Aiwyn

Implementation

DeliveryLead

$145–210k ~AI est. United States FULL TIME Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Lead candidates.

The Brief

“Delivery Lead at Aiwyn. Skills: Program ownership, Delivery leadership, Customer engagement, Cross-functional leadership. Own end-to-end success of complex, multi-product customer implementations. Develop and maintain comprehensive program plans”

What You'll Achieve.

End-to-end success of implementations; Program on schedule; Program on scope; Program aligned to delivery objectives; Customer confidence maintained; Scope integrity maintained; Risks resolved with urgency; Technical workstreams executed on time; Clearer picture for customers

Industry & Context.

Implementation
Problems you'll solve

Identify scope creep; Manage change control; Identify risks; Drive resolution; Identify misalignment; Adjust without losing control; Make judgment calls; Hold implementation engineer accountable; Hold technical workstreams accountable

What They're Looking For.

Must Have

6+ years implementation, program management, or professional services delivery, Proven experience managing multi-phase, multi-stakeholder implementation programs, Track record of executive-level customer communication and relationship management, Experience coordinating cross-functional delivery teams without direct management authority, Familiarity with technical implementation concepts

Nice to Have

PMP, PgMP, or equivalent program management certification

What You'll Do.

Own end-to-end success of complex

multi-product customer implementations

Develop and maintain comprehensive program plans

Coordinate multiple workstreams

and product deployments

Ensure implementation activity stays on schedule

Ensure implementation activity stays on scope

Ensure implementation activity aligns to delivery objectives

Act on program threats

Lead Advanced Implementation Delivery Trio

Drive alignment and accountability across functions

Coordinate across Implementation

Serve as primary delivery leader for enterprise customers

Facilitate executive-level conversations on program progress

Facilitate executive-level conversations on key decisions

Facilitate executive-level conversations on delivery strategy

Manage escalations with clarity and composure

Maintain customer confidence under pressure

Own scope integrity across the program

Identify scope creep early

Manage change control

Communicate tradeoffs to customer and internal leadership

Maintain a live risk register

Surface risks before they become fires

Drive risk resolution with urgency

Partner closely with Solutions Architect

Ensure proposed solution is executed as designed

Ensure Implementation Engineer has what they need

Execute technical workstreams on time

Identify misalignment between design and execution early

Drive misalignment resolution

Serve as a product expert and trusted advisor

Lead conversations on workflow changes

Guide firms on product configuration and usage

Translate operational requirements into implementation approach

Push back constructively on workflow requests

Establish and own operational rhythm of the program

Conduct milestone reviews

Conduct status reporting

Conduct executive readouts

Keep stakeholders informed without creating meeting overhead

How You'll Work.

Team & Collaboration

Cross-functional trio; Internal teams; Firm-side stakeholders; Implementation, Product, Engineering, Customer Success, and Support

Communication Scope

Executive-level conversations; Customer communication; Internal updates; Crisp updates; Specific asks; Escalations with point of view

Process & Methodology

Program management, Implementation planning, Scope management, Timeline management, Risk management, Change control

Full Job Description

About Aiwyn Who is Aiwyn and what do we do? 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. ABOUT THE ROLE The Delivery Lead is the Directly Responsible Individual for Aiwyn's most complex, high-stakes customer implementations. Where an Implementation Specialist owns a single-firm, defined-scope deployment, the IPM owns programs — rolling M&A playbooks, multi-phase enterprise rollouts, and multi-product deployments that span quarters and involve multiple internal teams and firm-side stakeholders simultaneously. This role sits at the center of Aiwyn's Advanced Implementation delivery model, leading a cross-functional trio alongside a Solutions Architect and Implementation Engineer. The IPM is accountable for the overall success of the program — scope, timeline, delivery quality, and customer confidence — while coordinating execution across every workstream. This is not a coordination role. It's an ownership role. The success or failure of the program lands here. WHAT YOU'LL OWN Program Ownership & Delivery Leadership Own the end-to-end success of complex, multi-product customer implementations. Develop and maintain comprehensive program plans that coordinate multiple workstreams, phases, and product deployments. Ensure all implementation activity stays on schedule, on scope, and aligned to delivery objectives. When something threatens the program, you see it first and act on it. Cross-Functional Leadership Lead the Advanced Implementation Delivery Trio — Solutions Architect and Implementation Engineer — driving alignment and accountability across each function without direct authority over the success of the project. Coordinate across Implementation, Product, Engineering, Customer Success,

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