Crossover

You would oversee portfolio dashboards, vendor scorecards, competitive technology procurement, and contract and invoice controls to support executive decisions across a $50M portfolio. | The role requires director-level ownership of 10+ initiatives with at least $5M in budget responsibility, management of multiple external technology vendors, and demonstrated experience with competitive procurement, SOWs, contract terms, and invoice validation. | You’ve built dashboards. Tracked milestones. Chased vendors. Flagged risks. But your reports hit a ceiling. You weren’t the one making the calls. 2 Hour Learning is building an AI-powered education model designed to help students achieve a full day of academic progress in just two hours. Making that model work at scale requires dozens of initiatives, technology partners, contracts, and investment decisions to move in sync. Your job is to make the execution layer trustworthy enough for executives to act on it. You will own the operating outputs behind those decisions: portfolio dashboards that expose slippage before it becomes a surprise, vendor scorecards tied to real contractual commitments, competitive bid packages that make trade-offs clear, and contract controls that prevent unsupported spend. AI will be part of your daily workflow, helping you standardize updates, detect anomalies, compare bids, analyze vendor performance, and validate invoices. This is not a PMO role built around meetings, process compliance, or polished status decks. It is for an operator who wants their work to have consequences. When a vendor underperforms, your evidence should make that obvious. When spend drifts from the contract, your controls should catch it. When executives need to make a $5M decision, your outputs should give them the confidence to make it fast. If that sounds like the level of ownership you have been looking for, apply. What You Will Be Doing • Own portfolio-level dashboards across 10+ concurrent initiatives, using AI to standardize updates, detect slippage, expose blockers, and maintain a trusted executive view of delivery, budget, and risk • Run recurring vendor performance reviews and maintain rubric-based scorecards that combine delivery, quality, cost, contractual commitments, and qualitative performance signals • Lead competitive technology-vendor procurement, including structured bid packages, normalized comparisons, scoring rubrics, SOW development, and evidence-backed recommendations • Govern contracts and invoices by tracking fee caps, milestones, acceptance criteria, and amendments, then validating invoices against signed terms before spend is approved • Use AI daily to analyze portfolio data, detect anomalies, surface underperformance, draft decision-ready outputs, and reduce manual PMO administration What You Won’t Be Doing • Producing status reports that executives read but never use to make decisions • Running a meeting-heavy PMO where coordination matters more than measurable execution • Treating vendor management as relationship maintenance while missed commitments go unchallenged • Passing contracts, SOWs, invoices, or procurement decisions to someone else because they look too commercial or technical • Using AI as an occasional productivity trick instead of a core part of how you operate Director Of Vendor Program Management Key Responsibilities Your mandate is to produce reliable, AI-powered dashboards, scorecards, procurement packages, and contract controls that give executives the clarity and leverage to hold vendors accountable, control costs, and accelerate delivery across a $50M EdTech portfolio. Basic Requirements • Directly owned a portfolio of 10+ concurrent initiatives with at least $5M in budget responsibility, including authority over budget allocation, vendor selection, or initiative prioritization • Managed 5+ external technology vendors at the same time, such as SaaS providers, AI/ML platforms, marketing agencies, or engineering firms • Built and maintained portfolio-level dashboards covering metrics such as delivery health, budget burn versus forecast, milestone completion, and major risks or blockers • Can point to a case where C-suite leaders used your portfolio data to make a go/no-go decision on a vendor renewal, budget reallocation, or initiative deprioritization • Directly led competitive technology procurement, including structured bid evaluation, vendor scoring, negotiation, and selection • Authored or co-authored SOWs with measurable deliverables, milestone payments, SLAs, acceptance criteria, or other performance-based terms • Negotiated commercial terms such as pricing, penalties, fee caps, or exit clauses and enforced those terms through invoice validation or corrective action • Strong written communication skills, with the ability to turn complex financial and operational data into concise recommendations executives can act on • Able to analyze financial and vendor-performance data quickly enough to recommend optimization, reallocation, or vendor elimination • Able to work US business hours Nice-to-have Requirements • Experience using AI-enabled dashboards, anomaly detection, predictive alerts, or natural-language analysis in portfolio management • Experience in EdTech, technology, consulting, or another environment managing complex portfolios of external technology partners • Fluency with portfolio and delivery tools such as Linear, Jira, or similar systems 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. Here’s How They’re Fixing It. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! 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 $100 USD/hour, which equates to $200,000 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. Crossover Job Code: LJ-5669-US-Miami-DirectorofVend.014

