About TestAssure
TestAssure is a fast-moving software company providing best-in-class automated testing solutions of workforce management rules. Our product services many of the world’s leading businesses and provides our customers highly quantifiable value, but it’s only just beginning. We’re looking to evolve our platform, improve UX, extend integrations, unlock new growth and ultimately deliver much more value to customers.
The Director of Customer Success will serve as a key member of the executive leadership team, reporting directly to the CEO and lead the company's customer success function.
Role Overview
Strategic Leadership
- Develop and execute a comprehensive customer success strategy aligned with business objectives and revenue goals
- Transform operations by implementing data-driven processes, playbooks, and success frameworks
- Define and track key metrics (NRR, GRR, CSAT, NPS, product adoption, health scores) and use insights to drive continuous improvement
- Partner closely with Sales, Product, Services and Marketing to ensure seamless customer journey and advocate for customer needs
Team Development
- Build a high-performance culture focused on customer outcomes, accountability, and continuous learning
- Establish clear goals, performance metrics, and career development paths for team members
- Lead a team of four customer success and customer support representatives
Operational Excellence
- Optimize customer segmentation, engagement models, and resource allocation strategies
- Implement and refine CS technology stack (CRM, CS platforms, analytics tools) to improve efficiency and insights
- Create scalable onboarding, adoption, and expansion playbooks that drive consistent customer outcomes
- Establish early warning systems and intervention strategies to reduce churn and identify expansion opportunities
Customer Engagement
- Own executive relationships with key accounts and serve as an escalation point for complex customer situations
- Conduct regular business reviews and strategic planning sessions with customers
- Gather customer feedback and insights to inform product roadmap and go-to-market strategies
- Serve as the voice of the customer internally, advocating for improvements across the organization
Requirements
Qualifications and Experience
- 7+ years in Customer Success, Account Management, or related customer-facing roles in B2B SaaS
- 3+ years in leadership positions, managing and developing high-performing teams
- Proven track record of improving retention rates, driving expansion, and optimizing CS operations
- Experience building scalable processes and implementing CS best practices in a growth-stage environment
- Strong understanding of SaaS metrics, customer health scoring, and data-driven decision making
- Prioritizing candidates in ET and CT given overlap with existing team working schedules
Skills & Competencies
- Strategic thinker with strong execution capabilities and attention to detail
- Excellent communication and presentation skills with the ability to influence at all organizational levels
- Data-driven approach to problem-solving with proficiency in CS platforms and CRM systems
- Strong business acumen with ability to connect CS activities to revenue outcomes
- Change management expertise with a track record of successfully transforming operations
- Collaborative mindset and ability to work cross-functionally in a remote environment
Travel
- Ability to travel for on-site, in-person leadership meetings five times per year
Nice to Have
- Experience in our specific industry or with similar customer profiles
- Background in revenue operations or sales enablement
- Familiarity with product-led growth strategies
- Experience with CS certifications or formal training programs
Benefits
- This is a full-time position where salary and equity will be based on experience; compensation will range from $170,000 to $210,000 USD per year.
- TestAssure offers employees a comprehensive benefits package including health insurance and a 401k / retirement plan with matching contribution.
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What We Do
The Brydon Group partners with entrepreneurs to acquire small businesses and support the effective transition of small businesses to the next generation of owners.
