PLAYER SELECT
ABOUT ME
Hey, I'm Ian — but most people call me Cub. I build things that are actually fun to use, coach people who want to grow, and generally try to make work feel less like work.
When I'm not in builder mode, you'll find me on a rugby pitch with North Shore RFC, getting choked out at Brazilian Jiu-Jitsu, or convincing myself the new song I'm writing on guitar is actually good. (The jury is still out. The critics are biased.)
I run on strong coffee, bad puns, and the deep satisfaction of watching something click for someone. I live on the North Shore with my wife Allanna, who keeps me from taking myself too seriously, and our two cats Beef and Pedro, who have not yet approved a single project I've shipped.
No cheat codes needed — just say hi.
WORK HISTORY
Financial Consultant
Fidelity Investments · Merrimack, NH · Feb 2025 – Present
- Assisted clients with 401(k) inquiries — balances, withdrawals, loans, maintenance
- Built rapport through empathetic listening and communication on every call
- Navigated proprietary systems to resolve customer issues efficiently
- Ranked top percentile in accuracy, efficiency, and customer satisfaction KPIs
Manager of Sales & Technical Enablement
SimpliSafe · Boston, MA · May 2022 – May 2023
- Built L&D processes from scratch: style guides, editorial guides, review processes
- PM'd full LMS and KM overhaul — audits, UX optimization, change management
- Created data-led development plans for 1,500+ field agents, supervisors, and leaders
- Developed Leadership Enablement Program for new and existing leaders
- Ran tri-weekly blind QA calls across cross-functional teams to drive performance
Senior Product Expert
Klaviyo · Boston, MA · Oct 2019 – Apr 2022
- Designed onboarding with 30/60/90 and 6-month checkpoints for support agents
- Delivered top-percentile CSAT and first-touch close rates consistently under SLA
- Coached agents on complex technical issues and customer interaction
- Founded 'Ticket Time' — follow-the-sun open office hours for 24/7 coverage
- Served on ERGs dedicated to equitable and welcoming workplaces
Technical Trainer
MBTA · Boston, MA · May 2018 – Oct 2019
- Designed curriculum for software implementation training alongside SMEs
- Authored role-specific technical manuals and reviewed all internal content
- Led team to highest pass rate, lowest retake rate, and highest satisfaction scores
Technical Support Supervisor
LogMeIn, Inc. · Boston, MA · 2015 – 2016
- Supervised 20-person tier II/III team across technical, sales, and fraud support
- Built an entirely new support model — restaffed, retrained, elevated standards
- Developed onboarding from scratch and expanded self-service knowledge base
- Improved overall performance metrics by 20%, reduced churn, raised CSAT
Professional Sabbatical — CX & Operations
Various Roles · North Shore, MA · Jun 2023 – Feb 2025
- Directed ops and staff training at Newburyport Brewery and The Modern Butcher
- Oversaw customer service, membership relations, and metrics at Choice Fitness and Lowe's
- Reinforced operational consistency through hands-on leadership and coaching
SKILLS & APPLICATIONS
📊 DATA, PROCESS & OPERATIONS
Qualitative & quantitative analysis
QA programs and feedback loops
Process documentation & optimization
Metrics, reporting & impact measurement
Cross-functional project management
🎓 LEARNING, ENABLEMENT & COACHING
Learning program design (adult methodology)
Coaching frameworks & manager development
Knowledge management & content strategy
Curriculum design, facilitation & TTT
Change management & rollout planning
🔧 PLATFORMS, TOOLS & TECH
LMS administration & optimization
Knowledge bases & internal documentation
CRM and ticketing systems
Shopify & Klaviyo ecosystems
Lessonly, Zendesk, Salesforce & more
Content authoring & learning tech
🤖 AI & EMERGING TECH
Generative AI tools & applications
Prompt design & workflow integration
AI risk management & responsible use
Human-in-the-loop system design
AI-augmented L&D and enablement
EDUCATION
M.S. · Organizational Leadership
Technical Project Management
Technical Project Management
Northeastern University
Leadership strategy, organizational behavior, and driving change across complex environments. Emphasized data-informed decision making, team development, and leading through ambiguity.
B.S. · Business Management
Human Resources Management
Human Resources Management
UMass Dartmouth
Foundation in business operations, management principles, and organizational strategy, with exposure to finance, marketing, and process improvement.
CERTIFICATIONS
Google Cloud — Generative AI Leader
Foundational generative AI concepts, model capabilities, prompt design, and enterprise applications. Responsible AI use, human-in-the-loop systems, and workflow integration.
NIST AI Risk Management Framework
Identifying, assessing, and mitigating risks in AI systems. Emphasis on governance, transparency, and responsible deployment aligned to industry standards.
Generative AI Certification — Udemy
Practical applications of generative AI across business use cases, including content generation, automation, and workflow optimization.
ATD Change Management Certification
Leading organizational change initiatives, stakeholder alignment, communication strategy, and driving adoption of new systems and processes.
ATD eLearning Certification
Designing effective digital learning experiences, instructional design principles, learner engagement, and building scalable training programs.
General Assembly Business Analytics
Applied analytics skills including data interpretation, visualization, and translating business questions into actionable insights.