Customer Success Specialist (Estimating)

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, Sequoia, 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.

Customer Success Specialist (Estimating) at Handoff

We’re hiring a Customer Success Specialist with experience in Construction Estimating to be the bridge between our AI product and the real-world needs of remodelers, builders, and contractors. In this hands-on role, you’ll apply your construction experience to help improve our AI estimates, support customers, and ensure that our tools actually work in the field.

This role is ideal for someone who has recently been in the trenches - estimating, managing residential projects, and working directly with clients - but now wants to transition into a tech-forward environment where your trade knowledge drives product development.

What you'll do

• Audit AI Estimates: Review AI-generated estimates and flag issues in pricing, scope, or logic based on real-world remodeling practices.
• Own Estimating Content: Help define and refine the scopes, cost libraries, and workflows that fuel our estimating engine.
• Triage & Troubleshoot: Be a front-line resource for customer support issues—resolving questions, spotting bugs, and escalating high-impact issues.
• Test & QA Features: Work with engineering and product teams to test new features, find bugs, and suggest improvements.
• Create Training Materials: Build help docs, internal guides, and video tutorials to empower both contractors and teammates.
• Coach New Customers: Help onboard contractors to Handoff—training them on the product and setting them up for success.
• Improve the AI Assistant: Review AI-chat transcripts, identify where conversations break down, and give feedback to improve clarity, accuracy, and usability.
• Collaborate Across Teams: Translate field expertise into actionable product insights, helping designers, PMs, and engineers build better tools.
• Champion the User Voice: Be a trusted advocate for contractors—ensuring we build with the customer’s perspective front and center.

About You

• 7+ years in residential construction—remodeling, custom homes, or design-build
• Deep experience with estimating, proposals, and project management
• Familiar with platforms like Buildertrend, JobTread, Joist, or STACK
• Comfortable using and explaining modern software tools
• Excellent written and verbal communication skills
• Curious, self-motivated, and eager to bridge construction and technology
• Bonus: Experience working with or supporting software product 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 - Choose your laptop!
• Team Offsites Around the World – In 2024, we gathered in Poland, Mexico, and Florida - where to next?

If you’re ready to bring your construction brain into a high-growth tech environment, we’d love to meet you. Let’s build something great together!