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Enterprise Training Lead at City Innovate, Remote

  • Full Time
  • Mid-level
  • Remote
  • Remote

Website City Innovate


Job Title: Enterprise Training Lead

City Innovate’s customers are seasoned government executives who are also on the cutting edge in their commitment to innovating very manual and complex document processes such as procurement, budgeting, grants and more.

We are looking for an experienced Enterprise Training Lead to design and deliver custom training programs to support software adoption and business process transformation for enterprise public sector customers.

The Enterprise Training Lead plays a crucial role in facilitating the successful adoption of our software products as customers undergo business process changes and broader change management initiatives during their journey with City Innovate. This role focuses on designing, crafting, and delivering comprehensive training programs that address the impact of software changes on people, processes, and technology.

What You’ll Be Doing

  • Needs Assessments and Business Process Mapping: 
    • Collaborate closely with Business Analysts, Project Managers, and other members of the Client Success team to uncover business needs, define the customer’s business rules and requirements, and map business processes to the product workflows.
    • Conduct thorough needs assessment reviews with internal teams to understand the specific requirements, challenges, and goals of each customer.
    • Analyze business processes to identify areas for improvement and alignment with the software solution.
    • Map customer business processes to the functionalities and workflows supported by the software solution.
    • Identify opportunities for process optimization, automation, and efficiency gains through software utilization.
  • Customized Training Program Design:
    • Design custom training programs tailored to the unique needs and business processes of each enterprise customer.
    • Deeply understand the current state and desired future state of the customer’s business processes, technology stack, and capabilities and design best-practice training plans that support the customer’s change management plans
    • Develop training materials, modules, and resources that align with the software solution and address specific business challenges.
    • Anticipate and address potential resistance to change within the organization and implement strategies to mitigate it.
  • Delivering enterprise in-person training
    • Collaborate closely with colleagues across the Professional Services team, Customer Outcomes team, and Consulting team to build and deliver on-site and live training courses tailored to the modules, user roles, and business processes in scope.
    • Develop and deliver customized training programs across learning modalities, including instructor-led workshops, hands-on simulations, and virtual learning programs across our modules.
    • Develop training materials, including presentations, handouts, and exercises tailored to specific organizational requirements.
    • Conduct engaging and interactive training sessions to educate users on product functionalities and best practices.
  • Collaboration with Training Specialist Delivering Virtual Standard Trainings:
    • Coordinate with the Training Specialist delivering virtual standard training to ensure alignment between customized training programs and standard training offerings.
    • Share insights, best practices, and lessons learned from custom training engagements to enhance the quality and effectiveness of virtual standard training.
    • Collaborate on identifying common challenges and developing solutions to improve the overall training experience for customers.
  • Engagement with Training Content Specialist:
    • Collaborate closely with the Training Content Specialist to provide insights and requirements for creating customized training materials and content.
    • Offer feedback and guidance on the development of training materials to ensure they accurately reflect the specific needs and business processes of enterprise public sector customers.
    • Leverage the expertise of the Training Content Specialist in instructional design and content creation to enhance the quality and relevance of custom training programs.
    • Provide input on the development of reusable training assets and templates that can be leveraged across different customer engagements.
  • Monitoring and Evaluation:
    • Evaluate training effectiveness and make adjustments as necessary to ensure learning objectives are met.
    • Maintain accurate records of training activities, participant progress, and feedback for reporting and analysis purposes.
    • Create internal feedback loops based on customer data to ensure materials are improved, customer learning gaps are addressed, and any risks are mitigated quickly by the appropriate team members.


Knowledge & Experience

The Enterprise Training Lead role requires a combination of instructional design expertise, technical proficiency, consultative change management, and client engagement skills to deliver impactful training solutions that drive software adoption and business transformation.

  • Business Process and Change Management 
    • Knowledge of change management principles and methodologies.
    • Ability to develop change management plans and strategies to facilitate software adoption and business process transformation.
    • Ability to analyze and map customer business processes to software functionalities.
    • Experience in identifying opportunities for process optimization, automation, and efficiency gains through software utilization.
    • Familiarity with process modeling techniques and tools.
    • A practical, working understanding change management methodologies and practices and human-centered change
    • The ability to write quickly and well to produce effective communications for audiences across varying channels and levels
    • Project management experience in successfully planning, managing, and delivering multiple, concurrent, and complex work streams in a matrixed organization
  • Instructional Design
    • Strong understanding of adult learning principles and instructional design methodologies.
    • Experience developing and delivering training as a part of large-scale change management program or organizational transformation, including the rollout of enterprise applications
  • Technical Proficiency
    • Ability to understand complex software functionalities and translate them into user-friendly training materials and programs.
    • Familiarity with enterprise-level software systems and their integration within organizational workflows.
    • Strong understanding of enterprise software training tools and methods
  • Project Management and Stakeholder Communication 
    • Ability to think both strategically and tactically, with strong analytical and problem-solving skills
    • Project management experience in successfully planning, managing, and delivering multiple, concurrent, and complex work streams in a matrixed organization Ability to prioritize tasks, meet deadlines, and adapt to changing project requirements.
    • Experience in tracking and reporting on training progress and outcomes.
  • Stakeholder management and Communication
    • Strong interpersonal and communication skills to engage effectively with stakeholders at all levels of the organization.
    • Ability to communicate complex concepts in a clear and understandable manner.
    • Experience in conducting stakeholder interviews, workshops, and presentations.
    • The ability to write quickly and well to produce effective communications for audiences across varying channels and levels
    • Outstanding verbal, written communication skills and ability to develop persuasive messages based on the information provided
    • Experience working in government or with public sector clients in preferred

Personal Attributes

  • Exercises independent judgment and takes action on it. Is quick to take ownership and leadership in coordination with other stakeholders and colleagues.
  • Has a sense of urgency and finds the most efficient way to move forward on a given task or effort
  • Displays excellent listening, interpersonal, written and oral communication skills.
  • Naturally curious, eager to learn and proactive in sharing knowledge with others.
  • Effectively prioritizes and executes tasks while under pressure
  • Demonstrates a high EQ, often described as the best collaborator and go-to person on a team
  • Process-oriented with an automation/efficiency mindset
  • Comfortable with ambiguity and working in a rapidly evolving startup environment.
  • Values the mission or City Innovate. Shares a true desire to improve how government operates and delivers on its mission.


  • Salary Range: $100,000-$140,000
  • Comprehensive medical, dental, and vision insurance
  • Retirement Plan
  • Unlimited PTO
  • Home office stipend

City Innovate is committed to diversity and equal opportunity in employment. We welcome all applicants irrespective of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

Interview Process:

  • Screening
  • Call with Hiring Manager
  • Case Study- Paid
  • 3 Cross Functional Interviews
  • Founder Interview

To apply for this job please visit

Enterprise Training Lead at City Innovate, Remote
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