Senior Director, Customer Success

Safe Software

About The Position

The Senior Director of Customer Success is responsible for defining and leading Safe Software’s North American post-sales strategy, ensuring customers achieve measurable outcomes while driving expansion revenue and strong net revenue retention. This role builds and scales a proactive Customer Success organization that transforms customer engagement into a predictable growth engine. We have an immediate opening and are excited to find the right candidate to join our team. Key Goals: Establish and scale a high-performing Customer Success organization across North America Drive net revenue retention and expansion through customer lifecycle excellence Embed a proactive, outcome-driven customer engagement model Build systems, processes, and metrics that enable predictable growth and visibility Serve as the executive voice of the customer across product and go-to-market strategy About The Team This role directly influences Safe’s revenue growth, customer retention, and long-term customer value. By aligning cross-functional teams and embedding customer-centric practices, the Sr. Director ensures a seamless customer experience and strengthens Safe’s position as a trusted partner to its customers.

Requirements

Bachelor’s degree in Business, Technology, or a related field (or equivalent experience)
8+ years of experience in Customer Success, Account Management, Professional Services, or post-sales leadership within enterprise SaaS
5+ years of experience leading and scaling multi-layered, distributed teams.
Experience leading Customer Success in complex, technical SaaS environments with a strong focus on adoption, value realization, and expansion.
Demonstrated success driving net revenue retention, customer adoption, and expansion revenue
Experience building or transforming Customer Success functions, including processes, metrics, and systems
Experience with Customer Success platforms and CRM systems (e.g., HubSpot)
Strong understanding of customer lifecycle management, health scoring, and revenue metrics (NRR, CSQLs, adoption)
Familiarity with data integration, analytics, or technically complex SaaS products (e.g., ETL, automation platforms)
Executive-level communication and stakeholder management
Cross-functional leadership and collaboration
Strong coaching, mentorship, and team development capabilities
Operational and strategic planning expertise

Responsibilities

Build, lead, and scale the Customer Success organization, including hiring and developing Strategic CSMs across regions
Own and execute net revenue retention and expansion strategy across the customer lifecycle
Drive onboarding, adoption, renewal, and expansion initiatives tied to measurable customer outcomes
Ensure all strategic accounts maintain active Mutual Success Plans aligned to business objectives
Foster a high-performance, customer-focused culture grounded in trust, accountability, and outcomes
Develop leadership bench strength through coaching, succession planning, and talent development
Continue to refine operating models, performance expectations, and success metrics across teams and customer segments
Define and manage KPIs, operating cadence, and reporting frameworks to provide visibility into Customer Success performance
Collaborate with RevOps to implement scalable systems, tools, and data models (e.g., health scoring, lifecycle tracking, CSQLs)
Leverage customer usage, health, and financial data to proactively manage risk and identify growth opportunities
Partner with Sales on account strategy, renewal motions, and expansion opportunities
Continuously evolve Customer Success strategies to align with business growth and market changes
Act as the executive voice of the customer, influencing product roadmap, support strategy, and go-to-market priorities
Partner cross-functionally with Sales, Product, Marketing, Support, and Finance to deliver a cohesive customer experience
Break down silos and ensure alignment across teams to improve customer outcomes
Manage executive-level escalations with clarity, urgency, and professionalism
Champion change management initiatives and foster a culture of continuous learning and improvement

Benefits

Meaningful Work: Make a profound impact across our business, workplace and data integration product.
A Supportive Environment: Feel empowered to share your ideas and implement them with high autonomy and team support.
Social Responsibility: Become part of a team that finds meaningful ways to give back. Take paid time off to volunteer for one of our Safe-organized opportunities that align with our core community initiatives.
Learning & Career Development: We believe in your continuous learning and growth. Take advantage of an annual learning budget and training programs paid for by Safe.
Flexible Working Hours: Flexible and remote-friendly work arrangements to fit your lifestyle. Work when you want, and how you want to.
Work-Life Balance: There's no place for burnout at Safe. Maintain a healthy balance of your personal and work life without splitting yourself in two. Enjoy 3 weeks of vacation to recharge, plus an additional paid 6 seasonal days off per year.
Health & Wellness: Extended health, dental, health or lifestyle spending, and counseling benefits from day 1. That’s right, no waiting period.
Family is important: We are dedicated to supporting our employees through parenthood and offer a Parental Leave Top-Up Program for new parents through childbirth or adoption.
Shared Success: Share in Safe’s success with our bi-annual profit sharing and RRSP/TFSA matching program.
An Accessible Commute: Regardless of your commute method, we’re located close to public transit, and provide complimentary parking and bike storage for our team!