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Full Job Description

Who is Aiwyn and what do we do?

Aiwyn is the first complete platform for modern accounting firms. Backed by top-tier investors like Bessemer, KKR, and Revolution, we’re one of the fastest-growing scale-up SaaS companies in the world. We build category-defining technology—and we’re doing it with world-class people, processes, and products.

To learn more, visit our website

This role:

As part of our Customer Support team, the Customer Escalation Manager at Aiwyn is responsible for overseeing, coordinating, and resolving high-impact and complex escalations identified through internal monitoring or customer channels. This role ensures escalated issues are prioritized and resolved efficiently, customers are communicated with transparently, and internal teams collaborate effectively to prevent recurrence and drive long-term improvements.

How We Investigate Issues:

Investigating escalations at Aiwyn requires operating within a highly integrated technical ecosystem. This work includes executing database queries, analyzing user session replays, reviewing application and network logs, and performing transaction-level investigations to identify root cause. The role frequently involves tracing source data from external systems through multiple integrations into Aiwyn’s database, diagnosing issues related to DNS configuration and mail servers, and understanding complex interactions with third-party systems including third party practice management systems, SafeSend, and Outlook. Successful candidates are comfortable navigating ambiguity and synthesizing data across systems to drive resolution.

Key Responsibilities:

• Monitor and triage inbound support tickets to surface critical escalations, recurring themes, and potential systemic issues.

• Act as the first point of contact for complex and high-impact customer escalations that exceed standard support channels.

• Own and manage the end-to-end escalation and problem management lifecycle in coordination with Product and Engineering teams, from identification to resolution, ensuring alignment with internal SLAs.

• Ensure escalated items are prioritized and routed appropriately across Support, Engineering, and Product teams.

• Manage customer communications regarding escalated issues through written and verbal channels (email, calls, virtual meetings).

• Serve as a trusted advocate for customers during escalations, preserving customer satisfaction while balancing internal priorities.

• Partner closely with Support Agents, Technical Support Engineers, Engineering, and Product leadership to orchestrate timely and effective resolution of escalations.

• Act as liaison to ensure escalations are visible to and supported by the appropriate resolver teams.

• Establish, document, and enforce escalation standards, including a “fix-forward” policy where relevant.

• Contribute to refining escalation workflows, playbooks, and internal runbooks.

• Analyze trends in escalations and problem occurrence to identify opportunities to reduce recurrence.

• Facilitate and support incident retrospectives, ensuring teams understand root causes, contributing factors, and follow-up actions.

• Guide teams through incident reporting and post-incident processes, helping ensure consistent execution and high-quality outcomes.

• Provide actionable recommendations to improve product usability, support processes, documentation, and customer onboarding, and ensure agreed-upon actions are tracked to completion.

• Manage risk escalation and ensure resolution trajectories minimize customer impact.

• Deliver timely reporting and insights on escalation performance, metrics, and adherence to SLAs, aligned with organizational goals.

Qualifications:

• 3–5+ years in escalation management, technical support, customer success, or related fields.

• Proven experience managing customer-impacting incidents in a production SaaS environment, including use of incident management tooling (such as incident.io) to coordinate responders, manage timelines, and drive post-incident actions.

• Curious and data-driven mindset with experience analyzing trends and reporting on outcomes.

• Strong ability to work with datasets, metrics, and reporting to debug issues, assess customer impact, and drive data-informed escalation and post-incident decisions.

• Familiarity with support platforms and issue tracking tools (e.g., Zendesk and Jira).

• Clear customer and internal communication skills, with the ability to simplify complex technical concepts.

• Excellent prioritization and organizational skills.

Preferred experience:

• Familiarity with SaaS platforms and cloud-based software solutions.

• Strong understanding of accounting principles and experience with accounting or accounts receivable software.

Benefits and Perks:

• The big-picture value proposition of this role is simple: join us, and you'll be paid competitively to have freedom in solving worthwhile, challenging problems alongside other A-players at a fast growing SaaS startup led by an experienced and successful co-founding team with industry experience.

Other benefits include:

• Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year. We encourage our team to recharge and explore the world beyond their home office walls.

• Remote, work-from-anywhere culture

• Flexible PTO

• World Class health benefits - we believe in fostering flourishing teams by providing benefits that go beyond the usual standards - Health, vision, dental, HSA/FSA, and mental health support.

• Stock options - every Full Time Employee has ownership in Aiwyn's future and success.

• 401(k) matching

Our Values:

• Relentless by Design

• Owners not Renters

• Trust at the Core

Learn more about Aiwyn:

• About us

• YouTube page

Aiwyn is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances.

Candidate information will be treated in accordance with our CCPA privacy notice which can be found here: https://www.aiwyn.ai/ccpa