Presales Podcast by Presales Collective

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