Deconstructing ClickUp’s GTM: A Journey Through Three Eras of Growth

Hello and welcome to The GTMnow Newsletter – the media brand of VC firm, GTMfund. Build, scale and invest with the best minds in tech.

By deconstructing a company’s go-to-market strategy and execution, you uncover:

• The decisions behind their breakout growth.
• The mistakes that almost derailed them.
• The hidden levers that aren’t obvious from the outside.

It’s a shortcut to pattern recognition, so founders and operators don’t have to learn every lesson the hard way.

ClickUp built a company around the rhythm of pure speed. In 2017, a tiny team shipped into beta in June, out of beta by September, and landed a first paying customer in November. The product wasn’t polished so much as in motion and users could feel it. By October 2019, “ClickUp 2.0” arrived, the kind of release that tells a community: this thing is growing new rooms every week.

What followed is the story of three eras: (i) the PLG foundation, (ii) layering sales on top of it, and (iii) systemizing for scale.

Let’s deconstruct the machine.

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ClickUp’s GTM: The Three Eras

Era 1: The PLG foundation (2017–2020)

The first era consisted of well-executed bottoms-up growth.

The goal was simple: build something people couldn’t help but share.

They operated in public with a relentless cadence. Zeb Evans (Founder & CEO) set the tone: “You should be able to see ClickUp get better every week.” They shipped over 200 features in a year, which was significantly above average at that point in time. The speed of shipping cadence built trust and trained users to expect progress.

Compounding mechanisms were the underlying growth lever:

• The Template Center wasn’t just a feature, it was a content engine and a time-to-value reducer.
• The Import Hub wasn’t just for onboarding, it was a direct attack on incumbents, disguised as a seamless transition.
• The Free Coaching Program wasn’t a sales tactic, it was a user retention strategy, catching teams at their most vulnerable moment.

Underneath it all sat a clear Hierarchy (Spaces → Folders → Lists → Tasks) that mapped to how work actually happens, making it easy for usage to spread from one person to an entire department.

The content engine ran at the same tempo. In 2020 alone, 227 blog posts shipped, comparison pages intercepted buyers at the moment of choice, and how-tos plus templates compounded organic traffic. Support moved just as fast: 396,904 tickets resolved in 2020 alone.

During this foundational PLG era, ClickUp demonstrated that the most effective “marketing” is a set of mechanisms designed to reduce time-to-value and make product progress unmistakable.

Era 2: Layering sales on top of PLG (2020–2021)

The product machine was humming. But then, a new signal emerged: hand-raisers.

Admins from large domains, already using the product, were asking for help. They needed support to roll out ClickUp at scale. These weren’t small teams, the deals were often 10x the LTV of self-serve users.

An important part to note here is that they layered on sales not a a strategic choice, but a response to demand. This approach is consistently echoed by companies that successfully went upmarket, including Vanta. You can hear their CRO, Stevie Case, share how demand dictated Vanta’s upmarket expansion in this conversation.

ClickUp’s first sales hire wasn’t to outbound upmarket, they were an inbound rep to meet demand that was already bubbling up inside the product.

This led to the true innovation of this era: Product-Led Sales (PLS). They fused product and sales, where usage events became triggers.

• A sudden spike in seat count? That’s a PQL.
• A new admin created? That’s a PQL.
• SSO/API turned on? That’s a PQL.

The machine was now fueled by both self-serve adoption and data-driven outreach. More on how Clickup blends PLG and sales-assist here.

The sales layer more than worked, it exploded.

Revenue grew ~9x in 2020. The user base doubled in the back half of the year. The company went from a $35M Series A to raising $100M and then $400M a year later.

The machine was firing on all cylinders. But that kind of speed can also be a recipe for chaos.

Growth exposed seams:

• Internal friction. The team jumped from ~200 to 500+ people. Processes couldn’t keep up. The chaos of a startup wasn’t a sustainable model for a scale-up.
• The “eight-layer cake.” Customers felt overwhelmed. An SDR, an AE, a CSM—all overlapping, all reaching out. The seamless, product-led experience was getting muddled.

