Planning Manager
Cypress HCM · United States · 5 days ago
RemoteRemoteProject Management$102.11–$113.79/hrContract
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
- 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
- Prowess in managing 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