In this exclusive CanadianSME Small Business Magazine interview, Jenna Poste, Vice President of Product at Wagepoint, shares how nearly two decades in B2B SaaS across fintech, security, and digital wellbeing shape her human‑centred approach to building simple, trustworthy payroll for Canadian small businesses. She explains why tools like integrated Timesheets and the My Wagepoint mobile app are key steps toward a unified time‑and‑pay platform, how automation and AI can quietly reduce compliance anxiety without adding complexity, and what Wagepoint’s refreshed brand and product roadmap mean for time‑pressed owners who want payroll, people, and time management that’s built for Canada—and built to just work.
You’ve spent nearly 20 years in B2B SaaS across sectors like fintech and digital wellbeing—how does that background shape your approach as VP of Product at Wagepoint, especially when you’re building tools for time‑pressed small business owners?
The common thread across everything I’ve worked on is that the stakes are always human. Whether you’re building for security, wellbeing, or financial operations, there’s a real person on the other end making decisions that affect their livelihood, their team, their family. That’s never felt abstract to me, and it shapes how I approach product from day one.
I’ve also spent a lot of time in spaces where trust is the product. If users don’t trust what the software is telling them, it doesn’t matter how well-designed it is. That’s very true in payroll. A small business owner running a pay run needs to know it’s right, with no room for ambiguity. Building that confidence into the experience, not just the underlying calculations, is something I think about constantly.
What drew me to Wagepoint is that the culture here already understood that. There’s a genuine commitment to building for the humans behind the business. My job is to keep that instinct sharp as the platform grows.
Wagepoint recently introduced the My Wagepoint mobile app and Timesheets—can you briefly explain what each of these products does and how they fit into your vision of a unified payroll, time, and people management platform for SMBs?
Both products came out of the same question: how do we make it easier for employee time to get into payroll?
Timesheets are built directly into Wagepoint 2.0 and included for all customers at no extra cost. Employees and contractors can submit time entries for approval, and once approved, those hours flow straight into payroll without having to chase anyone down. It also automatically calculates overtime based on the provincial and territorial rules that apply to each employee, which is a meaningful lift for any Canadian business with hourly workers.
My Wagepoint is our new mobile app, available on the App Store and Google Play. It gives employees and contractors on-the-go access to their time entries, paystubs, and profile information from wherever they are. For small business owners managing teams that aren’t desk-based, that kind of access changes what’s practically possible.
Together, they’re the first steps toward our broader vision: one platform where time, pay, and people are all connected. We’re building toward a future where a business owner doesn’t need to toggle between separate tools. Everything in one place, built for Canada, and designed to scale with them.
Small business owners often juggle payroll on top of everything else they do—based on what you’re seeing, what do they need most from a payroll provider today, and how do mobile‑first workflows change what’s possible for them and their teams?
Honestly, trust is what comes up most. Small business owners need to know their payroll is going to be accurate, compliant, and not going to consume hours of their week. It should be back of mind, something they trust is happening correctly, rather than something they’re anxious about every pay period.
What we’re seeing increasingly is that payroll doesn’t happen in a single place anymore. Teams are distributed, employees are on-site or in the field, and hybrid schedules are the norm. When the only way to interact with payroll information is through a browser on a laptop, it creates friction for everyone involved, especially employees trying to submit hours or access their pay information.
Mobile-first workflows start to remove that friction. When employees can submit hours from their phone right after a shift and easily access their paystubs and time records, the information payroll depends on becomes much easier to collect and share. It also reduces the back-and-forth that often slows things down for owners and bookkeepers when they’re trying to run a clean pay run.
There’s also a people dimension here that I think gets underappreciated. Giving team members easy access to their own paystubs and time records builds transparency and trust in the employment relationship, which matters a lot for small businesses competing for talent.
You’ve talked about trends in the Canadian SMB tech ecosystem, including automation and AI—where do you see these technologies having the most immediate, practical impact in payroll and time tracking, and where do you draw the line to keep things simple and human‑centred?
The most immediate impact of automation is in compliance, and that’s not a glamorous answer, but it’s the right one. Canada has genuinely complex payroll rules: different overtime thresholds by province, CRA remittance schedules, and T4 and T4A obligations. Automating those calculations and reminders removes a real burden from owners who don’t have a finance department to catch mistakes.
Timesheets are a practical example. Rather than an owner manually working out whether someone has hit their overtime threshold under BC or Ontario labour rules, the system handles it. That’s automation doing exactly what it should.
On AI, the biggest near-term opportunity is in helping businesses stay ahead of what they don’t know. Smart alerts, proactive compliance flags, surfacing patterns in time and attendance data. AI working quietly in the background, so people don’t have to think about it. I have spent a good amount of time in my career thinking about where AI adds genuine value versus where it adds noise, and in a small business context, the bar has to be: does this actually reduce someone’s anxiety, or does it just give them more to read?
We don’t add capabilities just to add them. Every feature has to pass a simple test: does it make someone’s day easier, or does it make them feel like they need a manual?
Wagepoint has just gone through a brand refresh and is adding dozens of remote roles while continuing to innovate its product—what excites you most about where the platform is headed next, and what message would you share with Canadian small business owners about how you’re building for them?
The brand refresh is an outward signal of something real. Wagepoint is growing up in a way that still honours what made it special in the first place: the warmth, the focus on small business, the genuine care for the people using the platform. What’s changing is the ambition and the capability behind it.
On the product side, what excites me most is how connected the experience is about to become. Looking ahead, we have a number of exciting updates in the pipeline – steps toward a platform where a Canadian small business owner can more easily manage their people, their time, and their pay.
I consider quite often how technology can either reduce people’s anxiety or quietly add to it. That question sits at the centre of everything we’re building here. The message I’d share with Canadian small business owners is simple: we’re building for you specifically. Not for enterprise companies with small teams, not for other markets. Every decision is grounded in the reality of running a business in this country, with Canadian compliance built in from the start. We know payroll isn’t why you started your business; our job is to make sure it never feels like the reason you regret it.
Disclaimer:
The views and opinions expressed in this interview are those of the interviewee and do not necessarily reflect the official policy or position of CanadianSME Small Business Magazine. Our platform is dedicated to fostering dialogue and sharing insights that inspire and empower small and medium-sized businesses across Canada.
