Strategy Director, Marketplace & New Programs

The Company:

Outschool’s mission is to inspire kids to love learning. In our fast-changing world, the traditional educational system struggles to meet the diverse and evolving needs of young learners. Outschool reimagines this system, offering flexible and engaging learning experiences as a supplement and alternative to traditional education. By connecting learners with a global community of teachers and peers through our online platform, we make learning personal, dynamic, and deeply human.

We've made significant strides since launching our marketplace of live online classes in 2017. Finding initial success with secular homeschoolers, we then expanded to enrichment learning to meet the needs of a wider audience, growing our business 16x since 2019. Post-pandemic, we have evolved our platform to power academic learning, incorporated AI, and have begun to grow our international community. We're proud to have served over 1.5M passionate learners with more than $100M in annual bookings.

Driving disruptive, positive change in education is rewarding and hard. Outschool team members are encouraged to challenge themselves, take risks, and grow in their careers. We look for talented people whose sense of urgency, innate curiosity, and determination to drive impact will help Outschool achieve outsized results in pursuit of our mission. We invite you to be part of an ambitious team dedicated to ensuring every learner can navigate the future with curiosity, resilience, and a love of learning.

The Role

Outschool is focused on strengthening and expanding its core marketplace while developing new educational programs and services that meet the evolving needs of families. We're looking for a Strategy Director, Marketplace & New Programs to help shape our marketplace growth strategy and turn new business opportunities into meaningful revenue growth.

In this role, you'll develop a deep understanding of Outschool's marketplace performance, customer behavior, economics, and underlying growth drivers. Working closely with Product, Growth, Marketing, Finance, and Operations, you'll identify opportunities to strengthen the existing business, improve our competitive position, and accelerate sustainable growth.

You'll also continuously evaluate the competitive landscape, emerging markets, and evolving customer needs to identify opportunities for new programs, bundled learning experiences, specialized services, and business models. You'll develop business cases, define new offerings, and establish a prioritized roadmap for marketplace expansion.

This is a strategic, commercially accountable, and execution-oriented role. You'll serve as the central business lead for new marketplace program initiatives, coordinating cross-functional development, launch, and commercialization. You'll establish clear revenue and enrollment objectives, monitor performance, and work across teams to ensure new offerings deliver measurable results.

You'll also collaborate closely with our Public Funding & Accredited Programs Strategy Director to identify opportunities that bring together marketplace offerings, public funding, and accredited educational models.

We're looking for someone with exceptional analytical capabilities, strong commercial judgment, and an entrepreneurial mindset who can connect deep business insights with practical execution and successful new programs.

Core Responsibilities:

• Understand and shape marketplace growth strategy: Develop a deep understanding of Outschool's core business, including revenue, gross merchandise value (GMV), customer acquisition, conversion, retention, educator supply, and marketplace economics. Help establish the strategic priorities and multi-year roadmap for marketplace growth and new programs.

• Identify opportunities to strengthen the core business: Analyze customer behavior, category performance, pricing, unit economics, competitive dynamics, and growth drivers. Work with Product, Growth, Marketing, Finance, and Operations to identify business challenges and recommend initiatives that improve marketplace performance and competitiveness.

• Evaluate new markets and growth opportunities: Analyze the competitive landscape, emerging education trends, underserved customer needs, and evolving business models. Assess total addressable markets (TAM), positioning, pricing, and revenue potential to identify attractive opportunities for expansion.

• Develop business cases and investment recommendations: Build financial models, revenue projections, and business cases for new programs, services, and market opportunities. Evaluate build, buy, and partner strategies and recommend investment priorities.

• Design new educational offerings: Lead the strategy and commercial design of new programs, bundled learning experiences, specialized services, and marketplace business models. Define target audiences, value propositions, positioning, packaging, pricing, delivery models, and financial objectives.

• Lead cross-functional program development: Serve as the central business lead for new program initiatives, working closely with Product, Growth, Marketing, Business Development, Finance, and Operations to translate concepts into business requirements, development plans, and launch-ready offerings.

• Drive program launches and revenue growth: Establish clear revenue forecasts, enrollment targets, launch milestones, and performance measures for new programs. Coordinate launches, monitor commercial results, and work with functional teams to optimize offerings, pricing, packaging, and go-to-market strategies.

• Collaborate across growth initiatives: Partner with the Public Funding & Accredited Programs Strategy Director to identify opportunities to integrate marketplace offerings with publicly funded, accredited, and tuition-based educational programs, ensuring clear ownership and coordinated execution.

