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Bobby Ip

New York, NY

With over 25+ years of IT experience, primarily focusing on the financial sector, I have held senior positions in Enterprise Strategy, Financial Management, Program Management, Enterprise Architecture and Engineering, and Production Operations for Investment Banks and Wealth Management firms.

Over the more recent decade, I have primarily worked alongside C-suite executives to provide Strategic Management Consultancy in order to define and implement new operating models, drive operational excellence, build business/technology teams, and enable technology capabilities to meet evolving clients needs.

My latest adventure is all about building and growing talent across the globe with a great team at my side.


Experience

Industry Lead, Financial & Professional Services Organizations

Toptal

I led a sales team comprised of Account Executives and Client Partners. I was responsible for defining client services and solutions to Financial and Professional Services Organizations with a 40+ million annual gross revenue target.

Nov 2023 - July 2024

Chief Business Officer, Americas

IT Consulting Solutions Group

I was responsible for all Business Development, Finance, Operations and Strategy for the ITCS Group's Americas region (US, Canada, Latin America) before ITCS Group regional operations were shut down in Oct 2023 and subsequently acquired by Smart IMS in 2024.

May 2022 - Oct 2022

Senior Director

Synechron (Acquired Citihub Consulting Oct 2020)

Led Cloud Consulting practice for Charlotte Business Unit which covered 3 of the top 5 largest clients by revenue within North America.

Oct 2020 - May 2022

Partner

Citihub Consulting (acquired by Synechron Oct 2020)

Led Business Development and Consulting engagements for our largest banking client within North America.

Aug 2010 - Oct 2020

Senior Windows Architect, Global Windows Engineering

Morgan Stanley - Global Wealth Management

Architecture & engineering lead for Windows technologies with ownership of End User and Retail Branch technologies.

Jul 2006 - Aug 2010

Analyst II, Global Enterprise Access & Desktop Services

Banc of America Securities

Provided technical solutions and support to Debt / Equity Research Line-of-Business.

Mar 2005 - Jul 2006

Systems Engineer, Infrastructure Services

Sony Music Entertainment

Architecture & engineering lead for distributed systems with specialty in automation and migration technologies.

Apr 2002 - Mar 2005

Systems Specialist, Private Banking

J.P. Morgan Chase & Company

Provided Desktop Level 1 and Level 2 operational support.

Jun 1998 - Dec 2001

Career Highlights

Management Strategy

Executives leverage my subject matter expertise and peer intelligence network to assess, define and execute on new Target Operating Models (TOM) to meet an organization's specific long term goals. To accomplish this, I often hold workshops with executive teams to set the short, medium and long term objectives for the organization, define the key performance indicators (KPI) and work with the various teams to build cohesive strategic roadmaps, focused on quick wins and consistent delivery. Often times, I will build / recruit key members, mentor existing leaders and work side-by-side with existing teams to ensure the new strategic direction is codified.

Notable Engagements

Organizational Challenge:  One of the largest multi-national Bank's infrastructure organization delivered new services through large scale programs and aggressively managing delivery teams. The teams were using traditional project management practices, coupled with a waterfall delivery methodology, which led to excessive administrative overhead and extremely long lead times. The LOBs (Line-of-Business) often needed new capabilities quickly to capture market share or meet ever evolving customer needs.

Solution Approach:

  • Execute on 3 key initiatives that tackled agile tooling, agile training and cultural change
  • The organization was already introducing SAFE Agile methodologies to the production application development teams and I needed to implement the same concepts tailored for their infrastructure teams
  • Common modern development tools needed to be adopted (i.e. Jira, Jenkins, Ansible, SonarQube) and augmented to support infrastructure team functional requirements
  • The culture needed to live and breathe an agile mindset through execution

Results:

  • Assisted with hiring and training of internal & external resources growing an infrastructure development team to over 25+ people
  • Implemented SCRUM practices and methodologies (ran sprint planning cycles, daily scrum calls, managed releases and retrospectives)
  • Published product roadmaps and executive presentations to ensure traditional program management and enterprise change control requirements were met
  • Transitioned SCRUM and development leading practices to long term internal staff

Organizational Challenge:  The largest American Bank recognized the need to implement a more comprehensive governance process to manage the risk of an exponentially growing adoption of Software-as-a-Service (SaaS), Infrastructure-as-a-Service (IaaS) and Platform-as-a-Service (PaaS) applications and services.

