Rick Aquilia Raleigh, North Carolina

Rick Aquilia

Customer Success & Technical Services leader for cybersecurity and SaaS

I'm Rick Aquilia — Richard Aquilia in full — and for the past decade I've helped software companies turn new customers into long-term ones, leading customer success and professional services teams at BrightGauge, ConnectWise, StrongDM, Forescout, MSPbots, and Compuquip, and building the reporting those teams run on.

My specialty sits where customers meet data: SQL-driven reporting, dashboards people actually trust, and the integrations that feed them. Today I also run Taproot Technology, my Wake County IT services business.

Portrait of Rick Aquilia (Richard Aquilia) in a charcoal suit and light blue tie against a brick wall

Rick Aquilia — Raleigh–Durham, NC

What I do

Ten-plus years across customer success, professional services, and the reporting layer underneath both.

Customer Success Leadership

Onboarding, adoption, renewals, and expansion for technical products — from founding a CS function from scratch to leading established teams serving enterprise accounts.

Reporting & Business Intelligence

SQL reporting and dashboard design for MSPs and SaaS teams — the BrightGauge and ConnectWise reporting world is where I built my name, one trustworthy number at a time.

Technical Services & Integrations

REST APIs, PSA and CRM data, and SaaS integrations. I speak engineer and executive in the same meeting, and I fix the data before blaming the dashboard.

Where I've worked

A decade in the MSP and cybersecurity software ecosystem. Select any company for the full story on the résumé tab.

Right now

Two tracks, same through-line: helping people get more out of their technology.

Taproot Technology

Founder of a local PC repair and IT services business serving Wake County, NC — diagnostics and repair, upgrades, custom builds, and small-business IT support, with firm pricing quoted before any work begins.

Visit the business site →

Open to the right role

I'm interested in customer success and technical services leadership roles — especially where reporting, data quality, and AI-readiness decide whether customers succeed. Raleigh–Durham based; remote-friendly.

Get in touch →

Off the clock

Work is only part of it. When I'm not wrangling data or building PCs, this is where you'll find me.

Comics & reading

Longtime Marvel reader with a book always going. My standing comics favorites are Fantastic Four — Marvel's first family — plus Spider-Man and Wolverine. On the prose side, the Girl with the Dragon Tattoo series is a longtime favorite, and I'm deep into Pierce Brown's Red Rising saga — currently counting down to Red God.

I solemnly swear that I am up to no good.

For L&S — wherever this finds you, know that you are loved, every single day. Always.

Mischief managed.

Guitar

I play guitar — my pride and joy is an American-made Fender Stratocaster. Classic rock and metal are home base, though I listen to a little bit of everything. My favorite guitarist is John Frusciante — the feel, the restraint, the way he always serves the song.

Gaming

Too many platforms, no regrets: PS5 on the TV, Steam Deck for the couch, Switch 2 for Nintendo nights, and a self-built gaming PC when I want to push the settings all the way up.

About Rick Aquilia

Rick Aquilia — full name Richard Aquilia — is a Customer Success and Technical Services leader based in the Raleigh–Durham area of North Carolina. Most people know him as Rick; Richard Aquilia is the name on the paperwork. His career in software began in 2015 at BrightGauge, the reporting and dashboard platform for managed service providers — the product now known as ConnectWise Reports and Dashboards. When ConnectWise acquired BrightGauge in 2019, Rick Aquilia continued with the combined company, rising to Team Lead for Integrations.

From there, Rick Aquilia brought the same playbook — disciplined onboarding, honest metrics, and reporting customers can trust — to infrastructure access at StrongDM and network security at Forescout, both as a Senior Customer Success Manager. He then returned to the MSP world as Head of Professional Services at MSPbots, and most recently served as the Founding Customer Success Manager at Compuquip, building its customer success function from the ground up.

Across every stop, the constant has been data: SQL queries, REST APIs, and dashboards that turn messy operational data into decisions. In 2026, Rick Aquilia founded Taproot Technology in Wake County, NC, providing PC repair, custom builds, and small-business IT services — and he continues to consult on the idea that now drives his work: making a company's data trustworthy enough for AI to be useful on top of it. He holds a BA in Criminal Justice from Long Island University Post (2012).