You would design and validate a gifted-school model, launch a prototype campus, build scalable programs and playbooks, and represent the model publicly. | The role requires a venture founder with at least $1 million in annual revenue ownership, deep gifted-student understanding, AI-first work habits, and regular travel to Austin. | You already built something from zero and took it to scale. Now you're looking for your next big bet—one that has both urgency and moral clarity. If you believe the U.S. education system is criminally under-serving gifted kids, and you’re ready to do something about it, keep reading. gt.school is redefining what school should look like for high-potential students. Our 2 Hour Learning model compresses the academic day into focused, mastery-based sessions—freeing up time for students to pursue real challenges. Now, we’re ready to build out a physical model campus that adds the missing pieces: leadership experiences, peer competition, performance-driven culture, and the kind of community these students have been missing. You’ll lead the design, validation, and public rollout of this model campus—with the goal of making it the prototype for a nationwide network. You'll also continue to build our virtual GT Anywhere program together with the team we already have in place. That means testing real-world programming, developing parent demand, building a culture that sticks, and crafting the playbooks to scale it all. We need someone with founder-level energy and credibility. Someone who understands that the best ideas mean nothing without relentless execution. Someone who can turn a sharp point of view into a school parents can’t stop talking about—and students can’t wait to attend. What You Will Be Doing • Designing and testing scalable programs that extend beyond academics—focusing on leadership, independence, and competition • Building and validating a physical model campus, including staffing models, space design, and operations • Developing parent-facing messaging, market strategies, and growth playbooks to fuel expansion • Defining, documenting, and scaling quality standards and cultural rituals across all future sites • Acting as the public face of the model—driving visibility through media, events, and partnerships What You Won’t Be Doing • Stepping into a traditional school role with classrooms, teachers, and a full-day schedule • Catering to families who want gifted-lite programs with AP classes and minimal challenge • Managing incremental change within existing institutions—we're not "fixing" schools, we're replacing them • Chasing superficial engagement metrics—we care about hard outcomes and deep learning, not just activity • Building everything remotely—you'll have flexibility, but will spend ~1 week/month in Austin to ground your work in reality Program Director Key Responsibilities Design, validate, and scale a high-performance gifted school model—starting with a single prototype campus and expanding to a national network. Basic Requirements • Built and scaled a high-impact venture from scratch (bonus if it involved physical operations or education). We are talking about at least 1M USD yearly revenue owned by you • Deep, personal understanding of gifted students—whether through family, professional experience, or lived reality • AI First mentality — Inclination to prioritize AI as the default solution for problem-solving, decision-making and work output generation at scale. • Proven ability to articulate a compelling vision and convert skeptics into believers • Based in the U.S., with ability to travel regularly to Austin (minimum 1 week/month) • Eligible to work in the U.S. without visa sponsorship About GT School GT School is revolutionizing education with AI, expert coaching, and 50+ years of learning science. They blend cutting-edge tech with data-driven insights to unlock every student's full potential. They're on a mission to disrupt the broken education system and unleash the true potential of gifted minds. Forget the one-size-fits-all approach that leaves brilliant students bored and disengaged. This school has tossed the rulebook and created a modern learning environment powered by AI and guided by dedicated mentors. Their personalized approach accelerates learning - 2-6 times faster than traditional classrooms. GT School students explore their passions, develop critical thinking skills, and learn to innovate. Because that's where genius lies. GT School is where gifted minds turn potential into power. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! 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. Crossover Job Code: LJ-5482-US-RoundRoc-ProgramDirecto.019

