ABOUT PROBOOK
Probook is the AI Operating System for the home services industry, transforming how plumbing, HVAC, and electrical businesses operate.
Our impact is real. Dispatching the right technician to the right job can mean the difference between a $300 "band-aid" fix and a $20,000 system replacement. By automating previously high-touch workflows around-the-clock, Probook ensures a consistent customer experience without the need for 24/7 live staffing. We unify our customers' processes into a single, scalable platform, giving businesses one place to run their entire dispatch operation.
Role Description
Probook is hiring a founding Head of Talent to build the recruiting engine for its next stage of growth. This person will own the systems, processes, and standards that make hiring repeatable at scale, while personally closing the company’s most important technical and leadership hires. The role spans intake discipline, scorecards, evaluation rubrics, ATS hygiene, hiring manager calibration, employer brand, and team development.
Probook needs a hands-on function builder who can protect a high talent bar under pressure, create engineering top-of-funnel from zero, and hire across engineering, product, sales, marketing, ops, and CS. This is a high-autonomy, CEO-reporting mandate for someone who has built an early-stage recruiting function before and is equally credible as a strategist, operator, and closer.
What You Will Own
The Build: You will get under the hood of the existing process and add the structure that makes great hires repeatable as we scale. Intake discipline, scorecards, SLAs, evaluation rubrics, and ATS hygiene are all in scope.
The Hiring Engine: You will drive the hiring engine that helps us scale to meet our market opportunity spanning engineers, product, sales, marketing, ops, and CS, from IC to VP. You'll personally close the marquee hires while building the systems that let the broader team run the rest with confidence.
The Bar: You will protect Probook's quality bar across every function and level. You'll calibrate it across roles you've never personally hired for and push back on hiring managers who want to lower it, without sacrificing speed.
Brand From Zero: You will own engineering top-of-funnel, which is our biggest sourcing challenge. With minimal marketing budget, you'll build the content, community, and engineer-as-ambassador playbook that turns Probook into a destination for talent.
The Team: You will partner with our two existing recruiters and recruiting coordinator, develop them as the function grows, and expand the team over time as our hiring volume increases.
Who You Are
"A Function Builder": You've stood up or evolved a recruiting function at a venture-backed startup before 100 people. You've managed recruiters at depth, not just had them report to you. You have opinions about tooling, process, and what separates a great recruiter from a good one, and you can defend those opinions to the engineer or operator who pushes back.
"Hands-on Closer": You'd rather close a critical hire yourself than route them through a coordinator. You've personally landed critical hires, run searches, or owned the first 50 to 80 hires at a startup solo. "I usually manage the process, not execute it" is not in your vocabulary.
"Bar Defender": You've actually pushed back on a founder or VP who wanted to move a candidate forward that didn’t hit the bar, and you can tell the story. You calibrate by going deep on prior best hires, not by reading a JD. Under velocity pressure, you don't fold; you offer alternatives.
"0-to-1 Brand Builder": You've built an employer brand at a company that didn't yet have one. You've organized meetups, run dinners that converted into hires, and convinced engineers to spend time on content without burning their week. You view a brand as a top-of-funnel multiplier, not a marketing line item.
"Cross-Functional": You've hired engineers, salespeople, ops, CS, and product, at every level, in the same company. You know that sourcing a Staff Engineer and an SMB AE are different sports, and you can speak credibly to both.
Requirements
7 to 15 years in talent acquisition or recruiting at a high-growth B2B SaaS company, with at least one stint as the founding or early talent hire at a venture-backed startup before 100 people.
Demonstrated track record of building or evolving a recruiting function: designing the system, not just executing inside one someone else built.
Personally hired top tier talent across technical (engineering, product) and non-technical (sales, marketing, ops, CS) roles in the same organization, at every level from IC to VP.
Has managed a recruiting team, including hiring, developing, and calibrating recruiters.
Has built employer brand from zero, with concrete examples of content, community, or candidate-facing initiatives that moved measurable inbound pipeline, ideally on the engineering side.
Tech-forward: fluent in modern AI-enabled recruiting tooling and comfortable using data to surface bottlenecks and resolve them quickly.
NYC Based: Excited to work in-office 5 days/week in our high-collaboration culture.
Why Probook
The Tailwinds: $700B industry with clear tailwinds: AI adoption, labor shortages, and generational transitions creating demand for operational modernization. We are defining the category, not fighting for share.
The Traction: $XXM ARR in 18 months. Product-market fit proven; now we're scaling.
Funding: $40M raised from Sequoia and Andreessen Horowitz
The Team: >60 people, our founding team comes from the space and has spent thousands of days onsite with our customers. We live the space. We're also becoming one of the most talent-dense start-ups in NYC (MIT, Harvard, UPenn M&T, Waterloo, Citadel, Palantir).
Compensation & Benefits
Base: $225,000 - $275,000 (Can flex depending on YOE)
Equity: Meaningful early-stage equity.
Health: Comprehensive medical, dental, and vision.
Perks: $500 monthly Ramp card for commuting, meals, gym, etc. (plus $25 in nightly meal delivery credit) and really good office snacks.
Access: Direct access to world-class investors and advisors.