Jon Cline

Salesforce Trails and Trials

We share wisdom, insights, and lessons from the entire arc of a Salesforce career path. From evaluating a Salesforce career, looking for jobs, preparing for interviews, gaining experience to getting hired, promoted, and increasing your value through leaving a legacy and succession. This show will help individual Salesforce professionals as well as Salesforce partners like ISVs and Marketing/Consulting Partners.

Author

Jon Cline

Category

Technology

Latest episode

Nov 18, 2025

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Episodes

#56 - Dreamforce wrap, new Agent Builder, Agent Script, Vibes booth stories 18.11.2025

In this post-Dreamforce episode of Salesforce Trails and Trials, hosts Erik, Jon, and Mike dive into the latest announcements from Dreamforce 2025. They discuss the evolution of AI in Salesforce, including Agent Force features, Agentforce Vibes for full-stack app development, and the new Agent Builder with enhanced scripting and observability. The conversation covers practical use cases for AI in...

#55 - From a resigned life to recruited and serving fellow vets. Trailblazer journey with Andrew Day. 11.11.2025

In this episode of Sales Force Trails and Trials, host John interviews US Air Force Veteran and Salesforce expert Andrew Day. Andrew shares his unique path from high school tech projects to military service, post-military career challenges, and eventual success in Salesforce. He discusses the importance of certifications, hands-on experience, and soft skills for veterans transitioning into tech. A...

#54 - Dreamforce preview, minisite for docs, hybrid AI model pipeline w/ Agentforce Vibes 28.10.2025

Jon, Erik, and Mike discuss opportunities for Dreamforce and lots of other topics including using AI to create navigable minisites for documentation.

#53 - Laughter Works: Kevin Hupschmann's Journey from Software Sales to Comedy to Workshop 14.10.2025

In this inspiring episode of Salesforce Trails and Trials, host Jon Cline chats with Kevin Hubschmann, entrepreneur and founder of Laugh. Events. Kevin shares his remarkable journey from an aspiring lacrosse player who got cut from his team to becoming an unexpected student body president, which ignited his passion for entrepreneurship and community leadership. He dives into his early career at an...

#52 - Efficient vs. Engaging in fast food, single user software 07.10.2025

## Podcast Title Navigating AI in Sales: Opportunities, Job Impacts, and Future Skills ## Short Summary In this episode of Salesforce Trails & Trials, host Jon welcomes guest Mike to discuss how AI is transforming the business landscape, emphasizing augmentation over replacement with analogies like McDonald's (efficiency-focused) versus Chick-fil-A (human-centered). Jon shares personal projects, i...

#51 - Intellectual Curiosity, Honesty, Trust with Matt Pieper 23.09.2025

Jon and Matt discuss the power of working a problem and gleaning the insights and character along the way.

#50 - Keep The Change - Trailblazer journey with Terri Sinclair 09.09.2025

A journey from trainer to coach and user to shepherd the Salesforce ecosystem.

#49 - Soft Skills and AI in 2025 World Economic Forum Future of Jobs Report 02.09.2025

Jon reviews data from the 2025 World Economic Forum report highlighting the top 10 core skills employers are looking for.

#48 - Mike's interactive resume, being a disinterested advocate, and LLM hallucination flaws 12.08.2025

We congratulate Mike on a big milestone and walk through his interactive resume and chosen demo to learn what others might do on their hiring journey. We also discuss ways to lead through the hype without pressuring others.

#47 - Swiss LLM as pub svc, packaging beyond AppExchange, key release highlights 29.07.2025

Join Jon, Erik, and Mike as they discuss recent news items around the Swiss public LLM initiative, ways to leverage packaging beyond the AppExchange, and a few key release highlights among other topics in the conversation. Listen in and subscribe here and via LI @ https://linkedin.com/in/joncline. Show notes always at www.salesforcetrailsandtrials.com.

#46 - Why Friction can help you flourish with Nick Romanos 15.07.2025

Jon Cline and Nick Romanos discuss why removing all friction from our physical and digital experiences actually reduces our enjoyment and capacity.

#45 - What is Technical Debt and why should you care? 08.07.2025

Jon provides a high level overview of technical debt, the negative impact it has on your Salesforce Org, and some symptoms you can recognize when it is impacting your business.

