Training & Enablement Specialist

The Training & Enablement Specialist is responsible for managing the customer onboarding journey from kickoff through go-live. This role serves as the primary point of contact throughout onboarding and is responsible for project coordination, customer communication, training delivery, adoption readiness, and go-live preparation. The Training & Enablement Specialist partners closely with the Configuration Specialist and internal stakeholders to ensure customers receive a structured, consistent, and successful onboarding experience that drives product adoption and long-term success. About Cloudpermit Cloudpermit is the fastest-growing community development, SaaS (software-as-a-service) company in North America. We provide local governments and their citizens with cloud-based software products for all land management processes, including permitting, code/zone enforcement, business licensing, city planning, and more. Headquartered in Reston, VA, Cloudpermit was founded 15 years ago and is growing rapidly across North America. Cloudpermit is committed to delivering efficient, accessible, and smart land management software for agencies and citizens nationwide. Key Responsibilities & Duties Essential Functions: Lead customer kickoff meetings and establish onboarding expectations, timelines, and responsibilities Serve as the primary customer contact throughout the onboarding lifecycle Develop, maintain, and manage customer onboarding plans and implementation timelines Conduct regular customer status meetings and communicate project progress, risks, and next steps Track customer action items and ensure timely completion of onboarding activities Coordinate onboarding activities with Configuration Specialists and internal stakeholders Deliver customer-facing User and Administrator training sessions Customize training delivery based on customer roles, workflows, and business processes Evaluate customer readiness and adoption throughout onboarding Conduct go-live readiness reviews and coordinate go-live activities Identify onboarding risks, customer challenges, and project delays and elevate appropriately Document onboarding progress, customer readiness, and project outcomes within internal systems Maintain a strong understanding of Cloudpermit products, onboarding methodologies, and implementation best practices Provide feedback on customer onboarding experiences, training effectiveness, and process improvement opportunities Support customer transition to Customer Success and Support following successful go-live Non-Essential Functions: Participate in internal training sessions, team initiatives, and knowledge-sharing activities Support development and refinement of customer onboarding materials, training content, and enablement resources Required Qualifications & Skills Experience with Cloudpermit software preferred; equivalent experience implementing or administering configurable permitting or municipal software will also be considered 3+ years of experience in Community Development, Municipal Government, GovTech, Professional Services, Customer Success, Training, Implementation, or related SaaS environments Experience leading customer-facing onboarding, implementation, training, or project initiatives Strong presentation, facilitation, and customer training skills Strong customer relationship management and stakeholder engagement skills Excellent written and verbal communication skills Ability to explain technical concepts and business processes in a clear, user-friendly manner Ability to manage multiple customer projects and priorities simultaneously Strong organizational, planning, and time management skills Strong problem-solving skills with the ability to proactively identify risks and coordinate solutions Technical proficiency with CRM platforms (e.g., Salesforce), Microsoft Office Suite, and cloud-based software platforms HTML/CSS experience preferred Work Environment & Physical Requirements Prolonged periods of working at a computer Frequent participation in customer meetings, training sessions, and project reviews Occasional travel may be required for customer onboarding engagements Company Culture Focus - We are focused on our passion, work ethic, and goals, so we can continue to push forward and create innovative software. Collaboration - We work and succeed as a team at Cloudpermit because we're stronger together. We accept each other's strengths so we can learn from one another and become better. Respect - Respecting our customers, and respecting each other, is of the utmost importance. We trust our team to do great work and stay open to new ideas. The Cloudpermit team is comprised of motivated, positive, and tech-savvy team members. We enjoy working as a team to solve problems and thrive on collective and personal success. At Cloudpermit, you will be assigned engaging and challenging projects and will have opportunities to give input and direction. The Cloudpermit work environment is inclusive, challenging, and rewarding. Competitive salary and benefits package Innovative and welcoming team Transparent and nurturing management Tremendous opportunity to grow professionally