Senior Technology Operations Lead

Senior Technology Operations Lead

Location: Worldwide (Remote/Hybrid) Reports to: CTO

CINC is a fully integrated cloud-based homeowners’ association accounting and property management software system that develops accounting, payment, banking, and management software solutions that support the running of the day-to-day activities of Homeowners Associations and Management Companies. CINC is the largest and most successful provider of solutions for this market.

Role Overview

The Senior Technology Operations Lead anchors the operating system of CINC’s technology organization. The role establishes and maintains the planning cadence, matures our engineering metrics and transparency (OKRs, DORA, Golden Signals), and partners with the CTO to deliver clear, data-informed communications to the ELT and Board. Success is bringing rhythm, clarity, and trustworthy data to how work is planned, reviewed, and communicated without unnecessary bureaucracy.

Areas of Responsibility for this role

This role connects day-to-day execution with leadership visibility through four pillars. You’ll introduce simple, repeatable mechanisms that improve focus, predictability, and accountability.

1) Delivery & Reliability Signals

· Establish and steward the engineering OKR framework (definitions, rollout, quarterly refresh, progress tracking).

· Define and maintain DORA metrics (deployment frequency, lead time, change failure rate, MTTR) with clear ownership and target bands.

· Stand up Golden Signals (latency, traffic, errors, saturation) and a practical SLO/SLA view for leadership.

· Build unified dashboards and a regular scorecard that integrates delivery and operational health.

· Ensure reliable data flow from Jira, Bitbucket, CI/CD systems, and observability platforms (e.g., Datadog/Grafana).

2) Customer & Portfolio Outcomes

· Partner with Product and Customer teams to surface adoption, active usage, retention/churn/NRR, roadmap predictability (hit rate), and cycle time to value.

· Integrate these product/portfolio indicators alongside engineering signals in the same leadership scorecard.

· Standardize metric definitions with Product to maintain consistency and comparability across teams.

3) Operating Rhythm & Governance

· Define and run the technology planning calendar: weekly ops syncs, sprint/iteration reviews, monthly business reviews, quarterly planning and retros.

· Introduce lightweight, reusable artifacts (concise briefs, decision logs/ADRs, risks/dependencies) to improve alignment and follow-through.

· Maintain a concise technology scorecard and R/Y/G status across key initiatives; track decisions and actions to closure.

· Promote clear ownership, capacity awareness, and dependency management across Product, Engineering, Data, and IT/Security.

4) Executive Communications & Accountability

· Partner with the CTO to prepare ELT and Board materials: memos, quarterly technology updates, roadmap/delivery summaries, risks/mitigations, and budget-impact highlights.

· Draft and refine high-visibility communications and internal notes.

· Standardize templates (MBR/QBR packs, Board deck sections, KPI pages) and maintain a single source of truth for technology KPIs and narratives.

Requirements and Qualifications

Core Profile

· Senior operator with strong judgment, discretion, and writing skills, able to draft for leadership and translate signals into clear decisions.

· Brings structure with a light touch; emphasizes operational excellence, transparency, and continuous improvement.

Experience

· 10+ years in Technology/Engineering Operations or Technical Program Management within software/SaaS.

· Demonstrated experience establishing and facilitating quarterly planning at the engineering-org level.

· Practical implementation of OKRs, DORA metrics and Golden Signals (definitions, instrumentation, dashboarding, and adoption).

· Comfortable maturing processes and tooling iteratively; aligns multiple teams around shared definitions and goals.

Skills & Tools

· Planning and facilitation across Product/Engineering/Data/IT; portfolio visibility and risk/dependency management.

· Excellent written communication; executive-ready slides and memos.

· Familiarity with Jira, Bitbucket, CI/CD systems, and observability/reporting tools (e.g., Datadog, Grafana, Looker, Mode, or similar).

· Strong analytics and storytelling, turning data into concise insights and recommendations.

Nice to Have (not required)

· Experience in high-growth or PE-backed environments.

· Collaboration across Platform, Product, Data, and Security teams.

· Familiarity with capacity or cost-to-serve views used in leadership packets.

Compensation

The compensation package includes a competitive base salary plus an incentive-based bonus.

CINC is an Equal Opportunity Employer of women, minorities, protected veterans and individuals with disabilities.