Willow

What is Willow? Willow is a voice dictation app that lets you type anywhere on your computer using your voice. People rely on Willow every day to write emails, respond in Slack, prompt AI, and move faster in their work. But dictation is just where we're starting. We're building the voice operating system. A system that writes for you today, takes actions for you tomorrow, and eventually anticipates what you need before you ask. Your voice becomes the primary way you create, communicate, and control your computer. We've proven adoption, from over 100,000 individual power users to enterprises like Uber. We're backed by Y Combinator, Box Group, and founders from Instacart, Reddit, Shopify, and HubSpot. Our enterprise motion is already gaining traction. We have active deals with household names, strong inbound demand, SOC 2 and HIPAA compliance, and a product that sells itself once people try it.  What we need now is someone to take that momentum and build a repeatable sales engine around it. The Role This is not a typical AE seat. You'll be the first dedicated sales hire at a company where the product already has real pull. Users are signing up, teams are expanding organically, and enterprise buyers are reaching out. The opportunity is to take something that's already working and make it systematic, scalable, and repeatable. You'll partner directly with the CEO and work alongside our GTM advisory team (Second Rodeo) to shape how Willow goes to market. Everything you build here becomes the playbook the company scales on. What You'll Own Run full-cycle deals from first conversation through close. You own the pipe, the relationship, and the outcome. Convert product-led demand into enterprise revenue. Willow has thousands of active users inside companies. Your job is to identify the highest-potential accounts, find and enable champions, and turn organic adoption into commercial deals. Build and execute the expansion motion. We've landed inside major logos. You'll map usage, identify new teams, arm champions with business cases, and drive department-by-department expansion. Systematize inbound and prioritize pipeline. Work with usage and signup data to build a scoring system that surfaces high-intent accounts and ensures nothing slips through the cracks. Navigate enterprise deal mechanics. Engage IT, security, and procurement stakeholders. Handle security questionnaires, negotiate contracts, structure pilots, and manage multi-threaded deal cycles. Shape the sales narrative. Collaborate with the founding team on positioning, objection handling, competitive differentiation, and pricing strategy. Your field insights directly influence what we build and how we sell. Document everything. Your learnings become the playbook. Templates, sequences, talk tracks, deal stage definitions. You're building the foundation the GTM team scales on. Who You Are You've sold into enterprise before. 2-5+ years in full-cycle sales, ideally at early-stage B2B SaaS or developer-focused/productivity companies. You know how to navigate multi-stakeholder deals with IT, security, and procurement. You've built before. Founding AE, first sales hire, or early GTM at a company where you had to figure things out, not just execute a playbook someone handed you. You understand PLG-to-SLG. You know how to take bottom-up product adoption and convert it into top-down commercial relationships. Champion enablement, usage-based scoring, and land-and-expand are second nature. You're a systems thinker who uses tools to multiply yourself. CRM hygiene, pipeline management, outbound tooling, AI-powered workflows. You don't just sell. You build infrastructure around how you sell. You communicate with clarity and empathy. You tailor your message to founders, IT directors, CTOs, and COOs. You build trust while driving urgency. You have a strong sense of ownership. You don't wait for someone to tell you what to do. When something is broken or missing, you fix it or build it. Bonus

What is Willow? Willow is a voice dictation app that lets you type anywhere on your computer using your voice. People rely on Willow every day to write emails, respond in Slack, prompt AI, and move faster in their work. But dictation is just the beginning. We're building the voice operating system: write with your voice today, control your computer with your voice tomorrow, and eventually let it act on your behalf before you even ask. We've proven adoption from individual power users to enterprises like Uber, Gusto, and Heidi Health. We're backed by Y Combinator, Box Group, and founders from Instacart, Reddit, Shopify, and HubSpot. We're scaling quickly, and you'll be joining early. The Role We're looking for a Growth & Content Lead to help scale how millions of people discover Willow. This is a Swiss-army-knife growth role. You'll work directly with the CEO to 10x what we've built across content, creators, affiliates, SEO, launches, paid creative, and