The setting
is a productivity software company for people who work in email all day. is its email app for Gmail and Outlook, with AI that drafts replies, sorts messages and surfaces follow-ups.
The upgrade flow is increasing purchases while leaving customers unsure what access they bought.
The default launch protects growth momentum, while clearer entitlement language protects trust after purchase.
Who you’d be doing this for
“I upgraded for the workflow I saw, then my team asked why the rest of it wasn’t there.”
Kavita Sengupta · Agency Account Director · a character in this brief
Manages client communication in Superhuman Mail and evaluates productivity tools for a small account team.
What is at stake
New subscribers are buying an upgrade with conflicting expectations about access. You must decide how much purchase momentum can move before customer understanding is proven.
Why it isn’t already fixed
Every obvious fix costs something else. That’s the part you’d have to decide.
- upgrade velocity vs. informed commitment
- cross-product discovery vs. clear access boundaries
- default-launch timing vs. validated comprehension
- premium simplicity vs. explicit entitlement detail
Why Superhuman
Superhuman Mail sits inside a suite where customers discover Grammarly and Superhuman Docs through connected activation journeys.
Written with these in mind
Not your kind of problem? 36 more at Superhuman, or browse every organization.
Where the organization context comes fromThe postings this brief was written from, and the reporting read before it.
The organization context comes from public information. The situation and characters are written for the brief.
Job postings it was written from
Public descriptions of the work at Superhuman. They are listed as sources, not as openings. The lines under a posting are its own words, where it meets this brief.
- Staff Product Designer, Go (opens in a new tab)
- As Superhuman grows into an AI-native productivity suite across Docs, Mail, and more, Go is the layer that helps people move from intention to execution—advancing ideas, producing useful outputs, and keeping momentum without constantly switching tools or contexts.
- Prototyping as thinking: Use interactive, high-fidelity prototypes to explore new interaction models, motion, and AI behaviors, treating prototyping as a core part of how ideas take shape.
- Staff Product Designer, Mail Growth (opens in a new tab)
- Superhuman offers a remote-flexible working model for this particular role on the Mail team.
- You’ll lead design for Superhuman Mail’s growth efforts, shaping onboarding, in-product activation, and purchase experiences for customers across our suite of collaborative products.
- Senior Product Designer, Growth (opens in a new tab)
- Own the design of key growth surfaces including onboarding, activation flows, referral programs, and upgrade moments across Superhuman’s product suite
- The company’s products include Grammarly’s writing assistance, Superhuman Docs’ collaborative workspaces, Mail’s inbox management, and Go, the proactive AI assistant that understands context and delivers help automatically.
- Growth Design Manager, Web & Acquisition (opens in a new tab)
- We started as Grammarly, and we’ve rapidly added new teams and products to our portfolio to become Superhuman — from Docs, Mail, Rows, and most recently GPTZero and Fathom.
- Lead the design of interactive web experiences — logged out product experiences, personalization opportunities, and other high-engagement web tools — that create real value for visitors from the moment they visit us and accelerate their path to becoming Superhuman customers.
- Senior Product Designer, Cross Activation (opens in a new tab)
- Collaborate with Product Managers to shape the vision and roadmap for cross-product activation initiatives, creating cohesive experiences that help users discover and engage with Grammarly, Superhuman Docs, and Mail as a unified suite.
- Design impactful onboarding, activation, upgrade, and early-lifecycle experiences that help users discover features, build habits, and realize value across the Superhuman suite.
This is the setup. The work is inside.
Running it puts you in the room: the full situation and its constraints, stakeholders who push back in their own words, and the decisions that are yours to make. What you produce becomes a Day One Plan — work you can show someone instead of describing.
Where similar work appears
Other live briefs connected to this one, and what connects them.
Similar problems at other organizations
Like this one, each of these is about people starting something and never quite finishing it.
Membership-step completion has fallen to 59%, and shoppers are reopening plan details before leaving.
You have to weigh a clearer buying decision against the shortest possible checkout path.
Seasonal accounts finish jobs during the trial but convert 10 points lower when closeout work never links to money collected.
You set the audience rules and proof points, without overstating what owners will earn.
Click-to-membership conversion has fallen from 8.0% to 6.1% for one-order trial members.
You have to weigh a concrete savings story against a simpler membership message with one send left.
The same setting, from another role
Each is set around Superhuman’s Superhuman Mail, written for a different role. They’re separate briefs, not the same scenario.
Enterprise feedback is being interpreted as competing one-off requests, delaying clarity on what blocks rollout.
You have to decide where AI groups evidence and where PM judgment remains the gate.
Enterprise displacement reviews keep producing competing interpretations of the same channel signals.
You must decide what AI recommends and what the strategist must still judge.
Recruiters are seeing Gmail replies while some threads in the mail client stay stale.
You must decide where a ranked suspect in the message flow stops being the system's finding and becomes the engineers' confirmed cause.
Other problems with a similar purpose
In each of these, as in this one, the aim is to make a bold growth decision that still holds up to scrutiny from the people it affects.
A trust-report campaign's top-testing headline rests on a benchmark from sampled customer data and unchecked machine-made categories.
You have to weigh the demand it could create against a claim you may not be able to back.
Non-designer participation is down 19% in large workspaces 120 days before renewal, and some of that is deliberate.
You have to pick rules that will hold for a quarter, without calling healthy customers at risk.
Next month, regulated and global accounts can only start through the new assessment, and its routing is not yet proven for them.
You weigh speed against tighter access, because retiring the old paths is hard to undo.
