Role Overview
The Senior Customer Enablement Specialist is an experienced, field-ready member of the Delivery team within Operations. In addition to providing remote onboarding support, includes on-site training engagements, multi-site rollouts, and hands-on workflow adoption for complex accounts.
This position requires approximately 35% travel to customer sites to lead in-person training, support high-stakes go-lives, and build the trusted-advisor relationships that drive long-term product adoption. The role reports directly to the VP of Product and Operations with a dotted-line to the Customer Enablement Lead.
This is not a sales or quota-carrying role. It is an operational and enablement-focused position responsible for measurable customer outcomes — from onboarding completion through sustained, independent usage of our route accounting software.
Key Responsibilities
Field & On-Site Training
- Travel to customer locations (~35% of time) to lead in-person onboarding, role-based training, and workflow adoption sessions
- Facilitate multi-day on-site rollouts for enterprise or complex accounts, coordinating logistics, agendas, and stakeholder alignment
- Deliver hands-on training tailored to customer teams including accounting, operations, dispatch, and route drivers
- Support live launch events on-site, providing real-time troubleshooting and user confidence-building
- Identify workflow gaps and adoption blockers in real time and address them proactively during field engagements
Customer Onboarding & Rollout
- Lead full-cycle onboarding from post-sale handoff through launch, including complex and multi-location accounts
- Conduct implementation coordination, configuration guidance, and readiness validation with technical and operational stakeholders
- Ensure customers achieve proficiency in core workflows: invoicing, payments, route reconciliation, reporting, and integrations
- Define and validate go-live success criteria, confirming customers operate independently before transitioning to Support
Training Development & Enablement Programs
- As directed by the Customer Enablement Lead, help develop, and maintain a comprehensive library of onboarding and training materials — including documentation, video walkthroughs, and role-specific quick-start guides
- Build and iterate on onsite training curriculum that scale across diverse customer types, including multi-site operations and advanced users
- Deliver advanced and refresher training sessions as customers expand usage, add users, or adopt new product features
- Contribute to team enablement playbooks, standards, and best practices in collaboration with the Enablement Lead
Ongoing Enablement & Post-Launch Engagement
- Lead periodic check-ins/enablement reviews for strategic accounts to reinforce best practices and surface expansion needs
- Act as a trusted product education resource, deepening customer knowledge and confidence over time
- Partner with Customer Success on broader account health and strategic expansion initiatives
Support Handoff & Cross-Functional Collaboration
- Facilitate formal customer transitions from Delivery to Support, ensuring complete documentation of configurations, workflows, known issues, and training status
- Conduct structured warm handoffs with clear customer expectations and full knowledge transfer
- Partner with Support to reduce repeat tickets through proactive education and improved enablement materials
- Collaborate with Product, Engineering, Customer Success, and Support to align on customer experience improvements
- Provide product feedback to product and engineering team based on interactions with users.
Required Qualifications
- 4+ years of experience in customer enablement, onboarding, implementation, training delivery, or customer-facing operations
- Proven experience in a B2B SaaS environment managing complex, multi-stakeholder onboarding engagements
- Comfortable leading in-person training and executive-level stakeholder conversations during on-site engagements
- Strong understanding of route accounting, distribution operations, or field service workflows (or ability to develop this expertise quickly)
- Excellent facilitation, presentation, and instructional design skills
- High degree of organization and self-direction; ability to manage multiple concurrent accounts and travel commitments
- Strong written and verbal communication skills; ability to translate technical concepts for non-technical audiences
- Willingness and ability to travel approximately 35% of the time, including multi-day site visits
Preferred Qualifications
- Experience with route accounting software, ERP systems, or distribution management platforms
- Background in creating structured training programs or learning paths
- Experience supporting enterprise or multi-site customer rollouts
Work Environment & Travel
This role is based in Turlock, CA or Denver, CO and is primarily office-based. Travel is approximately 35% and may include multi-day trips for on-site training events, launch support, and strategic account engagement. Travel is planned in advance and coordinated with customers and the Delivery team.
Pay: $75,000.00 - $80,000.00 per year
Benefits:
- 401(k)
- 401(k) matching
- Dental insurance
- Health insurance
- Health savings account
- Life insurance
- Paid time off
- Vision insurance
Application Question(s):
- Are you able to travel approximately 35% of the time?
Experience:
- customer operations : 4 years (Required)
Ability to Commute:
- Turlock, CA 95380 (Required)
Work Location: In person
