Senior Estimator

Senior Estimator at Handoff

Why join us? Handoff is the AI agent that runs a construction company. We help remodelers automate estimating, streamline operations, and win more work - backed by real-time cost data, intuitive design, and workflows that "speak contractor." With over 10,000 monthly active users and $6B in annualized project volume already flowing through our platform, we're becoming the trusted partner for the people who build our homes. We are backed by $25M+ raised from Y Combinator, Initialized, and Greycroft. Our team is distributed across hubs in Austin, São Paulo, and Buenos Aires, and we are deeply focused on building intuitive, high-impact solutions that make a real difference for our users.

We're hiring a Senior Estimator to own the quality of blueprint-based estimates delivered to our enterprise customers. In this role you'll ensure that takeoffs, scopes, and material/SKU matching meet customer-specific standards and can be executed quickly and accurately in the field.

This role is ideal for someone with strong residential construction and estimating experience who wants to move beyond the field and into a product-driven environment - where your expertise directly shapes how AI understands construction, materials, and real-world workflows.

What You'll Do

• Own Estimate Quality: Act as the primary point of contact between Handoff AI and enterprise construction teams, ensuring estimates meet customer-specific expectations.
• Validate Blueprint Takeoffs: Run structured quality checks on takeoffs and estimates, ensuring alignment with real-world scopes, quantities, and specifications.
• Improve Estimating Systems: Maintain and refine estimating knowledge bases, templates, and material classifiers to improve consistency and accuracy.
• Material & SKU Matching: Ensure contractor material lists are correctly mapped to enterprise vendor SKUs, including preferred brands, product lines, and availability.
• Debug Estimation Issues: Investigate failures by reviewing AI system logs, workflows, and outputs to identify root causes across logic, data, or configuration.
• Run Test Scenarios: Execute structured test estimates to validate improvements and ensure outputs meet defined quality thresholds.
• Translate Field Expertise: Convert contractor feedback into actionable insights for Product and Engineering teams.
• Document & Report Issues: Create clear, reproducible bug reports and prioritize improvements based on impact.
• Collaborate Cross-Functionally: Work closely with Product and Engineering to test features, improve workflows, and ship higher-quality outputs.
• Drive Continuous Improvement: Identify recurring failure patterns and propose scalable fixes to improve system performance.

About You

• 3+ years of residential construction experience (remodeling, custom homes, or design-build)
• 1–2+ years of experience in construction material purchasing or sales, with strong understanding of product selection, SKUs, and availability
• Hands-on experience with blueprint takeoffs using tools like PlanSwift, Bluebeam, or OST
• Familiarity with estimating platforms such as Buildertrend, JobTread, Joist, STACK, or CoConstruct
• Deep understanding of end-to-end residential construction workflows - from foundation through finishes
• Strong analytical and problem-solving skills, with the ability to break down complex issues into root causes
• Comfortable working with technical systems, logs, and structured workflows
• Excellent written and verbal communication skills, especially in cross-functional environments
• High ownership mindset with a bias for action and continuous improvement
• Bonus: Experience working closely with software, product, or engineering teams

What We Offer

• Competitive Salary + Equity
• Unlimited Paid Time Off (PTO)
• 401(k)
• Medical, Dental & Vision Insurance
• Life & Disability Insurance
• Flexible Spending Account (FSA)
• Dependent Care FSA (DC FSA)
• Relocation Allowance
• Top-Notch Equipment
• Team Offsites

If you've been in the field and know what a "good estimate" really looks like—and you're excited to help train AI to think the same way - you'll have an outsized impact here.

Join us in redefining how construction gets estimated, planned, and executed

Handoff is an Equal Opportunity Employer. Handoff is committed to the principle of equal employment opportunity for all employees and to providing employees with a work environment free of discrimination and harassment. Handoff will not tolerate discrimination or harassment based on any of these characteristics. Handoff encourages applicants of all ages. Handoff also participates in E-Verify.