Product Enablement Specialist
Bobyard
Product Enablement Specialist
Bobyard
AI-powered landscaping takeoff and estimation platform
About Bobyard
Construction is a trillion-dollar industry, but still runs on outdated software
Biggest bottleneck: cost estimating — takeoffs are still manual, slow, and error-prone
Lean team backed by 8VC, Primary, and Pear, building next-gen software for the built world
What you'll do
Build our Knowledge Center and LMS — Looms, guides, and articles that preempt questions
Own Intercom — respond to questions, troubleshoot fast, close the loop with empathy
Scale support with systems — kill repetitive work with automations, templates, and AI
Close the feedback loop — partner with Product/Engineering to log bugs and track fixes
Enable GTM — support Sales and CS with demos, feature deep dives, competitive insights
Know our users cold — deep expertise in the platform and how estimators/landscape pros get value
What we're looking for
2+ years in a customer-facing role (Support, Enablement, or Success preferred)
Excellent written and verbal communicator, no jargon
Proficient with Intercom (or similar), documentation/LMS tools, and Loom
Comfortable in a fast-paced startup where processes are still being built
Why Bobyard
Join a fast-growing AI startup transforming construction estimating
Report to Head of Post-Sales; work closely with Engineering and Product
Clear growth path into CSM or CS Operations
In-person, San Francisco
Compensation
$80k–$100k base + equity, full-time
Come build with us!
Bobyard offers an AI-powered takeoff and estimation platform for landscaping contractors. It automates the process of quantifying counts, lengths, and areas from landscaping plans so estimating teams can generate bids faster. The system uses AI trained on a large dataset of landscaping drawings to automatically extract measurements and quantities. A key feature is Pattern Search, which calculates square footage directly from plans. As a SaaS product, it provides tools to create accurate bids and scopes of work (SOWs), helping contractors increase their bidding capacity and streamline preconstruction tasks. Compared to competitors, Bobyard focuses specifically on landscaping, with automated measurement and SOW generation designed to speed up bidding and reduce manual work. The goal is to help landscaping professionals bid more quickly and accurately, enabling them to take on more projects and improve preconstruction efficiency.
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