Crossover

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

Own full-funnel enrollment growth and brand strategy for a gifted K–8 education platform. | 10+ years leading full-funnel marketing strategy with measurable conversion results and AI tool fluency. | This is not a position about managing campaigns. This is about owning growth. Most marketing leadership positions define success through impressions and volume of activity. This role defines it through enrollments. At gt.school, demand is already present. Families are searching for a credible, high-performance K–8 option designed for gifted learners. Our AI-powered approach accelerates mastery and allows students to focus on advanced interests and real-world capabilities. The product is proven. The market is prepared. What we require now is a marketing leader capable of converting this demand into meaningful scale. You will have full ownership of the enrollment engine for GT Anywhere and direct influence over brand strategy across virtual, campus, and summer offerings. Your mandate is clear: transform high-intent demand into 1,000 enrolled families while positioning gt.school as the authoritative name in gifted K–8 education. No playbook will be handed to you. You will design the funnel, establish positioning, lead experimentation, and create a dependable execution system using agencies, freelancers, and technology. You will work with autonomy and carry direct accountability for outcomes. If you seek ownership of a tangible target and the authority to construct the system that delivers it, let's talk. What You Will Be Doing • Taking full ownership of the enrollment funnel for GT Anywhere with direct responsibility for enrollments, conversion performance, and customer acquisition cost • Leading continuous experimentation efforts to detect and resolve high-impact conversion obstacles • Leveraging GenAI tools and AI-powered workflows to enhance marketing analysis, creative development, funnel diagnostics, and execution velocity • Developing the annual marketing strategy for virtual, campus, and summer programs, covering positioning, segmentation, channel allocation, budget planning, and measurable objectives • Creating a high-velocity execution framework that delivers consistently through agencies, freelancers, AI platforms, and marketing systems • Collaborating directly with enrollment and school teams to convert family insights into more effective messaging and higher-performing creative assets What You Won’t Be Doing • Leading awareness-focused campaigns without direct accountability for enrollments • Serving as a request handler for one-off marketing tasks with ambiguous return on investment • Relying on lengthy approval cycles or large bureaucratic structures to move forward • Focusing on vanity metrics that do not connect to enrolled families VP Of Marketing Key Responsibilities Develop and operate a full-funnel growth system that transforms existing demand into 1,000 enrolled families while establishing gt.school as the defining brand in gifted K–8 education. Basic Requirements • Bachelor's degree (BA or equivalent) • 10+ years of experience leading full-funnel marketing strategy and delivering measurable results in startup, technology, or high-growth settings • Proven accountability for hard conversion metrics including enrollments, revenue, customer acquisition cost, and conversion rates • Strong analytical capability in funnel performance with a history of identifying problems and prioritizing high-impact solutions • Experience establishing brand strategy, positioning, and messaging at the company level • Practical fluency with GenAI, including concrete examples of applying AI tools or AI-enabled workflows to enhance marketing productivity, execution speed, analytical quality, or business results • Demonstrated ability to design and manage scalable execution systems leveraging agencies, freelancers, AI tools, and marketing technology • Ability to work full-time (40 hours/week) in a remote capacity based in the United States 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 $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-5750-US-LosAngel-VPofMarketing