Solution Approach:

  • Define a new control function with senior stakeholders across IT, Finance, Risk and Compliance teams that would review and approve any new SaaS, IaaS or PaaS application before it's allowed into the Bank
  • Develop required tools and processes to support governance routines
  • Train stakeholders on the new process and support application owners as they leveraged the new control process

Results:

  • Defined the "Global Cloud Governance Forum" charter and secured buy-in from multiple senior stakeholders across multiple IT and non-IT control functions
  • Created required process overview, various training materials, process templates and executive presentations to support new governance routine
  • Built required application tooling and trained identified resources to run this new process routine
  • Managed the review of the first set of applications through the process, which required education to the application owners as well as support for development of materials to be presented to the forum
  • Adjusted the process to create a "fast-track" to accommodate proof-of-concepts (POCs) and "low risk" applications (production / go-live would still require the full process rigor)

Organizational Challenge:  A large multi-national Bank leveraged a Managed Services Provider (MSP) to perform network change, network monitoring and general operational support for one of the largest private networks in the world. The Bank had kept core architecture, engineering and security functions in house and wanted a long term path to avoid increasing MSP renewal costs.

Solution Approach:

  • Define a Target Operating Model (TOM) with new strategic resource hubs and identified new tooling required to support new functional requirements (with Agile practice requirements incorporated)
  • Determine insource strategy by identifying MSP provided functions that could be brought in-house and create transition plans for those functions
  • Define new functional roles and begin hiring resources in strategic locations
  • Execute RFPs (Request For Proposal) for functions that were better maintained outsourced

Results:

  • Built out new Agile functions with specific focused on change and release management teams to limit any organizational impact, as there were 1000's of changes implemented monthly
  • Existing MSP had a reduced scope negotiated, which resulted in multi-million dollar savings over the next renewal period
  • Onboarded additional vendors, where it made sense, to meet organizational financial goals, while reducing risk of delivery (hiring in a competitive market)

Technology Enablement

As a technologist and active practitioner, I often act as a Subject Matter Expert and help executives, architecture and engineering teams assess their current state, define their product roadmaps and execute on their roadmaps (hands-on). The strategy and solutions I champion provide the balance of security, compliance, risk and delivery capabilities aligned to intiative spends. When needed, I act as an external third party to manage, review, negotiate and reward RFPs to external vendor contracts.

Notable Engagements

Organizational Challenge:  As part of Digital Transformation, a large American Bank wanted to adopt Microsoft Azure as it's first Public Cloud Service Provider (CSP). Blazing a new trail within a large regulated organization required a methodical approach to ensure the proper risk, compliance and security requirements are in place as part of the service launch.

Solution Approach:

  • Perform "controlled experiments" to demonstrate cloud security and the Bank's required compliance controls are met
  • Connect CSP network to the Bank's network to facilitate CSP management and application integration activities
  • Develop required guardrails to ensure a consistent and managed adoption of CSP services (i.e. write required Infrastructure-as-Code automation)

Results:

  • Established policies and controls on over 60 different service capabilities required to launch any service (e.g. access management, logging, network security, etc.)
  • Established Microsoft Azure ExpressRoute between Bank and provider
  • Designed landing zones and provided access to these areas via Infrastructure-as-Code (IaC) APIs so application teams can self-provision
  • Integrated the Bank's SEIM (Security Event and Incident Management) products to leverage CSP native technologies so that existing security processes and practices were maintained (i.e. security event triggers and responses)

Organizational Challenge:  A large multi-national Bank had years of infrastructure automation created to develop OS images, configure them with scripts and deploy them on their internal private cloud. However, application teams would often need to create and layer on their specific business requirements once the infrastructure teams have provisioned their virtual servers and turned them over for appliction configuration. As part of the Cloud first strategy, the Bank required support for multiple cloud service providers and creating an API to abstract the IaaS components from the application stack in a programmatic way was most desired.