Coach K–8 students virtually on goals, motivation, and mindset; facilitate workshops, track progress, communicate with parents, and collaborate with the coaching team. | Requires a master’s degree, at least one year coaching or motivating K–8 students, six months working with gifted students, strong virtual communication, and comfort using performance dashboards. | You've already pushed your limits—on the field, on the stage, or in the boardroom. Now you're ready to make that excellence matter. As an academic coach at GT Anywhere, you'll guide students to do the unthinkable: love school, learn faster, and grow into confident, self-directed humans. And you'll do it from anywhere in the world. GT Anywhere is the virtual school for gifted students who are ready to accelerate. We pair AI-powered academics with high-touch coaching to deliver what traditional school can't: limitless learning velocity, depth in the sciences and humanities, and a community of intellectual peers. As an Academic Coach, you'll guide K–8 students who want to go faster. You're not teaching content—our tech handles that. You're the coach who builds belief, holds the bar high, and helps students discover what they're capable of. Every session matters. Every breakthrough counts. If you've ever pushed yourself to elite performance—on the field, on the stage, in the lab, or in business—and you want to help the next generation do the same, this is your role. What You Will Be Doing • Leading biweekly 1:1 virtual coaching sessions for each student, focusing on academic goal-setting, motivation, and mindset • Running open “office hours” where students drop in for real-time support, encouragement, or troubleshooting • Preparing and facilitating engaging virtual life-skills workshops for gifted students across age bands • Using AI tools and dashboards to track student progress, identify blockers, and adjust your coaching approach • Logging insights, flags, and strategy updates to ensure each student stays on a fast-growth trajectory • Communicating proactively with parents about student progress, goals, and concerns • Collaborating with your team to share strategies, escalate concerns, and constantly improve the coaching model What You Won’t Be Doing • Teaching lessons, grading tests, or assigning homework—our tech handles the academics • Delivering lectures or following a set curriculum • Babysitting or micromanaging disengaged students—we coach, not hover • Sitting through unnecessary meetings or bureaucracy • Coasting—this team is built for people who want to perform at a high level and make it count Academic Coach Key Responsibilities Drive measurable academic growth and engagement for virtual students by delivering high-frequency, high-impact mindset coaching in a fully remote, tech-powered model. Basic Requirements • Master’s degree in any field • At least 1 year of experience coaching, mentoring, or motivating K–8 students • At least 6 months working with gifted students in an educational, coaching, or mentoring setting • Proven high performance in any field—academics, athletics, entrepreneurship, or the arts • Strong virtual presence and ability to connect with students quickly over Zoom/Google Meet • Comfortable using dashboards and tech tools to track and adjust performance • Ability to maintain at least 80 percent overlap with US business hours Nice-to-have Requirements • PhD in any field • Background in performance coaching, sports psychology, or motivational work • Experience working with homeschool or alternative education families About GT School GT School is revolutionizing education with AI, expert coaching, and 50+ years of learning science. They blend cutting-edge tech with data-driven insights to unlock every student's full potential. They're on a mission to disrupt the broken education system and unleash the true potential of gifted minds. Forget the one-size-fits-all approach that leaves brilliant students bored and disengaged. This school has tossed the rulebook and created a modern learning environment powered by AI and guided by dedicated mentors. Their personalized approach accelerates learning - 2-6 times faster than traditional classrooms. GT School students explore their passions, develop critical thinking skills, and learn to innovate. Because that's where genius lies. GT School is where gifted minds turn potential into power. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! 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 $37 USD/hour, which equates to $75,000 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. Crossover Job Code: LJ-5732-US-Austin-AcademicCoach.006

