Technical Project Manager Jobs in Ocoee, FL (NOW HIRING)

Technical Project Manager

ABOUT THE ROLE

As a Technical Project Manager at 321, you will serve as the strategic leader responsible for planning, executing, and delivering complex technical projects including custom website development, enterprise system integrations, CRM implementations, and proprietary platform builds. You'll bridge the gap between technical teams and business stakeholders, translating strategic objectives into detailed technical requirements while managing timelines, budgets, and cross-functional resources to ensure successful delivery.

This role sits at the intersection of technical expertise, project leadership, documentation excellence, and AI-powered development methodologies. You'll bring deep understanding of software development lifecycles alongside proven ability to manage complex technical implementations. Your proficiency in AI-assisted development combined with strong technical writing skills will enable you to create comprehensive requirements documentation, guide development teams through AI-enhanced workflows, and deliver sophisticated solutions that leverage cutting-edge technologies. As part of an AI-first organization, you'll champion AI development practices, ensuring projects utilize intelligent tools to accelerate delivery, improve quality, and maintain competitive advantage.

WHAT YOU'LL DO

Technical Project Planning & Execution

• Own end-to-end project management for complex technical initiatives including custom website development, CRM integrations, API development, and proprietary platform builds like 321 AIM.
• Develop comprehensive project plans including scope definition, technical architecture, resource allocation, timeline milestones, risk management, and budget tracking.
• Lead technical discovery sessions with clients and internal stakeholders to understand business requirements, technical constraints, and success criteria.
• Translate business objectives into detailed technical specifications, user stories, and acceptance criteria that guide development teams.
• Manage project budgets and timelines, tracking actuals against estimates and proactively addressing variances to protect profitability.
• Coordinate resources across development, design, Client Success, and external vendors to ensure seamless collaboration and delivery.
• Facilitate agile ceremonies including sprint planning, daily standups, backlog grooming, sprint reviews, and retrospectives.

Technical & Functional Requirements Documentation

• Create comprehensive technical requirements documents (TRDs) that define system architecture, data models, API specifications, integration patterns, and technical constraints.
• Write detailed functional requirements documents (FRDs) that describe user workflows, business logic, interface requirements, and acceptance criteria.
• Document system integrations including API endpoints, authentication methods, data mapping, error handling, and testing procedures.
• Leverage AI tools to accelerate documentation creation, ensure completeness, and maintain consistency across technical specifications.
• Develop user stories, use cases, and process flows that communicate requirements clearly to both technical and non-technical stakeholders.
• Create data flow diagrams, system architecture diagrams, wireframes, and technical specifications using industry-standard tools and notation.
• Maintain living documentation that evolves throughout the project lifecycle, capturing decisions, changes, and lessons learned.
• Ensure documentation meets compliance requirements for regulated industries including HIPAA, SOC 2, and data privacy standards.

AI-Powered Development Leadership

• Champion AI-assisted development methodologies using platforms like Replit, GitHub Copilot, Cursor, and other AI-powered coding tools.
• Guide development teams in leveraging AI for code generation, debugging, testing, documentation, and optimization to accelerate delivery cycles.
• Architect solutions that integrate AI capabilities including natural language processing, machine learning models, predictive analytics, and intelligent automation.
• Evaluate and implement AI development tools and platforms that improve team productivity, code quality, and project outcomes.
• Define AI-specific requirements including model selection, training data needs, accuracy thresholds, and performance benchmarks.
• Stay current on AI development trends, frameworks, and best practices, sharing knowledge with technical teams and stakeholders.
• Assess technical feasibility of AI features, balancing innovation with practical constraints including cost, complexity, and time-to-market.

Website Development & CMS Projects

• Manage custom website development projects from discovery through launch including design, development, content migration, and deployment.
• Oversee CMS implementations and customizations across platforms including WordPress, HubSpot CMS, Webflow, and headless CMS solutions.
• Define website requirements including information architecture, user experience flows, responsive design specifications, and performance targets.
• Coordinate with Creative teams on design specifications, ensuring technical feasibility and maintaining design integrity through development.
• Manage website integrations including CRM connections, marketing automation, analytics, payment processing, and third-party services.
• Ensure websites meet accessibility standards (WCAG), SEO best practices, performance benchmarks, and security requirements.
• Plan and execute website launches including DNS management, SSL certificates, quality assurance, and post-launch monitoring.