Richard “Rick” Aquilia

Customer Success & Technical Services Leader

Raleigh–Durham, NC · rick.aquilia@gmail.com · (919) 434-4539 · linkedin.com/in/raquilia · github.com/raquilia

Summary

Rick Aquilia (Richard Aquilia) is a Customer Success and Technical Services leader with 10+ years in SaaS and cybersecurity — and a builder’s track record: first Customer Success hire at BrightGauge, founding CSM at Compuquip, Head of Professional Services at MSPbots. He has managed enterprise portfolios of $10M–$30M ARR and pairs executive-level success planning and renewals ownership with a rare second specialty: the SQL reporting and dashboard layer — the dashboards, QBRs, and monthly reporting that show whether any of it is working.

Certifications

  • Command of the Message® — Force Management (Nov 2022)
  • MEDDICC — Force Management (Nov 2022)
  • EMPOWERED: Product Leadership Workshop — Silicon Valley Product Group (Jul 2021)
  • INSPIRED: How to Create Tech Products Customers Love — Silicon Valley Product Group (Jul 2021)
  • SQL Querying Level 2 (Advanced) — New Horizons (Aug 2016)
  • SQL Querying Level 1 (Fundamentals) — New Horizons (Jun 2016)

Experience

Compuquip logo

Founding Customer Success Manager · Compuquip

October 2025 – March 2026

  • Founding Customer Success hire — built the CS function from the ground up, including the engagement model, cadence frameworks, QBRs, and internal playbooks.
  • Managed a portfolio of enterprise customers totaling $20M+ in contract value, serving as the primary point of ownership across technical, operational, and executive stakeholders.
  • Designed and led executive-level QBRs, shifting conversations from activity reporting to insight-driven discussions focused on risk, outcomes, and roadmap alignment.
  • Conducted customer discovery interviews across multiple segments, translating feedback into actionable service and experience improvements.
  • Owned customer communications for major company initiatives, service changes, and leadership transitions, and established escalation management frameworks with Product, Engineering, and Support.
MSPbots logo

Head of Professional Services · MSPbots

September 2024 – October 2025

  • Led three cross-functional departments — Migrations, Professional Services, and Assets — to strengthen operational efficiency and customer outcomes.
  • Directed customer migrations from competing platforms, minimizing disruption and accelerating adoption.
  • Oversaw delivery of custom SQL queries, dashboards, reports, and widgets tailored to each customer’s business requirements.
  • Built a customer feedback loop leveraging Canny, enabling data-driven product decisions and turning feedback into product enhancements, user stories, and reusable templates.
  • Reduced project resolution times by 80% with phased project plans and early requirements capture; automated Zendesk workflows cut aging tickets by 80% while sustaining a 100% customer satisfaction rating.
Forescout logo

Senior Customer Success Manager · Forescout

October 2023 – September 2024

  • Managed $25M ARR across 7 enterprise accounts, serving as a trusted advisor to champions and C-Level executives through onsite visits and tailored success plans.
  • Leveraged Gainsight to monitor user activity, usage trends, and health scores, proactively identifying risk signals like dwindling usage or user removals and prioritizing high-risk accounts.
  • Led QBRs to highlight progress toward goals, demonstrate ROI, and identify opportunities for deeper product adoption.
  • Collaborated closely with Sales to secure renewals and uncover expansion opportunities within existing accounts.
  • Coordinated cross-functional teams to resolve complex technical issues, manage escalations, and strengthen customer relationships.
StrongDM logo

Senior Customer Success Manager · StrongDM

February 2022 – October 2023

  • Managed $10M ARR across 35 enterprise accounts, collaborating with champions and executive stakeholders to drive adoption, align with strategic objectives, and maximize ROI through executive QBRs.
  • Guided customers implementing StrongDM for secure, Zero Trust access management across AWS and Azure, integrating identity providers and enabling just-in-time permissions.
  • Improved onboarding by defining clear success metrics at kickoff, aligning stakeholders and executives to enhance retention and satisfaction.
  • Leveraged Catalyst automation and health scoring to proactively identify risk — integration failures, user churn — and uncover expansion opportunities through usage analytics.
  • Partnered with Sales, Product, and Marketing to drive renewals, prioritize critical fixes and feature requests, and cultivate advocacy, raising CSAT and NPS.
ConnectWise logo