You will deliver life-skills workshops, coach students toward weekly goals using progress data, assess skill mastery, and document student progress across rotating campuses. | Requires a bachelor's degree, at least three years working with K–8 students, and willingness to travel to assigned U.S. campuses for one to three months at a time. | "All of my students came back in the top 1% for growth and achievement on their MAP scores." — Sam DePalo, Lead Guide, Alpha Fort Worth Texas Alpha is hiring. Most youth development careers reward you for staying put. This one rewards you for arriving. You will land at a different Alpha campus every one to three months, walk in as a stranger to every student, parent and colleague, and have them working at full standard inside a week. Alpha sends you where the network needs you, on site at campuses across the United States: one launching from nothing, or one running short-staffed. You do not choose the city. Accommodation is booked and paid for at every stop, and you earn a flat $120,000 wherever you live. You will be away from home every week outside of PTO. Alpha is a private school where students finish core academics in two hours a day using adaptive software. The rest of the day goes to life skills: public speaking, focus, collaboration, and giving and taking feedback. You will not teach math or reading. You will run one-hour workshops where students build, debate and present, then coach them one to one against their own progress data until they hit their weekly targets. Most people doing this work see one cohort in one city. You will see the whole network: which motivation strategies travel and which are local, and what separates a campus that is thriving from one that is struggling, because you will have worked in both inside the same year. You will also watch quiet students stand up and present to a room, in more than one state. Nothing prepares you faster to lead a campus of your own. If the road is the point rather than the price, apply. What You Will Be Doing • Run one-hour life skill workshops for K-8 students, adapting the provided curriculum to the cohort in front of you • Coach students one to one and in small groups using Coachbot analytics, weekly goals and incentives, until 90% or more hit their targets • Administer and score Test2Pass assessments so students prove the skill rather than just attend the session • Reach full standard inside your first week at each new campus, with names learned and rapport built • Hand over cleanly at the end of every posting, documenting per-student progress and every open intervention What You Won’t Be Doing • Teaching core academic subjects, lecturing from the front of the room, or grading • Writing curriculum from scratch: workshop plans, analytics and playbooks are provided • Running campus operations, facilities or admissions • Filling in as a substitute with no authority and no accountability for student results • Funding your own travel: accommodation is booked and paid for at every posting Youth Development Specialist Key Responsibilities Hold student outcomes at full standard at whichever campus is launching or running short-staffed. Basic Requirements • Based anywhere in the US, within reasonable reach of a major airport • Willing to be posted away from home one to three months at a time, with time at home only during PTO • Comfortable with Alpha assigning every posting, including the city and the campus • Bachelor's degree in any subject • At least 3 years working with K-8 students. Classroom experience is not required: camp counseling, coaching and youth program leadership all count • Able to describe one specific time you coached a K-8 student toward a goal, including the goal, what you did, and the result • Legal right to work in the US without visa sponsorship Nice-to-have Requirements • A track record of sustained mobility: travel-heavy field roles, touring programs, seasonal camp circuits, or service-year placements across multiple cities • Experience running youth workshops in camps, athletics, enrichment programs or youth leadership settings • Comfort reading student progress dashboards or learning analytics to decide where to intervene • Experience coaching a disengaged student to a measurable improvement you can point to About Alpha Join the team building school around student growth Alpha reimagines the school day around faster learning, stronger mentorship, and more time for students to build real-world skills. Roles with real student impact: Alpha hires teachers (guides), operators, admissions experts, school & curriculum leaders, and remote team members. Education work that pays like it matters: Alpha offers six-figure roles for people ready to help build a radically better school experience. A culture built for builders: Alpha is fast-moving, ambitious, and student focused. It’s for people who want to improve the system, not maintain it. Alpha is where you can do the most meaningful work of your career. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! Working with us This is a full-time, W2 employee position with immediate access to benefits (https://support.crossover.com/article/7581-w2-benefits-u-s-paychex-paid-only). All roles are year-long positions. The compensation level for this role is $120,000 USD/year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic. Crossover Job Code: LJ-5849-US-Phoenix-YouthDevelopme1.002

