Dennis O'Reilly

Experience

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  RentRedi

  Technical Support Manager

  Jul 2025 - Mar 2026

  RentRedi is a comprehensive rental management software for landlords and tenants, using data to enhance operations.

  • Reporting to Head of Sales and Support, managing a team of Technical Support Engineers and a dotted-line Software Engineer (Ops Duty), serving as the strategic bridge between Support and Engineering to expedite code fixes and PR generation for user-report
  • Streamlined incident management protocols and migrated case systems from Jira to Intercom, resulting in a 30% reduction in time-to-resolution for outages and a 36% improvement in case acknowledgment speed.
  • Architected the "Autopay" month-end monitoring rotation to safeguard revenue cycles; utilizing Sigma, Firebase, and GCP Logs Explorer to track revenue data, triage cloud function errors related to payments, and report anomalies to senior leadership and Da
  • Expanded team scope to own Google Cloud Platform (GCP) Error Groups and Sentry error logging, linking automated alerts to Jira to streamline bug reporting and accelerate engineering workflows resulting in a 14% increase in case closure rate.
  • Developed a specialized technical knowledge base for the Technical Support Engineering team, reducing triage time for known issues by 23%, tying individual goals to knowledge creation.

• Bowery Valuation

  Director, Technical Services

  Jan 2024 - Sep 2024

  Bowery Valuation provides fast, tech-powered commercial real estate appraisals in the U.S.

  • Reported to CEO, managed SaaS Product Support and IT teams; built a culture of cross-functional collaboration, reducing case backlog by 30% and improving team morale
  • Developed departmental structures, SOPs, incident management processes, Business Continuity Plan, Data Integrity Policy, and Disaster Recovery Plan, leading to improved CSAT and user experience
  • Created multi-channel case management system with automations, including bots with auto-response, and integrations with Usersnap, Jira, and Slack, improving response times
  • Built monitoring and alerts integrated with Slack and email for business-critical software, developed cross-functional incident response team which fostered a proactive approach and improved turnaround for incident response times
  • Improved CSAT engagement by 200% through automated offering and direct user interaction

• Bowery Valuation

  Technical Support Manager

  Mar 2022 - Jan 2024

  Bowery Valuation is a tech-enabled commercial real estate (CRE) appraisal firm that uses proprietary, AI-driven software to deliver faster, more accurate valuation reports for various asset types.

  • Reported to CTO, managed SaaS Product Support team, led with empathy, acted as backup for the team by engaging with users and solving cases
  • Created technical onboarding documentation, reducing ramp-up time for new team members from 6 months to 12 weeks, improving SLA’s: time to first response (87% to 100%), reducing time to resolution (96% to 100%), and engineering case deflection (from 70% to 82%)
  • Served as liaison for Engineering and DevOps; prioritized bug backlog and feature requests, provided backup for IT and Product Support teams, improving CSAT scores and user engagement
  • Created job descriptions, KPIs, and metrics; introduced automations
  • Built culture of documentation (Knowledge Base Council) for internal and external articles which increased user enablement and reinforced team knowledge, increased content by 633%
  • Instituted quarterly “Bug backlog Burn Down”, reviewed and validated engineering bug backlog, closing 8% on average
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  ICE Mortgage Technology

  Technical Support Manager

  Jan 2017 - Mar 2022

  ICE Mortgage Technology focuses on transforming the mortgage industry with technology solutions.

  • Oversaw global SaaS technical support team supporting enterprise clients in a call center environment; managed Agile sprints and release schedules, achieved 99% customer satisfaction from 2017-2022
  • Coordinated software upgrades, defined business requirements, and liaised with Engineering and Operations
  • ZenDesk administrator, Five9 administrator, maintained KPI metrics, presented to C-suite and B2B executives
  • Generated customer-facing release notes and incident advisories, built up-time status pages for production and pre-production domains, managed vendors
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  Capsilon

  Application Analyst 2

  Oct 2015 - Jan 2017

  Capsilon builds Intelligent Process Automation software for mortgage companies to improve efficiency.

  • Triaged software bugs for SaaS customers, supported multiple applications, developed an internal knowledge base, engaged with enterprise clients, maintained 100% personal CSAT, customer-focused approach.
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  McKesson

  Application Analyst Level 2

  Jul 2011 - Oct 2015

  McKesson Corporation is a leading healthcare services company primarily known as the largest pharmaceutical distributor in North America, delivering one-third of all prescription medications used in the United States.

  • Created and tuned SQL queries in Oracle DBMS
  • Executed procedure calls via JDBC connections
  • Facilitated interfaces between software and multiple third-party vendors
  • Monitored database performance and batch processes
  • Worked with development team on behalf of customers to facilitate and expedite defect and bug fixes, as well as enhancements to the EnterpriseRx software