Bookkeeper – Senior Estimator

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Wing Assistant

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B2B • SaaS • Productivity

Wing Assistant is a company specializing in providing virtual assistant services to businesses worldwide. The company offers a wide range of services including general virtual assistant work, executive assistance, customer service, bookkeeping, and digital marketing. Wing Assistant aims to enhance productivity for startups and enterprise teams by delegating tasks to dedicated virtual assistants, reducing operational load, and enabling businesses to focus on core activities. Their services are accessible via a subscription model, providing flexible and cost-effective solutions compared to traditional hiring methods. Clients benefit from a dedicated assistant model where the assistant works solely for their business, gaining a deeper understanding of their processes over time.

501 - 1000 employees

🤝 B2B

☁️ SaaS

⚡ Productivity

💰 $2.1M Seed Round on 2022-03

📋 Description

• Become proficient in Xactimate Estimating Software within the established onboarding period • Prepare detailed commercial roofing estimates from scope reports, drawings, field notes, and quantity takeoffs • Review historical data, price tables, and project documentation to ensure accurate estimation • Interpret project scopes, specifications, architectural plans, and site conditions • Estimate material quantities, labor requirements, equipment usage, and production rates • Collaborate with project managers, sales staff, and field personnel to clarify technical requirements • Build and maintain automation tools using Excel VBA, Google Apps Script, and spreadsheet functions • Streamline workflows related to estimating, data entry, reporting, and pricing updates • Support integration between various datasets, reports, and estimating platforms • Prepare historical estimates, price tables, line items, and structured datasets for training a web-based AI estimation tool • Work with technology teams to refine AI-generated estimates and improve accuracy • Assist in developing new AI-powered processes for estimating and scope interpretation • Apply general programming knowledge (Python, JavaScript, or similar languages) to support small tools, data transformations, or integrations • Troubleshoot scripts, maintain internal technical documentation, and support software setup as needed

🎯 Requirements

• At least 5+ years of proven experience as a bookkeeper with international clients • Experience or strong interest in learning Xactimate with the ability to become proficient quickly • Understanding of commercial roofing systems, materials, and estimating practices • Working knowledge of Excel, Excel VBA, Google Sheets, and Google Apps Script • Basic to intermediate programming experience (Python, JavaScript, SQL, or similar) • Analytical thinker with strong attention to detail • Ability to interpret scopes of work, quantities, and drawings • Comfortable working with large datasets and structured price tables

🏖️ Benefits

• Health Insurance (HMO) • Performance Incentives • Job Security and Stability • Paid Training • Inclusive Culture • Upskilling Opportunities • 100% Work-From-Home • Exceptionally Supportive Team • Opportunities for Career Growth • Fun Work Environment • Holiday & Overtime Pay