Presales Podcast by Presales Collective

The Future of AI in Presales: Beyond Demo Automation In this episode, Jack Cochran is joined by Nalin Senthamil, Founder and CEO of Storylane, to discuss the evolution of AI in presales beyond simple demo automation. They explore the hidden costs of demos, how the buyer themselves are becoming AI-powered, and the emergence of AI tools for sellers, much like Storylane has developed with RepEx Thank you to Storylane for sponsoring this episode! Visit Storylane.io to learn more. Follow Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Nalin Senthamil: https://www.linkedin.com/in/nalinpradeep/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack RepEx (AI buyer engagement platform): Available at https://www.storylane.io/ Key Topics Covered Nalin's Journey from Amazon AI Engineer to Demo Automation Founder The Hidden Cost Per Demo AI at the Infrastructure Level RepEx: The Next Generation of Buyer Engagement The Context Handoff Problem Presales as Strategic Advisors in 2026 Timestamps 00:00 Welcome 03:15 Nalin's Background: From Amazon AI Engineer to Storylane Founder  05:54 The Cost Per Demo Problem and Demo Automation Impact  13:24 What are we leaving behind with AI, and what remains human?  20:00 RepEx Launch: Beyond Traditional Chatbots  26:25 The Importance of Context in the Buyer Journey  28:54 How Presales Teams Can Prepare for AI Integration  30:15 Final Advice: Building Long-Term AI Capabilities in Presales

In this episode recorded at the Presales Collective Leadership Next Summit in November of 2025, Jack Cochran sits down with Gretchen Fitzgibbons, Senior Manager of Strategic Solutions Consulting at Airtable, to discuss what it means to be a courageous leader in presales. They explore how to make difficult decisions under pressure, navigate organizational politics with integrity, and build the support systems that enable consistent leadership. Gretchen shares powerful stories from her two decades of experience advising Fortune 500 customers and leading presales teams, including standing up for a team member being unfairly assessed and creating win-win solutions in challenging situations. Follow Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Gretchen Fitzgibbons: https://www.linkedin.com/in/gretchenfitzgibbons/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Sol/Con 2026: https://www.presalescollective.com/solcon-2026  Book mentioned: Think Again by Adam Grant: https://adamgrant.net/book/think-again/  Book mentioned: Thinking, Fast and Slow by Daniel Kahneman: https://www.goodreads.com/book/show/11468377-thinking-fast-and-slow  Key Topics Covered Redefining Courage and Leadership Making Tough Calls: Standing Up for Team Members Focusing on Your Team rather than on Yourself How to Prepare for a Leadership Role It's OK to be Wrong Developing Your Leadership Skills Grounding Principles for Leadership Timestamps 00:00 Welcome and Introduction 02:14 Defining Courage and Leadership in Presales 05:15 Making Tough Calls: A Story of Standing Up for What's Right 11:20 Focusing on Your Team rather than on Yourself 22:07 How to Prepare for a Leadership Role 27:40 It's OK to be Wrong 30:30 Developing Leadership Skills 37:42 Final Takeaways and Grounding Principles

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: info@4under3.io 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 migraf3@gmail.com 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: akash@tryopine.com 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  

In this episode, Jack Cochran and Matthew James are joined by Ben Pearce, founder of Elevated You, to discuss how technical professionals can effectively communicate with senior executives. They explore the critical differences between speaking to technical stakeholders versus C-suite leaders, covering everything from preparation strategies to delivery techniques. Ben shares practical frameworks for being relevant rather than just expert, emphasizing the importance of focusing on "what" and "why" instead of "how" when presenting to senior leaders. Thank you to Storylane for sponsoring this episode. Find out more about Storylane and how to build killer demos in 2 minutes at https://storylane.io 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 Pearce:https://www.linkedin.com/in/benpthoughts/ Links and Resources Mentioned Presales Collective Slack: https://www.presalescollective.com/slack Elevated You: https://www.elevatedyou.live/psc Tech World Human Skills Podcast: https://www.elevatedyou.live/twhs  Timestamps 00:00 Welcome 05:18 Why speaking to senior leaders is different 12:49 Being relevant vs. being an expert 16:19 Mastering delivery under pressure 25:04 Reading the room and course-correcting 32:53 De-risking and the human element Key Topics Covered The Technical Expert's Dilemma How technical expertise can become a curse when speaking to executives Moving from demonstrating knowledge to demonstrating relevance The Three-Part Framework for Executive Communication Relevance: Understanding what matters to your specific audience Compelling Content: Creating materials that speak to their priorities Excellent Delivery: Performing under pressure with confidence Preparation Strategies Mapping out personas and industries for reusable content The importance of team collaboration in content creation Practice vs. preparation: Why both are essential Reading the Room Starting with curiosity and mini-discovery Mirroring language and adapting on the fly Course-correcting based on real-time feedback The Punchline Problem Why building up to a big reveal doesn't work with executives Leading with impact: "Hitting them between the eyes" Getting to value within the first 90 seconds Risk Management and Trust Building Understanding that you represent organizational risk The "never get fired for buying IBM" mentality How human skills differentiate in an AI-driven world Building confidence through listening and problem-solving  

