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Project Overview

We are seeking a Delivery Coach to guide software delivery teams in adopting modern agile practices tailored for AI-first development workflows. Unlike traditional Scrum Master roles, this position emphasizes outcomes over ceremonies, flow over frameworks, and coaching over compliance. The Delivery Coach will support Enumerate’s project-based engagements under with clear deliverables and measurable success criteria.

Key Project Responsibilities

Delivery Enablement: Coach teams to deliver working software in iterative, value-driven increments, optimizing for GenAI-accelerated cycles.
Agility Beyond Scrum: Guide teams in adopting lean, and flow-based practices, tailoring approaches to GenAI-driven product development.
Experimentation Culture: Foster rapid prototyping, hypothesis testing, and continuous learning to leverage GenAI effectively.
Metrics & Outcomes: Define, track, and communicate delivery health metrics (throughput, predictability, cycle time) to stakeholders.
Collaboration Coaching: Act as a coach to Product Owners, Engineers, and Designers to ensure alignment, prioritization, and value delivery.
GenAI-Aware Practices: Incorporate best practices for integrating AI capabilities (e.g., prompt engineering, model iteration) into workflows.

Project Deliverables

Delivery playbooks and frameworks tailored for Enumerate’s AI-driven software projects.
Ongoing coaching sessions with delivery teams and leadership. - Project retrospectives and actionable recommendations for continuous improvement.
Documented metrics and delivery dashboards for visibility and decision-making.

Required Qualifications

Proven experience as a Scrum Master, Agile Coach, or Delivery Manager, preferably in technology-forward organizations.
Strong understanding of agile methodologies, lean practices, and modern delivery frameworks.
Familiarity with GenAI tools and workflows in software development.
Excellent facilitation, coaching, and stakeholder management skills.
Experience working with distributed/remote teams.

Preferred Qualifications

Background in software development, product management, or AI/ML projects.
Experience introducing new delivery practices into fast-paced, innovation-driven environments.
Ability to translate delivery metrics into actionable insights.

Engagement Terms

This role will be engaged under a Contractor of Record arrangement, structured as project-based work. The Delivery Coach will work remotely, collaborating with Enumerate’s distributed teams. Specific project scopes, timelines, and deliverables will be defined in each engagement agreement.

About Enumerate

Enumerate is a best-in-class provider of property management software and payments solutions for community associations. We make it easier to run associations by digitizing and optimizing their accounting processes, operational workflows, AR & AP payments, and resident engagement, ultimately reducing administrative tasks by over 75% with the use of AI and modern software workflows.

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