Storytelling as an Industrial Skill with Jon Billett

In this episode, Jack Cochran is joined by Jon Billett, Founder and CEO of StoryQuadrant, to discuss why storytelling in presales needs to be treated as an industrial skill rather than a soft skill. They explore Jon's framework for the four types of stories every SE should master, the danger of "Mad Libs" style customer stories, and why the most important story is the one told after you leave the room. Jon shares insights from his 15 years in presales and his unique background as a member of the Magic Circle, revealing how structure, rather than content, creates memorable presentations that drive deals forward. Follow Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Jon Billett: https://www.linkedin.com/in/jbillett/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack StoryQuadrant: https://storyquadrant.com/ Key Topics Covered Why Storytelling is an Industrial Skill, Not a Soft Skill The Story Quadrant Framework: Four Essential Story Types The Mad Libs Problem in Presales Discovery as Stepping Into Your Prospect's Story The Power of Contrast in Creating Memory What Makes Stories Retellable Timestamps 00:00 Welcome 03:16 Jon's Journey to Storytelling 06:31 Storytelling as an Industrial Skill 09:23 Overcoming the Belief: "I'm Not a Good Storyteller" 12:24 The Success Story Trap 15:59 The Mad Libs Formula Problem 18:13 Discovery Stories: Stepping Into Their World 21:20 Maximizing Your 5% of Face Time 23:10 Your Story: The Four-Minute Trust Window 26:51 Positioning Stories: Nobody Cares About Your Offices 27:40 The Story They Tell 30:30 One Technique to Implement Tomorrow: The Power of Contrast  

In this episode, Jack Cochran and Matthew James are joined by Nikhil Sarma, Founder of GTM Solutions Consulting, to explore why customer indecision has become one of the biggest challenges in enterprise sales. They discuss the factors driving buyer hesitation, how to diagnose value clarity vs. organizational issues, and practical strategies for helping customers build the confidence to move forward. Nikhil shares frameworks for understanding stakeholder dynamics, the importance of financial fluency for SEs, and why de-risking the implementation is often more important than the technology itself. Thank you to Storylane for sponsoring this episode. Get more information at https://www.storylane.io/  Follow Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Nikhil Sarma: https://www.linkedin.com/in/nikhilsarma/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack GTM Solutions Consulting: https://www.gtmsolutions.co/ The Jolt Effect Book: https://www.goodreads.com/book/show/61418641-the-jolt-effect  The Challenger Sale Book: https://www.goodreads.com/book/show/11910902-the-challenger-sale  Gartner Research on Buying Team Conflict Key Topics Covered The Factors Driving Customer Indecision in 2025 Value Clarity vs. Organizational Issues Understanding Stakeholder Levels (Operational, Manager, Executive) Discovery as a Two-Way Learning Process Diagnosing and Building Consensus Across Buying Teams De-risking Implementation as a Differentiator Financial Fluency for Presales Professionals Timestamps 00:00 Welcome 04:45 What's Changed about Customer Buying Behavior 09:50 The Jolt Effect and Challenger Sale Frameworks 13:56 Value Clarity Problems vs. Organizational Issues 20:03 Collaborative Whiteboarding for Discovery 25:17 De-risking Implementation Wins Deals 28:50 How to Connect with Nikhil

