How To Win in B2B in 2026 with Chris Cunningham, Founding Member at ClickUp | Ep. 378

B2B social isn’t broken…most brands are just playing it wrong. Daniel sits down with Chris Cunningham, founding member of ClickUp and the brain behind one of the most recognizable B2B social strategies today. Chris breaks down how ClickUp went from a scrappy pivot to a content powerhouse by betting early on creators, comedy, and consistency, even when everyone said B2B social wouldn’t work. From building an internal creator team to launching multiple niche media pages, Chris shares the exact operating system ClickUp uses to generate millions of organic impressions every month. You’ll also learn: Why B2B brands should copy B2C trends before they’re “acceptable” How ClickUp runs its weekly content machine from ideation to publishing Why creator-led pages and employee-generated content are the future of B2B marketing If you’re trying to build a brand people actually talk about (not just ads people scroll past), this episode is for you. CallRail is the lead engagement platform built for marketers who need clean attribution, smarter insights, and zero missed leads. From AI-powered call tracking and conversation intelligence to a 24/7 AI voice agent, CallRail helps teams maximize every inbound touchpoint and convert more leads into customers. https://www.callrail.com/proveit?utm_campaign=q4_2025_marketing_millennials_podcast&utm_medium=thirdparty_advertising&utm_source=marketingmillennials   Follow Chris: LinkedIn: https://www.linkedin.com/in/chrisclickup/ Follow Daniel: LinkedIn: https://www.linkedin.com/in/daniel-murray-marketing/ Sign up for The Marketing Millennials newsletter: https://themarketingmillennials.com/ Daniel is a Workweek friend, working to produce amazing podcasts. To find out more, visit: https://workweek.com/