Enterprise Customer Success Manager - North America

TRAILD · posted Oct 22, 2026

Open to candidates in Canada and United States

$100k–$140k · Full-time · Mid-level

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Must have

  • •2+ years in startup/scale-up, fintech or payments
  • •Manage high-value accounts ($100K+ ARR)
  • •Strong relationship & stakeholder management
  • •Commercial acumen, drive retention & expansion
  • •Data-driven storytelling for EBRs
  • •Project management & cross-functional orchestration
  • •Comfort working independently & adapting

Nice to have

  • •Experience in ERP, accounts payable, or payments
  • •Familiarity with Zendesk, HubSpot, Jira, Slack, Claude
Read the full posting

Traild: Who are we?

Traild is 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. Traild exists 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.

Traild is building the infrastructure behind modern finance, protecting and powering meaningful volumes of the world’s B2B transactions.

If you’re excited by high growth, real ownership, and building something that matters, Traild is the place to do the most impactful work of your career.

Hear how Traild customers speak about us here.

The Role: As Traild scales, our clients are getting bigger and more strategic. We already have an Enterprise Implementation role, and now we need an Enterprise Customer Success Manager to care for these accounts after go-live. This is the first role of its kind here, so you will help shape how it works as we learn what our largest customers need.

You will own a portfolio of high-value accounts, acting as trusted advisor and advocate for client leadership and day-to-day teams. You will build long-term success strategies, protect and grow revenue, and turn happy clients into public references. Expect ambiguity, change, and plenty of room to make your mark.

This is a full-time, remote and open to candidates across North America. Some early morning or evening calls will be needed to work with our development teams in APAC and EMEA.

Key Responsibilities:

  • Manage a portfolio of strategic and enterprise-level accounts as their primary point of contact and advocate.
  • Develop long-term success strategies with each customer, aligned to their goals and desired outcomes.
  • Drive revenue retention and expansion, partnering with Sales on upsell and cross-sell opportunities.
  • Manage churn - Spot at-risk accounts early using health, usage, and sentiment signals. Lead save plans with cross-functional support, and track churn reasons to feed back to Product, Support, and Sales.
  • Plan and deliver Executive Business Reviews (EBRs), building the value narrative for client leadership.
  • Manage escalations end to end: pull in Engineering and Product, turn client concerns into action, and keep stakeholders updated.
  • Follow up on roadmap commitments and interim fixes with Product and Engineering.
  • Monitor usage, health, and support activity daily to spot early escalation risks.
  • Spot trends across the customer base and share them with Product, Support, and Sales.
  • Turn successful clients into references
  • Contribute to documentation and mentor junior team members

Who You Are: You are a proactive and customer-obsessed professional who thrives on building relationships, solving problems, and driving customer value. You understand the customer journey end-to-end and excel at helping clients succeed post-onboarding. You are confident engaging with stakeholders at all levels and enjoy working in a fast-moving, scaling environment. You are at ease with executives, you think commercially, and you thrive in a start-up where the role is still taking shape and the path is not always clear.

Must have

  • 2+ years of experience in a start-up or scale-up, ideally in fintech or payments.
  • Experience managing high-value accounts ($100K+ ARR) in a customer success, account management, or similar client-facing role.
  • Strong relationship and stakeholder management skills, including executive presence and C-suite fluency.
  • Commercial acumen, with a track record of driving retention and expansion.
  • Data-driven storytelling: you can turn usage and health data into a clear value narrative for EBRs.
  • Project management and cross-functional orchestration across Support, Product, Engineering, and Sales.
  • Comfort working independently, managing your own time, and adapting as the role evolves.
  • The ability to de-escalate clients and own mistakes rather than assign blame.
  • Flexibility to take occasional early morning or evening calls with global teams.

Nice to have

  • Experience in the ERP, accounts payable, or payments space.
  • Familiarity with Zendesk, HubSpot, Jira, Slack, Confluence, Omni, and Claude. We know great customer success people come from all sorts of backgrounds. If you have transferable skills from other project management, onboarding, consulting or delivery roles, we'd still like to hear from you, please apply and use the relevant/transferable skills question in the application to tell us how your experience maps to this role.

Salary Range: The base salary range for this position is:

  • U.S. Candidates: $100,000 - $140,000 USD per year
  • Canadian Candidates: $100,000 - $140,000 CAD per year Compensation is determined based on experience, education, and geographic location. The final offer may vary within the stated range to reflect the candidate’s qualifications and market conditions in their area.

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