• Drive accountability and strategic decisions: Monitor performance of new initiatives, identify opportunities for expansion or improvement, and recommend continued investment, modifications, or discontinuation based on results. Present marketplace insights, business cases, strategic recommendations, and performance updates to executive leadership.

Desired Experience & Skills:

• 8+ years of experience in business strategy, growth strategy, product strategy, or new business development within consumer marketplaces, education, technology, or services businesses, including at least 3 years of experience leading a team or holding P&L responsibility.

• Strong analytical capabilities and demonstrated experience evaluating business performance, customer behavior, unit economics, and drivers of revenue growth.

• Demonstrated success identifying strategic opportunities and translating market and competitive insights into successful business initiatives.

• Experience developing business cases, financial models, market assessments, pricing strategies, and investment recommendations.

• Proven experience taking new products, programs, services, or business initiatives from opportunity identification through development, launch, and revenue growth.

• Strong cross-functional leadership skills, with the ability to align teams, influence priorities, and drive execution without direct reporting authority.

• Experience working closely with Product, Growth, Marketing, Business Development, Finance, and Operations.

• Entrepreneurial mindset, strong commercial judgment, and a demonstrated ability to translate strategy into measurable business results.

Other Considerations:

• Experience with consumer marketplaces, two-sided platforms, or educational services businesses.

• Experience analyzing marketplace dynamics, customer acquisition, retention, provider supply, and category economics.

• Experience developing bundled offerings, new service categories, subscriptions, or innovative commercial models.

• Experience launching and scaling new products, programs, or business lines within an established organization.

• Experience evaluating strategic partnerships, acquisitions, and build-buy-partner opportunities.

• Previous experience in startups, high-growth companies, or education technology businesses.

Compensation:

Outschool recruits across the US and Canada, and sets employee salaries to reflect local compensation and cost of living. In addition to base compensation, this role is eligible for equity and benefits. Additional details are provided during the interview process.

This role is available in the following US Pay Zones:

US Tiers

US Tier 1: San Francisco Bay Area, New York City, and Seattle Metro

US Tier 2: All California excluding San Francisco Bay Area, Boston Metro, Chicago Metro, Denver Metro, Austin Metro, Portland Metro

US Tier 3: All other cities and states

US Pay Zones

US Tier 1: This position is not available in this pay zone

US Tier 2: $183,600 - $207,000

US Tier 3: $162,000 - $182,250

Benefits & Culture:

At Outschool, we believe that taking care of one another enables us to do our best work. To us that means:

• Shared Financial Success: Competitive salaries, stock options, and retirement plans.

• Health: Comprehensive medical, dental, vision, disability, and life insurance.

• Wellness: Annual wellness stipend, access to coaching & therapy, and pet wellness plans.

• PTO & Family Benefits: Generous PTO and family leave policies.

• Hybrid & Remote-Friendly: Outschool has a distributed team across the U.S. and Canada and an office in San Francisco. Bay Area-based employees work in the office part of the week and receive commute-related benefits. Team members outside the Bay Area remain fully remote, with support for expensable home office setup and internet to stay connected no matter where you are.

• Lifelong Learners: Annual budgets for professional development and DEI learning; budgets for children to take Outschool classes.

• Community Impact: Outschool matches employee donations to eligible charities and supports Outschool.org’s nonprofit programs.

Outschool is an equal opportunity employer. We view diversity as a moral imperative and competitive advantage. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We plan and structure our interviews to directly assess skills and experience.

Benefits packages are included for full-time employees only. Please note benefits and perks may vary for employees based outside of the US and Canada.

Full-time employees must be a citizen or legal residents of the U.S. or Canada and reside in U.S. or Canada, unless specifically indicated otherwise.

Once you submit your application, Outschool will process your personal data to evaluate your candidacy for employment. Unless specifically indicated otherwise, we hire employees only in the U.S. and Canada. Applicants else where should be aware that we may discard your application upon submission or we may ask if you would like us to retain it later should there be consideration (this is not typical at all). If you are selected for interviewing, your data will be shared with interviewers and personnel involved in that process. If not hired, your application will be retained for one year in case there is another suitable role. You may opt out of this at any time. Please see our Employee/Applicant Privacy Notice for more detailed information. If applicable, as you progress through the process, we will be clear about what information is being asked for and what happens with that information.