Account Executive

About the role

Alternative Payments is seeking a highly motivated and experienced Account Executive to join our dynamic Sales team based in Toronto. This full-cycle sales role offers the opportunity to independently generate and manage your own sales pipeline, guiding prospects from initial outreach through to deal closure. As a key contributor to our growth strategy, you will be responsible for building strong relationships with potential clients, understanding their needs, and demonstrating how our platform delivers measurable business value. Your efforts will directly influence our market expansion and revenue growth, making this a vital position within our organization. The ideal candidate will possess a proven track record in B2B sales, especially within financial or technical software sectors, and will thrive in a fast-paced, target-driven environment.

Key facts

What you'll do

• Develop and execute a comprehensive sales strategy by proactively building and managing your own pipeline through outbound prospecting, including cold outreach via email, phone calls, social media engagement, and leveraging referrals and strategic partnerships.
• Take ownership of the entire sales cycle, from initial contact and qualification to product demonstrations, proposal development, negotiations, and closing deals.
• Maintain a high-velocity sales pipeline, ensuring accurate and up-to-date CRM data, and providing reliable monthly and quarterly sales forecasts to management.
• Identify and prioritize target accounts, develop tailored account plans, and navigate complex procurement processes involving security, legal, and finance teams.
• Engage with senior decision-makers such as CFOs, finance directors, and operations leaders, effectively communicating the value proposition of our platform and demonstrating its ROI.
• Collaborate closely with Marketing to refine messaging and campaigns, with Product teams to influence feature development based on customer feedback, and with Customer Success to ensure smooth onboarding and ongoing client satisfaction.
• Travel occasionally for client meetings, industry conferences, or team-building events, representing the company professionally and building rapport with prospects and clients.
• Consistently meet or exceed sales quotas, maintaining a well-documented and healthy sales pipeline, and tracking progress against targets.
• Contribute to the development of outbound sales playbooks, workflows, and best practices, sharing insights and strategies with team members to improve overall sales effectiveness.
• Participate in regular sales meetings, training sessions, and strategic planning activities to stay aligned with company goals and market trends.
• Assist in the onboarding and mentoring of new sales team members as the organization grows, sharing knowledge and best practices to foster a collaborative team environment.
• Stay informed about industry developments, competitive landscape, and emerging trends in payments, FinTech, and SaaS sectors to better position our offerings and identify new opportunities.
• Provide feedback to product and marketing teams based on customer interactions to help shape future product features and marketing campaigns.
• Maintain a professional and consultative approach in all customer interactions, ensuring a positive experience that fosters long-term relationships.
• Utilize modern sales tools and platforms such as Salesforce, Apollo, and LinkedIn Sales Navigator to identify prospects, track activities, and manage customer relationships effectively.
• Be adaptable and proactive in a fast-changing environment, demonstrating resilience and resourcefulness when facing challenges or obstacles.
• Uphold the company's values and commitment to diversity, equity, and inclusion throughout all sales activities and interactions.

Requirements

• A minimum of 5+ years of B2B full-cycle sales experience, with a demonstrated ability to self-source a sales pipeline and close complex, high-value deals.
• Proven success in consistently meeting or exceeding sales quotas within a B2B sales environment, particularly in technical, financial, or SaaS sectors.
• Strong outbound prospecting skills, including experience with email campaigns, cold calling, social media outreach, and in-person meetings.
• Deep understanding of selling technical or financial software solutions, with the ability to conduct value-based, ROI-driven discussions tailored to senior finance, operations, and procurement stakeholders.
• Excellent communication, presentation, and negotiation skills, with the ability to build credibility and rapport with C-level executives and other senior decision-makers.
• A proactive, ownership-driven mindset, capable of working independently, managing multiple priorities, and driving deals forward without constant supervision.
• Familiarity with modern sales technology stacks, including CRM platforms, prospecting tools, and sales engagement software.
• Eligibility to work in Canada, with proper authorization and documentation.
• Strong organizational skills, attention to detail, and the ability to manage multiple opportunities simultaneously.
• A customer-centric approach, with a focus on delivering value and building long-term relationships.
• Adaptability and resilience in a fast-paced, evolving sales environment.
• A growth mindset, eager to learn, improve, and contribute to the success of the team and company.

Nice to have

• Previous experience in FinTech, payments, B2B SaaS, or startup/scale-up environments, with an understanding of the unique challenges and opportunities within these sectors.
• Knowledge of SMBs, MSPs, or service-based businesses, including familiarity with accounts receivable/payable workflows and related financial processes.
• Experience mentoring or coaching junior sales team members, helping to develop sales playbooks, or establishing repeatable outbound sales processes in growing organizations.
• Comfort working in high-impact, fast-paced environments that require agility, creativity, and strategic thinking.
• Familiarity with industry-specific regulations, compliance standards, or security protocols relevant to payments and financial services.
• Multilingual skills or experience working with international clients, especially if the company expands its global footprint.

Skills & tools

• Salesforce CRM
• Apollo prospecting platform
• LinkedIn Sales Navigator
• Strong understanding of sales engagement tools and prospecting techniques
• Ability to leverage data and analytics to inform sales strategies
• Excellent written and verbal communication skills
• Ability to adapt to new technologies and sales methodologies

Practical notes

• Our benefits package includes unlimited paid time off, a yearly learning and development stipend, and equity opportunities to participate in the company's growth.
• Occasional travel may be required for client meetings, industry events, or team gatherings, with travel expenses covered by the company.
• All resumes are reviewed with a combination of human and AI assistance to ensure a fair and efficient process.
• We are committed to fostering an inclusive and accessible hiring process; please inform us if you require any accommodations during the application or interview stages.
• The role is based in Toronto and requires on-site presence in our office, with a hybrid work model (3 days in office per week).
• The company values diversity and is an equal opportunity employer, encouraging applications from all qualified candidates regardless of background.
• The position offers a competitive salary, performance-based incentives, and opportunities for career advancement within a growing organization.
• We believe in supporting our team members' professional growth and provide ongoing training, mentorship, and development programs.
• The company culture emphasizes collaboration, innovation, and a customer-first approach, fostering a positive and inclusive work environment.
• Our sales team works closely with cross-functional teams to ensure alignment and shared success, contributing to a vibrant and supportive company community.
• We prioritize transparency, open communication, and continuous improvement to help our team thrive and achieve their full potential.