Job Description
Probook is rewriting how the $700B home services industry operates, building the backbone for our country’s backbone: hard-working blue-collar Americans. We are one of the fastest growing start-ups in Applied AI - bootstrapped to $4M ARR in under 9 months with <5 people, profitable from day one, and backed by the world's best VCs.
Key Highlights - Quick deal cycle + strong ACV = easy commission (CEO did 6m in 9 months)
- Super IC Biller OR quick path to leadership
- Profitable since week 3 (De-risked and cash-flow positive)
- $XXM ARR by Dec ’25 — no GTM team. Real revenue & PROFITABLE!
- Stacked team: ex-quant traders, ICPC world finalists, IMO Gold medalist, Meta .01%, ex-founders.
- (Base/Bonus + Un-capped commission + Accelerators + equity)
- Path to 1M+ in total cash comp
What Makes This Rare Series B/C growth and PMF, but still only 20 people. You’ll be building a GTM motion 0→1 in a company with clear demand and without the threat of “pivot hell” most startups go through.
This role isn’t for everyone. As our first AE, you won’t just sell - you’ll help prove what works. You’ll be in the field with dispatchers and operators one day, then in a boardroom with private equity executives the next. You’ll grind through cold calls, test ICPs, break eggs, and help shape the GTM playbook from scratch. If you genuinely think this is you, let’s build.
What You’ll Do
- Own the full sales cycle — from outbound prospecting to closing enterprise-level contracts.
- Develop and execute strategic outbound campaigns targeting Probook’s ideal customer profiles; no SDR hand-offs.
- Run complex discovery and sales processes with both blue-collar operators and executive decision-makers.
- Craft and deliver compelling narratives that balance hard ROI with authentic storytelling.
- Exercise independent judgment to shape deal strategy, pricing, and negotiation approaches.
- Translate customer feedback into actionable insights that inform GTM strategy and product roadmap.
- Design and refine the GTM playbook — from ICP definition to outbound messaging and positioning.
- Lay the foundation for a scalable revenue engine and set the performance bar for future hires.
Who You Are
- 3–6 years of quota-carrying AE experience, ideally in a startup or builder-stage environment.
- Code-switcher: equally comfortable talking shop with frontline tradespeople or presenting to PE-backed executives.
- Proven builder: you’ve generated your own pipeline and exceeded quota — not just worked inbound.
- Relentless prospector: thrives in outbound-heavy environments and uses data-driven tactics to target high-value accounts.
- Discovery-driven: asks sharp, business-level questions that uncover pain and position you as a trusted advisor.
- Resilient and entrepreneurial: you’ve faced setbacks, iterated, and still delivered.
- Hands-in-the-weeds operator: you’ll set up CRM workflows, test outbound sequences, and iterate until you find what works.
- Independent and strategic: comfortable making judgment calls on deal structure, prioritization, and account strategy without needing top-down direction.
- Hungry for ownership and upside: this role is about proving and building — not maintaining.
Who You Are
Not - Order taker: if you need a pre-built pipeline or marketing machine, this isn’t the role.
- Script follower: if you can’t adapt your pitch to different buyers or think on your feet, you’ll struggle here.
- Comfort seeker: early deals are messy. You’ll cold call, get told no, adjust, and come back sharper.
Compensation & Benefits - $175K base / $350K OTE + commission + equity (path to $1M+ annual potential).
- Full medical, dental, and vision coverage.
- Monthly food stipend and office perks.
- Take-what-you-need PTO in a high-accountability culture.
- Career growth and ownership in a hyper-growth AI startup scaling nationwide.
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