211: Rachel Roberts | President of Sales, Check Point Software

212: Twelve Steps To Closing The C-Suite(Dan Customer Podcast)

Taking a break from the CRO interviews and going back to the 'roots' of the podcast, Dan is publishing his appearance on a customer podcast to talk about selling higher and closing CXOs! Studio interviews will return in 2 weeks. Audio only.

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”

210: Craig Bowman | SVP, Trellix

In this episode of Sales Is King, Dan sits down in the new Midtown Manhattan studio with Craig Bowman, SVP of Public Sector at Trellix and author of the new book Craft: CIA Elite Selling. Craig brings a wild career arc to the mic—from clandestine work with the CIA and the intelligence community to building high‑performing sales teams at Adobe and now leading public sector growth at scale. Craig unpacks how CIA tradecraft, “mission first” thinking, and AI can radically upgrade how you prospect, qualify, and win in complex B2B deals. Key topics covered * The CIA recruitment story: from a mysterious hotel lobby interview, underground parking garages, and VCR‑filled rooms to landing his first role under commercial cover. * Moving from intelligence to entrepreneurship: starting, scaling, and selling his own government contracting company, then returning post‑9/11 for a new mission. * Jumping into sales at Adobe: how he was recruited, doubled his salary, and built a new intelligence division by deeply understanding the mission—not just the tech. * “In the mud with the customer”: why Craig literally went to the southern border with CBP to understand the mission and coined his mantra about getting in the trenches. * Influence maps vs org charts: why the real power sits with the “knuckle‑draggers” in the back of the room, not just the CIO, and how to find and engage true influencers. * Frameworks without rigidity: his take on MEDDIC, Challenger, and why you coach the bottom half differently while using top performers as mentors to “shift the middle.” * The AI inflection point: how he rewrote his book mid‑stream to integrate AI, and why he now spends 70% of his time using AI agents as a personal chief of staff. * Craig’s live AI workflow: daily scripts that summarize email, corporate updates, and account intel; auto‑generated dossiers, personas, and value hypotheses. * The 90‑Second Takeover: how to send a pre‑meeting hypothesis of value, then open meetings with clarity, validation, and a working session instead of random discovery. * Humility as a superpower: the intern experiment that proved “humility emails” beat cold calls, and why genuine curiosity and asking for help unlock meetings. * AI from the buyer’s side: why your customers are already using AI to shortlist vendors and how you should be using AI the same way to qualify where you can truly win. * Metrics that actually matter: the question Craig asks every customer about how they’ll measure value 7 months after buying—then how he uses that in MEDDIC the right way. * The seven criteria of a successful seller: why he evaluates inputs (character, curiosity, rigor) rather than just outputs (pipeline, quota). * Mentors and pivotal leaders: from his grandfather and tough college professor to powerful women leaders in the intelligence community and sales leaders like Ken Karsten. Who this episode is for * Enterprise and public sector sellers trying to win complex, multi‑stakeholder deals. * Sales leaders looking to blend frameworks like MEDDIC with modern AI and real coaching. * Rev leaders who want their teams “in the mud with the customer” instead of stuck on Zoom. Listen for these takeaways * Why you must deeply understand your customer’s mission—and often physically go to the “border” or “boat”—before pitching technology. * How to build influence maps, not just chase titles on an org chart. * A tested AI + email play that interns used to book meetings your team “could never get.” * A simple question that turns MEDDIC metrics from guesswork into a mutual accountability pact. Connect with Craig * Book: Craft: CIA Elite Selling on Amazon (hardcover, ebook, and audiobook). * Bonus material & AI scripts: unlock the members section using the book, or message Craig on LinkedIn if you bought the audio version. If you’re tired of canned discovery, bad qualification, and random acts of prospecting, this conversation will change how you think about mission, AI, and what “elite selling” really looks like.