The State of Presales and Demo Technologies, and What's Coming in 2026 In this episode, Jack Cochran and Matthew James are joined by Justin McDonald, Co-founder and CEO of Saleo, to discuss how demo automation technology is transforming the presales landscape. They explore the evolution of presales over the past 20 years, the hidden costs of demo preparation (the "demo tax"), and how AI is revolutionizing how solutions engineers create and personalize demonstrations. Justin shares insights on building relational capital, the importance of in-person meetings, and why the future of presales lies in leveraging technology to spend more quality time with buyers. Thank you to Saleo for sponsoring this episode! Visit Saleo.io to learn more. Follow Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Justin McDonald: https://www.linkedin.com/in/justin-mcdonald-21a3aa6/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Saleo: https://saleo.io/ Mockaroo (dummy data generator): https://mockaroo.com/ Timestamps 00:00 Welcome 04:24 How has presales evolved over 20 years 09:20 Demo tax 13:37 The importance of in-person meetings 15:55 Breaking down the demo tax components 24:47 AI and Demo Data Agents 26:42 Trends reshaping presales in 2026 Key Topics Covered The Evolution of Presales Technology From manual data creation with tools like Mockaroo to automated demo environments The rise of presales as a respected profession with executive leadership Shift from multi-week prep and constant travel to efficient Zoom-based demos The Demo Prep Tax Multiple departments impacted: DevOps, product, engineering, and SEs Hard dollar costs: hosting demo tenants can cost millions at scale Demo data degradation: perfectly prepared demos degrade over time SE time is expensive, and hours spent on manual data preparation adds up Building Relational Capital Only 17% of sales time is spent with buyers (even less for presales) In-person interactions unlock opportunities that Zoom calls cannot EQ and relationship-building will separate good from great in the age of AI AI-Powered Demo Automation Demo Data Agent: generates personalized demo data with a single prompt Token-based customization for industry, vertical, and use case adaptation Data injection technology allows real-time demo personalization The Future of Presales AI will expand automation across the entire sales cycle Agentic and asynchronous AI tools will support SEs 24/7 SEs won't be replaced, their time will be used differently The demo data is the story: great storytelling requires great demo data  

In this episode, Jack Cochran and Matthew James are joined by Hannah Bloking, and Allison Macalik, co-founders of 4Under3. They discuss the universal challenge of imposter syndrome in the pre-sales profession, exploring how it manifests, why it affects nearly everyone, and practical strategies to address it. Hannah and Allison share insights from their workshops, including powerful techniques like the "lighthouse speaker" mindset and the importance of naming your imposter to take control of those negative thoughts. Thank you to Storylane for sponsoring this episode. Follow the Hosts and Guests Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Hannah Bloking: https://www.linkedin.com/in/hannahcfrisch/  Connect with Allison Macalik: https://www.linkedin.com/in/allisonmacalik/ Links and Resources Mentioned Storylane: https://storylane.io  Join Presales Collective: https://www.presalescollective.com/community-overview 4Under3: https://4under3.io/ Email: [email protected] Follow 4Under3 on LinkedIn: https://www.linkedin.com/company/4under3/  Timestamps 00:00 Opening 03:36 Why Focus on Impostor Syndrome 11:57 The Definition of Impostor Syndrome 14:45 Redefinining as a Phenomenon 20:15 Soft Skills is Important 24:50 The Lighthouse Speaker Mindset 27:15 Zip it, Todd! Key Topics Covered Understanding Imposter Syndrome The textbook definition: "The persistent inability to believe that one's success is deserved or has been legitimately achieved as a result of one's own efforts or skills" Why it's being reframed as "imposter phenomenon" rather than syndrome How it manifests differently for everyone The discovery that it affects people of all genders, levels, and backgrounds The Presales Connection Why imposter syndrome is particularly prevalent in pre-sales roles The challenge of being asked to be an expert when you're still learning Why internal demos to your own team are the hardest presentations to give The adrenaline rush of presenting and how it relates to imposter feelings Breaking the Silence Why people suffer in silence with imposter syndrome The power of creating space for vulnerability before major initiatives How company culture needs to embrace these conversations The importance of repeat workshops and ongoing dialogue Practical Techniques The Lighthouse Speaker vs. Spotlight Speaker: Thinking of yourself as lighting the way for others rather than being under scrutiny Naming Your Imposter: Giving your negative self-talk a name (like "Todd") to externalize and control it Reframing: Documenting what happens to realize most failures aren't actually about you Finding Your Person: Identifying someone who can hold you accountable when your imposter is talking The Workshop Impact Why companies become repeat customers How addressing imposter syndrome improves productivity and retention The connection between soft skills training and embracing new frameworks Creating internal communities (like AWS's "The Nest") for ongoing support Looking Forward The personal nature of addressing imposter syndrome The importance of daily practice and repetition How workshops facilitate conversations but individuals must do the work The evolving nature of imposter syndrome as AI and change management accelerate

