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  • Last week in B2B: ClickUp’s $300M playbook, SaaStr’s AI agent strategy, and the four fits of growth

Last week in B2B: ClickUp’s $300M playbook, SaaStr’s AI agent strategy, and the four fits of growth

Author

Ugi Djuric
September 29, 2025

Hey B2B folks,

This week’s theme? Building on stronger foundations.

From data quality to churn, from trust-led homepages to hiring strategies, the big wins came from teams fixing what breaks before scaling what works.

Meanwhile, ClickUp’s COO dropped a $300M ARR GTM playbook, SaaStr showed how 20+ AI agents can run an 8-figure business with a tiny team, and the new “consumer-to-enterprise” AI playbook is starting to take shape.

Also: lessons from Forbes’ AI 50 on PMF, reflections on churn, and a $90K/mo content ecosystem that proves consistency still compounds.

Let’s get into the best from last week:

Ops24.Ai sponsors this week’s issue.

Eight months ago, at our agency ContentMonk, we hired a Head of AI Engineering. Six months later, we’d built dozens of AI systems powering writing, sales, outreach, people ops, and even running The B2B Vault project.

Peers saw what we built and said, “You should offer this as a service.”

So we launched Ops24 — the AI automation and growth partner at the intersection of ops, growth, and AI.

We help B2B companies grow main KPIs, cut wasted hours, streamline ops, and save 6–7 figures a year. For example, Elogii added $300k in just 2 months after implementing our AI systems for sales & marketing, with no extra hires.

Now you can too. Book a free strategy call, and as a B2B Vault subscriber, get 20% off implementation.

  • How to spot signs of UX maturity regression
    Teams often think they’re maturing in UX, when in reality they’re sliding backward. This guide highlights the warning signs and provides guidance on how to address them. [Read here]

  • Why customer support shouldn’t handle your product feedback
    Feedback belongs to the product, not support. Here’s why and how to design better feedback loops. [Check the breakdown]

  • Fixing the foundation: The state of marketing data quality in 2025
    Bad data = bad decisions. This report highlights how data quality is eroding and what the best teams are doing to maintain high standards. [Read the report]

  • How Kellanova uses AI to predict creative performance
    Kellanova built AI systems that forecast creative outcomes before launch — and tie campaigns directly to KPIs. [See the case study]

  • PMF playbooks: Lessons from Forbes’ AI 50 startups
    The best AI startups achieve product-market fit by testing quickly, narrowing their focus early, and scaling later. Here are the common playbooks. [Read the insights]

  • The proof-led homepage that builds trust
    Forget flashy hero copy — this homepage strategy leads with proof, not promises, and converts better. [See the teardown]

  • What breaks GTM at scale (part 1/2)
    Scaling adds complexity, silos, and stalls. This series digs into what breaks GTM as companies grow. [Read part 1]

  • Reflections on two years of solving churn
    One founder shares two years of lessons on fighting churn — what worked, what failed, and what they’d do differently. [Check the reflection]

  • The GTM playbook for building a $300M+ ARR business (ClickUp)
    ClickUp COO Gaurav Agarwal reveals the plays that built their $300M+ ARR machine. [Read the playbook]

  • Hire better and faster: A step-by-step startup hiring strategy
    A practical guide for early-stage founders on how to design hiring systems that scale. [See the strategy]

  • SaaStr’s AI agent playbook
    How SaaStr runs 20+ AI agents to manage operations, scale revenue, and stay lean — proving what’s possible with agentic AI. [Read the case]

  • The four fits: A growth framework for the AI era
    Product-market fit isn’t enough anymore. This framework introduces four fits every AI-era company needs. [Check the framework]

  • My $90K/mo content ecosystem
    A content system that consistently prints $90K/month. Here’s how it’s structured. [Read the breakdown]

That’s a wrap for this week!

Loved this week’s issue? Share it with your peers.

See you next Monday!

Cheers,
Ugi from Ops24 and ContentMonk