Head of Customer Success, TrustFlight
Digital transformation services for aviation
Be an early applicant
Digital transformation services for aviation
21-100 employees
Be an early applicant
21-100 employees
Company mission
To be the trusted provider of digital workflow solutions to capture, store and share aviation data to improve safety and efficiency.
Role
Who you are
- Extensive experience in Customer Success, ideally 7+ years, with at least 3 years in leadership roles in B2B SaaS (mid-market preferred)
- Demonstrated ability to set vision and strategy, and deliver results through high-performing teams
- Experience managing departmental performance, budgets, and P&L
- Proven skill in building and scaling customer success frameworks, health scoring models, and automation playbooks
- Strong data-driven mindset; comfortable with analytics, success metrics, and reporting dashboards
- Solid background in collaborating cross-functionally with Product, Engineering, Sales, and Account Management teams
- Excellent communication skills, capable of presenting to senior stakeholders and customers alike
- Previous experience with AI-driven customer insights, support automation, and education platforms is highly valued
- Desirable: Experience in safety-critical, regulated software or technical B2B environments
What the job involves
- As Head of Customer Success, you will be responsible for the overall implementation, support, retention, and training of all SaaS customers at TrustFlight
- Reporting to the CEO, you will lead our Support, Implementation, Customer Success Management (CSM), and Training teams
- This role includes full accountability for the department’s performance, budget, processes, and team development
- You’ll collaborate closely with Product, Engineering, Marketing, Sales, and Account Management to ensure our customers achieve their goals and unlock long-term value
- Set and execute the Customer Success vision and strategy, aligned with TrustFlight’s objectives and growth ambitions
- Lead, mentor, and scale high-performing Support, Implementation, CSM, and Training teams
- Foster a culture of accountability, innovation, and continuous learning across the department
- Own the Customer Success department P&L, driving operational efficiency, service quality, and ROI
- Utilize customer data and insights to measure, optimize, and report on performance and engagement strategies
- Ensure customers achieve rapid Time-to-Value (TTV) and gain long-term benefits from our platform
- Oversee the CSM team to drive adoption, utilization, and proactive engagement using customer health scoring models and engagement frameworks
- Collaborate with Account Management to align onboarding, ongoing value realization, and new commercial opportunities
- Develop playbooks and proactive risk management strategies to deliver measurable customer outcomes
- Lead the Implementation team to deliver on-time, in-scope deployments that meet customer expectations and internal SLAs
- Standardize onboarding processes, reducing TTV through scalable automation and repeatable frameworks
- Maintain clear communication with Sales and Account Management to achieve customer success milestones
- Ensure Support provides timely, high-quality responses in line with SLAs and KPIs
- Scale AI-enabled tools (chatbots, predictive routing, intelligent ticket deflection) for efficiency and faster resolution times
- Analyze support trends and root causes to drive product improvements and enhance documentation
- Lead efforts to reduce inbound support volume with automation, UX feedback, and AI-powered self-service tooling
- Drive revenue through value-added training and enablement services for customers
- Build and maintain scalable education resources, including online learning portals, knowledge bases, and live training
- Implement AI-driven education tools and LMS platforms to promote self-service and reduce dependence on manual onboarding
- Launch and manage product certification programs to boost adoption and customer success
- Serve as the voice of the customer in discussions with Product, Engineering, and Sales, ensuring customer needs inform roadmap decisions
- Partner with Account Management for renewals, QBRs, and expansion, ensuring unified strategies for retention and advocacy
- Gather and structure customer feedback to influence product development and continuous improvement
- Transform satisfied customers into passionate advocates by building structured advocacy programs, customer advisory boards, and success stories that showcase the value of TrustFlight’s solutions
- As Head of Customer Success, you’ll be directly accountable for driving measurable business outcomes across three critical areas:
- Customer Retention & Expansion: Net Revenue Retention (NRR), Gross Revenue Retention (GRR), Churn Rate
- Customer Satisfaction & Support Efficiency: Net Promoter Score (NPS), Customer Satisfaction (CSAT), First Response Time (<1 hour), Average Resolution Time, Support Ticket Deflection Rate, Tickets Resolved per Agent, Cost per Ticket
- Onboarding & Implementation: Time-to-Value (TTV), Onboarding Completion Rate, Implementation Success Rate, Onboarding/Implementation CSAT, Cost per Implementation
Application process
- While we sincerely appreciate all applications, only those candidates selected for an interview will be contacted. No phone calls please
Salary benchmarks
Our take
TrustFlight develops intelligent workflow automation platforms and other tools with the aim of improving levels of efficiency and safety across the aviation sector. Currently, the company’s suite of products caters to maintenance programmes, technical support, tech and engine logs, and operational and equipment management.
It’s a slim sector to be operating in - and one would think it would pit TrustFlight head to head with a prohibitively strong slew of industry giants. TrustFlight, however, is seeing good growth - and has even partnered with the likes of Boeing to bring blockchain verification methods to aviation supply chains.
This integration of sourcing and the blockchain is proving a smart and lucrative bet across various industries, given the tightening regulatory focus on promoting supply chain oversight. It’s just one example of how TrustFlight is leveraging its deeptech expertise to digitally transform aviation. Developments in this sector won’t happen fast, but they are critical, and highly influential. TrustFlight has its sights set on becoming an important player in the space.
Freddie
Company Specialist at Welcome to the Jungle
Insights
Company
Company HQ
Coal Harbour, Vancouver, BC
Leadership
Karl Steeves
(Co-Founder & CEO)Prior to TrustFlight worked as a power electronics engineer with Jaguar Land Rover.
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