Director, Data Science & MLE

Summary

Join Calendly's Engineering team as the Head of Data Science & Machine Learning, leading AI/ML initiatives and driving innovation. You will develop and execute Calendly's AI and data science strategy, build and mentor a high-performing team, and collaborate with cross-functional teams. Responsibilities include overseeing AI/ML projects, ensuring ethical AI development, and engaging with stakeholders. This pivotal role leverages AI and data science to enhance efficiency and competitive advantage. The position requires significant experience in AI/ML, strong leadership skills, and deep technical expertise. Calendly offers a competitive salary and benefits package.

Requirements

• Advanced degree (Master’s or PhD preferred) in Computer Science, Data Science, Statistics, Engineering, or a related quantitative field
• 10+ years of experience in AI, machine learning, or data science, including significant leadership or management roles
• Proven track record of delivering complex AI/ML solutions at scale and driving measurable business outcomes
• Deep knowledge of modern AI/ML algorithms, frameworks, and best practices (e.g., supervised/unsupervised learning, deep learning, NLP, computer vision)
• Strong programming skills in languages such as Python, R, or similar
• Experience with data engineering, analytics platforms, and cloud-based AI/ML infrastructure
• Demonstrated ability to build, lead, and mentor high-performing technical teams
• Ability to develop and execute AI/ML strategies aligned with business goals and market demands
• Strong project management skills, including resource allocation, timeline management, and budget oversight
• Excellent verbal and written communication skills, with the ability to influence and collaborate across all organizational levels and with external partners
• Commitment to ethical AI development, data privacy, and regulatory compliance
• Passion for staying current with AI/ML advancements and fostering a culture of ongoing professional development

Responsibilities

• Develop and drive the Calendly’s AI and data science strategy, ensuring alignment with overall business objectives and market needs
• Lead the research, development, and deployment of advanced machine learning models, generative AI solutions to address complex business challenges and enhance product offerings
• Build, manage, and mentor a multidisciplinary team of data scientists, machine learning engineers, and researchers, fostering a culture of innovation, collaboration, and continuous learning
• Work closely with Product, Engineering, Design, Marketing, Sales, and Customer Success teams to integrate AI/ML initiatives across the organization and ensure seamless execution
• Oversee the end-to-end lifecycle of AI/ML projects, from ideation and prototyping to production deployment and monitoring, ensuring timely delivery and measurable business impact
• Establish and enforce best practices for ethical AI development, data governance, compliance, and risk management, ensuring transparency, fairness, and regulatory adherence
• Engage with internal and external stakeholders to understand business requirements, validate AI-driven solutions, and communicate technical concepts to non-technical audiences
• Stay abreast of emerging AI/ML technologies and industry trends, driving innovation and process improvements within the team and organization

Benefits

• Quarterly Corporate Bonus program (or Sales incentive)
• Equity awards
• Competitive benefits