#44 - Guest Episode: Gearset DevOps Diaries w/ Jon Cline 01.07.2025

Jack McCurdy and Jon Cline discuss solving the people puzzle in DevOps. This episode first appeared on the DevOps Diaries podcast.

#43 - AI Boom or Bubble, Poetry to Platforms, Co-op and Reflective AI, interview with Stephen Klein 24.06.2025

Stephen Klein, a guest on "Salesforce Trails & Trials," shares his 20+ year journey and AI insights. Klein's background includes a fine arts degree in poetry, valuing literature and art for distinguishing humans from AI. His diverse career path encompassed journalism (UMass Daily Collegian editor), early tech at Wang Laboratories, 12 years in advertising (built largest New England agency, European...

#42 - People First vs. AI First, Slack Data Changes, Co-op AI Coding w/ Cursor + Cline 17.06.2025

Jon and Mike catch up on trends, projects, and perspectives while Erik is on vacation.

#41 - Agentforce Testing Center, Cursor + Cline, Level-Up Your Role 10.06.2025

Mike Mikula joins Erik and Jon to discuss recent projects, learning, and trends.

#40 - Best Of: How to prepare for your Salesforce interview 03.06.2025

This was a big topic for many as Jon attended Tahoe Dreamin' and Texas Dreamin' so we are including it here as a reply. This episode of the "Sales Force Trails and Trials" podcast offers advice on acing a Salesforce job interview by leveraging soft skills. The hosts emphasize the importance of thorough preparation, including researching the company and its goals. They suggest demonstrating tenacit...

#39 - AI Snake Oil, Off-Platform Agents, a Google Gem, and harmony from Japan 27.05.2025

The Erik & Jon show returns with a wide ranging discussion of AI uses and a couple great books.

#38 - The Jon Cline Show: AI Hallucinations rising, risks of no playbook, People First prompt engineering. 20.05.2025

This episode of the Jon Cline Show focuses on the human side of technology and building stronger teams in an AI-driven world. Host Jon Cline discusses recent news in the AI world, including potential decreases in AI spending at Amazon and the increasing prevalence of AI hallucinations. As a continuation from a previous episode on why tech projects fail, the show delves into the most common risks a...

#37 - Construction Management to Cooperative AI: Trailblazer Stories with Akshay Panse and Omar Youssef 13.05.2025

This episode features the journeys of Akshay Panse and Omar Youssef, who found their way to the Salesforce ecosystem from diverse backgrounds in engineering and consulting. They discuss common bottlenecks and challenges in Salesforce implementations and the discovery process, often rooted in communication and managing varied client needs. To solve these pain points, they created Cloobot, an AI-pow...

#36 - Curiosity as curator: A Trailblazer's journey with Janeen Marquardt 06.05.2025

Janeen has navigated significant physical challenges throughout her life, undergoing over 30 surgeries, including multiple joint replacements and plates in her body. Her Taekwondo journey, pursued for achievement and mind-body connection, shows her resilience in pushing through limitations. She emphasizes that not all disabilities are visible and the importance of giving grace to others.

#35 - The Jon Cline Show: Top 5 Reasons Why Tech Projects Fail 29.04.2025

Jon Cline's show/podcast highlights significant tech project failure rates (45-95%, AI 70-85% in 2019) based on extensive data. Jon Cline argues people fail projects, not AI itself. He identifies top reasons: 1. Poor requirements/goals, 2. Ineffective communication/stakeholder management (citing Foxmeyer drug failure), and 3. Inadequate project management (favoring incremental delivery). Success r...

#34 - The Jon Cline Show: Klarna reversal, Caller is new on the team, Liberty Enhancing AI, NotebookLM superpowers 22.04.2025

This episode is sponsored by The Salesforce Recruiter (https://thesalesforcerecruiter.com/) and the People First AI Playground (http://www.joncline.com/trail).

#33 - Become Visible and Valuable with a Great Portfolio 15.04.2025

Leverage existing tools to expand your comfort zone and become experienced in using AI, CLI, and code co-pilot tools.

#32 - The Jon Cline Show: AI Transcription and Summary 08.04.2025

Learn more about your host and also key ways to leverage AI transcription and summary services without losing your People First Power.

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