Jeff Hatten

Senior Account Executive at 2Win! | Sales Humor Creator | Serial SaaS Founder

Jeff Hatten is a seasoned sales professional and serial entrepreneur based in Colorado Springs, Colorado, with over two decades of experience in B2B tech sales, leadership, and innovative content creation. Currently serving as Senior Account Executive at 2Win!, a globally recognized sales skills training company, Jeff helps SEs, AEs, and CSMs at top tech firms like Canva, Google, Microsoft, Okta, OpenAI, ServiceNow, and Shopify master key client interactions through programs like Demo2Win, Discovery2Win, Winning With Executives, and Success2Win. These modern, AI-adapted trainings focus on the 'how' of sales—connecting with audiences, influencing stakeholders, and adapting in real-time—delivering immediate impact with year-long support.[LinkedIn Profile](https://www.linkedin.com/in/hattenjeff) [2Win Website](https://www.2winglobal.com) Jeff's entrepreneurial journey is marked by bold ventures in video and SaaS. He founded Popr.ai (2022-2025), a platform for personalized GIFs and animations to boost LinkedIn DM conversations, driving trial signups through viral, humorous videos that amassed 56 million GIPHY views. Before that, as Founder & CEO of Bolt Video (2018-2022), he pioneered affordable B2B video content. Other startups include MeetHead (unique seller engagement tools), Vizoodeo (innovative B2B video), and a stealth project. Recently, he launched The Edutainment Studio, blending education and entertainment with funny, relatable videos for B2C2B brands on LinkedIn, TikTok, IG, and YouTube—starting at $4k/month, emphasizing fractional creators and audience-first storytelling.[Creative Shizzle Podcast](https://creativeshizzle.com/podcast/jeff-hatten-edutainment-journey/) [Popr.ai YouTube](https://www.youtube.com/watch?v=vbh3DJIVSts) His deep sales roots trace back to 2Win! Global, where he spent nearly two decades: as Founding Account Executive (2005-2014), building partnerships with marquee tech firms; Worldwide Sales Director (2014-2016), leading revenue and teams; and now back as Senior AE since March 2026. Earlier, at Excelsior Software, he sold enterprise solutions to K-12 education. Jeff's signature style? Infusing humor into sales. He hosts a retro sales game show, posts viral 'sales team humor' videos, and shares candid lessons—like shutting down Popr.ai due to product-market fit challenges, timing issues, and over-reliance on PLG without clear monetization.[LinkedIn Lessons Post](https://www.linkedin.com/posts/hattenjeff_i-had-to-shut-down-my-saas-biz-earlier-this-activity-7396676876959846400-abUD) With 11k+ LinkedIn followers, Jeff champions authentic, AI-leveraged human selling in discerning markets. His 'building in public' ethos—transparently sharing wins, flops, and metrics—builds community and accountability, turning sales' seriousness into therapeutic laughter while driving real GTM impact.[LinkedIn Live](https://www.linkedin.com/posts/revgenius_live-now-with-jeff-hatten-founder-atpoprai-activity-7042175910552231936-Qi_o)

Key Insights from Jeff Hatten

AI is taking over the world, but humans (who leverage AI) are as important as ever to help guide buyers.

— Jeff Hatten on AI in Sales

I had to shut down my SaaS biz earlier this year. And, it cost me a lot of $ and pride. But, I did learn a few valuable lessons.

— Jeff Hatten on SaaS Lessons

In this new attention economy, humor is the fastest way to stop the scroll and stand out in a sea of sameness.

— Jeff Hatten on Edutainment Marketing

Sales is serious. And it’s hard. That’s why laughing about it is therapeutic.

— Jeff Hatten on Sales Humor

Notable Quotes from Jeff Hatten

Humor is the fastest way to stop the scroll and stand out in a sea of sameness.

— Jeff Hatten

Sales is serious. And it’s hard. That’s why laughing about it is therapeutic.

— Jeff Hatten

Frequently Asked Questions about Jeff Hatten

How does 2Win! training differ from traditional sales methodologies?

While traditional methodologies focus on 'what' to do and when, 2Win! emphasizes the 'how'—connecting with audiences, influencing decisions, adapting to situations, and building confidence. Programs like Demo2Win teach structured Tell-Show-Tells and limbic openings for immediate use, with global facilitators localizing for regions and languages. Clients see results across sales funnels, supported by year-long coaching and AI tools like Wyn.[2Win Website](https://www.2winglobal.com)

What led to the shutdown of Popr.ai and key takeaways for founders?

Despite traction via humorous videos (56M GIPHY views) and PLG trials, Popr.ai closed due to unsolved product-market fit, lack of clear buyer commitment path, and suboptimal timing. Lessons: Validate monetization early, balance PLG with sales outreach, experiment boldly but pivot fast, and build transparently. Jeff applied this to Edutainment Studio, sharing metrics publicly.[LinkedIn Post](https://www.linkedin.com/posts/hattenjeff_i-had-to-shut-down-my-saas-biz-earlier-this-activity-7396676876959846400-abUD)

What is edutainment and how does The Edutainment Studio deliver it?

Edutainment merges education with entertainment via funny, relatable videos that subtly teach product value without hard sells. The Studio crafts scripts, casts talent, delivers bi-weekly batches for $4k+/month, tracking resonance on socials. Targets B2C2B brands; avoids risk-averse committees. Inspired by ClickUp, Tom Boston; contrasts meh B2B content drowning ICPs.[Creative Shizzle](https://creativeshizzle.com/podcast/jeff-hatten-edutainment-journey/)

Why focus on sales humor and what impact has it had?

Sales' intensity needs therapy; humor stops scrolls, builds relatability, drives indirect actions like Popr.ai trials. Videos garner massive views cross-platform (LinkedIn algo frustrations noted), fuel game show, position Jeff as authentic voice. Therapeutic for creators/viewers, enhances personal brand in crowded GTM space.[LinkedIn About](https://www.linkedin.com/in/hattenjeff)

Jeff Hatten — Areas of Expertise

  • B2B Sales Training
  • Sales Demos & Discovery
  • Edutainment Content
  • SaaS Entrepreneurship
  • Sales Humor & Videos
  • GTM Strategy
  • Guest

Jeff Hatten — Show Appearances

  • Mornings in the Lab (2024-08-21)

Jeff Hatten — Signal Brief

Signal Score: 6/100

Generated 2026-04-16T01:26:07.439Z