Design, validate, and scale a gifted-school model by building a prototype campus, developing programs and growth playbooks, and representing the model publicly. | Requires a venture built and scaled to at least $1 million in annual revenue, deep understanding of gifted students, AI-first problem-solving, and compelling vision-building. | You already built something from zero and took it to scale. Now you're looking for your next big bet—one that has both urgency and moral clarity. If you believe the U.S. education system is criminally under-serving gifted kids, and you’re ready to do something about it, keep reading. gt.school is redefining what school should look like for high-potential students. Our 2 Hour Learning model compresses the academic day into focused, mastery-based sessions—freeing up time for students to pursue real challenges. Now, we’re ready to build out a physical model campus that adds the missing pieces: leadership experiences, peer competition, performance-driven culture, and the kind of community these students have been missing. You’ll lead the design, validation, and public rollout of this model campus—with the goal of making it the prototype for a nationwide network. You'll also continue to build our virtual GT Anywhere program together with the team we already have in place. That means testing real-world programming, developing parent demand, building a culture that sticks, and crafting the playbooks to scale it all. We need someone with founder-level energy and credibility. Someone who understands that the best ideas mean nothing without relentless execution. Someone who can turn a sharp point of view into a school parents can’t stop talking about—and students can’t wait to attend. What You Will Be Doing • Designing and testing scalable programs that extend beyond academics—focusing on leadership, independence, and competition • Building and validating a physical model campus, including staffing models, space design, and operations • Developing parent-facing messaging, market strategies, and growth playbooks to fuel expansion • Defining, documenting, and scaling quality standards and cultural rituals across all future sites • Acting as the public face of the model—driving visibility through media, events, and partnerships What You Won’t Be Doing • Stepping into a traditional school role with classrooms, teachers, and a full-day schedule • Catering to families who want gifted-lite programs with AP classes and minimal challenge • Managing incremental change within existing institutions—we're not "fixing" schools, we're replacing them • Chasing superficial engagement metrics—we care about hard outcomes and deep learning, not just activity • Building everything remotely—you'll have flexibility, but will spend ~1 week/month in Austin to ground your work in reality Program Director Key Responsibilities Design, validate, and scale a high-performance gifted school model—starting with a single prototype campus and expanding to a national network. Basic Requirements • Built and scaled a high-impact venture from scratch (bonus if it involved physical operations or education). We are talking about at least 1M USD yearly revenue owned by you • Deep, personal understanding of gifted students—whether through family, professional experience, or lived reality • AI First mentality — Inclination to prioritize AI as the default solution for problem-solving, decision-making and work output generation at scale. • Proven ability to articulate a compelling vision and convert skeptics into believers • Based in the U.S., with ability to travel regularly to Austin (minimum 1 week/month) • Eligible to work in the U.S. without visa sponsorship About GT School GT School is revolutionizing education with AI, expert coaching, and 50+ years of learning science. They blend cutting-edge tech with data-driven insights to unlock every student's full potential. They're on a mission to disrupt the broken education system and unleash the true potential of gifted minds. Forget the one-size-fits-all approach that leaves brilliant students bored and disengaged. This school has tossed the rulebook and created a modern learning environment powered by AI and guided by dedicated mentors. Their personalized approach accelerates learning - 2-6 times faster than traditional classrooms. GT School students explore their passions, develop critical thinking skills, and learn to innovate. Because that's where genius lies. GT School is where gifted minds turn potential into power. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! 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. Crossover Job Code: LJ-5482-US-RoundRoc-ProgramDirecto.018

