Founding CSM (Customer Success Manager)

The Mission

Probook is building the operating backbone for the home services industry, helping plumbing, HVAC, and electrical businesses run smarter as they scale. The impact is tangible and immediate — better execution and timing directly translate into real revenue, stronger margins, and better outcomes for operators on the ground.

We’re tackling novel, greenfield problems and laying the framework for how AI gets applied in a $700B industry that has been historically underserved by modern software. If you want to work on foundational systems, see clear ROI from your work, and help shape a category from the earliest days, Probook is the place to do it.

The Mandate

• Proactive Account Stewardship Anticipate customer needs and issues before they escalate. Don't wait for customers to come to you. Understand their expectations, run regular business reviews, track leading indicators, and surface opportunities and risks early. Shift from reactive firefighting to proactive success planning.

• Renewal Machine Secure the base. Ensure your accounts renew their agreements early. Do not "force" renewals, engineer them through proactive success management that makes renewal inevitable.

• Commercial Animal Drive expansion. Embed Probook so deeply into customer operations that displacement is impossible and upsells are inevitable. Operationalize the "Land and Expand" motion by driving outcomes so successful that customers come to you to fill white space opportunities.

Who You Are

• World class relationship builder. You earn trust with economic buyers and day-to-day users. You become the trusted advisor customers turn to first.

• Commercially savvy. You spot upsell opportunities naturally, tie product features to ROI, and are comfortable discussing budget, delivering pricing, and asking for renewals. You build bulletproof business cases relevant to each customer's situation.

• Strategic account planner. You map stakeholders, understand customer business priorities, and align Probook value to their goals. You think several moves ahead.

• Proactive problem solver. You surface risks before they become fires. You don't wait for customers to complain.

• Outcome obsessed. You relentlessly track whether customers are achieving their success metrics and hold them accountable to realizing value.

• Technically sharp. You learn complex software quickly and don't make mistakes twice. You master new products as they evolve without constant hand-holding.

Requirements

• 3-5 years in account management, customer success, or account executive roles with B2B SaaS selling into MM or enterprise

• Proven track record of driving retention and expansion with measurable results (GRR/NRR)

• Experience managing high-touch customer relationships ($50K+ ACV) with multiple stakeholders and complex buying committees

• Comfort with commercial conversations: pricing, ROI discussions, contract negotiations, and asking for the business

• Willingness to travel occasionally for customer QBRs and relationship building

• NYC based: Excited to work in-office, in our high-intensity and high-collaboration culture

Why Join Probook?

• The Market: A $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. Cash-flow positive. Product-market fit is established; we are now optimizing for scale.

Compensation & Benefits

• Competitive Compensation: 120 - 145K (Can stretch depending on experience) + Equity

• Equity: Meaningful equity stake.

• Health: Comprehensive medical, dental, and vision coverage.

• Lifestyle: Monthly food stipend and unlimited office snacks.

• Access: Direct access to world-class investors and advisors.