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