Lead vendor program management with AI-powered dashboards, vendor scorecards, procurement, and contract governance to support executive decision-making. | Manage multiple vendor initiatives with budget responsibility, build dashboards, lead procurement, and enforce contract terms using AI tools. | You’ve built dashboards. Tracked milestones. Chased vendors. Flagged risks. But your reports hit a ceiling. You weren’t the one making the calls. 2 Hour Learning is building an AI-powered education model designed to help students achieve a full day of academic progress in just two hours. Making that model work at scale requires dozens of initiatives, technology partners, contracts, and investment decisions to move in sync. Your job is to make the execution layer trustworthy enough for executives to act on it. You will own the operating outputs behind those decisions: portfolio dashboards that expose slippage before it becomes a surprise, vendor scorecards tied to real contractual commitments, competitive bid packages that make trade-offs clear, and contract controls that prevent unsupported spend. AI will be part of your daily workflow, helping you standardize updates, detect anomalies, compare bids, analyze vendor performance, and validate invoices. This is not a PMO role built around meetings, process compliance, or polished status decks. It is for an operator who wants their work to have consequences. When a vendor underperforms, your evidence should make that obvious. When spend drifts from the contract, your controls should catch it. When executives need to make a $5M decision, your outputs should give them the confidence to make it fast. If that sounds like the level of ownership you have been looking for, apply. What You Will Be Doing - Own portfolio-level dashboards across 10+ concurrent initiatives, using AI to standardize updates, detect slippage, expose blockers, and maintain a trusted executive view of delivery, budget, and risk - Run recurring vendor performance reviews and maintain rubric-based scorecards that combine delivery, quality, cost, contractual commitments, and qualitative performance signals - Lead competitive technology-vendor procurement, including structured bid packages, normalized comparisons, scoring rubrics, SOW development, and evidence-backed recommendations - Govern contracts and invoices by tracking fee caps, milestones, acceptance criteria, and amendments, then validating invoices against signed terms before spend is approved - Use AI daily to analyze portfolio data, detect anomalies, surface underperformance, draft decision-ready outputs, and reduce manual PMO administration What You Won’t Be Doing - Producing status reports that executives read but never use to make decisions - Running a meeting-heavy PMO where coordination matters more than measurable execution - Treating vendor management as relationship maintenance while missed commitments go unchallenged - Passing contracts, SOWs, invoices, or procurement decisions to someone else because they look too commercial or technical - Using AI as an occasional productivity trick instead of a core part of how you operate Director Of Vendor Program Management Key Responsibilities Your mandate is to produce reliable, AI-powered dashboards, scorecards, procurement packages, and contract controls that give executives the clarity and leverage to hold vendors accountable, control costs, and accelerate delivery across a $50M EdTech portfolio. Basic Requirements - Directly owned a portfolio of 10+ concurrent initiatives with at least $5M in budget responsibility, including authority over budget allocation, vendor selection, or initiative prioritization - Managed 5+ external technology vendors at the same time, such as SaaS providers, AI/ML platforms, marketing agencies, or engineering firms - Built and maintained portfolio-level dashboards covering metrics such as delivery health, budget burn versus forecast, milestone completion, and major risks or blockers - Can point to a case where C-suite leaders used your portfolio data to make a go/no-go decision on a vendor renewal, budget reallocation, or initiative deprioritization - Directly led competitive technology procurement, including structured bid evaluation, vendor scoring, negotiation, and selection - Authored or co-authored SOWs with measurable deliverables, milestone payments, SLAs, acceptance criteria, or other performance-based terms - Negotiated commercial terms such as pricing, penalties, fee caps, or exit clauses and enforced those terms through invoice validation or corrective action - Strong written communication skills, with the ability to turn complex financial and operational data into concise recommendations executives can act on - Able to analyze financial and vendor-performance data quickly enough to recommend optimization, reallocation, or vendor elimination - Able to work US business hours Nice-to-have Requirements - Experience using AI-enabled dashboards, anomaly detection, predictive alerts, or natural-language analysis in portfolio management - Experience in EdTech, technology, consulting, or another environment managing complex portfolios of external technology partners - Fluency with portfolio and delivery tools such as Linear, Jira, or similar systems 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. Here’s How They’re Fixing It. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! 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 $100 USD/hour, which equates to $200,000 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. Crossover Job Code: LJ-5669-US-Chicago-DirectorofVend.011

