Director, Software Product Strategy & Engineering

About the Role

Oldcastle BuildingEnvelope is building a next-generation quoting and estimating platform that will transform how customers, sales teams, and estimators engage with our business. This platform will combine AI-powered workflows, guided configuration, and customer self-service capabilities to modernize a critical revenue-driving function.

As the Director of Software Product Strategy & Engineering, you will own the full product lifecycle—from vision and strategy through engineering execution and market adoption. This is a builder role where strategy and execution are inseparable. You won’t hand off plans—you’ll help bring them to life.

We’re looking for a leader who has successfully taken a product from concept to launch and adoption, and who is comfortable operating close to the engineering work to drive outcomes, not just deliverables.

What You’ll Own

Product Strategy & Roadmap

• Define product vision, roadmap, and prioritization across a multi-component platform


• Determine what gets built, in what sequence, and why


• Translate long-term strategy into clear, measurable quarterly deliverables

Product Engineering & Execution

• Partner directly with engineers, architects, and vendors to drive product development


• Create clear product requirements and participate in technical design discussions


• Identify and remove delivery blockers to keep progress on track


• Make informed tradeoff decisions across scope, timing, and functionality

Business Case & Investment Ownership

• Develop and own the financial model, including cost, ROI, and success metrics


• Build and present investment cases to executive leadership and stakeholders


• Define performance benchmarks to guide investment decisions throughout delivery

Go-to-Market & Adoption

• Lead rollout strategy, internal enablement, and external launch planning


• Drive user adoption across sales teams, estimators, and customers


• Incorporate real-world feedback into continuous product improvements

Stakeholder & Vendor Management

• Align cross-functional stakeholders across business units


• Manage vendor relationships and ensure delivery accountability


• Track and report against product performance and adoption metrics

Success Metrics

• Quote-to-order conversion rate


• Estimator productivity improvement


• Digitally influenced revenue growth


• Reduction in quote turnaround time


• Customer self-service adoption


• On-time delivery of roadmap milestones

Qualifications

Required

• 10+ years of experience in product management, product engineering, or digital product leadership


• Proven experience driving end-to-end software product delivery (concept through launch and adoption)


• Strong hands-on approach to working with engineering teams during the build process


• Demonstrated ability to develop and present business cases to executive audiences


• Experience leading cross-functional initiatives without direct authority


• Background in B2B environments with complex buyer and user dynamics

Preferred

• Experience in manufacturing, construction, distribution, or industrial environments


• Familiarity with CPQ systems, ERP-integrated quoting, or customer-facing platforms


• Exposure to AI-driven workflows, APIs, and cloud-based architectures


• Experience within a private equity-backed organization