Solution Approach:

  • Develop a thin API abstraction layer so that application teams do not need to build to specific CSP APIs
  • Ensure all the standards, required security and compliance requirements are enforced when leveraging Public Cloud services
  • Implemented a new Terraform based solution to support Infrastructure-as-Code (IaC) automation across multiple cloud providers

Results:

  • In less than 3 months, I helped design and deploy a lightweight Java based API that leveraged Terraform underneath to build landing zones and other required infrastructure based on application team requirements
  • The new API was extended to support calls for the Bank's internal container platform as well as Microsoft Azure Managed Kubernetes Service (AKS) over the course of it's evolution
  • As part of financial management controls, we wrote parts of "Netflix's Simian Army" to work against Azure
  • APIs were integrated with the Bank's IAM platforms and controls to create a consistent experience across multiple cloud providers

Organizational Challenge:  A large financial client required a new secure way to manage identities across internal application platforms and across multiple Cloud Service Providers (i.e. Azure, AWS, GCP). The new platform needed to be highly available with no downtime, as it would be critical to all application workflows, since it would store the required credentials in a secure manner.

Solution Approach:

  • Document functional requirements and identify required systems integration points within the Bank's ecosystem
  • After requirements gathering, HashiCorp Vault was chosen because of it's compatibility across multiple Public Cloud Service Providers and integration with common Hardware Security Modules (HSMs)
  • Deploy a highly fault tolerant system with multiple redundancies

Results:

  • Designed the platform and shepherded the new application and service through the Bank's rigorous security review processes
  • Deployed required infrastructure across multiple data centers and regions to support the high availability requirement
  • Determined and built automation to support all failure scenarios (e.g. network isolation, data corruption, general fault)
  • Built automation routines to support general operations and management (e.g. platform upgrades & releases, disaster recovery & failover, provisioning & deprovisioning of identities, etc.)

Organizational Challenge:  A financial client had a large private cloud infrastructure that required hundreds of hours for operations teams to build and configure servers each time they needed to expand. They needed to rationalize activities and develop a cohesive roadmap that would bring forward long term automation goals so that time to market for cloud expansion would be reduced to hours vs. weeks.

Solution Approach:

  • Build a cohesive modern architecture that can be used as a guide for product capabilities decisions
  • Adjust existing Product Roadmap to align to strategic organizational strategy
  • Implement a consistent intake, review and roadmap update process aligned to planning routines

Results:

  • Published an architectural diagram that could be used with various stakeholders to drive requirements discussions
  • Reviewed existing roadmap and adjusted priorities to align to new architectural principles (removed items that did not align to long term strategy)
  • Built customer engagement routines so that planning can be done in a proactive vs. reactive basis

Business Development

I bring to the table a unique perspective to building business, as I having spent my early career working for large enterprises and owning my own book of business as a Partner at Citihub Consulting. I believe that the best approach comes from building a strong partnership with key stakeholders and enabling them to be successful. The approach that has never failed me lies in finding mutual value and establishing trust as foundational ingredients. In my opinion, understanding the needs of your stakeholders and being agile are the best recipe to success.

Results

  • Built long term relationship with key technology executives as a trusted adviser (oldest relationship over 2 decades)
  • Brought on new client logos and expanded revenue in many key accounts
  • Defined new technical capabilities for consluting practices and built execution teams for delivery of those capabilities
  • Hosted many client workshops and roundtables as part of the business development activities
  • Build new sales teams and recruitment teams as part of growing new regions

  • Established key partnerships for strategic talent management (sourcing and training) and delivery
  • Built 3rd party vendor relationships with key sales and account teams to drive company and client requirements (e.g. Microsoft, AWS, Google)
  • Drive thought leadership through active participation in many industry forums (e.g. FINOS, EDMC, ONUG, etc.)

  • Led many responses to large multi-million dollar RFPs from the largest financial institutions
  • Created executive presentations and engaged stakeholders on various technical topics
  • Often identify opportunities outside of the RFx scope that have generated additional revenue

Transformation Management

I have worked in all facets of delivery of large scale transformation efforts from inception to execution and evolution. I specialize in building effective teams and aligning the delivery organizations to meet the demands of the business. Ultimately, I believe to manage large scale transformation efforts (multi-year in many cases), requires a strong command-and-control structure married with a realistic technology roadmap that enables consistent delivery.

