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  1. The Marketing Millennials
  2. How To Win in B2B in 2026 with Chris Cunningham, Founding Member at ClickUp | Ep. 378
How To Win in B2B in 2026 with Chris Cunningham, Founding Member at ClickUp | Ep. 378

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

The Marketing Millennials · Dec 26, 2025

ClickUp's Chris Cunningham unveils his B2B social playbook: building a content machine, using the ABCD formula, and proving ROI with small tests.

Treat Content Creation Like a Factory with a Strict Weekly Production Cadence

Sustainable, high-quality video content isn't about random inspiration. ClickUp implements a rigorous weekly schedule: Monday for analysis, Tuesday for pitching, Wednesday for scripting, Thursday for shooting, and Friday for planning. This operationalizes creativity and ensures consistent output.

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

The Marketing Millennials·2 months ago

A Viral Video Needs Five Elements: Shareability, Comment-Worthy Content, a Hook, Pacing, and a 'Button' Ending

A viral video's success hinges on more than just a strong opening hook. It must be inherently shareable, elicit comments, maintain engaging pacing, and conclude with a satisfying "button" that provides a clean, memorable finish and encourages a rewatch.

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

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

The Marketing Millennials·2 months ago

Secure Buy-in for In-House Creators By First Proving ROI with a Low-Budget Test

Before asking for a full-time creator headcount, de-risk the investment. Hire a talented creator on a freelance basis with a small budget. Use their initial viral hits and performance data to build a strong business case for a full-time role and a larger budget.

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

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

The Marketing Millennials·2 months ago

B2B Marketing's Next Big Thing Is Already Working in B2C

To predict future B2B marketing trends, look at what's currently successful in the B2C space. ClickUp's Head of Content, Chris Cunningham, applied this principle by pioneering B2B influencer marketing years ago, recognizing that consumer behaviors and effective channels eventually migrate to the business world.

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

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

The Marketing Millennials·2 months ago

Justify Brand Marketing Spend By Calculating Its Paid Media Impression Value

To sell leadership on brand initiatives with indirect ROI, translate organic performance into paid media equivalents. Calculate what the millions of impressions from a viral video would have cost via paid channels. Frame it as a cost-effective way to build brand and lower overall CAC.

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

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

The Marketing Millennials·2 months ago

Over-reliance on Immediate Attribution Guarantees You'll Lose to Patient Competitors

Companies fixated on immediate, last-click attribution will fail. Brand-building efforts like content marketing require patience. ClickUp's success came after months of investment before deals were explicitly sourced to TikTok, a timeline that impatient competitors would abandon too early.

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

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

The Marketing Millennials·2 months ago

B2B Content Teams Should Host 'Writer's Rooms' with External Comedians to Spark Ideas

To prevent creative stagnation, ClickUp's content team regularly brings external talent—like comedians or creators—into their ideation sessions. This "writer's room" approach injects fresh perspectives and helps "punch up" existing ideas, preventing the team from getting stuck in a creative rut.

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

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

The Marketing Millennials·2 months ago

Build a Media Ecosystem with Niche, Creator-Led Sub-Accounts, Not Just a Single Brand Page

Instead of centralizing all content on one brand account, ClickUp creates an ecosystem of pages like "ClickUp Comedy" and "ClickUp Memes." These niche accounts build their own dedicated audiences and can grow faster than the main brand page, creating multiple entry points into the ClickUp universe.

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

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

The Marketing Millennials·2 months ago

Balance Your Content Strategy with the ABCD Formula to Maximize Hits and Foster Innovation

A successful content mix isn't random. ClickUp uses a formula: A) Recreate your proven hits. B) Adapt what's working for others. C) Jump on relevant trends. D) Experiment with unconventional ideas. The goal is to turn "D" experiments into new "A" hits, ensuring a constantly evolving strategy.

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

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

The Marketing Millennials·2 months ago

Launch a Low-Budget Content Program by Hiring Micro-Creators with a Proven Viral Hit

To kickstart a content program without a large budget, identify micro-creators (under 25k followers) who have already produced 1-2 viral videos. They've proven they understand the algorithm but are still affordable. Offer a small monthly retainer for high-volume video production to test what resonates.

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

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

The Marketing Millennials·2 months ago