In this episode, Matthew James and Timmy Hendrickson are joined by Nalin Senthamil, Founder and CEO of Storylane, to discuss the future of pre-sales and AI driving influence beyond pipeline. They explore how demo automation is transforming the self-serve buyer experience, the changing role of solutions engineers, and how AI can create 10X impact in pre-sales workflows. Nalin shares insights on leveraging AI for demo personalization, managing complex product integrations, and why the traditional discovery call may be dying. 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 Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Timmy Hendrickson: https://www.linkedin.com/in/timmyhendrickson/ Connect with Nalin Senthamil: https://www.linkedin.com/in/nalinpradeep/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Storylane: https://www.storylane.io/ Timestamps 00:04 Welcome 01:08 Nalin's background and founding Storylane 03:08 What does a self-serve buyer experience look like? 08:18 How AI has changed presales 13:40 Training AI agents to answer technical questions 17:02 AI testing customer scenario 19:28 Overlooked use cases for demo automation 26:30 One workflow where AI can create 10X impact today Key Topics Covered The Death of Discovery Calls Why buyers are coming to conversations already educated How self-serve experiences span the entire buying journey The role of AI sales agents in initial discovery The Four Categories of SE Work Relationship building and strategic solutioning Demo delivery and POC management Administrative tasks and CRM updates Knowledge sharing and product insights AI as an SE Sidekick Demo preparation and tailoring automation Administrative task reduction Strategic thinking enhancement rather than replacement Demo Automation Use Cases Supporting different AE to SE ratios Managing complex product integrations Upsell and expansion opportunities Micro-demos for specific features Training AI for Technical Questions Leveraging tribal knowledge from Slack, Google Drive, and call recordings Importance of data quality and curation Automatic ingestion of organizational knowledge The Future of Pre-Sales AI enabling faster iteration and personalization Strategic partnership between CS and pre-sales for upsells The evolution from technical support to strategic advisory roles  

In this second part of our conversation with Raphael Joseph, former SE turned recruiter and founder of Brando Tech, Jack Cochran and Matthew James dive deep into why traditional job hunting methods no longer work in today's market. Raphael shares strategic insights on how SEs should approach job searching in 2025, treating themselves as products and leveraging their natural skills to navigate the competitive landscape. IMPORTANT: This is Part 2 of a two-part series. Make sure to listen to Part 1 first for the complete discussion on personal branding and LinkedIn optimization. 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 Raphael Joseph: https://www.linkedin.com/in/raphael-joseph-23044150/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Episode Sponsor: Opine - https://tryopine.com Timestamps 00:00 Welcome 04:42 What is "classic job hunting" and why it's dead 11:52 How to get on recruiters' radar 13:33 Starting your job search the right way 21:04 Treating job hunting like account management 27:23 Interview process changes and AI requirements 30:30 Why it's not a numbers game anymore Key Topics Covered The Death of Classic Job Hunting Why sending CVs to job postings no longer works How companies receive hundreds of applications they can't process The cycle of posting jobs, failing to hire, then using recruiters Why your application often goes unread The New Digital Job Hunting Approach Treating yourself as a product you're selling Building warm leads with hiring managers Using SE skills for job hunting: research, discovery, and value proposition The importance of targeted, high-touch approaches over spray-and-pray Working with Recruiters Effectively Why good recruiters provide 1-in-3 odds vs 1-in-300 direct applications How recruiters can prep you with insider knowledge The value of having internal champions in the hiring process Market Dynamics in 2025 Why it's now an employer's market The shift from growth-at-all-costs to profitability focus How COVID overhiring led to current oversupply of candidates AI's impact on hiring decisions and productivity expectations Interview Strategy in the Current Market Companies' increased specificity in requirements Why "must-haves" are truly must-haves now The importance of AI literacy and demonstrable skills How to address gaps in your experience strategically Leveraging SE Skills for Job Hunting Using research abilities to identify opportunities Applying discovery skills to understand company needs Creating value propositions for yourself as a candidate Avoiding the same mistakes SEs coach AEs to avoid  

