CS Strategist & Program Manager; Remote

Remote

KnowBe4 empowers the modern workforce to make smarter security decisions every day. Trusted by more than 70,000 organizations worldwide, KnowBe4 is the pioneer of digital workforce security, securing both AI agents and humans. The KnowBe4 Platform provides attack simulation and training, collaboration security, and agent security powered by AIDA (Artificial Intelligence Defense Agents) and a proprietary Risk Score. The platform leverages 15-years of behavioral data to combat advanced threats including social engineering, prompt injection, and shadow AI.

By securing humans and agents, KnowBe4 leads the industry in workforce trust and defense.

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.

• 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.

• 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 work streams, 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.
• 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.

• 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.

• 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…