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1. What Is Meet Oscar?
Meet Oscar is an AI email assistant built specifically for Gmail and Google Workspace. It handles your email communication by drafting accurate, on-brand responses that professionals can trust.
Unlike generic AI tools, Meet Oscar integrates your business documents and learns your communication style. It reads your pricing guides, policies, FAQs, and past correspondence to ensure every reply is factually correct.
The platform works directly inside Gmail. You don’t need to switch between apps or copy-paste information. It analyzes full email threads, understands context, and generates responses that match your exact voice.
Key capabilities include:
- Auto-sorting emails by priority
- Drafting replies in seconds
- Pulling accurate details from your uploaded files
- One-click approval system
- Calendly integration for scheduling
I found it particularly useful because it eliminates the back-and-forth of copy-pasting information from documents. Everything you need is referenced automatically.
It’s designed for high-stakes communication where accuracy matters most.
2. Who Created Meet Oscar?
Meet Oscar was co-founded by Giovanni Brees, who built the platform to solve his own business communication challenges.
According to their website, Giovanni needed an AI solution that could handle the specific demands of professional email. Generic AI tools weren’t connecting to crucial business documents like prices, policies, and contracts.
He wanted something that could reply in his exact voice while verifying facts against company documentation. That combination of verified context and precision became the foundation for Meet Oscar.
The company focuses exclusively on email management for professionals who need accuracy. Their approach differs from typical AI assistants because they built the system from the ground up specifically for Gmail.
They maintain Google CASA 2 approval and use 256-bit encryption to protect sensitive business communications.
The platform launched with a clear mission: eliminate the cost of manual replies and inaccurate AI for high-stakes professional communication.
Their website emphasizes that this isn’t just “ChatGPT in a new skin” but a purpose-built email agent.
3. How Much Does Meet Oscar Normally Cost?
Meet Oscar offers three pricing tiers based on your business size and needs.
The Starter plan costs $29 per month. It keeps one inbox organized, sorts and labels every email by priority, drafts replies in your voice, pulls accurate details from your uploaded files, and includes one-click approval inside Gmail plus Calendly integration.
The Pro plan costs $49 per month. This is their most popular option. It includes everything in Starter plus priority support for faster assistance when you need help.
The Enterprise plan has custom pricing. It’s designed for large organizations and includes unlimited email processing, custom AI model training for your specific needs, a dedicated account manager, custom integration support, 24/7 premium support, and an enterprise SLA.
Both Starter and Pro plans come with a 7-day free trial and a 30-day money-back guarantee. No credit card is required to start your trial.
Annual billing is available and saves you money compared to monthly payments, though the exact discount isn’t specified on their website.
4. What Are The Benefits Of Using Meet Oscar?
Meet Oscar delivers several powerful benefits for busy professionals and teams.
You get hours of your day back. Instead of manually crafting responses and hunting through documents for information, the AI handles it in seconds. This time goes toward revenue-generating activities.
Your inbox becomes instantly organized. Every email gets auto-sorted and labeled by priority. You immediately know what needs urgent attention versus what can wait.
You eliminate errors and awkward phrasing. The AI matches your exact tone and catches typos before you send. Your communications stay professional and polished.
You focus on strategic work instead of email triage. Critical client requests, deals, and correspondence get prioritized automatically.
Other key benefits include:
- Replies are factually accurate using your business documents
- Responses stay on-brand with your company voice
- Higher revenue wins from increased strategic focus
- Faster deal closures with immediate responses
- Better work-life balance with less inbox stress
5. What Are The Main Features Of Meet Oscar?
Meet Oscar includes seven core features that transform your email workflow.
Context Understanding reads full email threads and conversation history. It knows what was discussed previously so responses stay relevant and coherent.
Knowledge Base Integration learns from your uploaded documents. Drop in PDFs, DOCs, and TXT files containing pricing guides, company policies, FAQs, and SOPs. The AI pulls accurate details from these files when drafting replies.
Voice Matching adapts to your exact communication style. It writes in your tone, whether formal, casual, or somewhere in between.
Auto-Priority Sorting labels every email by importance. You see what needs immediate attention versus what’s just informational.
One-Click Approval works directly inside Gmail. Review the AI-generated draft and send with a single click.
Calendly Integration handles scheduling automatically within your email responses.
Enterprise-Grade Security includes Google CASA 2 approval, 256-bit encryption, zero data storage, and end-to-end encryption. Your emails never sit on their servers.
6. What Companies And Brands Use Meet Oscar?
Meet Oscar is used by leading brands and professionals across multiple industries.
Major companies using the platform include:
- Coca-Cola
- Monday.com
- Indeed
- Stripe
- HubSpot
- Blinkist
- Mojo
- Italic
The platform serves professionals in high-stakes communication roles. Nicole Barrett, a lawyer, uses it for accurate legal correspondence. Adam Ferrell, VP of Sales, relies on it for client communications that need to be both personal and correct.
Target users include:
Busy executives who need to prioritize strategic work over email management.
Sales professionals who handle high volumes of client inquiries and proposals.
Legal professionals who require factual accuracy in every response.
Growing businesses that want professional communication without hiring additional staff.
The common thread is that these users deal with communication where accuracy, speed, and brand consistency are critical. They can’t afford generic AI responses or time-consuming manual replies.
7. How Have They Benefited From It?
Users report significant improvements in productivity and communication quality.
Adam Ferrell, VP of Sales, says the platform ensures his replies are personal, correct, and on-brand. Generic AI sounded amateur, but Meet Oscar adapts to his exact professional voice while maintaining factual accuracy.
Nicole Barrett, a lawyer, gained instant inbox clarity. She describes getting “accurate, on-brand replies and instant priorities” that finally make her inbox manageable.
Time savings are substantial. Users get hours back in their day by eliminating manual email drafting and document searching.
Strategic focus improves. With email handled automatically, professionals can concentrate on closing deals, solving complex problems, and scaling their businesses faster.
Revenue opportunities increase. Less time in the inbox means more time on activities that directly generate income. Deals close faster with immediate, accurate responses.
The accuracy and brand consistency eliminate the need for time-consuming edits. Responses go out faster without sacrificing quality or professionalism.
8. Does Meet Oscar Come With A Satisfaction Guarantee?
Yes. Meet Oscar offers a 30-day money-back guarantee on all paid plans.
Their website clearly states: “If Meet Oscar Doesn’t Save You Hours, You Don’t Pay.” This shows their confidence in the platform’s value.
Additional risk-reduction measures include:
A 7-day free trial on all plans. You can test the full functionality before committing to a subscription.
No credit card required to start your trial. This removes the friction of signing up and eliminates concerns about unwanted charges.
Setup takes just 30 seconds. You can evaluate the platform immediately without complex onboarding.
Enterprise-grade security with Google CASA 2 approval and 256-bit encryption protects your sensitive communications.
Zero data storage means your emails never sit on their servers. This eliminates privacy and security risks.
I recommend starting with the free trial to experience the time savings firsthand. If you’re not satisfied within 30 days of purchasing, you can request a full refund.
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