Notable Engagements
  • End User Endpoint Migrations & Upgrades (Desktops, Laptops, Mobile Devices)
  • Mobile Device Management Platform Engineering & Rollout
  • Software Development Tools Rollout & Adoption
  • Private Cloud Automation Development & Implementation
  • Container Platform Global Expansion
  • Secrets Management Platform Engineering & Rollout (HashiCorp Vault)
  • Network Virtualization & Automation

Financial Management + Vendor Management

I often work with very closely with C-Suite Executives and technology teams in their financial planning and operational excellence programs bringing an objective 3rd party perspective. As I operate across multiple peer organizations, I can provide a unique perspective that can be invaluable during large vendor contract negotiation and often asked to lead end-to-end RFP as an objective stakeholder. The network of technologists I've built over the last 25+ years has proven invaluable in the decision making process.

Notable Engagements

Organizational Challenge:  A large enterprise was looking to reduce their overall budget for their Network Organization by 20-30% over the forward looking 3 years.

Solution Approach:

  • Establish an continuous process to evaluate saves opportunities
  • Identify required activities (e.g. contractual changes, technology policies, automation, license optimization, etc.) to reach financial goal over 3 years
  • Ensure all technology teams and roadmaps incorporate identified activities

Results:

  • Built inventory of spend that could be categorized into real-dollar savings
  • Established a new control gate as part of sourcing and procurement processes to ensure technology change costs align to long term financial goals
  • Mobilized self-funded initiatives to target saves opportunities

Organizational Challenge:  A large Bank had many technology vendors delivering similar capabilities and wanted to complexity in the environment so application development can be more nimble and deliver quicker.

Solution Approach:

  • Define strategic services and the technologies required to deliver those services
  • Review existing vendor lists to find opportunities for volume reduction
  • Integrate vendor costs into the Bank's Total Cost of Ownership (TCO) tool (i.e. Apptio)

Results:

  • Built an inventory of services and vendor products
  • Enriched inventory with data on internal integration touchpoints and criticality to the organization
  • Identified opportunities to reduce vendor spend or renegotiate contracts if vendor spend had increased due to scale of usage
  • Ensure all services and products are mapped into Apptio and new governance process exists to maintain the accuracy of the data within Apptio

Organizational Challenge:  A large American Bank wanted to adopt a Public Cloud Service Provider as part of it's Digital Transformation efforts.

Solution Approach:

  • Define requirements and identify applications as early adopters of Public Cloud
  • Buit business case and ensure funding is aligned to support the multi-year effort
  • Onboard new Cloud Service Provider vendor

Results:

  • New Public Cloud Service was defined with controls defined with security teams against over 60+ integration points
  • Enabled network connectivity between the Public Cloud Service Provider and the Bank
  • Performed "controlled experiments" to ensure controls function as desired
  • Built APIs to support automation required to setup "landing zones" for application teams
  • Onboarded new modern tools to manage Public Cloud infrastructure programatically (ensures all controls are followed consistently)


Skills & Education

Cloud Service Providers, Programming Languages & Tools

Frameworks and Methodologies

  • Information Technology Infrastructure Library (ITIL) v3
  • Scaled Agile Framework (SAFe) v4
  • Capability Maturity Model Integration (CMMI) Framework and Assessments
  • Threat Modeling and S.T.R.I.D.E. Methodologies
  • Site Reliability Engineering (SRE) and DevSecOps - Principles and real world execution
  • Objectives and Key Results (OKR) Principles and Execution Methodologies
 

New York University - Leonard N. Stern School of Business

Bachelor of Arts and Science
Major(s): Finance and Information Systems
Sep 1998 - Dec 2001
 

New Hyde Park Memorial High School

Blue Ribbon School Since 1992
Sep 1992 - Jun 1998

Interests

During the warmer months, I enjoy most of my time being outdoors on a golf course, on a tennis court, hiking and fishing. In the winter, I am an avid skier and novice snowboarder and chase the best mountains in the world.

When I have free time at home, I cook for family and friends with an obsession in making classic smoked barbeque. With any time left, I spend on keeping up with the latest technology trends through meet-ups, research and online learning platforms such as A Cloud Guru.