Era 3: Systemizing for scale (2022–present)

After two years of a rocket ride, the mission changed. The operating question shifted from “What worked?” to “What’s incremental?”

Things shifted from growth at all costs to allocation of dollars, touches and time.

Budgets were re-cut, the media mix was optimized, and first-party data became the most valuable asset. The result? CAC fell by ~3X.

They rebuilt the entire GTM as a single revenue system, organized across three clear segments:

• Self-serve SMB.
• Sales-assisted Commercial.
• Enterprise.

Each had a clear goal, but they all worked under one plan.

The final evolution was orchestration. They launched Project Constellation, a systems-first approach to GTM. It used product and account signals to prioritize actions across sales, success, and marketing. It was a single brain, a unified nervous system.

The results speak for themselves: ARR from ~$85M to $250M+. CAC down 50-66%.

Frameworks, mental models and playbooks

These are some of the frameworks, mental models and playbooks that ClickUp used throughout the three eras of growth.

Mental models (how to think)

Input KPI > Output KPI

Make shipping every week the behavior that drives growth (instead of chasing lagging outputs).

You can implement this by starting a Friday Ship Log – every team posts one shippable improvement.

Incrementality > Attribution

Fund what moves outcomes versus a control, not what a platform “credits.”
Use this when ad spend is high, CAC is fuzzy, channels claim the same wins. To implement, run a 2-week holdout on your biggest channel; reallocate to the highest incremental lift.

Signals > Opinions

Let product/account events call the play (not gut feel).
To implement this, define 4 starter signals (seat spike, SSO on, large import, usage drop) and route actions.

Mechanisms > Moments

Compounding programs (templates, imports, coaching, weekly releases) beat one-off launches.

To implement, pick one mechanism to build this month (e.g., Template Library v1).

Complexity Tax Index

A check against “too many touches.” Cap owners per account.
To implement, cap to ≤3 active owners on top accounts, and suppress conflicting touches.

Frameworks (how to structure)

Three-Lane Funnel (Creation / Harvesting / Retention)

One GTM system split into three lanes with distinct goals and owners.
To implement, tag every initiative to a lane. Then, pause anything untagged.

Payback by Segment

CAC payback thresholds by SMB/Commercial/Enterprise.

To implement, set thresholds, such as SMB <9 mo, Commercial <12 mo, ENT <18 mo; pause programs above threshold.

Guardrails + Primary

One outcome per lane, plus 2–3 guardrails that prevent dumb wins.
To implement, publish a traffic-light dashboard: Primary + Guardrails per lane.

Playbooks (how to execute)

Signals → Playbooks → SLAs (Project Constellation)

Turn signals into the next best action with timeboxes and controls.
Use when follow-ups are slow or opportunities or risks slip through cracks.
To implement, activate 4 rules with SLAs (e.g., seat spike → AE in 48h; usage drop → CSM in 72h) + holdouts.

PQL-First Territory

Prioritize accounts by product-qualified score, not firmographics.
To implement, ship a simple PQL score (weights for seats, admin, SSO, imports, collab events) and route ≥ 7.

Weekly Win Factory

Every lane ships one improvement each week (cadence across GTM, not just product).
To implement, commit 1 ship/week/lane (template, sequence, activation play) and review on Fridays.

Incrementality Test Pack

A repeatable way to prove which channels/plays truly add revenue.
To implement, pick one channel, define holdout and success metric, and move 20–30% budget to winners.

AI Adoption Loop (Replace / Reinforce / Reimagine)

A simple sequence to add AI where it improves payback.
To implement, choose 3 workflows to (1) replace manual steps, (2) reinforce existing flows, (3) reimagine an experience.

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This newsletter was written and edited by Sophie Buonassisi, Tetiana Paratsii, Paul Irving, Max Altschuler and the GTMfund team (not AI!).