewals, and a scaled‑up customer success organization​ Why net revenue retention, adoption, and engagement are becoming core metrics for customer success—and the debate over CSMs carrying quota​ Platform vs. best‑of‑breed: why integrations have become the number one buying criterion in B2B SaaS​ The explosion of buying committees: from an average of 4 to 11 stakeholders, and up to 17 people who can say “no” in an enterprise deal​ How top sellers orchestrate the ecosystem, multithread, and earn C‑suite meetings and trust​ Rachel’s career journey from Bay Area tech, marketing, and biz dev into enterprise sales and cybersecurity leadership​ “What’s different about AI and cybersecurity is that the bad guys have already figured out how to monetize it.”​ “If you’re not investing ahead of this AI wave, it’s not just about missing generational returns—it’s going to cost you dearly.”​ “Curiosity, grit, and operational discipline matter as much as domain expertise. You can learn an industry, but you can’t teach hunger.”​ 00:00 – Why AI has changed the cybersecurity game and the speed of attacks​ 01:00 – Introducing Rachel Roberts and Check Point Software​ 03:40 – Why Rachel joined Check Point and the AI security opportunity​ 04:20 – Re‑architecting go‑to‑market: hunters, ranchers, specialists, and customer success​ 08:00 – The evolving role and metrics of customer success​ 11:00 – How buyer conversations are changing: platforms vs. open garden​ 13:30 – Integrations as the top buying criterion in B2B SaaS​ 15:00 – Where Check Point is number one and how that shapes deal strategy​ 16:10 – Executive relationships, monolithic competitors, and winning at the top​ 18:00 – Larger buying committees and the rise of the “snipers” who can say no​ 20:00 – Wall Street’s AI fears and which software categories are most exposed​ 22:30 – AI, phishing, and the new risk profile inside the enterprise​ 26:30 – Giving sellers AI tools without leaking your crown jewels​ 28:10 – AI enablement, prompting as a skill, and adoption of tools like Copilot​ 29:10 – The ideal sales hiring profile today​ 32:00 – Rachel’s early career story and pivot into enterprise sales​ 35:20 – The “golden narrative thread” for changing industries and roles​ 36:30 – Why curiosity and problem‑solving power great sellers​ 39:45 – Mentors, presence, and operational discipline in leadership​ 41:30 – Leading global teams and communicating the “why”​

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211: Rachel Roberts President of Sales, Check Point Software is an episode from Sales Is King by Dan Sixsmith .

This episode is 00:44:27 long.

This episode was published on Mar 23, 2026.

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