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!
What We’re Looking ForWe’re seeking a Head of Content Strategy to join our Marketing team and help us define how Alternative Payments shows up across every touchpoint—products, verticals, channels, and campaigns.
This role is ideal for someone who thrives on strategic thinking, customer insight, cross-functional collaboration, and wants to take a hands-on role in shaping messaging architecture, guiding communication strategies, and elevating content quality across the organization.
This is a hybrid position based Downtown Toronto and is available to candidates who are eligible to work in Canada.
What You’ll DoLead and execute on content strategy initiatives across products (AR, AP, Analytics), verticals (MSP, Accounting, and beyond), and channels from research to rollout.
Conduct and synthesize customer, market, and competitive research to inform messaging, positioning, and content direction.
Collaborate with cross-functional teams including Product, Sales, Customer Success, Performance Marketing, and Design to deliver cohesive, high-impact messaging.
Own messaging architecture, including brand narrative, product positioning, audience personas, and communications strategies.
Establish and evolve brand voice, editorial standards, and content quality frameworks across the organization.
Provide strategic direction on channel strategy and content playbooks for product and vertical launches.
Mentor and support team members, elevating content quality and fostering a culture of strong storytelling and strategic thinking.
8+ years of experience in content strategy, brand strategy, or a related field within B2B SaaS, FinTech, or a high-growth startup environment.
Strong expertise in customer research, messaging frameworks, and positioning strategy.
Proven experience owning and driving content strategy at a company level (not just execution).
Strong communication skills to collaborate effectively across Product, Marketing, Sales, and executive stakeholders.
A proactive mindset with the ability to operate autonomously, make strategic decisions, and influence outcomes.
Experience developing brand voice, editorial standards, and scalable messaging systems.
Experience in FinTech, payments, or multi-product SaaS environments.
Familiarity with multi-product and multi-vertical go-to-market strategies.
Track record of mentoring teams and elevating content quality across functions.
Experience working alongside multimedia, performance marketing, and design teams.
Comfort working in fast-paced, dynamic, and high-impact environments.
Competitive salary tailored to your experience, skills, and expertise.
The total compensation range for this role is $125,000 – $145,000 CAD, 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 projects and collaborative 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.
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.
