Deployment Strategist

This role blends FDE, customer success, and sales. It is designed for a true Renaissance operator: someone who is execution driven, thrives in chaos, and wants direct ownership of outcomes.

Probook is rewriting how the services industry operates and building the backbone of how physical work gets done in the real world.

We work on first-to-market problems at the intersection of blue-collar work and cutting-edge AI. The services industry is a 700B market that software has ignored for decades.

This role is not for everyone. We want people who want to build something generational. People who want to be in the field with tradespeople, take full responsibility for customer outcomes, and learn what it 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, 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 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.