Manage and design community engagement systems to drive retention and advocacy. | Requires experience in community or customer success program management, digital communication channels, and data fluency. | At GT School, community is not a side initiative. It is our growth engine. Our parent network is our most defensible advantage. When families feel connected, valued, and invested, they stay longer, refer faster, and advocate louder. We are looking for a high-agency builder who can turn a collection of enrolled families into a self-sustaining ecosystem. In this role, you will design the systems that transform parents from customers into stakeholders. You will create the structures, rituals, and feedback loops that drive retention and referrals. You will not manage surface-level engagement. You will architect belonging. If you think in flywheels, measure sentiment, and believe that community should directly impact growth, this role gives you ownership over one of the school’s most powerful assets. What You Will Be Doing - Designing “sticky” engagement systems that move parents from passive observers to active contributors - Identifying highly satisfied families and equipping them to become structured referral ambassadors - Monitoring community health daily and intervening early with at-risk families - Translating parent sentiment into weekly strategic briefs that inform leadership decisions - Aligning academic milestones with intentional community “moments” that reinforce value - Responding to parent questions with clarity, empathy, and speed across digital channels - Creating and maintaining clear, high-impact parent-facing resources and knowledge content What You Won’t Be Doing - Managing passive social media engagement or chasing vanity metrics - Broadcasting one-way updates without building real dialogue - Operating as a reactive helpdesk or ticket closer - Reading from scripts or relying on templated responses - Troubleshooting technical bugs or acting as platform support Customer Community Manager Key Responsibilities Build and operationalize a parent community system that drives measurable retention, advocacy, and organic enrollment growth. Basic Requirements - A track record of designing and managing community, customer success, or multi-stakeholder programs - Strong program management skills with experience running end-to-end initiatives - Demonstrated ability to de-escalate sensitive parent concerns while extracting actionable feedback - Data fluency with experience using CRMs and engagement metrics to track impact - Exceptional writing skills with a clear, persuasive, human voice - At least 1 year managing digital communication channels such as email, chat, or helpdesk tools - Strong live virtual communication skills and the ability to build trust with parents over video calls - Based and authorized to work in the US - Willing to travel to GT School events around the US every month Nice-to-have Requirements - Experience building community or customer advocacy programs in a high-growth startup - Background in education or private school environments - Fluency with digital community platforms such as Slack, WhatsApp Business, Circle, or similar tools About GT School GT School is revolutionizing education with AI, expert coaching, and 50+ years of learning science. They blend cutting-edge tech with data-driven insights to unlock every student's full potential. They're on a mission to disrupt the broken education system and unleash the true potential of gifted minds. Forget the one-size-fits-all approach that leaves brilliant students bored and disengaged. This school has tossed the rulebook and created a modern learning environment powered by AI and guided by dedicated mentors. Their personalized approach accelerates learning - 2-6 times faster than traditional classrooms. GT School students explore their passions, develop critical thinking skills, and learn to innovate. Because that's where genius lies. GT School is where gifted minds turn potential into power. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! 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 $50 USD/hour, which equates to $100,000 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. Crossover Job Code: LJ-5748-US-Dallas-CustomerCommun.002

