Trilogy
Vice President of Strategic Operations, 2 Hour Learning (Remote) - $400,000/year
Trilogy, Chicago, Illinois, United States, 60290
Overview
Vice President of Strategic Operations, 2 Hour Learning (Remote) - $400,000/year USD
This range is provided by Trilogy. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.
Base pay range $200.00/hr - $200.00/hr
What You Will Be Doing
Owning one domain of the national launch plan: regulatory approvals, onboarding + systems, or financial operations
Leading cross-functional execution with full decision rights and accountability
Building playbooks where none exist — and pressure-testing them in real-time
Collaborating directly with founders, functional leads, and campus staff to deliver launch-ready infrastructure
Using AI tools and automation to streamline ops and accelerate execution
What You Won’t Be Doing
Playing advisor — this is not a strategy role
Working through layers — you\'ll have a direct line to decision-makers
Managing one market or workstream — you\'ll lead parallel efforts across geographies
Waiting for clarity — you\'ll create it
Delegating the tough calls — they\'re yours to make
Vice President Of Strategic Operations Key Responsibilities Own and deliver one core operational pillar of 2HL's national school launch — fast, clean, and at scale. We\'ll route you to the best-fit pillar, but your domain is yours to own.
Basic Requirements We\'re hiring across multiple ops verticals. All require speed, clarity, structured thinking, and the ability to execute with intensity.
You Should Bring
At least 3 years of experience at a top-tier strategy consulting firm (McKinsey, Bain, BCG)
Proven track record owning cross-functional operations in high-stakes, high-ambiguity environments
Clear spike in one or more: regulatory navigation, onboarding systems, or financial ops at scale
Structured thinker with strong execution bias — can go from plan to action without hand-holding
U.S. work authorization and willingness to travel ~1 week/month
Comfort using AI tools to streamline workflow and accelerate delivery
About 2 Hour Learning Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.
With students consistently ranking in the top 1-2% nationally and the top 20% achieving an astonishing 6.5x growth, they’re proving that smarter learning is possible. At 2 Hour Learning, it’s talent and performance that matter. They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system.
2 Hour Learning is reprogramming learning for the AI era.
Working with us This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $200 USD/hour, which equates to $400,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.
Chicago, IL
#J-18808-Ljbffr
This range is provided by Trilogy. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.
Base pay range $200.00/hr - $200.00/hr
What You Will Be Doing
Owning one domain of the national launch plan: regulatory approvals, onboarding + systems, or financial operations
Leading cross-functional execution with full decision rights and accountability
Building playbooks where none exist — and pressure-testing them in real-time
Collaborating directly with founders, functional leads, and campus staff to deliver launch-ready infrastructure
Using AI tools and automation to streamline ops and accelerate execution
What You Won’t Be Doing
Playing advisor — this is not a strategy role
Working through layers — you\'ll have a direct line to decision-makers
Managing one market or workstream — you\'ll lead parallel efforts across geographies
Waiting for clarity — you\'ll create it
Delegating the tough calls — they\'re yours to make
Vice President Of Strategic Operations Key Responsibilities Own and deliver one core operational pillar of 2HL's national school launch — fast, clean, and at scale. We\'ll route you to the best-fit pillar, but your domain is yours to own.
Basic Requirements We\'re hiring across multiple ops verticals. All require speed, clarity, structured thinking, and the ability to execute with intensity.
You Should Bring
At least 3 years of experience at a top-tier strategy consulting firm (McKinsey, Bain, BCG)
Proven track record owning cross-functional operations in high-stakes, high-ambiguity environments
Clear spike in one or more: regulatory navigation, onboarding systems, or financial ops at scale
Structured thinker with strong execution bias — can go from plan to action without hand-holding
U.S. work authorization and willingness to travel ~1 week/month
Comfort using AI tools to streamline workflow and accelerate delivery
About 2 Hour Learning Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.
With students consistently ranking in the top 1-2% nationally and the top 20% achieving an astonishing 6.5x growth, they’re proving that smarter learning is possible. At 2 Hour Learning, it’s talent and performance that matter. They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system.
2 Hour Learning is reprogramming learning for the AI era.
Working with us This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $200 USD/hour, which equates to $400,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.
Chicago, IL
#J-18808-Ljbffr