In this episode, Jack Cochran and Matthew James are joined by Raphael Joseph to discuss the critical importance of building a strong LinkedIn profile for PreSales professionals. They explore how the platform has evolved as a powerful career tool, especially in today's competitive job market. Raphael shares practical tips on crafting a professional presence that highlights your unique value proposition, explains the impact of consistent engagement, and offers advice on creating authentic content that resonates with hiring managers. 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 Raphael Joseph: https://www.linkedin.com/in/raphael-joseph-23044150/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Sponsor: Opine - https://tryopine.com Timestamps 00:00 Welcome and introduction to LinkedIn's evolution 01:50 Sponsor: Opine 03:06 Raphael's background and career journey 10:46 Why you should build your LinkedIn profile before you need it 21:11 Focusing on your ideal customer profile (ICP) 25:21 Engagement strategies: connecting, commenting, and posting 33:49 Overcoming nervousness about posting Key Topics Covered LinkedIn Profile Optimization Using your banner as prime real estate to showcase your unique value Crafting a clear headline that highlights your specialization Writing descriptions that focus on the value you provide The importance of professional photos and consistent branding Strategic Profile Positioning Reverse-engineering your profile based on your target roles Focusing on 3-4 key specializations rather than listing everything Using industry-standard job titles even if your company uses different terminology Making it easy for recruiters to find you through targeted keywords Building Meaningful Connections Connecting with 100-200 potential hiring managers weekly Engaging with their content through thoughtful comments and questions Creating a network before you need it for job searching Leveraging connections for opportunities when transitions occur Content Creation Strategy Starting with comments before moving to creating original posts Sharing authentic experiences from customer interactions Finding your niche audience within the PreSales community Focusing on consistency rather than viral metrics The Changing Job Market How market conditions have shifted from candidate-focused to employer-focused Why specificity now trumps broadness in skills presentation Standing out in a competitive environment through specialization Using LinkedIn as your primary job search tool rather than traditional resumes  

In this episode, Jack Cochran and Matthew James are joined by Karthik Krishna, Manager of Solutions Engineering at Freshworks and Presales Collective's Regional Community Leader for Chennai. They explore how Solutions Engineers can gain strategic influence in deal cycles beyond just giving demos and answering technical questions. Episode Highlights Karthik shares his journey from developer to pre-sales professional The evolution from "demo-giver" to strategic partner in deal cycles How SEs can co-own opportunities with Account Executives Navigating tough conversations when deals aren't a good technical fit Building credibility to increase your strategic influence Leveraging customer success and implementation teams for deal strategy About Our Guest Karthik Krishna is a Manager of Solutions Engineering at Freshworks, where he has built and coached distributed teams of SEs across companies of all sizes. He also serves as the Presales Collective Regional Community Leader for Chennai, recently hosting an event with over 60 SEs in attendance. Follow the Hosts and Guest Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Karthik Krishna: https://www.linkedin.com/in/karthikkrishna-s/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Presales Collective: https://www.presalescollective.com Timestamps 00:00 - Welcome and introduction 02:46 - Karthik's background and journey to presales 05:28 - What it means to "be in the room" for deal strategy 11:27 - Handling deals that aren't a good technical fit 16:30 - Building AE-SE relationships and trust 20:02 - Leveraging past customer experiences 27:14 - Growing strategic influence as an SE 32:30 - First experience in pipeline meetings and QBRs Key Topics Covered The Evolution of the SE Role From technical demonstrator to strategic partner Building relationships alongside technical expertise Flying "under the radar" while still influencing deals Co-Ownership vs. Support Understanding sales' responsibilities and pressures Taking appropriate accountability for deal outcomes Building a partnership model with Account Executives Strategic Influence Tactics Speaking up consistently, even when not initially heard Framing technical concerns alongside potential solutions Leveraging past experiences and customer success stories Cross-Functional Collaboration Involving product, implementation, and customer success teams Using collective wisdom to validate concerns Creating a "common voice" across departments Building Credibility Trust your instincts and speak up Demonstrate value through accurate deal insights Help teammates at critical junctures Bottom Line Solutions Engineers possess unique insights that can make or break deals, but gaining the opportunity to share those insights strategically requires building credibility, relationships, and influence over time. The most successful SEs find ways to contribute to deal strategy while respecting the unique pressures faced by their sales counterparts. Presales LIVE airs every other Tuesday. Join the Presales Collective Slack community to stay updated on future episodes, and follow the PSC LinkedIn page for upcoming shows.  

