Lead Customer Onboarding Manager - US​/Canada

Traild:
Who are we?

Traildis a high-growth SaaS company redefining how finance teams operate, combining AI, automation, and payments infrastructure to power the future of B2B finance.

Every year, businesses lose billions to fraud, errors, and mistakes.

Traildexists to solve this at scale, helping finance teams move faster, stay in control, and operate with confidence.

With rapid customer growth, global expansion across APAC, North America and EMEA, and continued investment in product innovation, we are at a defining stage of our journey.

This is an opportunity to help shape the next category leader in finance automation,control and security, building technology that transforms how businesses manage, move, and protect money. At the core of this is a powerful AI-driven platform, enabling finance teams to deploy intelligent agents that do the work, surface risk in real time, and continuously improve how financial operations run.

Traildis building the infrastructure behind modern finance,protectingand powering meaningful volumes of the world’s B2B transactions.

Ifyou’reexcited by high growth, real ownership, and building something that matters,Traildis the place to do the most impactful work of your career.

Hear how Traildcustomers speak about us here.

We’re looking for an experienced Lead Customer Onboarding Manager to lead mentor and grow our Customer Onboarding team in the America.

We are looking for someone who can lead the team, manage escalations and provide cross functional collaboration.

• Lead,coachand develop a team of Customer Onboarding Managers
• Set clear performance expectations, KPIs and onboarding standards
• Conduct regular performance reviews, mentoring and career development planning
• Support hiring, onboarding and enablement of new team members
• Foster a culture of accountability,ownership and customer-first thinking

• Act as the primary escalation point for complex, high-risk implementations
• Provide strategic guidance on solution design,configuration and rollout approach
• Proactivelyidentifyrisks across active implementations and intervene as needed
• Ensure consistent, high-quality execution across all onboarding engagements

• Design and continuously refine onboarding frameworks,playbooks and governance models
• Establish clear onboarding metrics (time-to-go-live, adoption, customer satisfaction, implementation quality)
• Improve processes to support global scale and operational efficiency
• Identify opportunities for automation and improved tooling

• Partner with Product and Technology teams to communicate implementation insights and recurring challenges
• Align with Customer Success,Salesand Support teams to ensure seamless customer handovers
• Contribute to strategic decisions that enhance the end-to-end customer journey

• Build strong relationships with senior customer stakeholders
• Provide executive-level updates during complex or strategic implementations
• Ensure customers achieve measurable business outcomes aligned to their goals

• 2+ years experience leading an implementation team
• Experience with SAP BI, Acumatica, Syspro or IFS required
• Proven ability to manage escalations and navigate complex stakeholder environments
• Strong operational mindset with experience building scalable processes
• Exceptional leadership, communication and stakeholder management skills
• Experience thriving in a fast-paced startup or scale-up environment
• High levelsof ownership, intrapreneurship and proactiveness
• Strong collaborator who embraces growth, hands-onexecutionand adaptability