Enterprise Account Executive

Alternative Payments is building the financial operating system for SMBs, consolidating the disconnected tech stack that holds service-based businesses back. 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'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. If you're energized by real problems, real customers, and real impact, we want to hear from you!

We're 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: you are entirely responsible for generating your own pipeline and carrying every deal from first touch through to close.

This role is ideal for someone who thrives on owning the entire sales motion — self-sourcing pipeline, running complex enterprise deal cycles, and closing — and wants to take a hands-on role in shaping our go-to-market strategy in a category we're actively defining.

You're a builder, not an order-taker. You know that in enterprise sales the best pipeline is the pipeline you create yourself, and you're energized by the challenge of getting into new accounts, mapping complex buying committees, and turning a cold conversation into a signed contract.

This role is an existing vacancy, available to candidates who are eligible to work in Canada in our downtown Toronto office 3x a week (Monday - Wednesday).

• Own your pipeline end to end. Generate your own pipeline through outbound prospecting, targeted account research, referrals, and partnerships — you are entirely responsible for building the top of your funnel, not waiting for leads to be handed to you.

• Run the full sales cycle from first outreach through discovery, demo, business case, negotiation, and close — with sole ownership of every deal in your book.

• Build and execute strategic account plans for enterprise and upmarket targets, mapping multi-stakeholder buying committees and navigating complex procurement, security, and finance 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 after close.

• Travel expectation: This role is expected to be on the road 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 as we grow.

• 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 (larger deal sizes, longer sales cycles, multiple decision-makers).

• Strong outbound and prospecting skills — you are comfortable and effective building pipeline from scratch across email, phone, social, and in-person channels.

• Proven experience selling a technical or financial software product, with the ability to lead value-based, ROI-driven conversations with senior finance and operations stakeholders.

• Strong communication and executive presence to build credibility and drive alignment across teams, regions, and stakeholders.

• A proactive, ownership mindset with the ability to operate independently, prioritize ruthlessly, and drive deals forward without hand-holding.

• Experience in FinTech, payments, B2B SaaS, or startup/scale-up environments.

• Familiarity with selling to SMBs, MSPs, or service-based businesses, and an understanding of accounts receivable / accounts payable workflows.

• Fluency with a modern sales stack (CRM, sales engagement, and prospecting tools).

• Track record of mentoring, building playbooks, or helping establish a repeatable outbound motion in an early or scaling sales org.

• Comfort working in fast-paced, dynamic, and high-impact environments.

• Competitive salary tailored to your experience, skills, and expertise.

  • The total on-target earnings (OTE) for this role is $300,000 (approximately $150,000 base + $150,000 variable), plus equity. The range displayed on each job posting reflects the approximate total target compensation for the position. 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.

At Alternative Payments, you'll do work that truly matters.

• Own your impact: Lead meaningful, high-impact deals and initiatives that are shaping the future of FinTech and redefining how businesses get paid.

• Collaborate: Work with a diverse, innovative team where every voice is heard and great ideas come from anywhere.

• Grow with us: Your career journey is top of mind. We prioritize internal growth and give you the space to shape your path based on your goals — whether that's deepening your expertise in your domain or exploring something new.

• Thrive in a supportive culture: As a scaling start-up, there's a lot to be done and initiative is key. We believe in shared learning, open communication, and building each other up. When one of us grows, we all do.

Want to see what we're actually building?

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.

• Transparency & Honesty: We communicate openly and truthfully with partners, investors, and each other so everyone understands where we stand and where we're headed.

• Resourcefulness & AI: We stay scrappy, find creative solutions, and make progress even when the path isn't obvious. We have a bias for action and seek out the information and resources necessary to make decisions and move quickly.

• Partnership: We win and lose together. We collaborate with our partners, investors, and teammates to tackle big challenges and reach shared goals.

• Revolutionary & Boldness: We challenge conventions, take calculated risks, and build better, stronger solutions that move our business and the industry forward.

• Accountability: We take ownership of our decisions and results. We follow through on our commitments knowing our work directly impacts our partners, our team and our business.

We're looking for candidates who are ready to step in and make an impact from day one. We know that sometimes people hold back unless they meet every requirement, but if you're excited about the role, bring relevant experience, and are ready to contribute, we want to hear from you!

All resumes are reviewed by our small but mighty talent team. While we may use AI tools to help prioritize applications, real people are behind every resume review and hiring decision. 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.