Strategy & Ops, Courses

Leland’s mission is to unlock human potential by making the world’s expertise more accessible. Our platform connects ambitious people with coaching, content, and courses that can can help them achieve their career and educational goals. Since our founding in 2021, we’ve helped tens of thousands of people reach their most ambitious goals, raised $19M from world-class investors, and built the industry leader in educational, career, and AI coaching.

In this Strategy & Ops role over Leland Courses, you will play a critical role in staffing, coordinating, and executing our cohort-based bootcamps covering topics in job recruiting, school admissions, test preparation, and AI upskilling. You will work closely with coaches on Leland's platform and collaborate with internal teams to create seamless, high-quality learning experiences for bootcamp participants — empowering them to achieve their career and academic goals. Our ideal candidate is someone who is detail-oriented, AI-native, customer-focused, and a resourceful executor who thrives in a fast-paced startup environment.

If you're a sharp, AI-native operator who's excited about building world-class learning experiences and has the skills to make them run flawlessly, we'd love to hear from you!

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  Staff bootcamps with qualified coaches and instructors, managing coordination and onboarding end-to-end.

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  Manage logistics for bootcamp operations, including scheduling, deadline tracking, materials distribution, and participant communications.

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  Coordinate with coaches to develop and maintain session curriculum, slide decks, and assignments — holding contributors to deadlines and quality standards.

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  Manage customer-facing communications via HubSpot and our CRM, ensuring a high-quality participant experience from enrollment through course completion.

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  Ensure our product is correctly configured and set up for each bootcamp cohort, partnering with the Product team on changes and testing.

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  Build and improve HubSpot workflows and automations to reduce manual work and scale operations.

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  Continuously audit and optimize bootcamp ops processes to improve efficiency and the customer experience.

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  Develop and maintain systems for updating flagship bootcamp materials across our admissions, recruiting, test prep, and AI upskilling categories.

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  Collaborate with our Growth team to support bootcamp marketing and enrollment efforts.

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  Contribute to data and reporting efforts focused on participant outcomes and course quality.

• Operationally rigorous: You care about the details, hold a high quality bar, and follow through on everything you own.

• AI-native: You use AI tools to automate workflows, solve operational problems, and move faster as a daily practice.

• Customer-oriented: Bootcamp participants are paying customers and you treat every touchpoint accordingly.

• A pattern recognizer: You study how things are already done, understand the reasoning behind them, and build on top of existing systems rather than starting from scratch.

• Scrappy and adaptable: You find creative solutions with limited resources and pick up new tools and processes quickly.

• A focused executor: You prioritize well, hit deadlines, and stay on task even when there are a hundred things competing for your attention.

• A thoughtful challenger: You follow the playbook, and you flag what isn't working when you see it.

• Experience with HubSpot, CRM platforms, or cohort-based programs is a plus.

• The chance to join a world-class team helping people achieve their career and educational dreams

• Work in a collaborative, high-energy environment where your contributions have a direct impact

• Operate in a fast-paced, AI-native environment

• We don't hire people who merely want to work for a great company; we hire people who want to make a great company

Leland is an equal opportunity employer. We encourage candidates of all backgrounds and demographics to apply.