Director of Product Engineering (Hybrid - 3 days onsite per week)
Overview:The Senior Director of Software Engineering is an executive technology leader responsible for defining and executing the long-term engineering strategy in alignment with the company's business objectives. This role oversees multiple engineering organizations through engineering directors and managers, ensuring scalable execution of the product and platform roadmap while driving operational excellence, innovation, and organizational effectiveness.
The Senior Director partners closely with executive leadership to shape technology investments, organizational design, workforce planning, and engineering strategy. This leader is accountable for engineering performance across multiple domains, organizational health, delivery predictability, engineering quality, financial stewardship, and leadership development while fostering a culture of innovation, collaboration, and continuous improvement.
The impact you'll make:- Develop and execute the long-term engineering strategy aligned with the company's vision and business objectives.
- Partner with the CTO and executive leadership to define technology investments, organizational priorities, and strategic initiatives.
- Lead organizational planning across multiple engineering functions to ensure alignment of resources with business needs.
- Establish engineering governance, operating rhythms, and decision-making frameworks that improve execution and accountability.
- Present engineering strategy, organizational health, investment recommendations, and business outcomes to executive leadership and stakeholders.
- Champion innovation by identifying emerging technologies, AI capabilities, and engineering best practices that create competitive advantage.
- Recruit, hire, develop, and retain exceptional engineering leadership and technical talent.
- Lead, coach, and mentor Engineering Directors, Engineering Managers, and senior technical leaders across multiple engineering organizations.
- Align organizational objectives with leadership development, succession planning, and workforce strategy.
- Foster a culture of ownership, accountability, inclusion, innovation, and continuous learning.
- Build scalable leadership pipelines that strengthen organizational capability and long-term succession.
- Lead organizational design, restructures, and workforce planning initiatives to support company growth.
- Conduct skip-level meetings to strengthen employee engagement and organizational effectiveness.
- Partner with People, Finance, and executive leadership on organizational planning and talent strategy.
- Establish enterprise engineering standards, architectural governance, and technical investment priorities across the organization.
- Provide executive technical leadership for the Weedmaps technology ecosystem.
- Drive modernization initiatives that improve platform scalability, reliability, security, performance, and developer productivity.
- Champion emerging web, mobile, cloud, AI, and machine learning technologies that support business growth.
- Set and drive the organization's AI strategy, partnering with Product, Data, and Machine Learning teams to deliver AI-powered customer experiences and AI-native engineering practices.
- Sponsor cross-functional technology initiatives spanning Engineering, Product, Design, Infrastructure, Developer Experience, Security, Data, and Operations.
- Develop technical strategies that improve engineering quality, operational efficiency, and speed of delivery.
- Represent Weedmaps within the industry through conferences, partnerships, and executive leadership forums.
- Own engineering operating plans, workforce planning, and budget forecasting across multiple engineering organizations.
- Partner with Finance to align headcount planning and technology investments with company objectives.
- Evaluate engineering investments to maximize business value and return on investment.
- Identify organizational risks and implement mitigation strategies that support business continuity and operational excellence.
- Balance strategic initiatives with execution priorities to ensure predictable delivery and sustainable organizational growth.
- Establish executive-level KPIs, organizational scorecards, and performance metrics that measure engineering effectiveness.
- Drive continuous improvement initiatives that increase engineering productivity, software quality, reliability, and delivery predictability.
- Lead organizational transformation efforts that improve engineering processes, culture, and operational maturity.
- Review organizational performance metrics to identify systemic opportunities for improvement across teams.
- Communicate engineering performance, strategic initiatives, organizational health, and business outcomes to executive leadership.
- Directly manages Engineering Directors and senior engineering leaders while indirectly leading a large, multi-level organization of engineering managers and software engineers.
- Provides strategic leadership across multiple engineering organizations, ensuring alignment with company priorities and long-term technology strategy.
- Owns organizational design, workforce planning, succession planning, and leadership development across multiple management layers.
- Holds decision-making authority over organizational structure, leadership appointments, budget planning, technical direction, and investment priorities.
- Leads executive-level performance management, talent reviews, compensation planning, and leadership calibration across engineering.
- Oversees hiring, onboarding, coaching, development, and performance management for engineering leadership while building scalable organizational capability.
What you've accomplished:- 12+ years of progressive engineering leadership experience in high-growth technology organizations.
- 7+ years leading Engineering Managers, Directors, and multi-level engineering organizations.
- Demonstrated success leading organizations of 100+ engineers across multiple functional areas.
- Proven experience developing engineering leaders while building scalable, high-performing organizations.
- Experience defining long-term engineering strategy and executing organizational transformation initiatives.
- Experience partnering directly with executive leadership to influence company strategy and technology investments.
- Experience owning workforce planning, organizational design, budgeting, and resource allocation.
- Proven track record implementing engineering governance, operational excellence, and continuous improvement initiatives.
- Experience shipping AI/ML-powered products including personalization, recommendations, search relevance, LLMs, and AI-native engineering practices.
- Demonstrated success leveraging AI-assisted development tools to improve engineering productivity, quality, and delivery.
- Strong understanding of modern software architecture, cloud platforms, distributed systems, security, and scalable engineering practices.
- Exceptional executive communication skills with the ability to influence leaders across all organizational levels.
- Experience leading globally distributed engineering organizations in Agile environments.
Bonus points: - Experience within marketplace, SaaS, or consumer technology organizations.
- Experience leading engineering organizations through rapid scale, organizational transformation, mergers, acquisitions, or IPO readiness.
- Experience integrating third-party LLMs, foundation models, and establishing responsible AI governance.
- Experience building AI-first engineering organizations and implementing enterprise AI strategies.
- Experience presenting technology strategy and organizational performance to executive leadership, Boards of Directors, or investors.
- Experience leading globally distributed engineering organizations across multiple regions and time zones.
The base pay range for this position is $230,060 - $259,500 per year, and a competitive bonus
2026 US Benefits for Full Time, Regular Employees:- Physical Health (Medical, Dental & Vision)
- 100% employer-paid premium for employees
- Up to 80% coverage for dependents
- Company HSA contribution with the High Deductible Health Plan
- 401(k) Retirement Plan (employer will match contribution up to 3.5% of employee contribution)
- Basic Life, Voluntary Life and AD&D Insurance options
- Supplemental, voluntary benefits
- Student Loan Repayment/529 Education Savings with a monthly company contribution
- FSA (Medical, Dependent, Transit and Parking)
- Voluntary Life and AD&D Insurance
- Critical Illness Insurance
- Accident Insurance
- Short- and Long-term Disability Insurance
- Pet Insurance
- Identity theft protection
- Legal access to a network of attorneys
- PTO, paid sick leave, and company holidays (including a 2026 holiday shutdown)
- Paid parental leave