Team Lead, Integrations · ConnectWise

October 2019 – February 2022

  • Owned the integrations product roadmap following the BrightGauge acquisition, prioritizing features through customer feedback, vendor insights, and strategic business alignment.
  • Managed vendor partnerships and monitored API changes across 40+ data sources, proactively preventing compatibility issues and maintaining integration reliability.
  • Implemented a customer-centric prioritization framework for triaging bugs and feature requests, balancing business impact with user experience.
  • Directed integration projects from requirements through development, testing, and deployment, managing product backlogs and sprint priorities.
  • Delivered product demos and roadmap presentations to stakeholders, driving alignment and product adoption.
BrightGauge logo

BrightGauge

January 2015 – October 2019 · Miami, FL (On-Site) · Three roles, promoted twice

Integration Developer

August 2018 – October 2019

  • Developed and maintained Python and Django integrations using third-party REST APIs, expanding connectivity with Salesforce, Microsoft Office, and Google Workspace.
  • Served as the technical escalation point for complex integration and SQL issues.
  • Supported AWS-based deployments and production reliability, troubleshooting complex API, data, and connectivity issues.
  • Delivered integration projects end to end — requirements through deployment — contributing to Agile development cycles.
  • Presented new features and integration capabilities to customers through webinars, driving adoption and feedback.

Team Lead, Professional Services

October 2016 – August 2018

  • Led Professional Services engagements translating business goals into dashboards, KPIs, and reports, mentoring a team of three on SQL and delivery best practices.
  • Led complex integration projects, including solutions consolidating 10+ datasets into unified data pipelines for advanced reporting.
  • Served as the technical escalation lead for data inaccuracies, resolving issues and protecting reporting integrity.
  • Acted as the technical liaison across Sales and Support while delivering billable implementation projects and customer training.
  • Translated business needs into scalable technical solutions, driving strong post-sales outcomes.

Technical Customer Success Manager

January 2015 – October 2016

  • First Customer Success hire — owned onboarding, implementation, training (1:1 and webinars), support, and health score development.
  • Redesigned customer onboarding processes to accelerate implementation and improve time-to-value.
  • Resolved 10,000+ support tickets, troubleshooting technical issues and guiding customers across a broad range of needs.
  • Developed custom SQL queries across PostgreSQL, MySQL, and Microsoft SQL Server for advanced reporting and data validation.
  • Consulted with customers on KPIs and reporting through biweekly training webinars, driving adoption and proactive churn prevention.

BrightGauge is the reporting and dashboard platform for MSPs — today ConnectWise Reports and Dashboards (formerly BrightGauge). Rick joined as its first Customer Success hire in 2015 and grew with it through the ConnectWise acquisition.

Skills

Customer Success

Onboarding & implementation, adoption and retention programs, QBRs / EBRs, renewals & expansion, escalation management, CS team leadership, building a CS function from scratch

Reporting & Data

SQL, dashboard and KPI design, PSA / CRM data (ConnectWise, Autotask), data-quality and AI-readiness cleanup, client-facing reporting

Technical

REST APIs and SaaS integrations, AWS fundamentals, Python & Django (working knowledge), professional services delivery, technical troubleshooting

Platforms

ConnectWise, BrightGauge / Reports and Dashboards, MSPbots, StrongDM, Forescout — and the MSP tool stack around them

Education

Long Island University Post BA, Criminal Justice · 2012

Entrepreneurship

Founder, Taproot Technology (2026) — PC repair, custom builds, and small-business IT services in Wake County, NC. raquilia.github.io/rick-it-website

Writing

Notes on customer success, reporting, and data

Occasional pieces drawn from a decade of post-sale work — mostly about why the numbers on the dashboard so often disagree with reality. First posts are in the works; these are the topics on deck.

MSP Reporting

Your PSA data is lying to you

Most bad reports aren't a dashboard problem — they're a data problem wearing a dashboard costume. Ticket statuses nobody updates, time entries written for billing instead of truth, agreements that don't match reality. How to find the lies before you automate them.

Dashboards

Dashboards executives actually read

One number per question, a definition somebody owns, and the discipline to delete the other forty widgets. What seven years of building reports for MSP owners taught me about the difference between a dashboard and a screensaver.

Data & AI

AI-ready is a data problem first

Every company wants AI working on its operational data; almost none have data an AI can safely work on. The unglamorous cleanup — deduplication, definitions, validation — that has to happen before the interesting part, and how to sequence it.

Contact

The fastest way to reach Rick Aquilia

Based in Raleigh–Durham, North Carolina. For roles and consulting, email or LinkedIn gets the quickest response; for Taproot Technology service, call or text works too.