Founding Deployment Strategist

The problem we’re solving

Probook is the AI dispatching software for the $700B home services space (think plumbers, electricians, HVAC technicians, etc). Matching technicians to the right jobs can mean the difference between a $300 toilet fix and a $20,000 system replacement yet this process is currently manual and rarely data-driven.

Probook automates the entire E2E process using AI.

The role

You will be working with customers every day. Period.

This includes, but is not limited to: onsite launches (4 days a week), business case building, process improvement, PE enterprise upsells, synthesizing case studies to evaluate patterns in our operations to further optimize, etc.

We’re looking for remarkable generalists to interface between product, engineering, and post-sale customers - to eventually take on a portfolio of 15-20 customers as we hyperscale.

We ask you to be technically cognizant of our software and product, and be able to onboard customers so they’re comfortable using Probook on an hourly basis (you will fly out weekly to client sites and to execute on this). After onboard, you’ll monitor product usage client ROI for weeks after to make sure clients retain.

Additional Info

Working experience: 1-4 years (looking for elite generalists)

Compensation: $150K - $180K

Equity: 0.1% - 0.15%

VISA sponsorship: TN Visa

On-site work policy: in-person NYC

Some of the problems you’ll be working on

Every week you will be traveling to 2 client sites (mon-tues, then wed-thurs) to help new Probook users get accustomed to our software and make their workflow transition as smooth as possible.

We’re still building out this client onboarding process with the goal of full self-sufficiency in the future. You would help identify bottlenecks, find workflows to streamline, and set a foundation for future DSs as we scale to 30/50/100 employees.

Growth opportunities within the company

Since you’ll be one of the first 10 employees of our company, you will eventually manage future Deployment Strategists across the regions our clients operate in. Our goal will be to reach 30 employees by the end of 2025 so your direct reports will inevitably grow each month.

In addition since you’ll be so closely involved with deployment, customer feedback, and user journey mapping, you’ll eventually be one of the key product thought leaders. As we offer more features and expand into new verticals, we expect you to be an instrumental voice in that.

This is expected to be a management position.

We also offer universal compensation raises as the team reaches new stepwise ARR goals.

Your skills & qualities

• 1-4 years of experience at a leading investment banking, consulting firm, high growth tech company. We’re looking for an individual who’s been surrounded by rapid progression.

• Can solve virtually any problem thrown at them: whether that be design a website from scratch, code a simple script to automate ROI reports, or build out an operating model spreadsheet to evaluate our current capacity.

• Customer Obsessed: You lose sleep when customer stones are left unturned.

• Grinder: You're ready to grind weekends to blow past $10M ARR.

• Low Ego: you hold yourself accountable before others have to. Self-excellence has always been your chip on your shoulder.

The team

Probook’s fully-bootstrapped team of 4 grew from 0 to $3M in ARR in our first 6 months of sales. We focus heavily on happy customers and executing with speed and diligence.

Our backgrounds are Penn M&T, Berkeley EECS, and ACM-ICPC world finalists.

We have an extreme bias towards executing with speed and diligence. Every one of us derives meaning and fulfillment from the work we do. And we hope to foster a working culture that no other startup can foster.

Come join the team if you:

• Can work 6 days in-office a week (New York City). We've gotten to where we are today through methodical and comprehensive grinding. The reward has been immense.

• Are relentlessly resourceful. While you'll be assigned specific objectives/KPIs, we expect you to be a versatile generalist at heart.

• Love to be self-sufficient. We empower each team member to have complete autonomy to solve the problems they're assigned. All information is transparently available to the whole team in our knowledge base.

We're not trying to burn anyone out, if you need 8 hours of sleep per day, you should do that. We understand humans need time to decompress and allow space for their own organic creativity to flourish, but we do expect Probook's mission to be a top priority in your life should you decide to join the journey we've embarked on.

More company info

Team size: 8 people

Website: www.probook.ai

LinkedIn: visit

Industry: AI & home services

Founding year: 2024

Office location: in-person NYC

Compensation Range: $150K - $180K