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 50,000 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

1. Run full-cycle deals from first conversation through close. You own the pipe, the relationship, and the outcome.
2. 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.
3. 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.
4. 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.
5. Navigate enterprise deal mechanics. Engage IT, security, and procurement stakeholders. Handle security questionnaires, negotiate contracts, structure pilots, and manage multi-threaded deal cycles.
6. 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.
7. 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 Points

• Experience selling horizontal productivity or collaboration tools (the kind of product everyone in a company can use, not just one department)
• Familiarity with usage-based pricing, seat-based enterprise deals, or hybrid models with true-up and activation mechanics
• Experience at a company that transitioned from PLG/prosumer to enterprise (Superhuman, Notion, Figma, Loom, Grammarly, etc.)
• Comfort working with AI-powered workflows and tooling to accelerate your own productivity
• A network in the startup, VC, or enterprise IT ecosystem

Why Willow

• The product sells itself. Users who try Willow become advocates. You're not cold-starting demand. You're converting organic enthusiasm into revenue.
• Real ownership. You'll shape how we sell, who we target, how we price, and how we scale. This isn't executing someone else's playbook.
• High scope. You'll work directly with the CEO and be a close partner on strategy, product, and customer development.
• Incredible logos and momentum. Trusted by teams at Uber, Gusto, and more. Backed by Y Combinator. Strong organic growth and an enthusiastic user community.
• GTM support built in. Our GTM advisory team provides deal coaching, pipeline strategy, and sales infrastructure support as you ramp.
• Big ceiling. You're building the GTM function. As the company grows, you grow into a leadership role.

How to Apply

Apply here and also reach out to Allan Guo (CEO) at allan[at]willowvoice.com if you’re proactive. Tell us about a deal you built from scratch and what you learned. We'd love to meet you.