Principal Engineering Manager - Applied AI

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 work spaces 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.

We are looking for a Principal Engineering Manager to join our growing Applied AI team. In this Age of AI, this is a rare opportunity to work at the cutting edge of Generative AI, Context Engineering and Agentic business capabilities. As the Principal Engineering Manager of the Applied AI team, you will be responsible for applying Generative AI to deliver Agentic capabilities in Highspot, growing and scaling the AI team, managing the planning and prioritization of upcoming Generative AI work, coordinating across multiple engineering teams, and coaching team members.

You will work with machine learning experts, data scientists, the leadership team, and product managers to drive the team's technical direction with planned AI engineering investments, to prioritize high-impact business outcomes and to deliver on new opportunities. You will know when to lean in and work hands‑on with your team and when to step out and direct the team to solve hard technical problems and to achieve business outcomes.

• Lead a team of Applied AI engineers that works at the bleeding edge of Generative AI to solve high‑impact business challenges.
• Apply Generative AI to solve hard unsolved challenges in the application of Agentic AI to real‑world business challenges
• Grow, coach, build and scale the Applied AI team
• Drive operational excellence to achieve enterprise‑grade scale, reliability, security, cost‑efficiency and performance.
• Drive technical direction for building a safe, scalable and reliable Agentic AI platform for all of Highspot
• Communicate complex concepts and the results of analyses in a clear and effective manner to technical and non‑technical audiences.
• Collaborate with other team members and cross‑functionally to share knowledge and discuss initiatives.

• 2+ years of experience in Generative AI and Agentic AI systems, including LLMs, context engineering, and modern vector‑based retrieval systems.
• 4+ years working as an engineering manager
• 8+ years working as a professional software developer
• A great understanding of Generative AI systems, best practices and experience in shipping Agentic AI into distributed, data‑intensive production systems
• Experience developing and operating Cloud services at enterprise scale
• Strong programming skills in Java, Python, C#, Typescript or equivalent programming language
• Substantial depth and breadth of management experience to lead and grow an Applied AI team
• Great collaboration with teams with different backgrounds/expertise/functions.
• Expertise in full product lifecycle; technical designs, project planning, iterative implementation, and successful product launches.
• Experience and passion for mentoring and encouraging collaborative teams.
• Experience in cultivating a strong engineering culture in an agile environment.

Base salary range: $240,870 -$297,652

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.

• 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…