Episode 181: Charting Your Presales Career Path with Miriam Graf In this episode, Jack Cochran and Matthew James welcome Miriam Graf, a presales veteran with 20 years as an individual contributor and 10 years in leadership roles. Miriam shares invaluable insights on navigating career growth in presales, from speaking up about your aspirations to recognizing when leadership is and isn't the right path for you. She discusses the evolution from being "the hero" to becoming a leader who helps others shine, and explores the diverse career opportunities available beyond traditional management roles. This episode is sponsored by Elvance. Find out more about them at https://elvance.io/  Follow Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Miriam Graf: https://www.linkedin.com/in/miriamgraf/ or email [email protected] Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Presales Podcast: https://www.presalescollective.com/podcast Timestamps 00:00 Welcome 06:53 Lessons to learn earlier 10:38 IC vs leadership 16:42 Expensive experience lessons 22:46 Variety of expertise is good 28:27 Focus on your industry and keep learning Key Topics Covered Speaking Up About Your Career Why waiting for someone to notice doesn't work How expressing interest puts you on the radar for future opportunities The importance of taking initiative on projects you're passionate about The Transition from Hero to Leader Why being the top SE doesn't automatically translate to leadership The emotional shift from personal accolades to team success Understanding if management is actually the right path for you Alternative Career Paths Beyond Management National expert or technical specialist roles Product management and product marketing opportunities Customer success, implementation, and demo engineering How presales skills translate across multiple disciplines Essential Skills for Career Advancement Soft skills: passion, communication, empathy, and listening Business acumen: understanding the "so what?" for your audience Technical skills: continuous learning and adaptability Learning Through Experience The value of trying roles outside presales How diverse experience makes you a better SE Why failures and tough feedback lead to growth Industry Expertise How to quickly learn an industry's key challenges The value of becoming a vertical expert Building credibility without years of industry experience

In this episode, Jack Cochran and Matthew James are joined by Rob Bruce, a presales leader at Syndigo with 20 years of experience, to discuss an innovative approach to presales operations: the Pursuit Desk. Rob shares how Syndigo has built a dedicated "concierge team" that handles RFPs, security questionnaires, reference coordination, and other time-consuming tasks, freeing solutions engineers to focus on discovery, solutioning, and building customer relationships. The conversation explores how to operate at the "top of your license," the role of AI in scaling pursuit operations, and practical advice for championing similar initiatives at your organization. Thank you to Elvance for sponsoring this episode: https://elvance.io Follow Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Rob Bruce: https://www.linkedin.com/in/robbruce/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Book: "Selling is Hard, Buying is Harder" by Garen Hess Timestamps 00:00 Welcome 04:29 What is a Presales Concierge 11:18 Presales culture 14:00 Working at the top of your diploma 17:10 How do you justify this 21:38 As focused as an F1 team 23:32 AI and the Pursuit Desk Key Topics Covered The Pursuit Desk Concept Functions as a presales concierge handling non-customer-facing tasks Manages RFPs, InfoSec documents, NDAs, reference coordination Creates centralized control over messaging and responses Operates on a global scale with cultural sensitivity Operating at the Top of Your License Focus on discovery, creative thinking, empathetic listening, and presenting solutions Eliminate time spent on administrative tasks that don't require SE expertise Reduce context switching and multitasking to maintain flow Maximize value delivery to customers and the organization Building the Business Case Find an executive sponsor to champion the initiative Measure impact through deal win rates and velocity Consider creative budget reallocation (travel budgets, etc.) Calculate ROI based on SE productivity and reduced burnout The Role of AI in Pursuit Operations AI handles first-pass RFP responses (80% completion) Pursuit desk personalizes and adds empathy (final 20%) Machine learning analyzes past deals for pattern recognition Go/no-go scorecards based on historical data Enables scaling without proportional headcount increases Presales Culture and Values Building trust through technical expertise and genuine personality Being a "chameleon" who adapts to different buyer needs Creating an environment where people feel welcomed and valued Mentorship and knowledge sharing across teams Preventing Burnout Eliminating nights and weekends spent on RFPs Reducing stress through better task distribution Enabling SEs to focus on work they're passionate about Creating sustainable workloads that retain top talent Measuring Success Tracking time spent on each RFP or pursuit activity Correlating effort to win-loss rates Building audit trails for continuous improvement Creating dashboards for data-driven decision making  

