Implementation Specialist

About the role
As an Implementation Specialist at Dockwa, you will own the critical bridge between sale and success—transforming new marina customers from contract signature to confident, productive platform users. You'll guide marinas through product configuration, data migration, system integration, and training, ensuring every implementation is tailored, timely, and sets the foundation for long-term retention.
This role reports to the Customer Success leadership team and sits at the intersection of Sales, Product, and ongoing Customer Success. You'll work closely with Account Executives during handoff, collaborate with Product teams on complex configurations, and partner with Marina Success Managers to ensure smooth transitions from implementation to steady-state support.
From helping marinas transition to digital contracts to configuring POS systems and migrating dock maps, you'll ensure each customer goes live successfully. Your work directly impacts time-to-value, product adoption, and gross retention—the metrics that determine whether we scale from $10M to $100M ARR.

Core responsibilities
1. Customer Onboarding & Implementation
Guide marina customers through product configuration, system integration, and go-live readiness
Migrate and configure customer data including rates, inventory, contracts, and dock maps
Configure POS systems and modular features (Service, Rentals, Fuel, etc.) based on marina operational needs
Manage implementation project timelines, ensuring on-time go-lives and minimal customer friction
Tailor onboarding experience to customer size, complexity, and technical sophistication
2. Training & Enablement
Conduct training sessions focused on product adoption and operational success across various user roles
Create and continuously improve training materials, onboarding documentation, and Help Center content
Deliver clear, effective training on product best practices for marina staff at all technical levels
Develop customer-facing resources that reduce support burden and enable self-service learning
Identify knowledge gaps and build enablement assets to address recurring customer questions
3. Cross-Functional Collaboration & Product Feedback
Work closely with Product, Sales, and Support teams to address implementation challenges and align messaging
Collect and synthesize customer feedback during onboarding to influence product improvements and roadmap priorities
Partner with Sales during handoff to ensure implementation expectations align with what was sold
Collaborate with Marina Success Managers to create smooth transitions from implementation to ongoing support
Surface implementation blockers, technical gaps, and customer experience issues to leadership
4. Process Development & Implementation Excellence
Manage multiple implementations simultaneously while maintaining quality and attention to detail
Build and refine implementation playbooks for different customer segments and product tiers
Identify patterns in implementation challenges and recommend process improvements
Contribute to scaling implementation operations as customer volume grows
What we're looking for
4+ years in Implementation, Onboarding, Customer Success, or similar customer-facing role, preferably in SaaS or technology-driven environments
Strong organizational skills with proven ability to manage multiple complex projects simultaneously
Excellent communication and training skills—ability to explain technical concepts clearly to non-technical audiences
Experience with CRM and implementation tools (Salesforce experience strongly preferred)
Detail-oriented approach to data migration, system configuration, and customer-facing documentation
Ability to balance multiple priorities, adapt quickly, and thrive in fast-paced environments
Passion for technology, boating, hospitality, or operations is a plus