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In this episode of Sales Is King, Dan Sixsmith sits down in San Francisco with Jack Caragol, a senior sales and GTM executive leader to explore the habits and leadership principles behind a career spanning Oracle, Symantec, Salesforce, ServiceNow, and Anaplan.
Jack shares how learning his customers’ business accelerated his early career, the lessons behind scaling a global business at ServiceNow, and his framework for balancing sales management, business growth, and people leadership.
They also discuss how AI is changing enterprise selling—from research and account planning to pricing and stakeholder engagement—and why business outcomes, customer trust, and critical thinking remain essential.
Timestamps
Dan Sixsmith sits down with John Belle, CRO of Justworks, to trace the unconventional path from accidental salesperson to Chief Revenue Officer. John shares hard-won lessons on leadership, hiring, and building a go-to-market engine — from his early days selling textiles to leading revenue at one of the fastest-growing HR tech platforms in the country. They dig into John's leadership manifesto, why CROs flame out, the student-teacher paradigm of value selling, and what AI can never replace in sales.
John Belle is the Chief Revenue Officer at Justworks, a platform that helps small businesses manage payroll, HR, and benefits. His career spans Symantec, CA Technologies, and PayPal, giving him rare breadth across enterprise, mid-market, and SMB sales. John is known for his "Who I Want Us to Be" leadership manifesto and his philosophy of professional impatience: moving fast with alignment, not recklessness.
The accidental salesperson: John chose sales because it paid more than finance ($32K vs. $28K) and kept him close to home. His first "sale" was actually a non-sale — a prospect who was interested but couldn't say yes. The lesson: don't accept no from someone who can't say yes.
Inside sales was harder than field sales: Moving to inside sales at Symantec was a lifestyle choice, not a skill-set downgrade. Selling over the phone required sharper listening and faster thinking.
Build a diverse resume on purpose: John intentionally worked across enterprise, mid-market, and SMB at different companies so his experience would transfer to any industry.
The CRO role is cross-functional: At Justworks, the biggest surprise was how much of the job involves product, marketing, underwriting, and customer success
Leadership is not being the top performer: John's first management role included bad hires and hard lessons. Trusting the team and learning to manage people is fundamentally different from being a great individual contributor.
The Wall Street Journal test: Would you be comfortable if your decisions appeared on the front page tomorrow? That's the integrity standard John sets for his team.
Go slow to go fast: As a change agent, diagnose the system before replacing people. Be a diagnostician, not a wrecker.
AI is not curious: The human edge in sales: curiosity, empathy, relationship-building is exactly what AI can't replicate.
The student-teacher paradigm: In value selling, the seller is the student and the buyer is the teacher. Your job is to understand the buyer's problem, not to teach them about your product.
Why CROs flame out: Expectations without agreement. When the board expects growth but hasn't aligned on strategy, or when a rigid playbook is force-fitted to the wrong stage, the CRO is set up to fail.
Definition of success: Seeing former team members go on to do great things. Building people, not just building numbers.
Quotes:
"Don't accept no from someone who can't say yes."
"Go slow to go fast. Diagnose before you change. Be a diagnostician, not a wrecker."
"AI is not curious. That's the opportunity."
"The seller is the student. The buyer is the teacher."
"CROs flame out because of expectations without agreement."
"Success is seeing your former team members go on to do great things."
Timestamps
0:00 — Cold Open:
The Student-Teacher Paradigm 1:02
Welcome & Introduction 1:49
Early Days: Getting Into Sales 3:26
First Sale & Sales Training 6:02
Early Sales Lessons & Mentors 7:23
Inside Sales at Symantec 9:05
Building a Career Path to CRO 12:12
Joining Justworks 13:37
Biggest Surprises at Justworks 16:45
First Leadership Role19:14
The Leadership Manifesto 22:35
Key Tenets: Leading with Integrity24:18
The Change Agent Question 27:50
Best Sellers at Justworks 30:30
AI and Curiosity in Sales 32:20
Value Selling: The Student-Teacher Paradigm 34:48
Rapid Fire: Professional Impatience 38:23
Lessons, Mentors & Scott Galloway 43:22
Why CROs Flame Out 46:04
Definition of Success 47:22
Wrap Up
Dan takes Sales Is King on the road to Del Mar Beach in San Diego for a conversation with Jen MacDonald, SVP of Americas at Talkdesk. Jen shares how she rebuilt Talkdesk's sales org for the shift to agentic AI, replacing 90% of leadership and 60% of AEs in 18 months and grew revenue anyway. They dig into hiring for AI-era selling, coaching with MEDDPICC, in-person prospecting tactics that are outperforming digital outreach, storytelling as a sales skill, balancing single motherhood with a demanding career, and her definition of success.
Timestamps:
Episode Summary
Dan sits down with Kevin Bogner along the Chicago River for a candid conversation about his 30+ year sales career: from 18 years at Microsoft to Philips, a CRO stint at a Vista Equity portfolio company, leading global sales at Outreach, and now building the SMB and commercial sales organization at Stripe.
Key Topics & Takeaways
The "How" vs. The "What" in SalesKevin's longtime mentor Geoff Nyheim (now a sales professor at DePaul) instilled a foundational principle: the what you do is table stakes. It's the how you do it that differentiates you and advances your career.
What the Best Sellers Do Differently
Motivating a Team of 125 Early-Career SellersKevin created a program called "Time to Shine": a weekly one-on-one walk to a shoe shine station near the Chicago Merchandise Mart with a top performer nominated by managers. He records a short best-practice interview, shares it on Slack every Friday, and fosters healthy competition. Simple, creative, and effective.
The Challenge of Staying Present as a LeaderKevin is candid about his personal challenge: carrying energy from one back-to-back meeting into the next. He's actively working on showing up fully in every conversation, whether it's a FY27 strategy discussion, a deal close, or a career conversation.
AI in Sales – Where It's Making the Biggest Impact
Structure vs. Freedom in Sales MethodologyKevin's take: structure matters, especially early in a career. But AI tools like Gong and Outreach are surfacing MEDDIC elements naturally from calls and emails, freeing sellers from checklist-style questioning and enabling more human conversations.
Value Selling at StripeStripe has a proprietary methodology called The Stripe Way, rooted in value selling. It includes AI-powered tooling that scores calls, emails, and decks against value-selling criteria, generating deal health scores and seller performance dashboards.
Notable Quotes
Note from the Host: This was Sales is King's first on-the-go recording. The iPhone ran out of storage and cut the interview short. Dan plans to reconnect with Kevin for a follow-up episode!
Tamara(Tamie) Adams, Chief Revenue Officer of Octave, joins host Dan Sixsmith in the New York studio during one of the most pivotal weeks of her career ,the day before Octave rings the bell on the NASDAQ. Tamie shares how she was recruited into a $1.6B carve-out from Swedish parent company Hexagon, and walks through the transformation she's driven across sales, customer success, enablement, and channel in her first nine months. The conversation covers her philosophy on CS as a driving force in revenue output, the evolving role of AI in enterprise selling, why negotiation has fundamentally changed, and what it really takes to be a successful CRO today. Tamie also reflects on her career journey from finance to Oracle to a PE-backed exit to Siemens and leaves listeners with her personal definition of success.
Timestamps
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.
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”
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
Who this episode is for
Listen for these takeaways
Connect with Craig
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.
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.
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
Highlights
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
Connect with Dan Sixsmith & Sales Is King
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