Implementation Specialist

Role Overview

• Own the full implementation lifecycle for multiple concurrent firm engagements, managing scope, schedule, dependencies, and stakeholder alignment from kickoff through go-live
• Maintain a living project plan in ClickUp capturing all milestones, task ownership, and critical path items — updated weekly and shared transparently with firm stakeholders
• Proactively identify, document, and escalate project risks before they become blockers; maintain a formal risk log with mitigation owners and resolution timelines
• Run structured project cadences: kickoff meetings, weekly status calls, internal delivery syncs, and go/no-go reviews prior to production cutover
• Facilitate clear, timely communication to firm stakeholders at all levels — from system administrators to CFOs — translating technical complexity into actionable decisions
• Manage change control when scope, timeline, or resource requirements shift; ensure changes are documented, approved, and reflected in the project plan
• Drive firm accountability on deliverables: data extracts, stakeholder availability, UAT sign-off, and cutover readiness approvals
• Produce structured status reporting for internal leadership, including RAG health indicators and escalation flags for at-risk engagements
• Coordinate with technical staff on staging environment provisioning, SSO configuration, and system deployment readiness
• Validate that environment-specific configurations are accurate before firm-facing testing begins
• Support the setup and testing of integrations, ensuring data flows are confirmed end-to-end prior to go-live
• Partner with technical specialists to manage the firm's data migration workstream, including historical data mapping from legacy PMS systems to Aiwyn equivalents
• Lead balancing and validation reviews with the firm: reconciling Open AR and Unbilled WIP reports, resolving discrepancies at the transaction, invoice, and client level
• Flag data issues that cannot be resolved before cutover and own the documented remediation plan and timeline
• Ensure production cutover balancing is completed and signed off before go-live is authorized
• Coordinate the full cutover execution plan, including scheduler management, domain configuration, and final validation steps
• Run the go/no-go decision process with internal and firm stakeholders, ensuring all readiness criteria are met before cutover is initiated
• Manage hypercare support in the immediate post-launch period, triaging issues and coordinating rapid resolution
• Configure the firm's system based on their chosen specifications and operational preferences
• Design and deliver tailored training sessions for firm staff, ensuring adoption of Aiwyn's software across relevant workflows
• Travel onsite when detailed workshops or executive-level training sessions are required (less than 10% of the time)
• Take ownership of internal improvement projects, contributing to SOPs, process documentation, and tooling enhancements
• Surface patterns across engagements to inform playbook development, risk frameworks, and implementation methodology improvements
• Collaborate cross-functionally with Product, Engineering, and Customer Success to resolve escalations and improve the customer journey

Requirements

• 3–5 years of experience in B2B SaaS implementation, professional services, or technical project management
• Demonstrated ability to manage multiple concurrent client engagements with competing priorities and deadlines
• Strong project management fundamentals: risk identification and escalation, milestone tracking, dependency management, and change control
• Exceptional written and verbal communication skills — able to translate complex technical concepts for non-technical stakeholders and drive decisions at the executive level
• Experience managing stakeholder relationships across all levels of a client organization
• Highly proficient in English with excellent written grammar and attention to detail
• Comfort working in ambiguous, fast-moving environments with the initiative to drive progress without all the answers in front of you
• Preferred Qualifications: Experience in the accounting firm or professional services technology industry, Familiarity with ETL concepts, data migration workflows, or system integration patterns, Experience with ClickUp or similar project management and CRM platforms, Exposure to cloud infrastructure concepts (SSO, API-based integrations, data pipelines) sufficient to facilitate technical conversations with engineering and firm IT teams

Tech Stack

• Cloud
• ETL

Benefits

• 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