The Marketing Millennials – Ep. 378

How To Win in B2B in 2026
Guest: Chris Cunningham, Founding Member at ClickUp
Host: Daniel Murray
Air Date: December 26, 2025

Episode Overview

In this high-energy episode, Daniel Murray sits down with Chris Cunningham, the creative force and social mastermind behind ClickUp’s viral B2B marketing. Together, they dissect how to shatter outdated B2B marketing myths, build share-worthy content machines, and dominate platforms like TikTok and Instagram using a “no BS” playbook. Chris candidly shares ClickUp’s journey from a pivoting startup to a recognized B2B brand, their approach to creator-driven content, and detailed tactics for winning in 2026 and beyond.

Key Topics & Insights

1. Chris’s Journey: From Agency Days to B2B Social Leader

[01:39-04:16]

• Chris’s initial collaboration with ClickUp CEO Zeb Evans began back in college, starting with social media promotion for a rapper, eventually leading them to agency work and finally, to building ClickUp.
• The team experienced several pivots, including an ambitious (and ultimately unsuccessful) Snapchat competitor, before focusing on building productivity tools.
• Quote:
  “Zeb has a near death experience ... he’s, like, ‘I don’t want to just be somebody who grows social. I want us to be people who change the world.’”
  — Chris Cunningham [03:32]

2. Breaking B2B Social Stereotypes

[04:37-07:12]

• Chris challenges the idea that B2B brands can’t be fun, creative, or big on social.
• Early bets on B2B influencer marketing paid off—mirroring B2C trends a few years later.
• The importance of testing with small budgets, looking for “signal” before scaling, and investing in a dedicated creator proved essential.
• Quote:
  “My number one rule is if something works in B2C, it’s probably going to work in B2B just a little bit later.”
  — Chris Cunningham [05:25]

3. The ClickUp Content Machine: A Weekly Workflow

[07:13-08:54]

• Mondays: Analyze what’s working/what’s not.
• Tuesdays: Team brainstorm and pitch new ideas.
• Wednesdays: Script refinement and role assignments.
• Thursdays: Marathon video shoot days (up to 5+ videos).
• Fridays: Chill, analyze, and plan posting schedules.
• Success comes from structured operations and consistent processes.
• Quote:
  “If you really want to win in content... You’ve got to build a machine. You need an operation.”
  — Chris Cunningham [08:38]

4. Ideation, Guardrails, and Writer’s Room Tactics

[08:54-12:14]

• Guardrails: Avoid over-branding (“no one wants an ad in every video”), steer clear of divisive topics, and prioritize fun and spontaneity.
• Regularly host “writer’s rooms”, often including external comedians or creators for fresh perspectives.
• Quote:
  “Sometimes our most viral videos just came from what we call letting them play.”
  — Chris Cunningham [09:36]
• Bringing in outsiders for ~50% of writers’ rooms prevents creative stagnation.

5. Serializing Content & The ABCD Formula

[12:14-15:27]

• Serializing viral concepts (e.g., “HR goes hard,” then “Finance goes hard”) to reach new audiences and extend successful formats.
• The ABCD content formula:
  • A: Proven “hits”—iterate and adapt.
  • B: Borrowed formats from elsewhere, adapted for your audience.
  • C: Current trends—quick wins, but shouldn’t dominate.
  • D: Experiment and push boundaries; your next “A” may start here.
• Quote:
  “When you strike gold, you need to capitalize on gold. You need to recreate it. But don’t do the same thing again. Find a new way to do it.”
  — Chris Cunningham [13:11]

6. Anatomy of a Viral B2B Video

[16:57-18:52]

• Key ingredients: Relatability & shareability, comments worth making, a strong hook/headline, good pacing, and a memorable ending (“button”).
• Shares are more valuable signals than likes.
• Quote:
  “If it’s contagious ... you want to hit share and send it to someone—that means it’s gonna be a good video.”
  — Chris Cunningham [17:21]
• Use platform analytics (e.g., video drop-off graphs) to refine and repost promising content.

