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About the Role

Alternative Payments is building the financial operating system for SMBs, consolidating the disconnected tech stack that holds service-based businesses back. We are seeking an Enterprise Account Executive to join our Sales team and help us win, expand, and deepen relationships with our largest and most strategic accounts. This is a full-cycle role responsible for generating pipeline and carrying deals from first touch through to close. This role is ideal for someone who thrives on owning the entire sales motion and wants to take a hands-on role in shaping our go-to-market strategy.

Responsibilities

Own your pipeline end to end, generating it through outbound prospecting, targeted account research, referrals, and partnerships.
Run the full sales cycle from first outreach through discovery, demo, business case, negotiation, and close.
Build and execute strategic account plans for enterprise and upmarket targets, mapping multi-stakeholder buying committees and navigating complex approval processes.
Serve as a trusted advisor to CFOs, finance leaders, and operations executives, translating Alternative Payments' platform into clear, quantified business value.
Collaborate with cross-functional teams — Marketing, Product, and Customer Success — to sharpen messaging, inform the roadmap, and ensure seamless handoffs.
Travel approximately 25% of the time.
Consistently hit and exceed quota, forecasting accurately and maintaining a clean, well-documented pipeline in our CRM.
Propose improvements and help establish the outbound playbooks, workflows, and best practices that will scale our enterprise motion.

Requirements

5+ years of full-cycle B2B sales experience, with a track record of self-sourcing pipeline and closing complex, multi-stakeholder deals.
Demonstrated success carrying and exceeding a quota in an enterprise or upmarket segment.
Strong outbound and prospecting skills across email, phone, social, and in-person channels.
Proven experience selling a technical or financial software product.
Ability to lead value-based, ROI-driven conversations with senior finance and operations stakeholders.
Strong communication and executive presence.
A proactive, ownership mindset with the ability to operate independently, prioritize ruthlessly, and drive deals forward without hand-holding.
Eligible to work in Canada.

Skills

FinTech
payments
B2B SaaS
startup/scale-up environments
selling to SMBs
selling to MSPs
selling to service-based businesses
accounts receivable workflows
accounts payable workflows
modern sales stack (CRM, sales engagement, and prospecting tools)
mentoring
building playbooks
establishing a repeatable outbound motion
working in fast-paced, dynamic, and high-impact environments

Location

downtown Toronto office

Work Type

full-cycle
hybrid (3x a week)
travel expectation: 25%

Experience Level

5+ years of full-cycle B2B sales experience
enterprise or upmarket segment

Salary/Compensations

Total on-target earnings (OTE) is $300,000 (approximately $150,000 base + $150,000 variable), plus equity.

Benefits

Equity opportunities
Unlimited PTO
Yearly learning & development stipend

About the Company

Alternative Payments is building the financial operating system for SMBs, consolidating the disconnected tech stack that holds service-based businesses back.
We've spent five years perfecting accounts receivable, and we're now expanding into accounts payable, AI-powered analytics, and beyond.
We're at an inflection point: 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.
We believe the best solutions come from diverse perspectives, deep collaboration, and a shared obsession with customer impact.
We prioritize internal growth and give you the space to shape your path based on your goals.
We believe in shared learning, open communication, and building each other up.
Our Values: Transparency & Honesty, Resourcefulness & AI, Partnership, Revolutionary & Boldness, Accountability.

Equal Opportunity

We're also committed to an inclusive and accessible process. If you require reasonable accommodation during the hiring process, please let us know upon being selected to interview.