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jaipinder singhJS
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jaipinder singh

@jaipindersingh

I lead enterprise digital transformations, cloud migrations, SaaS integrations, and complex platform cutovers.

Canada
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What I'm looking for

I'm open to connecting with technology leaders and enterprise program executives focused on digital transformation, cloud modernization, enterprise platforms, and complex cross-functional delivery.

At BMO, I lead five concurrent enterprise digital transformation programs across a $60M+ portfolio, including the AIR MILES-to-BMO Blue Rewards migration delivered with zero disruption to active members.

I've governed multi-partner platform integrations at Air Canada Aeroplan for TD Bank, Starbucks, and Uber, bridging SAFe Agile and Waterfall delivery across six partner organizations. I also coached Program Managers and Scrum Masters while improving backlog refinement, sprint predictability, and blocker resolution.

At Shepherds of Good Hope, I led Microsoft Azure cloud strategy and migrated 50,000+ Blackbaud donor records with 100% data integrity and zero fundraising downtime under NIST 800-53 controls.

I bring hands-on technical roots in software development, SQL reporting, computer networking, and technical support to program governance, risk management, compliance, vendor coordination, and executive decision-making.

Experience

Work history, roles, and key accomplishments

BMO logoBM
Current

Senior Project Manager — Technology PMO

Feb 2024 - Present (2 years 7 months)

Spearhead end-to-end PMO delivery for 5 concurrent enterprise digital transformation programs ($60M+ combined portfolio), aligning technical workstreams with PDLC frameworks, regulatory governance, and business objectives.
Directed the flagship AIR MILES-to-BMO Blue Rewards loyalty platform migration (Go-Live July 2, 2025), leading data mapping, system configurations, multi-partner integrations, a

Air Canada logoAC

Senior Project Manager — Aeroplan Partner Delivery

Dec 2021 - Jan 2024 (2 years 1 month)

Governed multi-organization integration programs—including TD Bank co-branded credit cards, Starbucks, and Uber platform partnerships—ensuring strict alignment with PCI-DSS and PIPEDA standards.
Established hybrid delivery guidelines bridging Air Canada's SAFe Agile framework with external partners' Waterfall methodologies to ensure seamless cross-organizational coordination.
Facilitated PI Pl

Shepherds of Good Hope logoSH

Program Manager & Agile Delivery Lead

Mar 2015 - Dec 2021 (6 years 9 months)

Directed enterprise Microsoft Azure cloud strategy and migration program, managing solution validation, security assessments, cutover execution, and post-migration hypercare.
Led the Blackbaud donor database migration (50,000+ core records) to cloud infrastructure, authoring data mapping specifications and validating UAT with 100% data integrity and zero fundraising downtime.
Ensured all progr

Rogers Communications logoRC

Project Manager — Agile Delivery

May 2013 - Feb 2015 (1 year 9 months)

Led cross-functional marketing and IT delivery teams, managing daily sprint ceremonies, backlog prioritization, and release predictability using Jira.

Seneca College of Applied Arts and Technology logoST

Graduated in Computer Networking and Technical Support

Jan 2011 - Dec 2012 (1 year 11 months)

Developed skills as a technical specialist in any computer support, local area network administration, and Internet management environment.

NAHAR GROUP OF COMPANIES logoNC

Software Developer

Nov 2006 - Jul 2010 (3 years 8 months)

Designed, coded, tested, and aggregated results from SQL queries to provide information to clients
Completed hands-on configuration and custom development of BI reports, using advanced queries to achieve reporting requirements, within performance constraints
Communicated technical information, both written and verbal, effectively to clients of varying technical experience
Investigated complex tech

Education

Degrees, certifications, and relevant coursework

SP

Seneca Polytechnic

Diploma, Computer Networking and Technical Support

2010 - 2012

PU

Punjab Technical University

B-TECH, Computer science and engineering

2001 - 2005

Punjab Technical University logoPU

Punjab Technical University

Bachelor of Technology, Computer Science and Engineering

2001 - 2005

Pursued a Bachelor of Technology in Computer Science and Engineering from 2001 to 2005.

Tech stack

Software and tools used professionally

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