Staff Software Engineer

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.

The Opportunity

This isn't a role where you'll optimize existing features—you'll define and ship the product capabilities that unlock our next phase of hypergrowth. The products you build in the next 12 months will serve tens of thousands of users and process hundreds of millions in transactions.

You'll own entire product surfaces end-to-end, set technical and product quality standards for the engineering org, and work directly with leadership to translate business strategy into shipped product.

Every feature you ship will directly impact our ability to capture market share at speed. You'll see your work drive millions in ARR in real-time, validated by direct customer feedback from our in-person onboarding process.

What You'll Do

Product Ownership & Delivery

• Own complete product surfaces from conception to production—backend systems, frontend interfaces, AI integrations, and everything in between

• Ship production AI products that automate complex workflows for thousands of service businesses

• Build features at a pace that would take quarters elsewhere—expect to move at startup velocity while maintaining staff-level quality

• Make product and technical decisions that balance user needs, business impact, and technical excellence

• Drive multi-month initiatives that unlock major product capabilities and revenue opportunities
  

Technical Leadership

• Design systems and product architectures that scale to 100x current usage

• Set the bar for product quality, technical craftsmanship, and user experience across the engineering org

• Build robust, scalable systems that enable the team to iterate faster on top of your foundation

• Integrate cutting-edge AI frameworks into customer-facing products, staying ahead of the rapidly evolving AI landscape

• Make critical technical decisions about architecture, infrastructure, and tooling that impact company trajectory
  

Strategic Impact

• Work directly with customers to understand workflows, identify pain points, and translate needs into shipped product

• Partner with leadership to define product strategy and prioritize initiatives that drive ARR growth

• Act as a force multiplier—your work should enable multiple engineers to ship better products faster

• Mentor engineers and raise the bar through code reviews, product critiques, and technical leadership
  

What We're Looking For

Technical Excellence

• 7+ years of product engineering experience shipping customer-facing products end-to-end

• Deep expertise in building complete product experiences—you're comfortable across the stack and can ship features independently

• Track record of building 0→1 products that reached meaningful scale, ideally as a founding or early engineer

• Expert-level coding fundamentals with sophisticated judgment about technical trade-offs and where to invest quality

• Battle-tested experience shipping production AI/ML products that customers depend on

• Strong product instincts—you know how to build features that users actually want and that drive business outcomes
  

Product Sense & Execution

• Exceptional product judgment—you understand what to build, how to build it, and when to ship it

• Proven ability to make high-stakes product and technical decisions with incomplete information

• Experience taking ambiguous customer problems and translating them into elegant, impactful solutions

• Strong technical communication—you can explain product decisions and technical trade-offs to both engineers and business stakeholders

• Extreme bias for action balanced with product quality—you ship fast without compromising user experience
  

Leadership & Impact

• Track record of setting product quality standards and raising the engineering bar at previous companies

• Experience as a product or technical leader who others look to for guidance on what "good" looks like

• History of building impressive products that demonstrate exceptional product sense and technical judgment (we actively evaluate for this)

• Ability to operate in high-growth, high-ambiguity environments where you define the playbook

• Comfort context-switching rapidly across multiple product areas and initiatives
  

Mission Alignment

• Genuine passion for building products that impact millions of working-class Americans

• Energized by the trades and home services industry—you want to modernize a massive, underserved market

• Willingness to engage directly with customers in the field—some of our best product insights come from on-site visits

Why Join Now?

This is the exact inflection point where legendary product leaders are made:

• Product greenfield: The features you ship will define the product for a greenfield space

• Direct impact: Small enough team that your product decisions ripple across the entire business

• Timing: In 12 months, the core product will be set. Right now, you can still define everything.

Why Join 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, ICPC world finalists, IMO Gold Medalists).

Compensation & Benefits

• Equity: Meaningful early-stage equity

• Salary: $250K – $300K

• 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