In this episode, Jack Cochran and Matthew James are joined by Art Fromm, author of "Making Seamless Sales" and sales enablement expert, to discuss how presales and sales teams can work together more effectively. Art shares insights from his 25+ years in sales enablement, exploring the common disconnects between SEs and AEs, and provides practical strategies for building stronger partnerships that drive better outcomes. The conversation covers the evolution from tribal knowledge to systematic collaboration, the importance of discovery before demos, and how to create value perception rather than just showing features. Art emphasizes that when teams work together properly versus teams that don't, there's a 37% difference in sales outcomes - a substantial opportunity sitting on the table. Connect with Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Art Fromm: https://www.linkedin.com/in/artfromm/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Art's Website: https://teamsalesdevelopment.com Team Sales Development: https://www.teamsalesdevelopment.com "Making Seamless Sales" by Art Fromm: https://teamsalesdevelopment.com/making-seamless-sales-book/ Timestamps 00:00 Welcome 03:55 Sol/Con East 2025 05:26 Making SEAMless Sales 11:27 Our Solutions Have No Value 24:02 You Only Get One Shot 29:42 Aren't We All Presales Key Topics Covered The SEAM Framework SE (Solutions Engineers) and AM (Account Managers) working together Breaking down organizational silos between presales and sales Creating systematic approaches rather than leaving collaboration to chance Moving Beyond the Demo Rush Why "we need to do a demo" often leads to failure The importance of proper qualification and discovery first How luck can reinforce bad habits in sales processes Creating Value Perception Understanding that solutions have no inherent value The Venn diagram of customer needs overlapping with solutions Turning "sell" into "buy" and "push" into "pull" The Trust Dynamic Presales comes with trust that can be lost Sales lacks trust that needs to be gained How proper discovery helps both teams build credibility Organizational Alignment Top-down (business focused) vs bottom-up (technical focused) approach Creating healthy overlap between sales and presales responsibilities The pyramid model of customer engagement levels Training and Enablement Moving beyond feature-function training to client success thinking Understanding the complete buyer journey from hello to consumption The concept of "solution enablement" as a continuous process

In this episode, Jack Cochran and Matthew James are joined by Wendy McHenry, Chair of WISE (Women in Solutions Excellence) at Presales Collective and Former Head of Global Solutions Engineering at CDATA, to discuss the critical need for supporting women in presales careers. They explore the challenges women face in a field where only 18% of solutions professionals are women, discuss unconscious bias in hiring and workplace environments, and highlight how WISE is creating support networks and career development opportunities to advance equity in the solutions field. To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. This episode is sponsored by Elvance. More information at https://elvance.io/  On the Show Today Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Wendy McHenry: https://www.linkedin.com/in/wendymac98/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack WISE Chapter Information: https://www.presalescollective.com/wise  Presales Collective LinkedIn: https://www.linkedin.com/company/presalescollective  Timestamps 00:00 Welcome 04:51 Why WISE? 09:12 Being a woman in sales today 12:57 You're not technical enough 16:16 Women leaving the profession 20:33 How is WISE helping? 27:55 What's happening next? Key Topics Covered The Current State of Women in Presales Only 18% of solutions professionals globally are women Many women are the only woman on their SE team Higher attrition rates during layoffs disproportionately impact women Unconscious Bias and Workplace Challenges "Not technical enough" bias applied differently to women Interview panels dominated by men Social environments that may exclude women The importance of calling out bias when witnessed WISE Mission and Structure Started as an ERG at Salesforce, now part of Presales Collective Open to anyone who cares about supporting women in solutions careers Regional chapters like Women in Solutions Consulting Australia/New Zealand Company-specific chapters at organizations like Salesforce and Pegasystems Creating Change and Allyship How to be an effective ally in supporting women's careers Starting WISE chapters at your company (or expanding to broader sales/tech groups) The importance of diverse account teams and client representation Free career coaching and mentorship available through WISE council

