About the Role

At 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 Responsibilities

Project Management & Delivery

• 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

Environment Setup & System Configuration

• 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

Data Migration & Validation

• 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

Production Cutover & Go-Live

• 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

Firm Training & Enablement

• 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)

Internal Contribution

• 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

Qualifications

• 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
  

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:

1. 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.

2. Remote, work-from-anywhere culture

3. Flexible PTO

4. 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.

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

6. 401(k) matching

Our Values:

• Relentless by Design

• Owners not Renters

• Trust at the Core

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