Deployment Strategy Associate

Probook is rewriting how the services industry operates and building the backbone of how physical work gets done in the real-world. We are one of the fastest growing start-ups in Gen AI - bootstrapped to $4M ARR in under 9 months with <5 people, profitable from day one.

We’re tackling first-to-market problems at the intersection of blue-collar work and bleeding-edge AI, creating generational change in a $700B industry that has been ignored by software. Every customer deployment is done in person and our growth comes from execution and word of mouth, not GTM spend.

This position isn’t for everyone. We’re only looking for serious builders who want to be at the foundation of something generational - people who want to be in the trenches with tradespeople, own customer outcomes end-to-end, and learn what it truly takes to build and scale a hyper-growth company from the inside.

What You’ll Do

• Lead on-site customer deployments (2–4 days/week travel).
• Drive customer success post-implementation calls, meetings, and proactive support.
• Translate messy real-world workflows into product improvements.
• Take full ownership of account health, retention, and expansion.
• Grow into leading and scaling deployment teams.
  
  

Who You Are

• 1–4 years’ experience in banking, consulting, sales engineering, or similarly high-pressure environments.
• Persuasive, assertive, and outcome-driven.
• Comfortable with complex technical products; quick to master new systems.
• Selfless teammate: ego low, standards high.
• You are a firefighter: Fast growth means a million fires burning. We’re comfortable around heat.
• Customer obsessed, meaning you ready to sleep to ensure a top .1% service
• Proactive about identifying and solving problems before they turn into larger issues
  
  

Compensation & Benefits

• 120 - 150K Base salary Equity (Can stretch in comp for the right candidate)
• Career growth upside in a hyper-growth AI startup.
• Medical, dental, vision.
• 1K in monthly food stipend
• Take-what-you-need PTO office perks.
  
  

This is not just a job. It’s a proving ground for people who want intensity, ownership, and the chance to build something enduring at the ground floor.