How does HeyHelp learn my writing style?

HeyHelp analyzes your past email threads and monitors the manual edits you make to its drafts. Over time, it mimics your tone, vocabulary, and preferred way of responding.

Do I need to manage my own AI API keys?

It depends on your plan. The Pro plan includes all-inclusive AI usage with no key required. The Connect plan allows you to bring your own API key from Google, OpenAI, or Anthropic to pay only for what you consume.

Is HeyHelp secure and private?

Yes, HeyHelp is a Google Verified App and is CASA Tier 2 certified. It uses end-to-end encryption and enterprise-grade infrastructure to ensure your email data remains confidential.

Does it work with Outlook or other email providers?

Currently, HeyHelp is built exclusively for Gmail and Google Workspace to provide the deepest possible native integration.

What is the definition of a 'User' for pricing?

HeyHelp follows the Google Workspace definition. Each dedicated user seat (e.g., name@yourcompany.com) requires one license.

Nobody owns this listing yet

HeyHelp is live in the directory, but no verified owner controls the page.

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Email management

Freemium

HeyHelp

An AI executive assistant for Gmail that triages your inbox, drafts personalized replies, and manages scheduling to save you over an hour of manual email work every day.

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Rating

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3 months ago

Listed

Email management

Productivity

Gmail assistant

AI drafting

Inbox triage

Meeting scheduling

Executive assistant

Workflow automation

Tool information

Provider

HeyHelp

Platforms

Web

Gmail

Languages

English

Added to directory

3 months ago

Last updated

about 1 month ago

Rating

Not available

Pricing

Freemium

About HeyHelp

What the tool does and who it's for

HeyHelp is an AI executive assistant designed specifically for Gmail that automates inbox management and drafting. It acts as a personal triage layer, automatically tagging and archiving incoming emails, drafting context-aware replies in your personal tone, and managing meeting scheduling. Built by the team behind DragApp, it integrates natively into the Gmail interface, requiring no new applications to learn. The tool utilizes advanced models like Gemini, GPT-4, and Claude, allowing users to choose their preferred AI engine while maintaining enterprise-grade security with CASA Tier 2 certification.

Key capabilities

AI Triage: Automatically sorts, tags, and archives incoming emails based on priority.

Smart Drafting: Prepares email replies in your unique voice by learning from past threads.

Self-Learning: Evolves over time by observing your manual edits and tagging corrections.

Flexible AI Engines: Choose to power your assistant with Google Gemini, OpenAI, or Anthropic models.

Native Integration: Works directly inside the Gmail UI without the need for external apps.

AI Scheduling: Suggests meeting times and creates calendar events based on email context.

Follow-up Automation: Tracks unreplied emails and drafts timely follow-ups to keep deals moving.

CASA Tier 2 Certified: Meets high-level Google security standards for data protection.

Pricing

Freemium — plans below

Free Trial

7-day full access
No credit card required
AI sorting and drafting
Gmail integration

Pro (Locked-in)

Pro (Standard)

All Pro features
Billed monthly or annually ($20/mo)
No API quota limits
Continuous updates

Connect (Lifetime)

199

One-time payment
Bring your own API key
Pay-as-you-go AI costs
Full feature access for life
Choice of Gemini, Claude, or GPT

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