Sales Enablement & Training Manager

Company Overview Construction is one of the largest industries in the U.S., but also one of the least technologically advanced. Every year, firms spend over $60B on teams creating cost estimates for bids. The process relies on tedious "takeoffs"—manually measuring and counting materials from drawings. Bobyard automates takeoffs using computer vision and NLP, cutting estimate time significantly while reducing errors. We're a small team backed by Primary, Pear, and 8VC, building software for the construction industry. Position Overview We're hiring our first dedicated Sales Enablement & Training Manager to build the training, tooling, and content infrastructure behind our sales org. You'll own onboarding and ramp for new AEs and SDRs, sharpen our messaging for a notoriously hard-to-sell buyer (skeptical, hands-on, trade-vertical decision makers), and make sure reps have what they need to run a consistent, effective sales process — from first call to close. This is a high-ownership, build-from-scratch role. You'll work closely with Sales, Marketing, and Product to translate what's working in the field into scalable playbooks, and you'll have a direct line to leadership on what's moving the needle. Responsibilities - Build and own onboarding for every new AE and SDR, across every trade vertical we sell into - Partner with our Sales Engineers to design and run a certification program reps have to pass before running demos or calls solo - Partner with Sales leadership to identify skill gaps by stage of the funnel and build targeted training to close them - Sit in on live calls and give reps specific, individual coaching — this is hands-on, not just content - Partner with Product on launch readiness — making sure reps can sell new features and verticals from day one - Build and maintain trade-specific playbooks that make it easier for new reps to sell - Track ramp time and quota attainment by cohort, and use it to prove what's working and cut what isn't - Own the enablement tech stack – ensuring reps are equipped and trained on the tools they use daily - Coach managers on how to reinforce enablement content in 1:1s and deal reviews What We're Looking For - 3-5+ years in sales enablement, sales training, or a related revenue role (AE/SE background a plus), ideally at a startup that's scaled quickly - Experience building a training program from the ground up, not just maintaining an existing program - Strong instincts for translating complex or technical product value into simple, repeatable selling language — especially for a buyer that isn't software-native - Comfortable with sales tooling and data (HubSpot or similar CRM; comfort with reporting/analytics a plus) - Bonus: experience selling into construction, trades, or other traditionally offline/skeptical-of-software industries Benefits - Competitive salary ($120K–$145K base), Bonus, 401K, and equity options - Comprehensive medical, dental, and vision coverage, plus flexible PTO - Direct impact on how the sales team grows, with ownership of the enablement function from the ground up - Work alongside a driven team building something new in a large, underserved industry SF-based role: full-time, in-person in San Francisco (4 days/week) We think our product stands out and the industry is ready for it. If you're excited to help us prove that out, we'd love to talk. Comp Philosophy We are proud to offer competitive, top-of-market compensation because we want to celebrate the dedicated people who ship amazing work and drive our success. Our individual compensation is thoughtfully tailored based on your role, experience, and contributions, alongside performance-based rewards.