Planning Manager
Cypress HCM
Overview The Planning team is the strategic and operational backbone of Fraud and Safety Operations (FSO). We drive the planning systems, roadmap execution, and cross-functional coordination that keep FSO moving with speed and discipline. Our mission is simple: deliver a clear, well-resourced plan so that FSO can focus on what matters most, delivering peace of mind to every guest and host on the platform. Every member of our team is expected to be coachable, highly organized, proactively communicative, and committed to operational excellence, both as an individual contributor and as a trusted cross-functional partner. The Difference You Will Make: FSO's planning process is complex, multi-phase, and high-stakes, running across various stakeholders, four strategic pillars, and a Global Operations lens. As a Planning Manager, you own the tactical mechanics that make this process work. You will drive the day-to-day execution of FSO's annual and biannual planning cycles, building and maintaining the roadmap, coordinating initiative inputs from across FSO and cross-functional (XFN) teams, mapping work back to OKR targets and metrics, and ensuring every milestone, review gate, and deliverable lands on time. This role gives our Planning lead the space to focus on strategic direction and executive engagement, knowing the engine is running cleanly behind the scenes. Duties Own and maintain the full milestone plan across all planning phases, track progress against key deadlines, and proactively flag risks or slippage to the Planning lead before they become escalations Collect and organize initiative submissions from FSO pillar teams and XFN partners, flag duplicates and gaps, and prepare first-pass above/below-the-line prioritization materials for leadership review Compile all above-the-line initiatives with confirmed DRIs, go-live dates, OKR connections, and metrics targets; keep the roadmap current and accurate throughout the planning cycle Ensure every prioritized initiative is connected to at least one KR target, surface misalignments, and support the Planning lead in resolving tensions before executive review Work directly with FSO leads to capture strategy inputs, confirm KR owners, and track capacity baselines and carry-over assessments Track all cross-functional dependencies from prioritized initiatives, identify POC owners and commitment levels, and follow up with XFN partners to confirm commitments Prepare materials for planning forums, strategy workshops, review sessions, and FSO leadership meetings, including agendas, pre-read decks, consolidated data inputs, decision trackers, and post-session outputs Support the development of the CFO Annual Plan deck and business review deliverables by synthesizing roadmap data and OKR progress into clear, exec-ready narratives Work with pillar leads to identify ongoing initiatives likely to carry into the next planning period and flag them as pre-committed capacity Requirements 6-8+ years of experience in program management, roadmap planning, or a highly cross-functional planning operations role Hands-on experience building and maintaining roadmaps in Airtable, Asana, Jira, or similar tools; comfort with multi-level tracking, field logic, and reporting views is a strong plus Strong analytical skills with the ability to work with OKR frameworks, initiative data, and capacity inputs to surface insights and alignment gaps Proven ability to manage complex, multi-phase workstreams with competing deadlines and multiple stakeholder groups Strong proficiency with Google Suite (Docs, Sheets, Slides), including comfort with templates and lightweight automation Excellent written and verbal communication skills, with the ability to distill complex planning inputs into clear, action-oriented artifacts and exec-ready materials Track record of operating in fast-moving, cross-functional environments where proactive communication and disciplined follow-through are non-negotiable Highly organized self-starter with a strong bias toward documentation, structured process, and context preservation across planning cycles Compensation $102.11- 113.79/hr W-2 Req#: 37405847 #J-18808-Ljbffr
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$170k - $215k
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$114k - $170k
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...clarity, and narrative precision to translate our ambition into a plan the whole organization can execute against. Reporting to the... ...are: 6-10 years of experience in strategy, with a background in management consulting, corporate strategy, or a combination of both...Work at office
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