Project Manager/Executive Assistant to VP of Engineering

Project Manager/Executive Assistant to VP of Engineering (ConnectWise) We are looking for a Project Manager/Executive Assistant to work alongside the VP of Engineering and develop data‑driven decision‑making processes for the engineering, product, and operations teams. Company 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, 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 activities for small and medium sized businesses, such as backup and restore, security, and administrative tasks on Microsoft 365 tenants. Role Overview We are seeking an energetic individual to build, maintain, and evolve the metrics, dashboards, analyses, and reporting infrastructure that inform leadership’s strategic decisions. This position focuses on analytics, reporting, and collaboration with stakeholders, rather than direct project delivery. Key Responsibilities Design, implement, and maintain dashboards and scorecards to reflect 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 Qualifications 6+ years of experience in a technical or data‑oriented role (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 the ability to simplify complex analyses into digestible narratives for senior audiences Strong stakeholder management skills, with the 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 Preferred Qualifications (Bonus) 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 data‑quality tooling) Additional Information / Personal Profile High level of self‑organization Attention to detail Structured work approach Excellent communication skills Employment Details Seniority level: Mid‑Senior level Employment type: Full‑time Job function: Project Management Industries: IT Services and IT Consulting Referrals increase your chances of interviewing at Sigma Software Group by 2x. #J-18808-Ljbffr