GTM campaigns. This role is a mix of growth, content, and ops. You'll come up with ideas, run experiments, create content, manage creators, build systems, and help turn Willow into a much larger consumer and prosumer growth engine. You'll: You'll build and execute Willow's content strategy across TikTok, LinkedIn, X, YouTube Shorts, and other channels where Willow can grow. You'll create content yourself, manage creators and UGC partners, write briefs, test hooks and formats, and study what drives reach, conversion, and retention. You'll build our creator and affiliate programs: sourcing the right partners, onboarding them, improving their content, tracking performance, and scaling from dozens of partners to hundreds. You'll work closely with our paid ads and influencer experiments, turning strong organic ideas into paid creative and using performance data to sharpen our messaging. You'll help lead SEO / AEO, product launches, events, and GTM campaigns. When we ship something new, you'll help plan the campaign, coordinate assets, drive distribution, support events, and turn the launch into real growth. What We're Looking For You have viral sense. You understand why some ideas spread and others do not. You can look at a post, video, landing page, or campaign and quickly see what would make it sharper. You're a creator. You can write, edit, brief, package, and ship content. You understand hooks, pacing, clarity, taste, and distribution. You're an operator. You like moving fast, working through ambiguity, and figuring things out. You can run experiments, manage people, build systems, and turn early traction into repeatable growth. Strong signals: Personal track record: 10k+ followers, a side project with real traction, or content that has reached a meaningful audience Previous founding team member or early growth employee at a high-growth consumer, prosumer, or PLG company Experience scaling an influencer, creator, affiliate, or UGC program efficiently 2+ years working with content creators, creator partnerships, social content, or growth campaigns Strong writing, taste, and ability to turn messy ideas into clear campaigns Passion for productivity, AI, voice technology, or new computer interfaces In-person in San Francisco. We're building in person. Before You Apply Research the product. Download Willow, try it, and understand why this matters and how we grow. We want people who already get it. Know what you're signing up for. We're an intense environment. We optimize for learning, achievement, and career growth, and that means we work very hard. If you want to be challenged and grow fast, we'd love to hear from you. Reach out proactively. Don't just submit an application. Reach out and show us how you think.

About Willow Willow is a voice-first productivity app that lets you type anywhere on your computer using your voice. People rely on Willow every day to write emails, respond in Slack, prompt AI, take notes, and move faster through their work. We’ve proven adoption from individual power users to enterprises like Uber, Gusto, and Heidi Health. We’re backed by Y Combinator, Box Group, and founders from Instacart, Reddit, Shopify, and HubSpot. We’re scaling quickly, and you’ll be joining early. The Role We’re looking for a Founding ML Research Engineer to build Willow’s personalization layer. This role is for someone who believes the hardest unsolved problem in AI products is not raw model capability, but context and user modeling. Foundation models are getting better every month. The open question is how to build an AI system that understands a specific user in the flow of their work. You’ll work on the systems that turn Willow from “great dictation” into a personalized communication and intent layer. Today, a user can say something rough like: “Tell my boss I’ll come in at 6.” Willow should understand the screen, the relationship, the app, the user’s tone, their past edits, their communication style, and produce the message the user would have written if they had taken the time to write it well. What You’ll Work On You’ll help build systems for: 1. Personal writing and behavior models that learn from edits, preferences, workflows, tone, formatting, and user actions 2. Intent-to-action systems that turn rough user intent into high-quality execution 3. Multimodal context understanding across voice, screenshots, app state, selected text, workflows, and historical behavior 4. Retrieval and memory systems that understand what context matters in a given moment This is not a pure research role and not a generic ML infra role. You should be excited to take ambiguous ideas, ship quickly, learn from real-world usage, and iterate aggressively. What We’re Looking For You are unusually excited by personalization, context, workflows, and user modeling. You think deeply about questions like: 1. How does an AI system learn what a user actually means? 