Sales Is King

Hosted by Dan Sixsmith

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184

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Oct 2026

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About the show

The podcast, Sales is King, features interviews with sales and marketing leaders who share their insights on the latest trends and challenges in the B2B space. The podcast covers a wide range of topics, including AI, value selling, sales enablement, and personal branding. The guests offer actionable advice on how to succeed in today's competitive market. The podcast is popular with not only C-Level executives, but also thousands of sellers across multiple industries.

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October 26, 202646 min

215: John Belle | CRO, Justworks

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

September 23, 202637 min

214: Jen McDonald | SVP, Americas | Talkdesk

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: 0:00 – Intro & Setting the Scene 0:39 – Jen's Role at Talkdesk & the Agentic AI Shift 1:52 – Rebuilding the Sales Team for the AI Era 4:02 – Career Origins: 13 Years at ADP 7:39 – Balancing Single Motherhood & Sales Career 9:30 – SAP Years & Leading Through COVID 13:32 – Winning Deals: In-Person, Humility & Relevance 15:18 – What Top Sellers Do Differently 17:50 – Coaching Struggling Sellers & MEDDPICC 19:36 – Personal Selling & Customer Retention 21:39 – Improving NRR & Customer Advisory Boards 26:15 – Math vs. Art: The MEDDPICC Debate 27:45 – The Art of Storytelling in Sales 29:09 – Role Models & Risk-Takers 32:37 – Career Turning Points & Getting Tapped on the Shoulder 35:02 – Defining Success: The Three Buckets 36:53 – Closing Thoughts & Culture at Talkdesk

August 10, 202618 min

213: Kevin Bognar | SVP, Stripe

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 Sales Kevin'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 Curiosity – Always-on learners who use technology, listen to Gong calls, and constantly sharpen their craft Cross-functional orchestration – The best AEs are "resource brokers," pulling together CSMs, specialists, professional services, and executives to deliver value Multi-threading with sequence in mind – It's not just who you involve, but in what order . Kevin shares how he sent daily stakeholder updates on his biggest deal, scripting who talks to whom and when Authenticity over improvisation – Thinking on your feet includes being comfortable saying "I don't know, but I'll find out" Motivating a Team of 125 Early-Career Sellers Kevin 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 Leader Kevin 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 Strategy and ICP targeting – Using AI to monitor deal patterns in real time (fastest activation, highest usage, fastest close) and identify emerging verticals like GLP-1 distributors, cannabis, and gaming Lookalike prospecting – The best sellers use AI to find the next customer that looks exactly like their last great win Interview signal – Kevin asks every candidate how they're using AI, both to assess their skills and to learn from them Structure vs. Freedom in Sales Methodology Kevin'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 Stripe Stripe 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 "The how we do what we do as sellers is what really advances your career." "The best sellers are resource brokers. They bring all the best people to the table." "I value authenticity. Thinking on your feet includes being able to say 'I don't know.'" "Football teams don't hit the field with just the first play. They hit the field with the entire drive." 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!

June 29, 202638 min

212: Tamara Adams | CRO, Octave

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 0:00 — Introduction 0:27 — Octave rings the bell on the NASDAQ: a $1.6B carve-out from Hexagon 1:07 — How Tamie was recruited as CRO 3:16 — First moves: assessing systems, personnel, and data 5:06 — State of Customer Success coming in 5:43 — Rebuilding channel sales and alliance partnerships 8:11 — CS as a true profit center: 200% pipeline growth 14:39 — AI for selling: research, prompting, and the risks 17:29 — The art of storytelling in sales 19:17 — How negotiation has changed 25:36 — CRO tenure: why it's 18–22 months and how to break through 27:42 — Top skills required for a successful CRO today 29:17 — Tamie's origin story: race cars, finance, and Oracle 35:10 — The first CRO role: PE-backed, move with speed, exit to Siemens 37:22 — Definition of success: "A little bit of grit and a little bit of grace"

March 23, 202644 min

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”

February 23, 20261 hr 5 min

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.

January 28, 202649 min

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.

December 1, 202550 min

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/ Okta newsroom and updates: https://www.okta.com/newsroom/ Connect with Dan Sixsmith & Sales Is King Dan Sixsmith on LinkedIn: https://www.linkedin.com/in/dansixsmith/

