About the RoleOldcastle 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 OwnProduct 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
QualificationsRequired- 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
What OBE Offers You- Benefits that benefit you - industry competitive benefits at the lowest cost to the employee
- Work-life balance - PTO and holidays, including floating holidays you can choose
- Compensation that rewards your hard work - A pay-for-performance culture with potential for annual raises and bonuses
- Training - We will equip you with the knowledge and skills you need to succeed