7. Testing, Experimentation, and New Plays for 2026

[20:53-23:23]

• Testing new formats: “Creator-led” adjacent pages (e.g., ClickUp Comedy, Tips with ClickUp); some may outgrow the main brand account.
• Big on EGC (Employee Generated Content), with 15+ ClickUp staff creating content, especially on LinkedIn.
• Bets for 2026: Micro-media brands, short films, long-form episodic content, and diversifying beyond the brand’s main social.
• Quote:
  “EGC—I’m all in on employee-generated content. I have 15 of my employees creating content now ... it’s a great way to make content, especially on LinkedIn.”
  — Chris Cunningham [22:00]

8. Building an Ecosystem of Brand & Niche Pages

[24:14-25:54]

• Multiple interconnected accounts (e.g. ClickUp Comedy, ClickUp Memes) join-posting with the main ClickUp account, creating a “universe” of content hubs with different angles and audiences.
• Quote:
  “It’s building a big ecosystem that all still goes back to one place, ClickUp, and is still very well branded.”
  — Chris Cunningham [25:03]

9. Empowering Creators Internally & Selling Social Strategy Upwards

[28:05-31:38]

• New B2B marketers should:
  • Decide if their brand’s strength is humor, education, or utility.
  • Research emerging creators, reach out for test projects at manageable costs.
  • Monitor results and “sell” organic success to leadership by comparing to paid CPMs and impact on CAC.
  • Scale up successful creators and retain them (competitors will poach!).
• Quote:
  “Once you have a video that hits a couple times ... you go to your board and say: ‘Hey, I got 10 million impressions for us last month. What is that worth to you?’”
  — Chris Cunningham [30:29]

10. On Attribution, ROI, and Taking Brand Risks

[35:08-37:12]

• The “marketing hill” Chris will die on:
  • Long-term brand plays beat short-term attribution-obsessed thinking.
  • Marketers must be allowed to test and iterate; true results compound over quarters, not weeks.
• Quote:
  “You always lose to companies like us who don’t [over-optimize for attribution], because it takes time to see some of these results... The hill I will die on is: you can’t just overly track attribution immediately. Last click, all that. You gotta just take the risk, keep going, keep iterating.”
  — Chris Cunningham [35:23], [36:36]

11. The Real Role of AI in Social Content (2026 Perspective)

[32:13-34:15]

• Chris uses AI to streamline and ideate—but does not believe it can replace genuine creator-driven content yet.
• AI works for memes, quick visuals, and production shortcuts, but lacks taste and humor.
• Quote:
  “I don’t think [AI] writes the best content ... people are screaming for more real. They’d almost rather you just walk out and talk on your phone.”
  — Chris Cunningham [32:28], [33:23]

Notable Quotes & Memorable Moments

• On Serializing Content:
  “That’s where you mess up ... if you’re just creating A’s ... eventually the content will get exhausted. You need to look for B’s, C’s, and always be trying new D’s.”
  — Chris Cunningham [14:14]
• On Creator-Led Brand Universes:
  “ClickUp Comedy might pass ClickUp’s main page in followers ... people love it so much, it proves we were right to bet on comedy.”
  — Chris Cunningham [24:53]
• On Realness Over AI Automation:
  “Right now people want creators ... they’re craving something real, hearing real conversation.”
  — Chris Cunningham [33:23]

Actionable Playbook (Summarized)

1. Study what works (B2C trends first), test small, and go all-in on signals.
2. Structure content ops like a real media company—analyze, pitch, script, shoot, evaluate weekly.
3. Mix proven hits (A), borrowed models (B), trends (C), and wild-card experiments (D) every week.
4. Expand ecosystem—don’t rely on just brand account; create niche pages, empower employees, collaborate cross-brand.
5. Pitch up successes internally through organic reach, cost savings, and brand cachet—not just bottom-funnel leads.
6. Use AI as a helper for ideation/automation—not for driving genuine, shareable creators’ content.
7. Don’t obsess over attribution in the short term; brand growth compounds and pays off long-term.

Where to Find Chris & ClickUp

• ClickUp: @ClickUp (and associated pages like @ClickUpComedy)
• Chris: @cunningham (Instagram); Chris ClickUp (Twitter, LinkedIn); chris@clickup.com

RECOMMENDATION:
If you’re in B2B marketing, listen to this episode for a clinic on modern brand building—especially if you want your content to actually get traction, not just impressions.
“If you’re just wanting to go share and give, it will win every single time.” — Chris Cunningham [39:12]