209: Andrew Brown | CRO, RedHat

In this episode of Sales Is King, host Dan Sixsmith kicks off the show’s 10th year and the launch of a brand new studio with a powerhouse guest: Andrew Brown, Senior Vice President and Chief Revenue Officer at Red Hat. Andrew shares how Red Hat is driving double‑digit growth with its hybrid platforms, automation, and AI capabilities—while staying anchored in long‑standing values like freedom, courage, commitment, and accountability. He also breaks down how AI is really changing sales, what separates top sellers from the middle of the pack, and why “happy customers” is his simple, non‑negotiable definition of success. * Red Hat’s growth engines in 2025 * Three core platforms: Enterprise Linux, OpenShift (containerization/virtualization), and automation. * Why true hybrid (on‑prem, private cloud, hyperscalers) is resonating with customers globally. * The acquisition of Neural Magic and how Red Hat is playing in AI inference. * Values that customers actually feel * How Red Hat’s long‑standing values—freedom, courage, commitment, accountability—show up through products and people, not posters. * Stories from customer visits (including India) where clients proactively praise the team, not just the tech. * The call to become CRO and first 90 days * How Andrew was tapped from IBM by Rob Thomas to run “anything that touches revenue” at Red Hat. * Why he changed almost nothing at first: two ears, two eyes, one mouth—used in that ratio. * Moving the organization from “growing” to truly unlocking the next growth curve, with alignment on one vision and one belief. * What really separates top sellers from the middle * Active listening as a true differentiator—probing pain, impact, and outcomes versus just hearing words. * Never settling: aiming beyond the renewal, operating on the “front foot,” and treating success and failure the same way. * A sports mindset: being ready for the clutch moments, orchestrating stakeholders, and failing at least 50% of the time but getting back up. * How AI is reshaping sales at Red Hat * Building and buying: Red Hat’s own AI assistant embedded in sellers’ workflow (Slack → CRM opportunity creation) plus tools like People.ai to free managers from data validation and focus them on coaching. * The big challenge: not building AI models, but getting them into production at scale with governance, cost control, and the right deployment (cloud vs. on‑prem). * Why only a small percentage of AI projects show real value today—and what needs to change. * Channel and ecosystem as revenue multipliers * Why a significant share of Red Hat’s revenue runs through partners and how they’re enabled pre‑ and post‑sales. * Technical certifications, revamped partner programs, and advisory boards to keep value and alignment high. * Customer success and value realization * Consolidating scattered customer success pockets into a central, technical CS team that engages the day after the contract is signed. * Focus on hands‑on deployment, embedding Red Hat tech in customer architectures, and rescuing under‑utilized hybrid commitments. * The direct link Andrew sees between CS, value realization, and recurring revenue uplift. * Andrew’s personal journey and leadership lessons * From aspiring soccer player to IBM intern to CRO at Red Hat. * Doing an MBA nights/weekends to bridge technology and business outcomes in C‑level conversations. * Early “bad” first management role and learning from white‑space, door‑to‑door style selling. * Influences from Lou Gerstner and other mentors: keep it simple, communicate clearly, don’t define your life only by work. Andrew Brown is Senior Vice President and Chief Revenue Officer at Red Hat, where he leads all revenue‑touching functions globally across sales, services, and ecosystem partners. Prior to Red Hat, Andrew spent nearly three decades at IBM in a variety of technical, sales, and leadership roles, combining a deep technology background with a strong commercial track record.

208: Jon Addison | CRO, Okta

In this episode of Sales Is King, host Dan Sixsmith sits down with Jon Addison, Chief Revenue Officer at Okta, to unpack how identity is becoming mission-critical in a world of AI agents, distributed work, and rising security expectations. Jon shares how Okta is evolving from product to platform, why identity is central to securing AI, and what it really takes to lead large, global go-to-market organizations today. The conversation ranges from AI ROI and agent security to sales leadership, relationship selling in a post‑pandemic world, and Jon’s unconventional path from door‑to‑door sales and technical roles into the CRO seat. Key Topics * Okta’s mission and why identity sits at the center of security and AI.  * The early, messy phase of AI and agents and why standardization and consolidation are coming.  * How Okta thinks about securing AI agents for 20,000+ customers through policy, platform, and design.  * Moving from “product company” to “platform company” and what that means for GTM, partners, and customers.  * Jon’s view of the CRO role: being a change agent, driving parallel transformations, and balancing data with instinct.  * The “Formula to Win” (Focus, Compete, Lead) and the decision to specialize across Okta and Auth0 buying personas.  * Why enterprise selling is going “back to relationships” in an era of hyper‑informed, AI‑enabled buyers.  * Skill vs. art in sales: practice, rehearsal, and the X‑factor of human connection and courage.  * Methodologies, MEDDIC, and how frameworks and creativity can and should coexist.  * Jon’s career path: door‑to‑door sales, technical consulting, product management, Oracle, LinkedIn, and now Okta.  * How to think about talent, instincts, and building high‑performing, international sales teams.  * Jon’s definition of success: growth, unlocking potential in reps, and meaningful customer outcomes.  Highlights * AI and agent deployments are still in early, fragmented stages, and most enterprises are experimenting without yet seeing consistent ROI—creating a big opening for vendors who can standardize and secure these environments.  * Okta sees AI agents much like cloud apps in the early days: scattered pilots that will eventually need centralized identity, policy, and governance—an area where its platforms are already embedded.  * The CRO role is fundamentally about being an empowered change agent: driving multiple transformation streams at once, building trust across functions, and having the courage to move fast without creating “one‑way doors.”  * Specialization across platforms (Okta vs. Auth0) and buying personas is unlocking deeper expertise, better customer conversations, and sharper competitive positioning.  * Enterprise sellers will increasingly face highly educated buyers who have already self‑researched with AI, which shifts the seller’s value from information transfer to relationship, insight, orchestration, and outcome design.  * World‑class sellers treat sales like a craft: they rehearse, review call recordings, seek coaching, and study both customers and industries the way elite athletes study film.  * Strong sales cultures blend a clear methodology and shared language with individual creativity, ambition, and “brave” outreach that truly differentiates the experience for customers.  Guest Bio – Jon Addison Jon Addison is the Chief Revenue Officer at Okta, where he leads the global field organization and is responsible for driving worldwide growth. He brings over 20 years of sales leadership experience from roles at LinkedIn, Oracle, and other global technology firms, and is focused on building high‑performing teams, scaling platform‑led go‑to‑market motions, and helping customers modernize and secure identity in the age of AI. Connect with Jon and Okta * Jon on Okta’s leadership page: https://www.okta.com/company/leadership/jon-addison/ [https://www.okta.com/company/leadership/jon-addison/]  * Okta newsroom and updates: https://www.okta.com/newsroom/ [https://www.okta.com/newsroom/]  Connect with Dan Sixsmith & Sales Is King * Dan Sixsmith on LinkedIn: https://www.linkedin.com/in/dansixsmith/ [https://www.linkedin.com/in/dansixsmith/]