Implementation Operations Analyst

About Aiwyn

Aiwyn is building the operating layer for accounting firms — automating the workflows that sit between client engagement and getting paid. Our platform spans Payments, Engagements, and Practice Management, and we're deploying it inside some of the most respected accounting firms in the country, including Big 4 and Top 25 firms.

We're growing fast, and operational clarity is what keeps growth from becoming chaos.

About the Role

The Implementation Operations Analyst is the person who makes sure the VP of Implementation always knows what's actually happening across the org — not through status updates, but through data.

This role owns the reporting layer for the entire Implementation organization. That means pulling data from ClickUp, HubSpot, Pendo, and Notion into a coherent weekly picture, identifying the themes and patterns that matter, and bringing them forward proactively — without being asked. The VP of Implementation relies wholly on this person for the reporting and operational insight that comes out of the org.

This is not a BI engineering role. It's an analytical ops role. The data already exists — the job is to make sense of it, surface what it means, and communicate it clearly. The best candidate for this role reads a dashboard and immediately asks "why" and "so what" — and then goes and finds the answer.

What You'll Own

Portfolio Reporting & Monitoring Maintain a weekly implementation portfolio view across all active implementations — covering RAG status, cycle time by product line, projected go-live dates, and IS capacity utilization. Build and maintain the ClickUp dashboards, list views, and custom fields that give real-time visibility into portfolio health. Ensure the data is clean, current, and trustworthy.

Theme Identification & Analysis Synthesize data from ClickUp, HubSpot, and Pendo into a regular themes brief for the VP of Implementation. Not a data dump — a narrative. What is the data telling us? Where are implementations stalling? Which product lines are trending red? Which customer segments are highest risk? Flag anomalies before they become fires: deals that are off-pace, handoffs with missing data, go-lives likely to slip.

Leadership & Board Readout Support Own the data preparation for QFE slides, L10 scorecards, and board-level implementation metrics. Ensure every number is accurate, consistent, and told with the right context. Build and maintain the single source of truth for implementation KPIs: cycle time by product line, on-time go-live rate, IS capacity and utilization, NPS at go-live and CS handoff, time-to-first-value, and sales-to-kickoff lag.

Data Integrity & Operational Cadence Audit ClickUp data quality on an ongoing basis — ensure Implementation Specialists are logging correctly, dates are accurate, and project boards reflect reality. Build the operational cadence that makes reliable reporting possible: what gets logged, when, by whom, and how it flows into the reporting layer. Partner with the Director of Implementations to ensure process documentation accuracy aligns with how work is actually tracked.

Cross-Functional Data Liaison Pull HubSpot deal data to track sales-to-implementation handoff quality and time-to-kickoff trends. Pull Pendo usage data to surface adoption signals that correlate with implementation health. Coordinate with Finance and Operations on implementation labor cost data when needed to support capacity modeling and planning.

What We're Looking For

You are proactive by default. You don't wait to be asked what the data says — you already know, and you're ready to tell the story behind it. You have an instinct for what matters and what's just noise, and you can write a clean, direct narrative that a VP can act on.

You're organized and systematic. You understand that good reporting is only as good as the data behind it, and you take data quality as seriously as the analysis itself. You've built reporting cadences from scratch before and you know what it takes to get a team to log consistently.

You're comfortable working across tools and pulling data from multiple sources without needing a data engineer to do it for you. You're a power user of project management platforms and spreadsheets, and you know how to build views and dashboards that actually get used.

You're a strong communicator. The weekly brief you produce should be something leadership actually wants to read — concise, specific, and actionable.

Qualifications

• 3–5 years in operations, implementation, customer success operations, or a similar analytical ops role at a SaaS company

• Expert-level proficiency in ClickUp or a comparable project management platform

• Working knowledge of HubSpot or a comparable CRM for pulling pipeline and handoff data

• Exceptional written communication — able to translate data into a clear, readable narrative

• SQL not required, but comfort with data at a conceptual level is important

• Prior experience in accounting technology, fintech, or professional services is a plus

Why Aiwyn

This is a role with real visibility and real impact. You'll sit close to leadership, see across the entire implementation org, and directly shape how the VP of Implementation understands and manages the business. If you're someone who finds clarity in data and satisfaction in building the systems that keep a growing org honest, this is the role for you.

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