Full-Time
Posted on 10/31/2025
AI writing assistant across apps
$260k - $340k/yr
San Francisco, CA, USA
Hybrid
Grammarly is an AI-powered writing assistant used by individuals and teams to improve writing across more than 500,000 applications and websites. It offers a range of subscriptions—Grammarly Free, Premium, Business, and Education—that provide real-time suggestions for grammar, style, tone, and clarity, integrated through browser extensions, apps, and other tools. The platform supports over 30 million users and 70,000 professional teams daily, with a strong emphasis on security and privacy as it serves many Fortune 500 companies. Grammarly’s approach combines automated language checks with tone and contextual guidance to help users communicate more effectively. The company differentiates itself through a large global user base, enterprise-grade security, and a proven track record with major customers, aiming to expand adoption across individuals and organizations to improve written communication at scale.
Company Size
1,001-5,000
Company Stage
Debt Financing
Total Funding
$1.4B
Headquarters
San Francisco, California
Founded
2009
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401K / Retirement Plan
Half Baked #577: 401(k) recovery, Stitch x Claude... Plus Bootstrapping an AI company to a $1.2B valuation Mar 30, 2026 Welcome to Half Baked, the newsletter serving up startup ideas as talked about as OpenAI going public later this year? In today's edition: * | AI agents that recover lost funds * | The Google Stitch + Claude Code design workflow * | Bootstrapping an AI company to a $1.2B valuation + more * | Meta model, $170M raise, market update + more * | A cooler way to get around Let's goooo Half Baked x Grammarly: This week Gethalfbaked has partnered with Grammarly to offer one Half Baked reader a new MacBook Neo to support them on their founder journey. To be considered, just: Shoutout to last week's winner Andrew Ali. Good luck! Gethalfbaked is Hiring: Gethalfbaked is looking to hire a new Head of Content at Half Baked. If that sounds like something you'd be interested in, let Gethalfbaked know here. AI agent for 401(k) recovery. The Problem: The other day I sat down with a financial advisor to talk about something riveting...my 401(k). He asked me a pretty simple question - how many retirement accounts have I had with different companies. I told him I wasn't sure and he looked at me the way a doctor looks at someone who hasn't had a checkup in a decade. And it turns out a lot of Gethalfbaked are in the same boat. There's $1.65 trillion of Americans' money sitting in forgotten 401(k)s. In the UK? £26.6 billion. And trying to recover these funds is a bit of a pain...scrolling through government websites, calling HR departments, finding old tax forms. Well luckily for Gethalfbaked this is the kind of monotonous work agents can do in 2026. Here's what Gethalfbaked is thinking. The Solution: The Idea: An AI agent that autonomously hunts down every 401(k) you've ever had. * Connect your IRS account and VaultTrace pulls your full W-2 history to identify every employer you ever had a retirement plan with - then autonomously contacts HR departments, cross-references the National Registry, DOL Form 5500 database, and state unclaimed property registries to track every retirement account down. * One-click consolidation rolls everything into a single account with zero paperwork, with ongoing monitoring and escheatment alerts forever after * Long term, the company could open its retrieval infrastructure as an API - letting HR platforms embed 401(k) finding directly into employee onboarding and allow people to invest these recovered funds too. Nice. Business Model: Free to search, $99 flat fee per account successfully recovered. The average recovered pot is worth $9,500 - a $99 fee is an easy sell. End Goal: Acquisition by Fidelity, Betterment, or Robinhood looking to own the retirement consolidation funnel. 6-10x revenue multiple - realistic $50-150M exit. Rate this idea. How to make AI writing actually sound like you. You're probably using AI to write emails, pitch decks, investor updates...and just about everything else. The problem? So is every other founder, and your readers can tell. Grammarly fixes that. What it does: * Humanizer rewrites AI text to match your natural voice * Reader Reactions previews how your message lands before you hit send * Works across email, docs, and browser with zero tab switching 40M+ people use Grammarly and it's 100% free to start. The Google Stitch + Claude Code design workflow. The Context: Most AI-built apps have the same problem - the features work but the UI looks like it came off a production line. This workflow uses Google Stitch 2.0 to generate a complete design system and a single markdown file to lock your design language across every screen, so Claude Code stops drifting every time you prompt it. Step-by-step: * Drop screenshots of your existing app (or 2-3 Dribbble inspiration images if starting fresh) onto the Stitch canvas, then write one focused prompt describing your app and the design direction you want - dark mode, minimal, editorial, whatever fits - and generate