Enterprise Account Executive

ABOUT PROBOOK

Probook is the AI Operating System for the home services industry, transforming how plumbing, HVAC, and electrical businesses operate.

Our impact is real. Dispatching the right technician to the right job can mean the difference between a $300 "band-aid" fix and a $20,000 system replacement. By automating previously high-touch workflows around-the-clock, Probook ensures a consistent customer experience without the need for 24/7 live staffing. We unify our customers' processes into a single, scalable platform, giving businesses one place to run their entire dispatch operation.

The Role

Enterprise Account Executives at Probook close deals by understanding the customer and the product and making both connect. You own the full sales cycle: discovery, evaluation, negotiation, and close. You are not a demo jockey. You are a problem solver who builds trust fast and earns the right to move fast with it.

You will have SDR support generating pipeline and marketing backing you in the field. In exchange, you are expected to manage your patch with precision, keep your process airtight, and hit your number. You will never sell what you would not buy. If you care about the craft of sales and want to sell a product customers actually love, this is the role.

Who You Are

• You own the full sales cycle without needing to be managed through it. You are self-directed and process-driven by instinct, not instruction.

• You understand complex workflow technology and can translate that into business value for operators who are not technical.

• You build trust quickly. Your EQ is a competitive advantage in sales situations, not an afterthought.

• You have operated in early-stage environments before. You know how to close with limited resources and incomplete information.

• You are a deal-team player, not a lone wolf. You work closely with SDRs, Sales Engineers, and leadership to advance opportunities.

• You are high-energy, gritty, and entrepreneurial. You take initiative and do not wait for permission.

What You Will Own

• Account Planning: Know your patch better than anyone at the company. Map accounts that fit the ICP, identify key contacts, and develop and iterate your value hypothesis throughout each evaluation.

• Pipeline Management: Use Probook's sales process to manage your pipeline with rigor. Understand the reality and risk of each deal based on stage exit criteria. When stuck, ask for help proactively.

• Collaboration: Work closely with SDRs, Sales Engineers, Professional Services, and leadership to build, advance, and close opportunities. Deal team culture is central here.

• Client Relationships: Own the relationship from initial engagement through close, renewal, and expansion. You are the constant.

Requirements

• NYC Based: Excited to work in-office 5 days/week in our high-collaboration culture.

• 5+ years of software sales closing experience, with demonstrated success selling complex workflow technology solutions.

• No less than 1 year of enterprise sales experience.

• Demonstrated intellectual capacity to understand underlying technology and articulate how it fits a customer's specific business needs.

• Demonstrated EQ and relationship-building skills: the ability to get to trust quickly.

• Proven grit and entrepreneurial spirit in early-stage or resource-constrained environments.

• Comfortable with up to 10 to 20% domestic travel.

Why Join Probook?

• The Tailwinds: $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. Product-market fit proven; now we're scaling.

• Funding: $40M raised from Sequoia and Andreessen Horowitz

• The Team: >60 people, our founding team comes from the space and has spent thousands of days onsite with our customers. We live the space. We're also becoming one of the most talent-dense start-ups in NYC (MIT, Harvard, UPenn M&T, Waterloo, Citadel, Palantir, ICPC world finalists, IMO Gold Medalists).

Compensation & Benefits

• Equity: Meaningful equity.

• Salary: $300K OTE (base + commission).

• Health: Comprehensive medical, dental, and vision.

• Perks: $500 Monthly stipend (food, gym, Uber, etc), plus $25 in nightly meal delivery credit and really good office snacks.

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