October 6, 202537 min

207: Marilee Bear | CRO, Gainsight

In this episode, host Dan Sixsmith interviews Marilee Bear the CRO at Gainsight. Marilee reflects on her first year at the helm, discussing the company’s impressive growth trajectory, recent strategic acquisitions, and the challenges and opportunities presented by a major leadership transition. Marilee shares actionable strategies for improving net revenue retention, such as leveraging data-driven insights, fostering cross-functional collaboration, and investing in customer education. The conversation also explores the impact of AI on sales processes. Marilee offers candid leadership insights, discussing the importance of transparency, adaptability, and building a culture of continuous learning. She also recounts her career journey, from her early ambitions and formative experiences to the pivotal moments that led her to lead a major SaaS company, offering advice for aspiring leaders in the tech industry. Timestamps: Welcome and Introductions (00:00:01) Dan welcomes Marilee Bear who reflects on her first year at Gainsight, company growth, and recent leadership changes. Company Growth, Acquisitions, and Leadership Transition (00:00:30) Marilee discusses acquisitions, repositioning Gainsight for growth, and the CEO transition from Nick Mehta to Chuck Apathy. Team Structure and Business Unit Model (00:02:04) Explanation of new hires, business unit model, and leadership structure within product and customer success teams. Integrating Customer Success into Revenue Organization (00:03:21) Describes shifting customer success under the revenue team and the industry trend of CS as a revenue driver. Defining Roles and Realigning the Revenue Team (00:05:25) Outlines the jobs-to-be-done exercise, clarifying roles across sales, CS, and other go-to-market functions. Customer Success as a Pipeline Engine (00:06:24) Details how CS now contributes to pipeline generation and the metrics used to measure CSM impact. Net Revenue Retention (NRR) Challenges (00:07:29) Discussion of industry-wide NRR declines and the need for strategic retention and value delivery. Retention Strategies and Multi-threading (00:08:21) Emphasizes proactive retention, business value demonstration, and multi-threading within customer organizations. Competitive Landscape and Expansion Focus (00:12:29) Explains how competition now includes internal build vs. buy, and the importance of expansion within existing customers. Convergence of Sales and Customer Success Roles (00:13:53) Observes the merging responsibilities of CS and sales, with CS teams adopting more sales-like approaches. State of B2B Sales and Impact of AI (00:14:25) Explores ongoing challenges in B2B sales, the impact of generative AI, and the need for business acumen. Reaching C-level Executives and Sales Best Practices (00:17:00) Shares the difficulty of accessing executives, the importance of detective work, and value-driven outreach. Effective Sales Outreach to Executives (00:19:12) Marilee describes what makes sales outreach compelling: offering choices, concise meetings, and understanding executive preferences. Marilee’s Career Journey (00:21:31) Covers her early ambitions, work history from restaurants to Oracle, Akamai, Zendesk, and her path to Gainsight. Retention and Customer Success Experience (00:25:54) Highlights her experience with retention at Akamai, building CS teams, and her initial exposure to Gainsight. Key Career Lessons and Leadership Growth (00:28:54) Shares lessons on authenticity, operational rigor, and the importance of direct feedback and self-improvement. Leadership Philosophy and Team Management (00:33:58) Discusses leading diverse teams, empathy, balancing encouragement with accountability, and fostering a feedback culture. Definition of Success (00:36:00) Marilee defines success as delivering the best outcomes for customers, company, and self, in that order. Closing Remarks (00:36:43) Dan thanks Marilee, wraps up the episode, and previews future collaborations.

August 21, 202541 min

206: Sam Jacobs| CEO + Founder of Pavilion

Summary In this episode, Dan Sixsmith interviews Sam Jacobs, CEO and founder of Pavilion, discussing his journey from working as a finance executive to building a thriving community for go-to-market executives. They explore the challenges faced by leaders in today's fast-paced environment, the importance of community, and the evolving landscape of sales and AI. Sam shares insights on the future of Pavilion, the role of media in building connections, and his personal definition of success. Takeaways Pavilion was born out of the need for community among go-to-market executives. Job security for senior leaders is decreasing, leading to increased anxiety. AI is transforming the sales landscape, but the need for community remains. Pavilion aims to equip operators with the tools and resources they need to succeed. The community has grown significantly, especially during the pandemic. Sam emphasizes the importance of having a strong network for job security. The future of sales will see a wider gap between great and average sellers. Pavilion is evolving to create an elite membership tier for experienced operators. Sam's success is defined by personal fulfillment, professional growth, and meaningful relationships. Chapters 00:00 Introduction to Pavilion and Sam Jacobs 03:02 The Journey to Pavilion: Early Ambitions and Experiences 06:13 The Birth of Pavilion: From Idea to Community 09:13 Navigating Challenges: The Role of Community in Uncertain Times 12:03 The Evolution of Pavilion: Growth and Community Dynamics 15:08 Building an Elite Community: Focus and Future Directions 19:56 The Importance of Technical Fluency in Sales 21:38 The Changing Landscape of B2B Sales 24:26 The Rise of New Companies and Sales Opportunities 28:31 Navigating Anxiety in the Business World 34:27 Building a Media Property for Operators 38:28 Defining Success in Business and Life 41:23 Introduction to Sales Dynamics 41:23 Understanding Customer Needs