Sr. Director, Engineering

About Highspot
Highspot is pioneering the category that is fundamentally changing the way companies increase sales productivity. On a mission to transform the way millions of people work with sales enablement, Highspot is committed to building breakthrough software with a spark of magic. We believe a great place to work is about more than the work – it's about what the company stands for, and how it authentically represents its values in the real world. To this end, we have put intentional focus on creating equitable workspaces for each of our employees. Our goal is to create a culture where everyone feels a deep sense of belonging and is empowered to be an agent of change, with the ability to transform themselves, their workplace, and their world.

About The Role
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—one that starts with personalized training paths and AI-graded practice, extends to analyzing real-world performance with conversational intelligence, and culminates in data-driven coaching that demonstrably improves outcomes. Your leadership will be instrumental in empowering sales managers to become world-class coaches and enabling every seller to bridge the gap between learning and execution. As a key member of the Product leadership team, you will bring your technical expertise and people management skills to foster a culture of innovation and deliver a unified solution that directly connects enablement efforts 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.
• Effectively collaborate with key partners in your product area, including Designers, Product Managers, and TPMs
• Uphold and build upon Highspot's culture, ensuring that Engineering is a welcoming, inclusive place, and that we not only meet our DE&I goals but lead Seattle's tech industry with our commitment to diversity
• Bring your technical expertise to bear as you work to manage the evolution of Highspot's software; ensure that our architecture and stack are optimized to keep pace with the demands of hyper-growth; position your product area (and support adjacent product areas) for continued high-availability, security and reliability across multiple worldwide data centers
• Deeply understand the strategic value and the market opportunity of your product area; leverage your expertise to define KPIs and growth plans for your organization
• Create a collaborative environment where all levels of engineers can contribute in meaningful ways
• Partner with the Services team to understand what drives customer joy in your product area and ensure your team works to address customer concerns in a timely manner
• Advocate for the tools, process, and resources the core dev team needs to enable their ongoing success and unlock their ability to innovate
• Mentor and guide the professional and technical development of the managers and engineers on your team
• Define clear roles and responsibilities that ensure efficient decision-making, careful analysis of trade-offs, and a responsible balance of strategic business objectives, unique customer needs, operational necessities, and product quality
• Ensure architects, stakeholders, and SMEs are appropriately involved in decisions
• Ensure decisions are communicated within and outside team
• Enforce accountability through empathetic, relevant, and objective performance targets and timely feedback and coaching
• Advise the broader Product leadership team on the relative costs and benefits of various projects competing for Engineering resources

Your Background

• Minimum of 10 years in senior engineering leadership roles, including managing engineering managers, and recent experience in the B2B SaaS industry
• An academic background in Computer Science or related discipline, or equivalent experience
• Extensive experience developing and scaling cloud-native applications and infrastructure
• Experience in product domains related to AI/ML, learning management systems, data analytics platforms, or conversational intelligence is a significant plus.
• Proven success in attracting and retaining top engineering talent from diverse backgrounds
• Proven success as a partner and collaborator who prioritizes the success of the team over individual aspirations
• Entrepreneurial spirit, priding yourself on getting things done with a high level of quality
• Previous 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
• Experience building software in languages such as TypeScript, Python, Ruby, Java and Clojure

Base salary range: $266,000 - $329,609

Employees may also be eligible for bonuses, stock options, and other forms of compensation.

The above represents total expected compensation for this role. Actual compensation will depend on various job-related factors, including, but not limited to, location, experience, and job qualifications.

Highspot also offers the following employee benefits for this position:

• 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 (paid days off 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 Statement
We are an equal opportunity employer and value diversity at our company. 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, physical or invisible 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, hit the 'apply' button.