Lead vendor and portfolio management with AI-powered dashboards and contract governance to support executive decision-making. | Requires direct ownership of multi-million dollar portfolios, multiple vendor management, procurement leadership, and strong executive communication skills. | You’ve built dashboards. Tracked milestones. Chased vendors. Flagged risks. But your reports hit a ceiling. You weren’t the one making the calls. 2 Hour Learning is building an AI-powered education model designed to help students achieve a full day of academic progress in just two hours. Making that model work at scale requires dozens of initiatives, technology partners, contracts, and investment decisions to move in sync. Your job is to make the execution layer trustworthy enough for executives to act on it. You will own the operating outputs behind those decisions: portfolio dashboards that expose slippage before it becomes a surprise, vendor scorecards tied to real contractual commitments, competitive bid packages that make trade-offs clear, and contract controls that prevent unsupported spend. AI will be part of your daily workflow, helping you standardize updates, detect anomalies, compare bids, analyze vendor performance, and validate invoices. This is not a PMO role built around meetings, process compliance, or polished status decks. It is for an operator who wants their work to have consequences. When a vendor underperforms, your evidence should make that obvious. When spend drifts from the contract, your controls should catch it. When executives need to make a $5M decision, your outputs should give them the confidence to make it fast. If that sounds like the level of ownership you have been looking for, apply. What You Will Be Doing - Own portfolio-level dashboards across 10+ concurrent initiatives, using AI to standardize updates, detect slippage, expose blockers, and maintain a trusted executive view of delivery, budget, and risk - Run recurring vendor performance reviews and maintain rubric-based scorecards that combine delivery, quality, cost, contractual commitments, and qualitative performance signals - Lead competitive technology-vendor procurement, including structured bid packages, normalized comparisons, scoring rubrics, SOW development, and evidence-backed recommendations - Govern contracts and invoices by tracking fee caps, milestones, acceptance criteria, and amendments, then validating invoices against signed terms before spend is approved - Use AI daily to analyze portfolio data, detect anomalies, surface underperformance, draft decision-ready outputs, and reduce manual PMO administration What You Won’t Be Doing - Producing status reports that executives read but never use to make decisions - Running a meeting-heavy PMO where coordination matters more than measurable execution - Treating vendor management as relationship maintenance while missed commitments go unchallenged - Passing contracts, SOWs, invoices, or procurement decisions to someone else because they look too commercial or technical - Using AI as an occasional productivity trick instead of a core part of how you operate Director Of Vendor Program Management Key Responsibilities Your mandate is to produce reliable, AI-powered dashboards, scorecards, procurement packages, and contract controls that give executives the clarity and leverage to hold vendors accountable, control costs, and accelerate delivery across a $50M EdTech portfolio. Basic Requirements - Directly owned a portfolio of 10+ concurrent initiatives with at least $5M in budget responsibility, including authority over budget allocation, vendor selection, or initiative prioritization - Managed 5+ external technology vendors at the same time, such as SaaS providers, AI/ML platforms, marketing agencies, or engineering firms - Built and maintained portfolio-level dashboards covering metrics such as delivery health, budget burn versus forecast, milestone completion, and major risks or blockers - Can point to a case where C-suite leaders used your portfolio data to make a go/no-go decision on a vendor renewal, budget reallocation, or initiative deprioritization - Directly led competitive technology procurement, including structured bid evaluation, vendor scoring, negotiation, and selection - Authored or co-authored SOWs with measurable deliverables, milestone payments, SLAs, acceptance criteria, or other performance-based terms - Negotiated commercial terms such as pricing, penalties, fee caps, or exit clauses and enforced those terms through invoice validation or corrective action - Strong written communication skills, with the ability to turn complex financial and operational data into concise recommendations executives can act on - Able to analyze financial and vendor-performance data quickly enough to recommend optimization, reallocation, or vendor elimination - Able to work US business hours Nice-to-have Requirements - Experience using AI-enabled dashboards, anomaly detection, predictive alerts, or natural-language analysis in portfolio management - Experience in EdTech, technology, consulting, or another environment managing complex portfolios of external technology partners - Fluency with portfolio and delivery tools such as Linear, Jira, or similar systems 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. Here’s How They’re Fixing It. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! 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 $100 USD/hour, which equates to $200,000 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. Crossover Job Code: LJ-5669-US-Chicago-DirectorofVend.010