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About the RoleAt Aiwyn, our Implementation team is pivotal to our company's success. As an Implementation Specialist, you'll serve as the primary owner of the end-to-end implementation experience for accounting firms onboarding onto Aiwyn's platform. You'll combine rigorous project management discipline with deep technical engagement — managing timelines, surfacing risks, driving firm readiness, and coordinating across internal and external stakeholders to deliver a world-class go-live experience.This role sits at the intersection of project management, client services, and technical execution. You will own the implementation lifecycle from kickoff through production cutover, while partnering closely with technical staff on data migration, environment setup, and integration work.What will you do in this role?At Aiwyn, our Implementation team is pivotal to our company’s success. You will be a key member of our fast-growing and high-performing Go-To-Market (GTM) organization working to deliver an unparalleled experience to our customers and integration partners as we work to 1) onboard and educate new firms in using our software modules, 2) advise firms on best operational practices when using Aiwyn’s software, 3) provide the customer a transparent, supported experience as they go-live with our products.In this role, you will primarily be working with representatives from our customer firms to manage the Implementation process, acting as the primary lead for interfacing with customers throughout implementation, configuring their system based on their chosen specifications, training the firms on what to expect from the experience of using our software and testing the data flowing through our software. You will also be integral in designing and refining our standard operating procedures as well as contributing and leading internal development and improvement projects.Key ResponsibilitiesProject Management & DeliveryOwn the full implementation lifecycle for multiple concurrent firm engagements, managing scope, schedule, dependencies, and stakeholder alignment from kickoff through go-liveMaintain a living project plan in ClickUp capturing all milestones, task ownership, and critical path items — updated weekly and shared transparently with firm stakeholdersProactively identify, document, and escalate project risks before they become blockers; maintain a formal risk log with mitigation owners and resolution timelinesRun structured project cadences: kickoff meetings, weekly status calls, internal delivery syncs, and go/no-go reviews prior to production cutoverFacilitate clear, timely communication to firm stakeholders at all levels — from system administrators to CFOs — translating technical complexity into actionable decisionsManage change control when scope, timeline, or resource requirements shift; ensure changes are documented, approved, and reflected in the project planDrive firm accountability on deliverables: data extracts, stakeholder availability, UAT sign-off, and cutover readiness approvalsProduce structured status reporting for internal leadership, including RAG health indicators and escalation flags for at-risk engagementsEnvironment Setup & System ConfigurationCoordinate with technical staff on staging environment provisioning, SSO configuration, and system deployment readinessValidate that environment-specific configurations are accurate before firm-facing testing beginsSupport the setup and testing of integrations, ensuring data flows are confirmed end-to-end prior to go-liveData Migration & ValidationPartner with technical specialists to manage the firm's data migration workstream, including historical data mapping from legacy PMS systems to Aiwyn equivalentsLead balancing and validation reviews with the firm: reconciling Open AR and Unbilled WIP reports, resolving discrepancies at the transaction, invoice, and client levelFlag data issues that cannot be resolved before cutover and own the documented remediation plan and timelineEnsure production cutover balancing is completed and signed off before go-live is authorizedProduction Cutover & Go-LiveCoordinate the full cutover execution plan, including scheduler management, domain configuration, and final validation stepsRun the go/no-go decision process with internal and firm stakeholders, ensuring all readiness criteria are met before cutover is initiatedManage hypercare support in the immediate post-launch period, triaging issues and coordinating rapid resolutionFirm Training & EnablementConfigure the firm's system based on their chosen specifications and operational preferencesDesign and deliver tailored training sessions for firm staff, ensuring adoption of Aiwyn's software across relevant workflowsTravel onsite when detailed workshops or executive-level training sessions are required (less than 10% of the time)Internal ContributionTake ownership of internal improvement projects, contributing to SOPs, process documentation, and tooling enhancementsSurface patterns across engagements to inform playbook development, risk frameworks, and implementation methodology improvementsCollaborate cross-functionally with Product, Engineering, and Customer Success to resolve escalations and improve the customer journeyQualifications3–5 years of experience in B2B SaaS implementation, professional services, or technical project managementDemonstrated ability to manage multiple concurrent client engagements with competing priorities and deadlinesStrong project management fundamentals: risk identification and escalation, milestone tracking, dependency management, and change controlExceptional written and verbal communication skills — able to translate complex technical concepts for non-technical stakeholders and drive decisions at the executive levelExperience managing stakeholder relationships across all levels of a client organizationHighly proficient in English with excellent written grammar and attention to detailComfort working in ambiguous, fast-moving environments with the initiative to drive progress without all the answers in front of youPreferred QualificationsExperience in the accounting firm or professional services technology industryFamiliarity with ETL concepts, data migration workflows, or system integration patternsExperience with ClickUp or similar project management and CRM platformsExposure to cloud infrastructure concepts (SSO, API-based integrations, data pipelines) sufficient to facilitate technical conversations with engineering and firm IT teamsBenefits and PerksThe 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 cultureFlexible PTOWorld 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) matchingOur Values:Relentless by DesignOwners not RentersTrust at the CoreAiwyn 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
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