In this episode, Jack Cochran and Matthew James are joined by Akash Ganapathi, CEO of Opine, to discuss how AI strategies differ between startups and enterprises in the presales space. They explore the myth of AI replacing SEs, the importance of specialization vs. generalization, and how AI can help presales teams manage more revenue per team member while focusing on strategic, relationship-building activities. Follow Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Akash Ganapathi: https://www.linkedin.com/in/akash-ganapathi/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Opine: https://tryopine.com/ Contact Akash directly: [email protected] Timestamps 00:00 Welcome 04:35 Why AI strategy differs for startups vs enterprises 09:27 Debunking the myth of AI replacing SEs 18:35 The human element in buying and selling 24:35 How enterprises can leverage existing knowledge bases 28:12 The paradox of considering AI for every task 32:14 Future predictions for 2026-2027 Key Topics Covered Startup vs Enterprise AI Strategy Startups benefit from generalist approaches and bottom-up experimentation Enterprises need specialized, top-down AI strategies to avoid redundancy The role of specialization vs wearing multiple hats The AI Replacement Myth Why the "AI SE" that replaces human SEs doesn't work SEs do much more than just answer technical questions The importance of relationship building and strategic thinking Current AI Limitations Context window constraints (around 1 million tokens currently) Retrieval Augmented Generation (RAG) accuracy at ~75% Why breakthrough improvements are needed for true automation The Future of Presales with AI More revenue managed per team member Shift toward hiring less experienced SEs with AI enablement Focus on strategic consulting rather than administrative tasks Practical AI Implementation Draft-and-approve workflows for deliverables Automating account research, meeting prep, and RFP responses Using AI for onboarding and knowledge enablement Mid-Market Recommendations Lean toward enterprise-style, forward-looking strategies Enable not just current team but future hires Focus on cross-organizational enablement (AEs, product, marketing)  

In this episode, Jack Cochran and Matthew James are joined by Ben Hills, Founder and CEO of Iris, to discuss how to scale presales teams effectively while avoiding burnout. They explore the difference between healthy high performance and unsustainable overwork, the role of AI in streamlining repetitive tasks like RFPs, and practical strategies for building scalable processes that enhance rather than replace human expertise. To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT. Follow the Hosts Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Ben Hills: https://www.linkedin.com/in/benjaminhills/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Iris: https://heyiris.ai/ Timestamps 00:00 Welcome 04:04 Iris 05:14 Ben's background 14:29 Healthy high performance vs burnout 21:55 Common scaling mistakes and the headcount trap 29:14 Effective AI tools for presales teams 35:04 The future of AI-to-AI RFP processes 37:46 Final advice on embracing AI Key Topics Covered Understanding Burnout vs. High Performance Why burnout isn't just about hours worked The importance of connecting work to larger purpose and outcomes Creating time-bound periods of intense work with clear endpoints Scaling Without Adding Headcount The "mythical man month" problem in presales Building playbooks and processes before hiring Separating "in the business" vs "on the business" work The Rocks, Pebbles, Sand Framework Planning for big quarterly tasks (rocks) Managing predictable weekly activities (pebbles) Handling unexpected fire drills (sand) AI Tools That Actually Work RFP automation and response generation Call transcript analysis for product feedback Demo automation with synthetic data Why AI SDRs haven't lived up to the hype The Future of RFPs and AI Model Control Protocol (MCP) for AI-to-AI communication Maintaining personalization in automated processes The buyer's perspective on RFP proliferation