multiple variants to curate from. * Once you're happy with the designs, go to Design Systems in the right-hand panel, click into design.md, and copy the entire file - this is your auto-generated typography scale, color palette, component rules, and spacing specs in one place. * Create a design.md file in the root of your project and paste it in - from this point forward, Claude Code will reference this file on every prompt and your design language stays consistent across every new screen and feature. * Connect Stitch to Claude Code via MCP (grab the install command from the Google Stitch docs, create an API key in Stitch Settings, and paste both into your Claude Code terminal), then prompt Claude to rebuild your UI directly from the Stitch frame source code. Become the calmest, most credible voice in the room on AI. AI should help you think better, not drown you in jargon. Mindstream is a human-first newsletter that turns complex topics into plain language, examples, and checklists you can use immediately. Whether you're a bridge builder aligning execs and engineers, a strategic navigator sizing up your next bet, or a practical learner building confidence one issue at a time, each brief respects your time and your intelligence. Five minutes to read, instant value to apply, and zero hype to filter out yourself. Founder fuel. Money Shot: This MIT dropout bootstrapped his company to a $1.2B valuation. Here's how. Prompt Drop: This prompt can turn Claude into your virtual CEO. 🆓 Founder Resource: Boris Cherny (creator of Claude Code) just shared a bunch of his favorite hidden and under-utilized features in Claude Code. Very cool. Founder Deal: Get a 45-day free trial of Wispr Flow on Gethalfbaked, its most used AI tool at Half Baked. Founder finds. Meta just unveiled TRIBE v2, a foundation model trained to predict how the human brain responds to any sight or sound. Meta's ad targeting is about to get ridiculous... Redpoint just released their 2026 Market Update, giving the latest read on where they think the market is heading. Brian Chesky thinks AI founders are leaving money on the table. Most AI capital is chasing B2B, but he believes the real opportunity is in consumer products people use every day. Aaron Levie's recent piece on the "capability overhang in AI" (that models can already do far more than most companies are actually deploying, and the gap is widening every week) is well worth a read. Drunk business idea: motorized cooler. * Enjoy a cold beer in the sunshine? Wish your cooler had wheels...and a motor...and went 16 mph? * Introducing CruzinCooler(TM), the world's first rideable electric cooler scooter. It's a full-size cooler with a 1000W motor, three wheels, and a top speed that'll get you a noise complaint in most campgrounds. It holds your beers and even brings you to the party. * CruzinCooler(TM)- the frost and the furious. That's all folks! Before you go just a few public service announcements: * Have an idea you want feedback on? DM me to discuss it or book in for Office Hours here. * Looking to sponsor Half Baked? Just fill out this form and Gethalfbaked'll get back to you asap. See you soon, John and Darragh | The Half Baked Team
Grammarly faces lawsuit over AI tool using academics' identities. Promoted by Amazon Alexa EdTech Skills Challenge
Superhuman disables controversial Grammarly AI feature. Superhuman has disabled Grammarly's "Expert Review" feature that impersonated real writers and academics, following outrage and a class-action lawsuit against the company. The tool, launched in August, used AI to generate feedback credited to specific experts without their consent. Living authors expressed outrage, leading to a class-action lawsuit against Superhuman. CEO Shishir Mehrotra announced the decision to suspend the feature on LinkedIn on March 11, 2026. The controversy highlights the legal risks of AI systems that scrape personal data to create commercial products. The feature relied on publicly available information from third-party LLMs to mimic experts. It displayed names of both living and deceased individuals alongside a disclaimer. The disclaimer stated the references were for informational purposes only and did not imply endorsement. The feature allowed users to select experts based on subject matter. It included figures ranging from scientists to fiction authors. Users received feedback generated to appear as if it came from these individuals. The tool did not seek permission from the people named. Mehrotra stated the agent was designed to help users discover influential perspectives. Grammarly initially attempted to mitigate backlash by allowing writers to opt out of the platform. This response failed to satisfy many critics. A class-action lawsuit is currently underway against Superhuman regarding the tool. Mehrotra said the company is reassessing the feature before any potential reintroduction. Grammarly is a widely used writing assistant. Superhuman, primarily an email productivity app, acquired Grammarly in a major industry deal. The acquisition positioned Superhuman as a broader productivity platform. The company faces ongoing scrutiny regarding its use of AI and user data.
