Product executive · SaaS, platforms, payments and applied AI

I lead product through major change.

Over more than 20 years, I’ve led product from a 12-person computer-vision startup to portfolio leadership at a late-stage SaaS company. Along the way, I’ve launched a new kind of image search, rebuilt and migrated a core platform, built Product from scratch, and led global retail payments across software, hardware and operations.

See my experience How I lead

Melina Stathopoulos wearing red glasses and a teal blouse — Melina StathopoulosToronto

The work I do best

Several parts of the company are tied up in the same problem.

The problem may show up as an overloaded roadmap or a launch that keeps slipping. I want to know what is holding it up. The cause could be the platform, a commercial commitment or work split across teams that cannot decide for one another.

I start by learning how the company makes money and where customers are getting stuck. I ask the people who live with the technical constraints to explain them directly. The answer may change the roadmap or which team owns the work. Sometimes it means ending the work altogether.

The situations I know well

01
The company has several products now. Customers need them to work together.
02
A core product or platform needs to be rebuilt or replaced while customers and the business still depend on it.
03
Growth now depends on serving larger customers or entering new countries. That changes what the product has to do and what the company has to support.
04
Major customer commitments, near-term revenue opportunities and necessary platform work are competing for the same teams.
05
The Product organization no longer fits the work it is being asked to do.

Experience

What I was responsible for, in practice.

Clio

Senior Director, Product

2024–2025

Clio: Helping customers use several Clio products together.

At Clio, I initially led Mid-Market, Core Product, Product-Led Growth and International. I started weeks after its Series F; five months later, I temporarily led the broader product portfolio and reported to the CEO.

I worked with Clio’s VP of Design on longer-range product strategy and organization design. One important problem was how Clio’s products could work together instead of feeling separate. Across Core Product and Product-Led Growth, my teams built the first multi-product onboarding pilots and features designed to work across products.

When I took on the broader portfolio, I set clear expectations for what teams needed to have ready for each planning cycle and how we would review progress. My teams and I kept go-to-market leaders up to date as plans changed and made it clear when we needed a decision.

My International teams also brought Clio Draft to Australia and other APAC markets (opens in a new tab).

Shopify

Senior Product Lead

2020–2023

Shopify: Bringing integrated retail payments and hardware to new markets.

At Shopify, I initially led Retail Payments and Checkout. I led product strategy and market sequencing as we rebuilt Shopify’s platform for in-person payments on Stripe Terminal. Our teams worked closely with Stripe as both companies developed their retail products. We helped shape Terminal while building the capabilities Shopify needed to bring integrated payments and hardware to new markets. The work required country-specific certification, careful rollout and keeping payments reliable as the underlying platform changed.

My teams launched integrated retail payments in Australia, New Zealand and Germany, relaunched them in the UK and Ireland, and expanded the Canadian offering with full Interac chip-and-PIN support. By Q3 2021, Shopify reported that Shopify Payments penetration in POS had risen above its overall Shopify Payments penetration. I additionally took on Hardware and global hardware operations.

Shopify’s 2021 international retail rollout My Interac conversation on the Canadian work Shopify’s Q3 2021 payments-penetration statement

Loopio

Senior Director, Product Management (Head of Product)

2018–2020

Loopio: Building the Product function from scratch.

I was Loopio’s first Product hire after Series A and built its first five-person PM team. The company was growing quickly, and people needed to see why one piece of work had displaced another. When we discussed the roadmap with the founders and teams across the company, we looked at both what customers needed and what would help the business grow.

I worked with Design and Engineering to improve onboarding so new customers could start using Loopio more easily. We added integrations with Salesforce, Slack and Microsoft Teams so customers could use Loopio alongside tools they already relied on.

FreshBooks

Product Manager to Senior Director

2011–2017

FreshBooks: Rebuilding the product, then bringing customers with us.

At FreshBooks, I was the second Product Manager and helped define and win support for a ground-up rebuild. I led discovery and the first customer-facing version, which launched to real customers under the BillSpring name and developed into the new FreshBooks.

I later created the customer-migration function and kept the first cohorts deliberately small. We watched where billing, data, existing pricing and familiar ways of working made the change confusing or risky, then improved the experience before opening it to more customers.

Old and new systems ran side by side for a long time. It was messy, but it allowed us to move customers in small groups and pause when we found a problem. I later led product for Transactions and Payments.

Forbes on the FreshBooks rebuild The customer migration experience was shortlisted in the Disrupting category of the 2018 Interaction Awards

TinEye

First Product Manager

2004–2010

TinEye: Building a new kind of image search.

I got into Product almost by accident. I was studying film and joined a tiny computer-vision company part-time to help pay for my thesis film. The supposed temporary job turned into a career. TinEye began with an unusual idea: search the web using an image instead of words. I worked on the earliest product decisions and helped bring it to market.

Once it launched, I read every piece of customer feedback we received. At that stage, that was our research system. It showed us what people thought the product was for, what they were actually trying to do with it and where they got stuck.

TinEye was the first product I helped create from nothing. It is also where I learned to stay very close to the people using what we built.

Public sources

The parts I can point to directly.

Company plans and internal decisions stay with the companies. These are the sources I can share.

How I lead

I give people the context behind a decision.

I give people as much context as I can. If a customer commitment or technical constraint is shaping the work, the person leading it should know. I also tell them when the pressure is commercial or the executive team disagrees.

I stay close enough to the work to ask useful questions and help make the reasoning stronger. Coaching happens in the actual work. Directors should own the decisions within their scope. If every difficult call comes back to me, I have not given them enough room.

Product, Design and Engineering should be involved while the problem is still taking shape. The work is better when each function gets to help shape the answer.

When it works, people know what they own, why it matters and when to ask for help.

I like people who tell me what is actually happening, especially when it is inconvenient.

“Bring bad news early, while we still have choices.”

Evidence

I look at the data, and I figure out the “why, though” before I decide what to do.

Communication

I put the request at the top. If I need a decision, I say which one and include the evidence needed to make it. I do not send someone a pile of links and ask them to reconstruct my argument.

Decisions

I use reviews to get to a decision or make the work better. If people leave with the same confusion they brought in, I change the review. I have no interest in polishing a deck for its own sake.

Developing leaders

I give leaders work with real scope and stay close enough to help when it gets difficult, without taking the decision away.

A little more about me

What I’m like to work with.

I like complicated systems and plain language. I enjoy the tragedy and joy of getting to the heart of a juicy problem.

I ask a lot of questions. I say what I think. I am perfectly happy to be proven wrong, and I like working with people who are equally direct.

The work

Where I’m most useful.

I’m most useful when I have enough of the system in view to make informed decisions and then follow them through. That usually spans product direction, UX and customer experience, pricing and packaging, and data and experimentation. I’m also comfortable stepping into adjacent systems like billing or infrastructure, or into org design when structure (or a lack of it) is getting in the way of good decisions. I care less about where the boundary of “Product” sits and more about whether I have the context and backing to improve the outcome.

I’m based in Toronto. Depending on the situation, I may be leading this work inside a company, advising a leadership team through a specific decision, or teaching from what I’ve learned.

If you’re working through one of these problems, I’m always interested in comparing notes.

Contact

Get in touch

If something here made you think we should talk, I would be glad to hear from you. Use the short form below, or write directly if you prefer.

melina.stathopoulos@gmail.com