We're looking for a hands-on Head of Sales to run the entire sales cycle solo, set up sales systems, and recruit AEs/BDRs. You'll prospect, qualify, demo, and close 5- and 6-figure ACV deals. Experience in full-cycle B2B SaaS sales with $20K-$150K ACV wins is required.
Key Highlights
Technical Skills Required
Benefits & Perks
Job Description
About UX Pilot AI
UX Pilot AI is a profitable, bootstrapped product-led SaaS that turns ideas into actionable design in minutes. More than 14 000 designers and founders rely on us to ship better experiences, faster. We’re fully remote, async-first, and obsessed with deep work and quick delivery.
Why we’re hiring
Word-of-mouth and self-serve growth got us here, but a dedicated revenue engine can take us 10 × further. We’re looking for a hands-on Head of Sales who will:
- Run the entire sales cycle solo today from first touch to closed-won.
- Set up the systems and automations (HubSpot, Zapier, sequences) that scale tomorrow.
- Recruit and onboard the first AEs/BDRs once the playbook is humming.
- Collaborate closely with Growth and Tech, and can actively demo our product
What you will tackle
- Full-cycle selling
- Prospect, qualify, demo, negotiate, and close 5- and 6-figure ACV deals.
- Beat ambitious ARR targets as a team of one.
- Outbound engine
- Build cold-email and LinkedIn sequences; test copy, cadences, and channels.
- Double down on what converts; kill what doesn’t.
- CRM & reporting
- Own HubSpot setup - pipelines, stages, dashboards, automated tasks.
- Deliver analytics, learning and funnel metrics weekly.
- Process & playbooks
- Document repeatable discovery, demo, and negotiation flows.
- Ideate on how we can win big entering teams from our relevant user base
- Customer feedback loop
- Channel real-time insights from prospects to Design & Engineering.
- Influence roadmap with customer-validated data.
- Future hiring
- Define roles, timing, and onboarding plans for the first sales hires.
- Lead recruiting and mentoring once headcount is approved.
You might be the one if you have a few or all of these
- Spent 5+ years in full-cycle B2B SaaS sales with $20 K–$150 and + K ACV wins.
- Built a sales motion in an early stage startup, and took it 5-20mil ARR
- Built HubSpot integration (or similar) from scratch, with automations and dashboards you actually use.
- Cold outreach is your superpower - your emails and DMs get replies.
- Understand how to create market demand in collab with Growth - you didn’t just happen to get leads to close passively
- Savvy and can demonstrate the product to anyone middle of the night
- Strong xp working with US clients
- Bonus: Experience selling to product, design, or engineering leaders.
What’s in it for you
- $80k–$140k, plus commission on actively sourced deals
- Anything you need - gear, tools, learning budget - to make your work shine.
- 100 % remote, async culture, zero corporate BS.
Ready to apply?
- Send a brief hello, tell your story, and brag about wins you’re proud of (numbers welcome!). Reach our hiring manager at roberto@uxpilot.ai - we read every note and reply quickly.
Similar Jobs
Explore other opportunities that match your interests
natulim
codedesign
Director of International Strategy and Sales Enablement - Expansion Solutions
