Enterprise Account Executive

About the role

Alternative Payments is seeking a highly motivated and experienced Enterprise Account Executive to join our dynamic Sales team based in Toronto. This role is integral to our growth strategy, as you will be responsible for managing the entire sales cycle, from initial lead generation through to closing complex deals with our most significant enterprise clients. Your expertise will help define and execute our market approach within the rapidly evolving financial technology sector. You will work closely with cross-functional teams, including marketing, product, and customer success, to ensure a customer journey and to drive revenue growth. This position offers an to contribute to a fast-paced, innovative environment where your efforts directly impact the company's expansion and success.

Key facts

What you'll do

• Take ownership of your sales pipeline, proactively sourcing and developing leads from initial contact through to contract signing, ensuring a steady flow of new business opportunities.
• Manage all stages of the sales process, including conducting discovery calls, delivering compelling product demonstrations, developing tailored business cases, negotiating terms, and closing deals with enterprise clients.
• Develop and execute strategic account plans tailored to each enterprise client, navigating complex approval processes that involve multiple stakeholders across finance, operations, and executive levels.
• Engage with CFOs and senior finance leaders to understand their needs and demonstrate the value proposition of our platform, positioning it as a critical solution for their financial operations.
• Collaborate closely with marketing, product, and customer success teams to refine messaging, develop targeted outreach strategies, and ensure a smooth transition from sales to onboarding and ongoing customer success.
• Travel approximately 25% of the time to meet with clients face-to-face, attend industry events, and build strong relationships with key decision-makers.
• Consistently meet or exceed sales quotas by maintaining accurate and up-to-date CRM records, providing reliable forecasts, and adjusting strategies as needed to achieve targets.
• Contribute to the development of outbound sales strategies, sharing best practices and insights to improve overall enterprise growth efforts.
• Maintain a deep understanding of our platform's features and benefits, staying informed about industry trends and competitor activities to position our offerings effectively.
• Build long-term relationships with clients, ensuring high levels of customer satisfaction and identifying opportunities for upselling and cross-selling.
• Participate in regular sales meetings, training sessions, and strategic planning to continuously improve sales techniques and product knowledge.

Requirements

• A minimum of 5 years of B2B sales experience, with a proven track record of sourcing leads independently and closing complex enterprise deals.
• Demonstrated success in consistently meeting or exceeding sales quotas in an enterprise sales environment.
• Strong outbound prospecting skills across various channels, including email, phone calls, social media, and in-person meetings.
• Experience selling technical or financial software solutions, with the ability to lead value-based discussions with senior finance and operations personnel.
• Excellent communication skills, including the ability to articulate complex concepts clearly and persuasively to C-level executives and other senior stakeholders.
• A confident and professional executive presence that fosters credibility and trust with clients.
• A proactive, self-driven attitude with the ability to work independently, prioritize tasks effectively, and manage multiple deals simultaneously.
• Familiarity with CRM systems and sales engagement platforms to track activities, manage contacts, and forecast sales accurately.
• Ability to adapt quickly to changing priorities and work in a fast-paced environment.
• Strong problem-solving skills and a customer-centric mindset focused on delivering value.
• Willingness to travel as needed to meet with clients and attend industry events.

Nice to have

• Prior experience in FinTech, payments, B2B SaaS, or startup environments, providing a solid understanding of the industry landscape.
• Knowledge of SMBs, MSPs, or service-based businesses, including familiarity with accounts receivable and payable workflows.
• Experience working with modern sales tools such as CRM platforms, sales engagement software, and prospecting tools to streamline outreach and follow-up.
• Mentoring experience or a history of establishing scalable outbound sales processes within a growing organization.
• Comfort working in dynamic, high-impact settings where adaptability and resourcefulness are essential.
• Understanding of the regulatory environment, including compliance considerations relevant to financial technology.

Skills & tools

• CRM systems for managing contacts, sales activities, and forecasting.
• Sales engagement platforms to automate and optimize outreach efforts.
• Prospecting tools to identify and connect with potential clients effectively.

Practical notes

• Candidates must be eligible to work in Canada to qualify for this role.
• The company offers a comprehensive benefits package, including unlimited paid time off (PTO), a yearly learning and development stipend, and equity opportunities to align employee success with company growth.
• Alternative Payments values transparency, resourcefulness, partnership, boldness, and accountability in its culture and daily operations.
• While AI tools may assist in initial application screening, all hiring decisions are made by human reviewers to ensure the best fit.
• The company is committed to providing accommodations throughout the hiring process upon request, ensuring an inclusive environment for all candidates.

About the company

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