2. How do you build systems that feel genuinely personalized instead of generically helpful? 3. How do you evaluate trust? You probably have some combination of: 1. Strong applied ML or research engineering ability 2. Experience with LLMs, VLMs, agents, speech, personalization systems, retrieval, or multimodal systems 3. Strong product intuition and taste We care much more about technical depth, product intuition, and speed than credentials or years of experience. Why This Matters The first major computer interface was the keyboard. The second was touch. The third is voice. But the opportunity is larger than voice itself. Voice matters because it captures intent naturally and with very low friction. By living directly inside user workflows, Willow gains something most AI systems do not have: continuous, real-world context. We believe this becomes increasingly important as AI systems become more autonomous. Foundation models will become extremely good at long-horizon execution, but the highest-frequency interactions on a computer are different: fast, contextual, ambiguous, and deeply personal. That requires understanding not just the task, but the user: their workflows, preferences, communication patterns, and intent in the moment. Exactly what Willow can capture.  Before You Apply Try Willow. Use it in your real workflow. Dictate messages, emails, prompts, and notes. Think about what it would take for software to truly understand your intent. We’re an intense, highly ambitious, in-person team in San Francisco. We optimize for learning, ownership, speed, and exceptional work. You’ll have significant responsibility, direct ownership, and the opportunity to shape the future direction of the company very early. Don’t just submit an application. Reach out and show us how you think.

What is Willow? Willow is a voice AI company building the application layer for how knowledge workers communicate at work. Our first product is a voice dictation tool that caught fire immediately with world-class retention. People who adopt Willow replace up to 80% of their typing at up to 4x the speed through voice. Engineers use it to prompt AI tools like Cursor, Claude, and ChatGPT. Busy professionals use it for email, Slack, and everything in between. Our second product is a scribe that takes what you mean and turns it into finished communication across every platform, in your voice, in seconds. Willow lives on every surface you work on, builds context and personalization over time, and is becoming capable of far more than transcription. Instead of writing, you express intent. Willow handles the rest. Eventually Willow becomes the voice operating system for your computer. We are seven figures in ARR, 100k+ in users, growing 30% month over month, with Fortune 500 enterprise companies like Uber. We’re a small, fast, and highly technical team from Stanford and YC in San Francisco. The Role We're looking for a Product Designer who can think in systems and own product surfaces end-to-end. You'll be in the room making product decisions. The bar is high. Our users are fast, opinionated professionals who notice when something is one click too many or one animation too slow. Great design here is about removing friction between thought and output, and that requires someone who genuinely cares about both craft and outcomes. What You'll Do Own problem areas from concept to launch - flows, wireframes, and high-fidelity specs Collaborate tightly with engineers and founders to prototype, test, and ship across core product surfaces Define success criteria and ship work that moves activation, retention, or conversion Partner with engineering to ensure designs are feasible, performant, and maintainable Run user research, study analytics, and conduct usability testing to validate solutions before they scale Move fast and light with quick prototypes and lean experiments, with a strong eye for brand and modern, clean, sleek aesthetic What You'll Bring 3+ years of end-to-end product design experience, ideally on productivity or workflow tools, with a portfolio of shipped work Proficiency in Figma and modern prototyping tools with ability to produce clear specs close to engineering A metrics-minded approach — you set success criteria, track outcomes, and know whether your work moved the needle Familiarity with modern productivity and personal tools (Notion, Linear, Superhuman) and intuition for how knowledge workers actually work Strong visual design and brand instincts, with comfort evolving design systems that are aesthetic, clean, and scalable Experience on a small, fast-moving team where you owned projects from research to shipped UI To Apply Download Willow and use it. Understand why it matters from the inside. Know what you're signing up for. We're a small team moving fast in San Francisco. We optimize for learning and growth, and that means working hard. Don't just submit an application. Make sure to attach your best portfolio and show us how you think.