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By Eleanor Bennett


3 min read

For the next interview in our series speaking to technology specialists from around the world, we’ve welcomed experienced CTO, Leonard Trigg. Leonard is a member of the Harbourfront executive management team and serves as the firm's Chief Technology Officer.

Joining the industry in 1995 Leonard has a background in enterprise technology, finance and operations. Leonard previously served as the Chief Operating Officer and Director at Vertex One Asset Management Inc. Prior to being appointed COO he supported Vertex for 16 years as a consultant and outsourced Chief Technology Officer.

Tell us about the business you represent? What is the vision?

Harbourfront Wealth Management is a Canadian-owned independent advisory firm servicing growth-oriented advisors and high-net-worth clients. Founded in 2013, the company is headquartered in Vancouver, BC, and has a rapidly growing network of 22 branches across Canada. It is a member of the Harbourfront Group of Companies, which also encompasses a sub-advised Canadian Asset Management firm specializing in alternative investments, and Harbourfront Wealth America, a US registered investment advisor.

What notable IT challenges have you overcome?

  • Migration to hybrid/remote workforce
  • The rapid expansion of the firm
  • Increasing cybersecurity threats
  • Data acquisition/analytics and integrating with legacy banking infrastructure.
  • Moving security analysis more inside of the firm

What are your plans to expand your service?

We are constantly welcoming new advisor teams, expanding our fund offerings and adding to our national footprint.

Being the CTO, what does your day to day responsibilities look like?

  • Supporting the various departments of the firm
  • Refining data connections and deploying, data analytics and reporting projects
  • Analyzing and enhancing cybersecurity and infrastructure reporting and logging
  • Overseeing a large selection of existing vendors while analyzing new vendor solutions

What advice would you give aspiring CTOs and entrepreneurs?

I think a valuable skill is first understanding that technology is a toolset, and it's our job to best figure out how to use those tools to streamline, support and improve the business.

Once you refine the core technology and staff you then must focus on supporting the core business visions and services. This second phase is challenging as you must evaluate developing internal solutions versus partnering with vendors. Vendor management requires you to understand all the players in the space and then how they can strategically integrate with your other internal systems and other external vendors.

One thing I would also like to mention is the mindset of looking for opportunities to improve the business constantly, not just technology. For example, you may be a system engineer aspiring to be a CTO and you are tasked with migrating on-premise file servers to a cloud-based system. This is an opportunity to look at the target team's file structure and to help educate them on how to consolidate, organize and streamline their files. It is also an opportunity to look at their current files and processes and suggest automation and refinement.

How do you think the role of the CTO has evolved in the last five, ten, fifteen years?

As technology has continued to play a larger and more encompassing role in business, a CTO is now expected to fully understand all facets of the business and to support all departments and initiatives. At one time the CTO’s focus was more niche to just infrastructure and basic software, now with all the critical business processes running on in-house or external software, it is the CTO that must help execute the larger vision.

What new challenges are CTOs facing today?

Security and supporting a hybrid work model I would say is the number one challenge, as companies migrated to a hybrid model things must be efficient and secure. In coordination with that, we have seen an ever-expanding cyber security threat, requiring a larger investment in time and resources to protect the organization.

What do you see as the hottest trends within your industry today?

  • Hybrid work and the migration to the cloud (Office 365, Google)
  • Migration to SharePoint from on-premise servers
  • Migration to collaborative tools like Slack and Teams, with live data and systems integration into the chat rooms.
  • Cybersecurity and defending a hybrid workforce in the face of ever-increasing volume and complex threats.

Do your technical teams or do you use log analysis as part of your role? If you do, how do you find this helps day to day operations?

Yes, we analyze usage and access reporting from multiple systems to try and spot anomalies. We also use monitoring software to confirm system availability and unusual usage patterns.

We have also relied on Microsoft’s extended security tools for the last few years to control access, and monitor for issues.

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