Senior Self-Serve Strategist

We are monday.com, a global software company transforming how businesses run. Our product suite can adapt to the needs of diverse industries and use cases within one powerful platform, empowering ~245,000 customers worldwide to reimagine how work gets done, drive greater efficiency, and scale like never before.

With over 2,500 employees across the globe, we grow by prioritizing transparency and knowledge sharing. We care about the impact you make, not the hours you clock, so we encourage initiative, ownership, and fresh thinking. We back our people with flexible work, wellness and mental health support, and a work environment built on collaboration.

We're building a new, innovative Tech Touch segment to manage the majority of our accounts, and we're looking for a senior strategist to be the architect of this motion. This role is critical to addressing our current retention and adoption challenges, and your primary mission will be to drive significant improvements in our Gross Revenue Retention (GRR) and monthly loss metrics.

You will serve as the strategic voice for the self-serve model, defining how our digital engines and AI agents proactively engage customers to drive adoption, improve their experience, and mitigate churn. You'll work at the intersection of customer needs and technology, providing the vision and strategic direction that allows us to scale our impact in a dynamic and ever-changing environment.

Key Responsibilities:

• Architect the Digital Retention Strategy: Design the end-to-end self-serve experience for existing customers, from automated onboarding flows to proactive, AI-driven interventions, with a clear focus on maximizing customer lifetime value and reducing revenue loss.
• Define Business Requirements for Technology: Serve as the primary business stakeholder for all self-serve technology. You will define the strategic requirements for our Risk Engine, AI agents, and digital enablement programs, working closely with product, data, and engineering teams to translate them into a prioritized roadmap.
• Partner with Cross-Functional Stakeholders: Act as a key strategic partner to teams across the organization—including Customer Success, Product, Marketing, and Data & Analytics—influencing them to align on a unified strategy to improve retention.
• Lead with Data & Insights: Partner with our centralized data and analytics team to define and track key business metrics, including Gross Revenue Retention (GRR), churn rate, and monthly revenue loss. You will use data to continually optimize the customer experience and identify new opportunities for growth.
• Scale the Customer Experience: Lead the effort to define the content, messaging, and communication flows for our self-serve tools and automated campaigns, ensuring they are helpful, on-brand, and designed for maximum impact.

• 5-7 years of experience in a senior-level role within a SaaS or technology company.
• You likely have a background in one of the following areas:
• Digital Customer Success: Designing and scaling tech-touch customer success models.
• Self-Serve GTM: Managing and optimizing the post-sale customer journey for retention and expansion.
• Customer Retention: Directly improving retention metrics for a large, low-touch customer base.
• Demonstrated expertise in churn analysis and the creation of proactive retention strategies that directly impacted GRR.
• Professional Skills:
• Exceptional strategic planning skills with a track record of translating high-level business goals into concrete, data-driven action plans.
• Deep understanding of how to leverage AI, automation, and digital adoption platforms to solve business challenges.
• Strong analytical skills with the ability to define KPIs and interpret complex data to inform strategic decisions.
• Soft Skills:
• Strategic Mindset: The ability to think beyond a single project and understand how all initiatives fit into the broader business strategy.
• Strong Communication & Influence: The capacity to collaborate effectively with and influence both technical and non-technical stakeholders across the organization.
• Innovative Thinking: The ability to design new solutions from scratch and articulate a clear vision for the future.
• Adaptability: The ability to thrive and innovate in a fast-paced, ever-changing environment.