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.
We’ve achieved strong product-market fit in our first year, with most sales coming from inbound word of mouth and extremely fast sales cycles for ACVs of our size. We’ve scaled to this level of ARR with sales as an afterthought. We’re now looking for a rockstar to scale with us through true hypergrowth.
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.
Full-cycle ownership: from prospecting to close, no SDR hand-offs.
Source, qualify, and develop pipeline - outbound heavy in early days.
Run complex discovery and sales cycles with both blue-collar and executive stakeholders.
Deliver compelling pitches that balance storytelling with hard ROI.
Translate customer feedback into actionable insights for GTM strategy and product.
Iterate and prove out the playbook: ICP targeting, outbound messaging, pricing, and positioning.
Lay the foundation for a GTM engine that scales - be the bar-setter for future hires.
2–6 years of quota-carrying AE experience
Code-switcher: can build rapport with frontline tradespeople and hold a room with PE-backed execs.
Strong track record of quota attainment and pipeline ownership. You’ve built pipeline, not just inherited it.
Relentless prospector: comfortable cold calling, emailing, and grinding for meetings.
Discovery-driven: ask sharp questions that make prospects feel understood and position you as the authority.
Resilient: you’ve faced setbacks, rebuilt, and still closed business.
Hands-in-the-weeds builder: willing to set up your own CRM workflows and test outbound sequences, but pragmatic enough not to “systemize everything” before proving it works.
Hungry for ownership and upside. This is not a cushy AE role - it’s about proving and building.
Who You Are NOT
Order taker: If you need a full pipeline handed to you, this isn’t the role. You’ll be expected to generate demand from scratch.
Script follower: We don’t have perfectly polished decks or sequences. If you can’t adapt your pitch to different buyers - from small shops to PE execs - you’ll struggle.
Comfort seeker: Early deals are messy. You’ll cold call, get told no, iterate messaging, and still need to come back hungry the next day.
150-180K Base + Commission + Equity
Career growth upside in a hyper-growth AI startup.
Medical, dental, vision.
Monthly food stipend.
Take-what-you-need PTO + office perks.
What We Do
Increase flip rates, boost ticket sizes, and reduce windshield time— all without scaling your dispatch department.
Probook learns from your historical sales data and sends your technicians to the right calls every time.
Our dispatcher-friendly interface overlays your dispatch board so you never have to leave ServiceTitan.
Dispatchers can now focus on higher-value tasks like verifying job info and keeping customers updated.
See why top operators nationwide trust Probook!
