Implementation Specialist - Onboarding & Training

Role Summary
As an Implementation Specialist – Onboarding & Training, you own the customer’s journey end to end: from kickoff through system implementation, integration, and full training completion. Rather than handing customers off between an implementation owner and a trainer, you carry the relationship yourself — configuring MarketMan, setting up POS and API integrations, uploading and validating inventory, then training the team until they are running confidently and independently on the platform.

This role is primarily dedicated to our Square customer segment, where you will develop deep expertise in the Square integration and its onboarding motion. You will not be limited to that segment: you will also support customers on other POS platforms (Toast, EPOS Now, and others) as business needs require. You will work closely with Sales, Support, Training, Data Processing, Customer Success, and Product, and act as a key feedback channel back into the product.

What You Will Do
Own the End-to-End Customer Journey
•    Single owner: Serve as the primary point of contact for the customer from kickoff through training completion and early live use.
•    Plan and drive: Build and execute implementation and training plans with clear milestones, timelines, owners, and success criteria for each account.
•    Portfolio management: Manage a portfolio of concurrent customers at different stages, prioritizing effectively to keep every account moving toward go-live.
•    Clean completion: Confirm that implementation and training milestones are fully met — not just delivered — before transitioning the account to Customer Success or Support.

Implementation & Integration
•    Configure the MarketMan system for each customer: inventory, suppliers, recipes, locations, users, and permissions.
•    Own POS and API integration setup end to end, with deep specialization in the Square integration and working proficiency across Toast, EPOS Now, and other supported platforms.
•    Partner with the Data Processing team to get customer inventory and item lists processed, validated, and uploaded accurately and on schedule.
•    Identify and resolve issues during and after implementation; escalate to Technical Support or R&D with clear, reproducible detail when needed.
•    Maintain accurate documentation of configuration decisions, integration setup, and customer-specific requirements.

Training & Enablement
•    Deliver engaging training across formats — 1:1 sessions, cohort-based (1:many) sessions, and webinars — covering inventory counts, purchasing, invoice scanning, recipe costing, and reporting workflows.
•    Tailor sessions to real restaurant scenarios and to the customer’s own data, so training maps directly to how their operation runs.
•    Verify competency before sign-off, and run refresher or re-training sessions where adoption lags.
•    Guide customers toward scalable, self-serve learning: help centre articles, on-demand video, and in-app guidance — and contribute to building and improving those assets in collaboration with the Training team.
•    Document recurring questions and friction points, and turn them into reusable materials that reduce repeat, preventable support contacts.
Adoption, Risk & Growth
•    Monitor usage and engagement signals through onboarding and early live use to proactively surface adoption gaps.
•    Flag churn risk early, with documented context and a clear action plan.
•    Identify expansion signals — additional locations, users, or modules — and surface qualified opportunities to Customer Success or Sales.

Collaboration & Feedback
•    Coordinate with Sales for handoff context and customer goals, with Support for post-live continuity, and with Customer Success on account strategy.
•    Relay structured customer feedback to Product, particularly on integration behaviour, onboarding friction, and feature gaps.
•    Keep records, project status, and customer insights current in Salesforce and project tracking tools so program status is always reportable.
•    Participate in product, support, and customer success syncs, and share trends observed in the field.

What You Will Bring
Required
•    2–3 years of experience in implementation, onboarding, customer training, enablement, or a similar technical customer-facing role.
•    Demonstrated comfort with integrations and data: imports/exports, field mapping, spreadsheets, and troubleshooting data discrepancies.
•    Strong facilitation and presentation skills, with the ability to train non-technical users clearly and patiently.
•    Solid project management ability — running multiple accounts and deadlines simultaneously without losing momentum or detail.
•    Excellent written and verbal communication, plus strong problem-solving instincts.
•    Working knowledge of tools such as Salesforce or HubSpot, Jira, Google Workspace, and project tracking platforms.
•    Ability to work independently, take ownership, and operate with a customer-first mindset.
•    Bachelor’s degree in Business, Hospitality, Computer Science, Engineering, or a related field — or equivalent practical experience.

Advantage
•    Background in SaaS and/or restaurant technology.
•    Hands-on familiarity with Square POS (or Toast, EPOS Now, and comparable platforms).
•    Restaurant or hospitality operations experience — inventory management, food cost control, purchasing, or kitchen management.
•    Exposure to instructional design, LMS platforms, or training content creation.
•    Ability to write and speak Spanish