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Role Description

We are seeking a high-caliber VP of Customer Success to lead our global CS organization through a period of strategic transformation. Reporting to the COO, you will be responsible for moving the team from reactive "firefighting" to a proactive, outcome-oriented machine. This role requires a unique blend of "High-Touch" mastery and technical scalability, focusing intensely on Gross Dollar Retention (GDR) and the architectural integrity of our customer journeys. You will serve as a champion for the CS function, ensuring operational boundaries are maintained while scaling our impact through AI and data-driven insights.

What You’ll be Doing…

• Strategic Leadership & Outcome Architecture: Transform the CS organization by implementing robust Customer Success Plans (CSPs) that are customer-validated and tied directly to measurable business impact.
• Segmented Value Delivery: Identify and define value-driven segmentation of our customer base, creating raving fans for our customers by providing the right depth of value-focused support to them in achieving their people analytics goals.
• GDR Ownership & Commercial Strategy: Drive a relentless focus on Gross Dollar Retention. You will coach leaders and CSMs to build a pipeline of paid service growth (CSQLs), transitioning the mindset from "free support" to value-based professional services.
• Risk & Data Governance: Build and refine risk frameworks within Gainsight (or similar) that prioritize action over description. Leverage health scores to provide "no surprises" renewal forecasts to the executive team 6–9 months in advance to maintain best-in-class customer renewal KPIs.
• Global Team Development: Oversee a diverse team across NA, APAC, and EMEA. You will be responsible for mentoring front-line leaders and implementing a structured career pathing matrix for CSMs.
• Operational Scaling: Lead the integration of AI-assisted models and tech-touch workflows to increase team efficiency without compromising the "High-Touch" experience for our enterprise portfolios.
• Cross-Functional Advocacy: Act as a firm but collaborative voice for the CS department, building a strong partnership with Sales, Product, and Marketing to ensure the team remains focused on retention and customer health.

Qualifications

• 10+ years in Customer Success or Account Management, with at least 4 years in a senior leadership role within a high-growth SaaS environment.
• Proven track record of managing distributed teams across multiple time zones and cultures.
• Deep understanding of SaaS metrics ($LTV$, $CAC$, $NRR$) and the ability to translate data into actionable playbooks.
• Ability to build relationships with C-suite stakeholders at Tier-1 enterprise accounts.
• Extensive experience overseeing portfolios with individual account values ranging from $100K to $3M+ ARR, particularly those requiring high levels of customer education and consultative partnership.
• A proven history of managing high-performing, culturally diverse teams across multiple time zones (NA, APAC, EMEA).
• Demonstrated success in transitioning legacy CS teams from reactive modes to proactive, data-driven outcomes.
• Professional stamina to be measured primarily on GDR; you understand that this metric only goes down and requires a proactive, "protect-at-all-costs" mindset.
• Exceptional ability to serve as an executive sponsor for Tier-1 accounts, managing high-stakes escalations and maintaining C-suite relationships.
• Advanced experience with Gainsight, PlanHat, or Totango, with a specific focus on turning daily activities into predictive analytics.
• A "forever learner" who actively explores how AI can augment CRM workflows and improve the overall customer experience.
• While HR domain experience is helpful, we prioritize candidates with a background in complex, high-stakes SaaS environments.

Requirements

• Base salary range for this role is $190-$240K CAD. Pay band is commensurate with geographic location and experience.