Staff Software Engineer

About Probook

Probook is building AI infrastructure for the $700 billion home services industry.

We've scaled from 0 to $10M ARR in under 18 months while remaining cash-flow positive from day one. Our ambition isn't modest—we're building the fastest-growing, most talent-dense startup in NYC and the dominant platform in home services.

The Opportunity

We're hiring a Staff Product Engineer to own the product experiences that will scale us from $10M to $100M+ ARR.

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
  

Who Thrives Here

We're a high-performance, in-office team in NYC built around three core values:

Blue Collar – We build products with real impact for people in the trades. We jump on customer calls, visit job sites, understand workflows intimately, and translate that into features that drive real business value.

3-Month Runway Mentality – We move with urgency and execution focus. We make thoughtful product decisions but optimize for shipping customer value today. Perfect is the enemy of shipped.

Low Maintenance – We maintain an exceptionally high product and engineering bar, own our commitments completely, and do whatever it takes to deliver. We're on the same team, with zero politics and total accountability.

Every person at Probook is an A-player with a proven track record in high-stakes environments. We operate with intensity, hold ourselves to the highest standards, and measure success by outcomes, not output.

Why Now

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

• Proven traction : $10M ARR in 18 months, 100% word-of-mouth growth, cash-flow positive

• Product greenfield : The features you ship will define the product for a $100M+ revenue company

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

• Massive opportunity : $700B market, <1% penetrated by modern software

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

You're joining at the stage where:

• Your product decisions will shape what millions of users experience daily

• You'll define product quality standards for a growing engineering org

• You'll have direct access to customers, leadership, and business metrics

• You can still own entire product surfaces end-to-end.

Benefits

• Competitive salary and meaningful equity

• Full medical, dental, and vision coverage

• Unlimited PTO

• 1K monthly stipend on Ramp