Sean Pollock

VP Engineering at Fig. Fintech systems, scaled engineering teams.

I'm an engineering leader in Toronto with a decade in Canadian fintech. At Fig I run engineering, data, infrastructure, security, and IT. Before that I spent six years at Wealthsimple, most recently leading the team behind Wealthsimple Cash.

Advisory work →LinkedIn ↗

About

I lead engineering and technology at Fig, a Canadian consumer lending fintech. Over the past three years I've built the organization from the ground up — the in-house team, the loan origination system, the data platform, the security program. The systems process around 50,000 applications a week and run one of Canada's first fully automated personal loan experiences, from underwriting through funding.

Before Fig, I spent six years at Wealthsimple. I started as one of two engineers on the US product, moved into management, and eventually led Wealthsimple Cash — four teams, 25 engineers, over a billion dollars in client balances, and a finance category #1 on the iOS App Store. Along the way I founded or led the International, US Back-office, Advisors, CX Engineering, Book of Record, and STAR teams.

My approach is product-driven and pragmatic. Ship quickly, validate with real usage, and invest in robust systems where scale actually demands it. I care about simplicity, strong developer experience, and architectures that let teams move fast without accruing unnecessary complexity. I'm most useful in environments that need both hands-on technical leadership and organizational scaling.

Fractional CTO & Advisory

I take on a small number of advisory engagements alongside my role at Fig. If you're a founder or CEO who needs senior technical judgment — for a specific decision, a recurring seat at the table, or a short intensive project — these are the shapes of engagement I offer.

Fractional CTO / technical leadership

Retainer engagements with early-stage teams that need senior technical judgment in the room — architecture decisions, roadmap pressure-testing, team structure, hiring. Typically 1 day a week.

Engineering team building

Hiring plans, role scoping, interview design, and coaching for first-time engineering managers. Drawing on the team I built at Fig and the four teams I grew at Wealthsimple.

Technical due diligence

Pre-acquisition or pre-investment diligence on software companies: architecture, team, security posture, delivery practices, technical debt, and integration risk. Written reports with clear risks ranked.

Architecture and MVP reviews

Focused reviews of an existing system or a planned MVP. Covers scalability, data model, build-vs-buy calls, and the handful of decisions most likely to cause pain later. Delivered as a written assessment with prioritized recommendations.

Vendor and tooling selection

Structured evaluation of critical vendors — loan origination, payments, KYC/AML, data warehouses, observability. I've built the in-house alternatives to several of these and know where vendors are worth it and where they aren't.

Process and delivery coaching

Working with engineering leaders on the operating rhythm: planning, standups, on-call, deployment cadence, incident response, career development. Pragmatic, not dogmatic about any particular framework.

Engagement models

Retainer

Ongoing part-time engagement, typically 1 day per week.

Project

Fixed scope and fixed fee, 2–6 week engagements (diligence, reviews).

Advisory

A few hours a month, async-heavy, for founders who want a second opinion on call.

Good fit

— Seed to Series B software companies, especially in fintech or adjacent regulated spaces

— Canadian context (though I work with companies based anywhere)

— Founders who want a sounding board, not a yes-person

Not a fit

— Anything needing full-time availability or daytime on-call

— Pure staff-aug coding work — I don't ship features, I help you ship them

— Situations where someone needs me to tell them their existing plan is correct

Reach out on LinkedIn →

Experience

Built the engineering and technology organization from the ground up. Replaced an external dev shop with an in-house team, reducing cost by roughly $2M a year, cutting cycle time from 7+ days to 24 hours, and increasing deployment frequency 8×.
Architected and built a custom loan origination system and client portal, eliminating key vendor dependencies, improving underwriting latency from 20s to 1s, and unlocking ~$3M/year in savings.
Led a company-wide data transformation on Snowflake, dbt, and Metabase — real-time visibility and self-serve analytics across the business.
Established security and IT foundations, including near-full automation of MDM and SSO/SAML, and achieved SOC 2 Type II in partnership with a vCISO.

