What this role is

This is a growth role with direct impact on revenue.

You will own how users move from signup to activation, from activation to paid, and from paid to expansion. Email is your primary lever, but you will influence the full lifecycle across onboarding, engagement, upgrade, and retention.

If users don’t activate, convert, or stay, you will understand why and fix it.

Why this role matters

Cal.com already has strong top-of-funnel growth. The opportunity now is to convert more of that demand into active, paying, and expanding users.

This is where most companies leave money on the table.

If you do this well:

• Activation improves

• Conversion increases

• Retention compounds

• Revenue follows

Few roles offer this direct line between your work and company growth.

What you’ll do

Own the lifecycle

• Design and run flows across onboarding, activation, upgrade, and retention

• Map the full user journey from signup to long-term usage

Drive activation

• Improve time to first value

• Identify where users drop off and fix it

• Ship flows that get users to their first successful booking

Drive conversion

• Turn active users into paying customers

• Test pricing, offers, and messaging within lifecycle touchpoints

• Increase trial-to-paid conversion

Drive retention and expansion

• Re-engage inactive users

• Increase usage across features and teams

• Support expansion through targeted lifecycle campaigns

Write and ship

• Write clear, direct-response email copy

• Build and launch campaigns quickly without heavy dependencies

• Use AI tools to increase speed and output

Measure and improve

• Track performance across activation, conversion, retention, and revenue

• Run experiments and iterate based on results

The shape of the role

This role combines lifecycle strategy, copywriting, and growth.

You should be able to:

• write emails that drive action

• design flows that move users forward

• analyze performance and decide what to do next

You will have high ownership and minimal approval layers. You are expected to ship, measure, and improve continuously.

What winning looks like

Users reach first value faster

• Activation rates increase

• Trial-to-paid conversion improves

• Churn decreases

• Expansion revenue increases

Lifecycle becomes a consistent, measurable driver of growth

Who this is for

You:

• Have run lifecycle or email programs that drove real outcomes

• Can write clear, conversion-focused copy

• Think in funnels, not campaigns

• Are comfortable owning metrics tied to revenue

• Use AI tools to move faster

Who this is not for

• This is not a brand or newsletter role

• This is not a role focused on design or long-form content

• This is not a fit if you prefer planning over shipping

About Cal.com

Cal.com is building scheduling infrastructure for the internet.

We power how time gets scheduled across teams, products, and platforms.

If Stripe handles payments, Cal.com handles time.

Details

• Remote, async-first

• $60k base + performance bonus + equity

Why work at Cal.com?

We’re building Cal.com not just as a product, but as a place to do great work and live a good life.

• 🌐 Work from anywhere, anytime, fully remote & async

• 💸 Earn the same salary no matter where you live

• 📅 No standups, no micromanagement, no unnecessary calls

• 🪩 Real flexibility, take time for life stuff, no approval needed

• 💻 Work in your own flow, pajamas welcome

• 🧘 30 paid OOO days per year (wherever you are in the world)

• ✈️ Yearly team retreats in beautiful locations

• 🏡 People-first culture, stable, family-friendly, kind