Director of Professional Services

* Project Portfolio Management
+ Define and operationalize implementation methodologies appropriate for Enterprise Resource Planning (ERP), Point of Sale (POS), and Student Information System software implementations with contract values ranging from less than $10,000 to over $500,000 and durations from 1 month to 18 months
+ Lead PS team members in the execution projects and perform direct customer-facing project management duties as required.
+ Ensure successful project delivery aligned with revenue targets and client satisfaction.
+ Manage remote, cross-functional teams of Application Consultants, technical specialists, and SMEs across all product lines.
+ Apply project management frameworks with internal rigor while remaining approachable and relationship-centered in all customer-facing interactions, particularly with K-12 and higher-education institutional leaders.



* AI Strategy & Adoption
+ Treat AI adoption as a strategic imperative — embedding AI tools throughout the PS lifecycle from SOW creation and project planning through execution, testing, training, and closeout.
+ Leverage AI tools to scale implementation capacity, enabling a small PS team to support a growing number of large, complex projects without linear headcount growth.
+ Continuously evaluate and implement AI tools that accelerate project planning, automate documentation generation, and improve cross-project visibility.

Qualifications


* Proven experience leading complex software implementation projects in ERP, Point-of-Sale, Student Information Systems, or comparable vertical market software domains.


* Demonstrated success in building and scaling PS delivery processes from the ground up in a small-team, high-growth environment.


* Strong financial management capability, including hands-on experience with percent-complete (EAC) revenue recognition, PS P&L ownership, WIP management, and revenue forecasting.


* Demonstrated comfort operating a PS team at a revenue-to-operating-expense ratio of 2x or greater.


* Concrete, hands-on experience applying AI tools in a project management or PS delivery context, with the ability to speak to past applications, outcomes, and a forward-looking vision.


* Experience managing remote, cross-functional teams with accountability across distributed environments.


* Servant-leader with the ability to apply structured methodologies internally while remaining approachable and relationship-centered with K-12 and higher education customers.


* Results-driven, capable of defining relevant KPIs and milestones, then measuring progress to achieve long-term goals.

Preferred Qualifications


* Vertical market software experience; Education technology (K-12 and/or higher-education) considered a strong asset.


* Familiarity with IFRS revenue recognition policies.


* Experience with project tracking tools (e.g.,...