Sales Is King 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”