Huckleberry is everyone's executive AI coach: private, voice-first, and always available. It helps professionals develop and outperform in their role, whether that means preparing for a feedback conversation, navigating conflict, thinking through a career decision, or getting unstuck in real time without waiting for a scheduled session. Unlike traditional coaching, it's always available and accessible beyond the executive few. Unlike generic AI tools, Huckleberry is built for real coaching: grounded in proven frameworks, personal context, and real feedback. We're headquartered in Portland and Auckland, on a mission to coach the uncoached. Headquartered in Portland, Oregon and Auckland, New Zealand, we're on a mission to help coach the uncoached.
On-site · Ottawa
Provide AI-driven career coaching to individual contributors to improve visibility and professional growth. Help users navigate difficult career conversations and implement structured development plans.
On-site · Ottawa
The role focuses on integrating continuous AI coaching into the existing L&D stack to bridge the gap between knowledge transfer and behavioral change. It involves implementing reinforcement layers, pre-conversation preparation, and expanding coaching coverage across the entire organization.
On-site · Ottawa
The role focuses on providing AI-driven coaching solutions to scale professional development for managers and high-potential individual contributors. It aims to bridge the coaching gap by offering real-time support for critical workplace conversations and leadership growth.