Today's episode was recorded during Presales Collective's AI-Powered Presales Summit on March 26th, 2025. In this episode, Jack Cochran (General Manager, Presales Collective) and co-host Matthew James discuss the ethics and trust issues surrounding AI in sales environments with guest Diana Capello, Director of Solutions Consulting for US and Demo Engineering at Eightfold. The discussion explores how AI is transforming the presales landscape, from creating demo environments to navigating AI buying committees and addressing hiring practices in tech. Diana shares insights from her 20-year journey in AI, offering valuable perspectives on maintaining customer trust while leveraging AI tools. 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. 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 Diana Capello: https://www.linkedin.com/in/dianacappello/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Presales Collective newsletter: https://www.presalescollective.com/newsletter Book Recommendation, "AI Superpowers" by Kai-Fu Lee: https://www.goodreads.com/book/show/38242135-ai-superpowers  Presales Collective's YouTube channel: https://www.youtube.com/c/PreSalesCollective Presales AI Summit recordings, available on the PSC YouTube channel: https://www.youtube.com/@presalescollective7795  Timestamps 00:00 - Introduction 01:27 - Welcome Diana Cappello 04:10 - Maintaining customer trust while using AI 06:50 - Explaining how AI works to customers 11:45 - Navigating AI councils in enterprise sales 20:34 - AI in hiring processes 27:43 - Book recommendation 31:10 - Q&A  

In this episode, Jack Cochran (General Manager, Presales Collective) and guest co-host Allison Macalik dive into the topic of "Presales People in Disguise" with Alex Nation. They explore the journey into presales roles, the importance of effective discovery techniques, the power of silence in customer interactions, and the unique relationship between presales professionals and sales teams. Alex shares valuable insights from her career transition from retail to tech, highlighting key skills that have made her successful in the presales world. 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. Find us: Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Allison Macalik: https://www.linkedin.com/in/allisonmacalik/ Connect with Alex Nation: https://www.linkedin.com/in/alexandranation/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Presales Collective newsletter: https://www.presalescollective.com/newsletter Timestamps 00:00 - Introduction 02:48 - Alex's background and journey into presales 08:59 - The importance of being a presenter pain point gatherer 10:40 - The power of effective discovery 14:24 - The art of silence in customer interactions 20:26 - Presales vs. Sales 26:20 - Advice to younger self 29:25 - How to find Alex Key Topics Covered Career Transitions into Presales Alex's journey from Nordstrom to tech Finding your strength as a "presenter pain point gatherer" The accidental path many take into presales roles Effective Discovery Techniques The importance of listening more than speaking How good discovery differentiates vendors Building trust with customers through purposeful questions The Power of Silence Using silence as a negotiation technique Training yourself to be comfortable with pauses Demonstrating confidence through patience Presales and Sales Dynamics Developing empathy for sales counterparts Understanding the complete customer lifecycle Working together for customer success Career Development The unique pressures and rewards of presales Developing flexibility and resilience Creating paths for women in presales  

In this episode, Jack Cochran and Matthew James are joined by Manisha Raisinghani, Founder and CEO of SiftHub, to discuss how AI is transforming the Presales landscape. They explore how SiftHub's AI sales engineer helps solutions teams consolidate tribal knowledge, automate repetitive tasks, and increase productivity. Manisha shares insights on leveraging AI for RFPs, POCs, and competitive intelligence, while emphasizing that AI serves as a sidekick to enhance SEs' strategic value rather than replace them. 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 Manisha Raisinghani: https://www.linkedin.com/in/manisharaisinghani/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack SiftHub: https://www.sifthub.io/  Timestamps 00:00 Welcome 03:34 Manisha's journey to founding SiftHub 08:12 SE to AE ratios in different organizations 13:10 The changing role of SEs in relationship building 15:06 Three main buckets of SE work and how AI can help 16:30 The evolution of tribal knowledge 20:40 SaaS proliferation and knowledge fragmentation 26:51 How SEs can leverage AI effectively 31:02 Using AI to analyze POCs and RFPs Key Topics Covered The Evolution of Tribal Knowledge From undocumented information to knowledge scattered across platforms How AI can consolidate knowledge from Slack, Salesforce, call recordings, and more Leveraging recorded conversations to preserve context and insights SE Challenges and AI Solutions Managing repetitive questions from sales teams and product managers Handling documentation tasks and RFP responses Creating custom solutions across different industries and regions The Changing SE Role Shift from technical support to relationship building Evolving buyer journeys requiring deeper technical engagement Balancing solutioning, question-answering, and demo responsibilities Measuring AI Impact Time savings on RFP responses and repetitive questions Using freed-up time for strategic activities and better customer engagement Supporting more deals simultaneously with AI assistance AI as a Teammate Using AI to enhance rather than replace SE capabilities How AI can work 24/7 across global teams The future of visual and diagram-based AI assistance