Alternative Payments

Head of Outbound

Toronto · Mid

Work authorization required$185k-$225kDetected 79 days ago

SalesforceSalesOutbound SalesAccountingAR/VRCommunicationCollaborationMentoringAccounts Payable

About the role

Starting with MSPs, we've spent five years perfecting accounts receivable, and we're now expanding into accounts payable, AI-powered analytics, and beyond.
We believe the best solutions come from diverse perspectives, deep collaboration, and a shared obsession with customer impact.
This is a hybrid position requiring a minimum of 3 days in office based in Toronto, ON and is available to candidates who are eligible to work in Canada.

Design BDR outbound playbooks for each segment: signal-based targeting, sequence architecture, cold call scripts, and email positioning tailored to different buyer personas.
Build rigor and accountability across the BDR team - daily/weekly operating cadences, activity standards, pipeline inspection, and performance management.
Collaborate across Marketing, Partnerships, and Events to drive a strategic approach to outbound efforts.
Work with Head of New Markets to build GTM plans for new verticals: define the buyer, the pitch, the outbound motion, and the pipeline targets.
Build the mid-market and enterprise outbound motion alongside the existing SMB process.
5-10 years in B2B SaaS or fintech sales, including time where your job was building or running outbound programs across multiple segments.
Proven ability to leverage AI to drive team efficiency and prove outcomes with tangible results.
Experience building outbound motions across multiple verticals simultaneously.
Lead meaningful, high-impact projects and collaborative initiatives that are shaping the future of FinTech and redefining how businesses get paid.
We collaborate with our partners, investors, and teammates to tackle big challenges and reach shared goals.

You know the difference between a sequence that books meetings and one that gets ignored.

The total compensation range for this role is $185,000 - $225,000 CAD (OTE), plus equity.
Within the range, individual pay is determined by factors including relevant skills, experience, education/training.
Equity opportunities so you can share in our growth and success.
Unlimited PTO and flexibility when you need it the most.
Yearly learning & development stipend to help you grow and do your best work.
We believe in shared learning, open communication, and building each other up.

closing the loop on money movement and laying the foundation for a platform that will reshape how service businesses operate financially.
We're growing fast, thinking big, and building a global team that wants to be part of something that lasts.
If you're energized by real problems, real customers, and real impact, we want to hear from you!
As a scaling start-up, there's a lot to be done and initiative is key.
When one of us grows, we all do.
We made a short video so you don't have to take our word for it.
Get a glimpse of our product, our people, and the problems we're solving, then decide if it sounds like your kind of place.
We challenge conventions, take calculated risks, and build better, stronger solutions that move our business and the industry forward.
We're looking for candidates who are ready to step in and make an impact from day one.

This listing is sourced directly from Alternative Payments's careers page and normalized into a canonical job model.