Senior Account Executive, Canada (Toronto-based)

Katana is a remote-first, AI-first SaaS company that builds powerful inventory and manufacturing software for 1,500+ businesses that make and sell physical products around the world.

We've just stepped into an exciting new phase of expansion - moving beyond small merchants into a larger market of modern, multi-channel, multi-location businesses. With that growth comes bigger opportunities, more complex problems, and the chance to shape how we scale. Our 100+ person team across 10+ countries is building what's next -together.

And that's where you come in.

If you're good at what you do, you've probably already hit the ceiling. The territory is carved up. The playbook is handed to you. The biggest logos belong to the reps who got there first, and your job is to run someone else's motion, inside someone else's process, with your name nowhere near the result.

This role is the opposite of that.

Real ownership. At a larger company, you run someone else's playbook to the letter. Here you shape one that's still taking form - and your name is on the result.

Speed. Test an angle Monday, see it in pipeline by Friday. No committee is gating your process, no 6-month approval cycle.

Visibility. Direct line to Commercial Leadership. Your wins are seen and attributed, not absorbed into team output.

A credential that travels. "I shaped Katana's enterprise sales motion as the company moved upmarket" is a better story than being Account Executive #47 at a recognizable name - and that first-mover story counts for even more this early in the AI era.

This isn't a role for someone who wants a bigger version of the job they already have. It's for someone who's ready to own something that matters - at a company moving fast enough that your work shows up in the results within months, not years. If you want to shape a motion while it's still taking form, not inherit a finished one, this is the rare seat where you actually can.

About the role

This is a new role - and a foundational one.

You will be the first dedicated Account Executive for Advantage - our new enterprise go-to-market motion at Katana. You are not joining an established enterprise team - you are the enterprise team. You'll own our enterprise sales motion end-to-end, running complex, multi-stakeholder deals with mid-market businesses that are scaling beyond what basic tools can handle - from qualification through close. You'll sell custom-scoped engagements to companies ready to invest in a purpose-built solution, and you'll own a book of high-value deals in a motion that's being built in real time.

To be clear about scope: this isn't a farming or account-management seat. This role requires a rare combination - someone who can run a complex enterprise deal and go find their own business when the moment calls for it. We want the rep who closed the deal, not the one who supported it. The learning curve is real, the opportunity is real, and the impact you have on how this company grows upmarket will be visible from day one.

The motion is already live - and still taking shape. You'll sharpen it, scale it, and make it yours.

What you'll do

• Own a pipeline of mid-market enterprise deals targeting CA$15K–CA$50K ACV.
• Run discovery that goes deep - quantifying pain, mapping stakeholders, and building business cases in the prospect's own numbers.
• Navigate buying committees across Operations, IT, Finance, and the C-suite.
• Position confidently against enterprise alternatives.
• Scope and negotiate custom, SOW-based engagements.
• Manage longer sales cycles with disciplined follow-through between every touchpoint.
• Introduce expansion and ongoing engagement opportunities during the initial deal scope.

Source your own pipeline

• Source and develop your own pipeline when needed. This role requires a hunter mentality as much as a closer one - you don't wait for inbound, you go find it.
• Consistently hit and exceed quota on a dedicated enterprise motion.

What success looks like

First 30 days: You're not warming up on the sidelines. You've ramped fast on the product, ICP, and our motion, and you're already active in live deals from the pipeline waiting for you - running discovery, meeting buying committees, moving real opportunities forward. You're asking sharp questions about where the motion is still being figured out.

By 6 months: You've closed meaningful business from the existing pipeline, and your own self-sourced deals are now in play alongside it. You're running the full motion end-to-end and shaping a repeatable process that's yours - not one you inherited. You can articulate exactly why each deal is moving or stalling, and what you're doing about it.

By 12 months: You're consistently hitting and exceeding quota, your self-sourced pipeline is a reliable engine rather than an exception, and the way you sell has become part of how we sell. You've turned a motion that was still being built into one that works - and set the bar for everyone who follows.

What we're looking for

What you can do

• You close complex SaaS deals in the CA$15K–CA$50K+ ACV range, and you can walk through exactly how each one came together - the discovery, the stakeholders, the moment it nearly died and what you did about it.
• You carry a quota north of CA$500K and consistently hit it - and you can explain the process behind the number, not just the number.
• You navigate a real buying committee - an Operations Manager, a CFO, and a CEO in the same deal - reading what each one actually needs and getting to a signed order without losing the room.
• You run structured discovery (MEDDIC, SPICED, or your own equivalent), separate the presenting symptom from the underlying pain, and quantify that pain in the prospect's own numbers - so urgency comes from the math, not from pressure.
• You build and defend an ROI-driven business case in front of a C-suite and senior decision-makers.
• You position and win against entrenched ERP and enterprise operations platforms - naming where they're slow, heavy, or overkill, and reframing the decision around fit and time-to-value.
• You scope and price a custom engagement from a messy, ambiguous set of requirements - building a commercial structure that holds up deal-by-deal rather than read off a fixed price list, and negotiating terms that survive scrutiny.
• You source your own pipeline - you spot a trigger event, engineer a referral, or build an outbound angle - and you can point to deals that started with you, not with an SDR or an inbound form.
• You're based in Canada, in or around the Greater Toronto Area (Eastern time zone).

Nice to have

• You know the operations buyer - the world of inventory, supply chain, or manufacturing software - well enough to speak their language from the first call.
• You've sold in a high-growth environment where the motion was still taking shape, so ambiguity reads as opportunity rather than risk.

Mindset & Ways of Working

• A closer, not a relationship manager. You've built your own process, you know why it works, and you can explain it.
• Builder first - ready to own something, and clear that shaping a motion as it scales is worth more than another year at a recognizable name.
• Diagnostic under pressure. When a deal goes quiet, you know exactly why and exactly what to do about it.
• Pulled toward the opportunity, not running from a job. You build urgency without manufacturing it.
• Adaptable - we change often and fast, and this should energise you not scare you.

Compensation

• Base salary: CA$106,380–CA$130,020, depending on demonstrated skill and seniority.
• Variable equal to 100% of your annual base salary (OTE:$212,760–$260,040).

What we offer

• A competitive, market-aligned base salary
• Employee Stock Option Program - you share in what you build
• Time off that's genuinely encouraged: statutory annual leave aligned with local requirements, with a global minimum of 4 weeks, 3 paid health days annually, and your birthday off — because it should actually feel like a day off
• Fully paid 1-month sabbatical + 1,000 EUR travel budget after every four years at Katana - time to reset, explore, or focus on personal growth
• Home office stipend to help you create a setup that works for you
• Health & wellness package through Sun Life
• Modern tools and tech, including AI-enabled tools that help you work smarter and stay focused on high-impact work