CSM Strategist & Program Manager (Remote)

Remote positions open to the US only.

The CSM Strategist & Program Manager sits at the intersection of Customer Success strategy and operational execution. This is a high-impact individual contributor role operating at a senior manager level, acting as the connective tissue between CSM leadership, cross-functional partners, and the broader business. Serving in a capacity akin to a Chief of Staff meets strategic operator, this role owns the strategic planning rhythm, drives critical CSM initiatives from concept through completion, and ensures the right work gets done at the right time. This role requires someone who thrives on ambiguity, moves fast, and translates high-level strategy into concrete execution plans without losing the big picture.

Responsibilities:

Strategic Planning & Chief of Staff Functions

• Own and drive the CSM annual and quarterly planning process, including OKR development, roadmap prioritization, and executive alignment.
• Serve as a strategic partner to CSM leadership, preparing briefings, decision memos, and exec-ready presentations for leadership reviews, QBRs, and board materials.
• Identify strategic gaps, risks, and opportunities across the CSM organization and develop recommendations for leadership action.
• Manage the CSM leadership operating cadence — agendas, follow-ups, decision logs, and cross-functional coordination.
• Act as a trusted proxy for CSM leadership in cross-functional forums, representing CSM priorities and driving alignment with Product, Sales, Marketing, and Finance.

Program Management & Execution

• Own end-to-end program management for strategic CSM initiatives — scoping, planning, resourcing, risk tracking, and delivery.
• Develop and maintain program charters, project plans, RAID logs, and stakeholder communication plans.
• Drive clarity and accountability across workstreams, ensuring cross-functional owners are aligned and on-track.
• Proactively surface blockers and risks to leadership with recommendations for resolution.
• Build scalable playbooks and frameworks that operationalize strategic priorities across the CSM organization.

CSM Strategy & Insights

• Partner with CSM Analytics and Finance to synthesize data into strategic insights that inform CSM strategy — retention trends, expansion opportunities, health metrics, and customer segment performance.
• Develop business cases and ROI frameworks for new CSM investments and motions.
• Lead strategic research and benchmarking to inform CSM best practices and competitive differentiation.
• Support the development and iteration of the CSM model, including coverage models, segmentation strategy, and engagement frameworks.

Requirements:

• 5+ years of experience in Customer Success, strategy, consulting, chief of staff, or a related field within a B2B SaaS environment.
• Preferred: Prior experience in a Chief of Staff, Strategy & Operations, or CSM Strategy role at a high-growth SaaS company.
• Preferred: Experience supporting VP or C-suite executives in a fast-paced environment.
• Preferred: Background in cybersecurity, security awareness, or adjacent technology markets.
• Preferred: MBA or equivalent advanced degree.

Required Technical & Core Skills:

• Proven ability to manage complex, cross-functional programs from inception to delivery with multiple stakeholders.
• Strong strategic thinking skills — comfortable working with ambiguous problems and translating them into clear frameworks, recommendations, and execution plans.
• Exceptional written and verbal communication skills, including the ability to craft exec-ready narratives and presentations.
• High degree of ownership and bias to action; ability to drive projects forward autonomously.
• Proficiency with program management tools (e.g., Asana, Jira, Monday.com) and presentation tools (PowerPoint, Google Slides).
• Ability to synthesize quantitative and qualitative data into actionable insights.
• Preferred: Familiarity with CSM platforms (e.g., Gainsight, Salesforce) and CS metrics (NRR, GRR, NPS, CSAT, time-to-value).

The salary for this position ranges from $120,000-$160,000, which will vary depending on how well an applicant's skills and experience align with the job description listed above.