System Integrations & API Development

• Lead complex integration projects connecting CRM platforms (HubSpot, Salesforce, High Level), marketing automation tools, and business systems.
• Define integration requirements including data synchronization, real-time vs batch processing, error handling, and data validation rules.
• Work with development teams to design and implement RESTful APIs, webhooks, and middleware solutions that enable seamless data flow.
• Document API specifications including endpoints, authentication methods, request/response formats, rate limits, and error codes.
• Manage third-party integrations and vendor relationships, ensuring SLAs are met and integration points remain stable.
• Develop integration testing plans, coordinate QA activities, and validate data accuracy across connected systems.
• Monitor integration performance and reliability, addressing issues proactively and implementing improvements.

Quality Assurance & Risk Management

• Develop comprehensive testing strategies including unit testing, integration testing, user acceptance testing, and performance testing.
• Create detailed test plans and test cases that validate functionality against requirements and acceptance criteria.
• Utilize AI-powered testing tools for automated test generation, bug detection, and quality assurance at scale.
• Coordinate UAT sessions with clients and stakeholders, managing feedback and ensuring issues are resolved before launch.
• Identify and manage project risks including technical constraints, resource availability, third-party dependencies, and scope creep.
• Implement change management processes that assess impact, maintain scope control, and protect project timelines and budgets.
• Ensure projects meet security standards, compliance requirements, and data protection regulations relevant to regulated industries.

Stakeholder Communication & Leadership

• Serve as primary point of contact for technical project communication with clients, internal teams, and external vendors.
• Lead client meetings including kickoffs, status updates, demo sessions, and strategic planning discussions.
• Translate complex technical concepts into business language that non-technical stakeholders can understand and act upon.
• Provide regular project status reporting including progress updates, milestone tracking, risk assessments, and budget reporting.
• Facilitate decision-making when technical trade-offs arise, presenting options with clear pros, cons, and recommendations.
• Build trusted advisor relationships with clients through consistent delivery, proactive communication, and strategic guidance.
• Mentor junior team members on project management methodologies, technical documentation, and AI development practices.

WHAT YOU HAVE

• 5+ years of experience in technical project management, preferably managing web development, software projects, or system integrations in an agency or professional services environment.
• Strong technical background with understanding of software development, system architecture, APIs, databases, and modern web technologies.
• Deep expertise in AI-assisted development including hands-on experience with Replit, GitHub Copilot, Cursor, or similar AI-powered development platforms.
• Proven ability to write comprehensive technical and functional requirements documentation for AI-enhanced applications and intelligent systems.
• Understanding of AI/ML concepts including model integration, training data requirements, API-based AI services, and practical AI implementation constraints.
• Experience managing custom website development projects across various CMS platforms and modern web frameworks.
• Expertise with CRM platforms (HubSpot, Salesforce, High Level) including custom integrations, API development, and complex implementations.
• Strong understanding of API design, RESTful services, authentication protocols, data modeling, and integration patterns.
• Proficiency with project management methodologies including Agile, Scrum, Waterfall, and hybrid approaches.
• Advanced skills in technical documentation including technical specifications, system architecture diagrams, data flow diagrams, and API documentation.
• Experience with project management tools (ClickUp, Jira, Asana, or similar) and documentation platforms (Confluence, Notion, or similar).
• Understanding of web security, HTTPS, authentication, data encryption, and compliance requirements for regulated industries (HIPAA, SOC 2).
• Strong analytical and problem-solving skills with ability to troubleshoot complex technical issues and identify root causes.
• Excellent communication and presentation skills with ability to facilitate meetings, build consensus, and influence stakeholders.
• Experience with AI-powered project management and documentation tools that accelerate planning, requirements gathering, and delivery.
• Demonstrated ability to manage project budgets, track profitability, and make decisions that balance quality with financial constraints.
• Experience working with regulated industries including healthcare, legal services, or financial services is highly valued.
• Proficiency with version control systems (Git), CI/CD concepts, and modern development workflows.
• PMP, CSM, CSPO, or similar project management certification is a plus.
• Continuous learner who stays current on AI development tools, project management trends, and emerging technologies.
• Self-motivated leader who can drive projects forward without direct authority over technical resources.
• Detail-oriented with exceptional organizational skills and ability to manage multiple complex projects simultaneously.

REPORTING STRUCTURE

This position reports to the SVP of Strategy. This position coordinates technical resources across development, Creative, Digital, and Client Success teams.