Led the engineering organization for Wealthsimple Cash. Built the team to 4 squads and 25 engineers across mobile, web, and backend.
Shipped integrations with bank partners — direct deposit, PAD, bill pay, e-transfer, cheque clearing — and a spend card program.
Went viral, hit #1 in iOS finance multiple times, signed up 100k+ clients, and safekept over $1B in client balances.

Founded or led International (US/UK), US Back-office, Wealthsimple for Advisors, CX Engineering, Book of Record, and STAR.

One of two engineers on the US product; merged into International Platform.

Led the dev team and owned ML. Built engineering culture from scratch — agile, CI/CD, interview process, learning objectives.
Architected a distributed, Kubernetes-based crawler and OCR pipeline (Terraform, Docker, Kafka, HBase, Scrapy, Tesseract, scikit-learn) that scaled to tens of millions of documents.
Built an SVM classifier tagging documents across 15 categories at >95% accuracy.

Industry-first NLP algorithm to extract positional information from unstructured aircraft maintenance text, which won the company a marquee customer.
Prototyped an ML classification system that expanded the addressable market.
Took the backlog from 400 to 100 tickets in the first six months.

How I think

Build the smallest system that could work, then invest where scale actually demands it.

Most technical debt comes from premature sophistication, not from shipping fast. I lean toward monoliths over microservices, boring databases over novel ones, and managed services over self-hosted — until the business has a specific reason to choose otherwise. The job is to keep the option to scale, not to pre-build for it.

Vendors are a tool, not a strategy.

Buying is right when the problem isn't your differentiator and the vendor is mature. Building is right when the vendor's roadmap doesn't match yours, or when the integration surface is larger than the thing itself. I've replaced vendors with in-house systems that paid back in a year, and I've killed build projects that should have been a SaaS purchase. Getting this call right is one of the highest-leverage things a technical leader does.

AI spend needs the same rigor as any other infrastructure investment.

Everyone's adopted AI tooling. Fewer companies can tell you what they're getting for it. The interesting work in 2026 is figuring out where AI genuinely changes the math — and where it's a line item that feels productive. That means picking the high-leverage places to adopt aggressively, carving out space for teams to experiment without it becoming a free-for-all, and measuring outcomes in something more meaningful than "developers say they like it." The companies that treat AI adoption as an engineering discipline pull ahead of the ones that treat it as a vibe.

Technical decisions are business decisions.

The best architecture choices are the ones that match where the business is trying to go — not the ones that are technically elegant in isolation. I spend as much time with finance, operations, and product as I do with engineers, because the right answer to "should we build this?" usually isn't a technical question.

FAQ

What is a fractional CTO?

A fractional CTO is a senior engineering executive who works with a company part-time, usually one to two days a week on an ongoing basis. They're embedded in the leadership team but don't replace a full-time CTO — they're used when a company needs senior technical judgment but isn't at the stage to hire one full-time, or when the existing CTO needs a peer to think with.

What stage of company do you work with?

Mostly seed through Series B, though I'll take earlier-stage conversations if the problem is interesting. I'm most useful to companies that have a working product and need to scale the engineering organization, or are about to raise and need to sharpen their technical story.

Are you available full-time?

No. I run engineering at Fig and take on a small number of advisory engagements alongside that role. Typical commitments are four to eight hours a week, or fixed-scope projects delivered in two to six weeks.

Do you work with companies outside Canada?

Yes. I'm based in Toronto, but advisory work is almost entirely remote. I have the most pattern-matching for Canadian fintech because that's where I've operated, but the engineering leadership work travels.

Do you write code in engagements?

Rarely. My job is to help teams make better decisions and ship faster — not to ship features myself. Occasional exceptions for diligence or prototyping, but if you need someone to write production code, I'm not the right hire.

How do I get in touch?

The fastest way is a message on LinkedIn. I try to respond within a few business days. Include a sentence or two about what you're working on and what kind of help you're looking for.