From Co-Pilot to Orchestrator: AI and the Evolving SE Role with Manisha Raisinghani

In this episode, Jack Cochran welcomes back Manisha Raisinghani, Founder and CEO of SiftHub, exactly one year after her first appearance on the show. Together they explore the dramatic shift in how AI is being used by solutions engineers. Manisha shares what it means for SEs to become Forward Deployed Engineers, how vibe coding is changing live customer interactions, and what enterprise leaders are getting wrong about AI adoption. She also offers concrete first steps for SEs and SE leaders who feel like they're behind. Thank you to SiftHub for sponsoring this episode! Visit sifthub.io to learn more. Follow Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Manisha Raisinghani: https://www.linkedin.com/in/manisha-raisinghani/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack SiftHub: https://sifthub.io/ Sol/Con (PSC Annual Conference, Chicago): https://www.presalescollective.com/solcon-2026  Paytm (referenced in board discussion): https://paytm.com Key Topics Covered How AI Shifted from Co-Pilot to Workflow Orchestrator Vibe Coding and the Forward Deployed Engineer Democratizing Institutional Knowledge AI Transformation at Enterprise Scale Making SE Value Visible with Data Where to Start if You Feel Behind Timestamps 00:00 Welcome & Intro 03:58 One year later: the headline shift in AI and SE workflows 07:20 Vibe coding — what it is and why SEs should care 10:23 The rise of the Forward Deployed Engineer 14:01 How SiftHub has evolved: from retrieval to reasoning 20:23 Lessons from the Paytm board on enterprise AI adoption 24:43 Sales: the most blamed, least understood function 28:40 First steps for SEs and SE leaders who feel behind  

In this episode, Jack Cochran and Matthew James continue their conversation with Micah Joel, diving deep into the metrics that matter when building and justifying a demo engineering team. Micah shares practical approaches to measuring the value of demo engineering, from simple time-saving calculations to sophisticated surveys that capture SE satisfaction and retention indicators. The conversation explores how to frame these metrics in terms that senior management cares about, moving beyond technical accomplishments to demonstrate real business impact.   Micah emphasizes the importance of thinking "top down" when building a demo engineering organization, focusing on what leadership values most: productivity, cost savings, and revenue growth. He shares real-world examples from his time at Salesforce's Q Branch, including how to measure the value of demo environments, how to identify unexpected patterns in the data (like deals where demo engineers get involved), and how cultivating relationships with SEs creates goodwill that extends beyond the numbers. The discussion also covers how demo engineering impacts go-to-market speed for new products and how to position the team as mission-critical support for field teams rather than just a technical function. Follow Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James https://www.linkedin.com/in/matthewyoungjames/  Connect with Micah Joel: https://www.linkedin.com/in/micahjoel/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Sol/Con 2026 (Chicago, August 2026): https://www.presalescollective.com/solcon-2026 Presales Collective Podcast: https://www.presalescollective.com/podcast Key Topics Covered Establishing baseline metrics for demo engineering through time-saving calculations Using SE surveys to measure demo environment value and satisfaction Identifying retention indicators at 3-year and 7-year tenure marks Reducing technical barriers to hiring SEs through better demo tooling Thinking "top down" to align metrics with senior management priorities Measuring go-to-market speed and time-to-revenue for new products Building goodwill and political capital with SE teams Branding your demo engineering team with effective metaphors Course-correcting when metrics don't align with expectations Positioning demo engineering within the organization structure Timestamps 00:00 Welcome  02:55 Measuring time saved with tooling  09:20 Reducing technical hiring barriers  13:50 Building the overall business case  18:30 When metrics don't line up  21:20 Product-to-Market (P2M)  27:40 Final thoughts on top-down thinking  

In this episode, Jack Cochran and Matthew James sit down with Micah Joel, GTM leader and demo engineering pioneer, to explore what it means to build a dedicated demo engineering function from scratch. Micah shares his journey from theater kid to SE to leading Salesforce's legendary Q Branch, and unpacks why demo engineering might be the most underutilized lever in presales today. They cover the difference between deal-focused and infrastructure-focused demo engineers, how to structure the team, why blended teams fail, and how a mature demo engineering org can swim upstream into product strategy to reduce time-to-revenue. This is part one of two. Part two will focus on measuring and proving the value of a demo engineering team. Follow Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Micah Joel: https://www.linkedin.com/in/micahjoel/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack SoulCon 2026 (Chicago, August 2026): https://www.presalescollective.com/solcon-2026  Presales Collective Podcast: https://www.presalescollective.com/podcast Key Topics Covered Micah's Background: From Theater to SE to Demo Engineering What Is Demo Engineering and How Is It Different from Being an SE? When Does an Organization Need a Demo Engineering Team? The Two Sides of Demo Engineering: Deal Support vs. Infrastructure/Scale How to Hire and Structure the Team Demo Engineering as a Talent Pipeline and Retention Strategy Swimming Upstream: Demo Engineering's Role in Go-to-Market Strategy Common Mistakes and How to Avoid Them Timestamps 00:00 Welcome 02:48 Intro Micah Joel 05:42 Demo engineering definition 08:33 When do you need a DE team? 11:13 Deal side vs. infrastructure/scale side 15:48 Demo engineering as SE retention 23:55 Swimming upstream 27:11 Final advice

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: [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