Project Manager / Executive Assistant To Vp Of Engineering (Connectwise)

We are looking for an Project Manager / Executive Assistant to VP of Engineering to work alongside the VP of Engineering and develop data-driven decision-making processes for the engineering, product, and operations teams.

You will build and maintain metrics, dashboards, and KPI frameworks, turning complex data into clear insights that will guide strategic planning.

This position focuses on analytics, reporting, and collaborating with stakeholder, rather than on direct project delivery.

You’ll have a strong influence on executive-level decisions, gain exposure to cross-functional teams, and help evolve data measurement and observability practices across the company.

Customer

ConnectWise is the world’s leading software company dedicated to the success of IT solution providers. Their vision is to power a thriving IT ecosystem that transforms what’s possible for SMBs and do this by empowering IT solution providers with unmatched software, services, and community to achieve their most ambitious vision of success. The tools being developed are used by IT service providers to automate their activities for small and medium sized businesses (SMBs), such as backup and restore, providing security, and performing administrative tasks on Microsoft 365 tenants.

Project

We are seeking an Project Manager / Executive Assistant to work alongside our VP of Engineering, driving data-driven decisions across engineering, product, operations, and related teams. In this role, you will not be responsible for executing or managing specific project delivery, but rather will build, maintain, and evolve the metrics, dashboards, analyses, and reporting infrastructure that inform leadership’s strategic decisions.

• Your core mission will be to provide high-visibility, actionable insights. You will coordinate with multiple teams to collect, validate, and interpret data;
• propose new KPIs and measurement strategies;
• identify trends, risks,and opportunities;

and present your findings to Senior leadership or directly to the team on monthly business review meetings in a clear, compelling way.

You will act as a force multiplier, enabling the VP and Senior leadership to monitor progress, spot deviations early, and course-correct, while fostering alignment across stakeholders on how success is measured and communicated.

Requirements

Will be a plus

Personal Profile

Responsibilities

propose and drive enhancements, including new instrumentation, tooling, or process changes