Director of Product Engineering

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.

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

Why Work at Weedmaps?

Life at Weedmaps means innovation and heart. Come join us if you care about the plant, the people who love it, and are ready to let your talent shine. We foster a bustling and collaborative culture that revolves around an environment that focuses on the benefits of weed, and the community that supports it. 

You too can have a hand in shaping the industry’s future; ready to roll with us? 

See how we’ve grown—our journey, leadership team, and what’s next at Weedmaps.com/corporate 

About Weedmaps:

Founded in 2008, we’ve grown from a small startup to a global leader in the cannabis industry.  Our dedication to transparency, education, and community has set us apart, and today, we proudly serve cannabis to consumers and businesses in the U.S. and worldwide. 

“Freedom to choose. Freedom to access. Freedom to enjoy.”

Notice to prospective Weedmaps job applicants:

Our team has been made aware of incidents involving LinkedIn, Telegram, and Facebook accounts impersonating Weedmaps recruiters. These individuals are attempting to use our company name to solicit payment from prospective candidates interested in applying for jobs at our company. Our team is actively working to combat these attempts, but in the meantime, please be mindful of the following:

• Our recruiters will always communicate with candidates through an @weedmaps.com email address.

• CORRECT: jlebowski@weedmaps.com

• INCORRECT: jlebowski@gmail.com

• Our recruiters will NEVER ask for or attempt to solicit payment from applicants in order to apply, interview, or work for Weedmaps.

• If you are interested in a role at Weedmaps, please apply through our established channels.

• Weedmaps Careers Page or LinkedIn

If you are unsure if a communication is legitimate, please contact our recruitment team at talentops@weedmaps.com and they will happily confirm for you. Thank you for your vigilance and we appreciate your interest in working with us!  

Weedmaps is an equal opportunity employer and makes employment decisions on the basis of merit. The Company prohibits unlawful discrimination against employees or applicants based on race (including traits historically associated with race, such as hair texture and protective hairstyles), religion and religious creed, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, military status, veteran status, uniformed service member status, sexual orientation, transgender identity, citizenship status, pregnancy, or any other consideration made unlawful by federal, state, or local laws. The Company also prohibits unlawful discrimination based on the perception that anyone has any of those characteristics, or is associated with a person who has or is perceived as having any of those characteristics. Our company uses E-Verify to confirm the employment eligibility of all newly hired employees. To learn more about E-Verify, including your rights and responsibilities, please visit www.dhs.gov/E-Verify.

Applicants are entitled to reasonable accommodations under the terms of the Americans with Disabilities Act and applicable state/local laws, unless the accommodation presents undue hardship. Please email us at peopleoperations at weedmaps.com if you would like to confidentially discuss a potential accommodation during the interview process.