Overview Senior Director, Engineering at Highspot. We are seeking a Senior Director to lead the strategy, innovation, and development for our Training and Coaching pillar. In this role, you will own the product vision for a complete, AI-driven learning ecosystem that transforms how revenue teams develop and master critical skills. You will guide your teams in building a continuous feedback loop—personalized training paths and AI-graded practice, analyzing real-world performance with conversational intelligence, and data‑driven coaching that improves outcomes. Your leadership will empower sales managers to become world-class coaches and help every seller bridge learning and execution. As a key member of the Product leadership team, you will bring technical expertise and people management skills to foster a culture of innovation and deliver a unified solution that connects enablement to quota attainment, win rates, and predictable revenue growth. What You'll Do Lead, mentor, and inspire a high-performing organization of engineers and managers, setting the technical vision and execution strategy for our AI-driven Training and Coaching products. Collaborate with key partners in your product area, including Designers, Product Managers, and TPMs Uphold Highspot’s culture, ensuring that Engineering is welcoming and inclusive, and lead DE&I efforts in alignment with our goals Guide the evolution of Highspot’s software, ensuring architecture and stack support hyper-growth, high availability, security, and reliability across multiple data centers Define KPIs and growth plans for your organization based on strategic value and market opportunities Foster a collaborative environment where engineers at all levels can contribute meaningfully Partner with Services to address customer concerns and drive customer joy in your product area Advocate for tools, processes, and resources to enable ongoing success and innovation Mentor the professional and technical development of managers and engineers on your team Define clear roles and responsibilities to balance strategic business objectives, customer needs, operational necessities, and product quality Involve architects, stakeholders, and SMEs in decisions and ensure effective communication Maintain accountability through relevant performance targets and timely feedback and coaching Advise the broader Product leadership team on project costs and benefits when allocating Engineering resources Your Background Minimum of 10 years in senior engineering leadership roles, including managing engineering managers, with recent experience in the B2B SaaS industry Academic background in Computer Science or related discipline, or equivalent experience Extensive experience developing and scaling cloud-native applications and infrastructure Experience in AI/ML, learning management systems, data analytics platforms, or conversational intelligence is a significant plus Proven success attracting and retaining top engineering talent from diverse backgrounds Proven ability to partner and collaborate, prioritizing team success over individual goals Entrepreneurial mindset with a focus on delivering high-quality results Experience designing and building software products at scale Deep understanding of the SDLC for SaaS applications Working knowledge of modern object-oriented and functional programming languages (e.g., TypeScript, Python, Ruby, Java, Clojure) Compensation and Benefits Base salary range: $266,000 - $329,609. Employees may also be eligible for bonuses, stock options, and other forms of compensation. The total compensation depends on location, experience, and qualifications. Highspot offers benefits including: Comprehensive medical, dental, vision, disability, and life benefits Health Savings Account (HSA) with employer contribution 401(k) matching with immediate vesting on employer match Flexible PTO 8 paid holidays and 5 paid days for Annual Holiday Week Quarterly Recharge Fridays for mental health recharge 18 weeks paid parental leave Access to coaches and therapists through Modern Health 2 volunteer days per year Commuting benefits Equal Opportunity We are an equal opportunity employer and value diversity. We do not discriminate on the basis of age, ancestry, citizenship, color, ethnicity, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, disability status, political affiliation, veteran status, race, religion, or sexual orientation. Did you read the requirements as a checklist and not tick every box? Don’t rule yourself out. If this role resonates with you, click the apply button. Location: Bellevue, WA or Seattle, WA

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