Grammarly, now part of the rebranded Superhuman company, has introduced an "expert review" feature that offers AI-generated feedback styled after real authors and academics—both living and deceased. Users can receive critiques from simulated versions of figures including Stephen King, Neil deGrasse Tyson, Carl Sagan and editor William Zinsser. The feature provides no actual involvement from these individuals, with a disclaimer stating references are "for informational purposes only" and don't indicate affiliation or endorsement. The company says the AI examines users' writing and surfaces expert content to help shape their work, pointing users towards influential voices. The legality of training AI on these individuals' works remains unclear and has sparked criticism. University of Birmingham professor Vanessa Heggie called the practice "obscene", accusing the company of trading on names and reputations without permission.
ASU teams Up with Grammarly to deploy agentic AI assistant. Arizona State University recently partnered with Grammarly to integrate agentic AI into teaching and learning, becoming the first university to deploy Grammarly's Superhuman Go AI platform. Superhuman Go is an agentic AI assistant designed to solve campuswide challenges such as siloed data and information, tool fragmentation, and contextualized student support, Grammarly explained in a news announcement. ASU will have early enterprise access to Go, "pressure testing" the platform's capabilities to ensure it meets the needs of higher education institutions. Utilizing Go, students, faculty, and staff will be able to "extract, organize, and act on knowledge within their organizational context," Grammarly said. ASU plans to build its own custom agents on the platform, including a tool that will help with course and instructional design as well as tools "that can add student value wherever they are reading, writing, or communicating on their devices." In addition, ASU faculty will partner with Grammarly to create a new AI-native assignment workspace that "reimagines written assignments with AI support" in the AI era. Instructors will be able to configure assignments to their course needs, creating coursework that allows students to brainstorm, research, write, and revise with AI guidance. The goal: "to provide a model for how higher education and technology vendors can use AI to support authentic learning and support students, faculty, and administrators as they navigate AI integration," Grammarly said. "There is no doubt that AI is radically reshaping how we teach, learn, and work," commented Nancy Gonzales, executive vice president and university provost at ASU, in a statement. "ASU's expertise in educational technology and innovation, combined with our scale and technical sophistication, requires us to take responsibility for how these technologies shape the educational process. We are proud to take the leadership role with partners like Grammarly to ensure that AI improves and expands the success of our students and enriches the teaching experience for our faculty." "Arizona State University has been an invaluable partner in defining what agentic AI means for education," said Jenny Maxwell, head of Grammarly for Education. "Its willingness to test early versions of our product, provide detailed feedback, and push us to think differently about how AI can support both learning and operations has been crucial to building a platform that actually works for higher education. This partnership represents what's possible when a forward-thinking institution collaborates closely with an AI-native company." Rhea Kelly is editor in chief for Campus Technology, THE Journal, and Spaces4Learning. She can be reached at [email protected]. * Organizations Face Obstacles to Cloud Infrastructure Readiness in the Face of Increase in AI-Driven Workloads Enterprise cloud teams are hitting barriers to scaling and resilience as AI-driven workloads surge, according to a new report from ControlMonkey. * The Shadow AI Threat: Why Higher Ed Must Wake Up to Risks Before the Headlines Hit The most concerning issue with artificial intelligence may not be in the tools themselves, but in how quietly they're being used without oversight. * McGraw Hill Intros AI-Powered ALEKS for Calculus McGraw Hill has expanded its lineup of ALEKS digital learning products with ALEKS for Calculus, bringing AI-powered personalized learning support to the calculus classroom. * "Engineering and the Good Life" at Santa Clara University An ethics across the curriculum program at Santa Clara University's School of Engineering supports ethical reflection in engineering design and encourages each student to consider what it means to them to be an engineer.