Executive Assistant to VP of Engineering

We are looking for an 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 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.

• Design, implement, and maintain dashboards and scorecards to reflect the progress toward strategic objectives
• Define, refine, and evolve KPIs, SLAs, OKRs, and other metrics frameworks in collaboration with engineering, product, operations, and business teams
• Aggregate, cleanse, and correlate data from multiple systems (e.g. JIRA, monitoring, data warehouse, internal tools, and financial systems)
• Analyze trends, variances, and anomalies. Perform root cause analyses, and propose actions or changes to processes or focus
• Produce regular reports (weekly, monthly, quarterly) for the VP, the executive team, and cross-functional stakeholders
• Partner with stakeholders to vet and align on metric definitions, reporting cadences, and data interpretations
• Assist in setting targets, thresholds, and goals for key metrics, and monitor progress toward them
• Monitor the health of metrics (data quality, signal stability, outlier detection, alerting) and drive remediation when issues arise
• Identify gaps in current measurement capabilities; propose and drive enhancements, including new instrumentation, tooling, or process changes
• Serve as the "go-to" analytics/metrics liaison between the VP and various teams (engineering, product, operations, finance)
• Assist in preparing executive-level narratives and presentations, translating complex data into impactful stories
• Stay abreast of industry best practices in metrics, observability, dashboards, and data analytics. Implement innovations and continuous improvements

• 6 years of experience in a technical or data-oriented roles (e.g. analytics, reporting, technical product management, program management with a strong focus on metrics)
• Strong experience working with cross-functional engineering, product, or operations teams
• Experience analyzing large data sets, identifying trends and anomalies, and performing root cause analysis
• Excellent verbal and written communication skills, with ability to simplify complex analyses into digestible narratives for Senior audiences
• Strong stakeholder management skills, with ability to influence across multiple teams without direct authority
• Comfortable working in ambiguous, fast-moving environments
• Experience in defining and refining KPIs, SLAs, OKRs, and similar measurement frameworks
• Advanced level of English

WILL BE A PLUS

• Bachelor's degree in computer science, engineering, data science, statistics, business analytics, or a related field (or equivalent experience)
• Experience in technical domains (e.g. cloud, infrastructure, SaaS, and dev tools)
• Familiarity with data warehouses, ETL processes, instrumentation, event tracking, observability, and monitoring systems
• Experience working with program management tools (e.g. Azure DevOps, Jira, Confluence, and Asana)
• Prior experience reporting to Senior executives or being part of an executive-facing analytics and insights team
• Prior experience with metrics governance (defining metric ownership, ensuring metric consistency, handling metric versioning, and maintaining metric catalogs)
• Experience in tooling improvements for measurement (e.g. instrumenting new metrics, automating data collection, and adopting of data-quality tooling)

PERSONAL PROFILE

• High level of self-organization
• Attention to detail
• Structured work approach
• Excellent communication skills