Head of Sales

Portfolio+; Whitchurch-Stouffville; On-site; CAD 100,000 - 140,000; Full time

Job summary

A leading financial technology firm in Ontario is looking for a Head of Sales to drive revenue growth and manage client relationships. The ideal candidate will have over 10 years of experience in sales within the financial services industry, a strong business acumen, and a track record of exceeding sales targets. This role offers an opportunity to lead a high-performing team and contribute to the company's strategic direction.

Qualifications

• Minimum of 10 years in sales or account management in financial services.
• Proven ability to meet and exceed sales targets.
• Strong understanding of B2B enterprise sales.

Responsibilities

• Define and execute sales strategy to meet revenue targets.
• Manage the sales pipeline to ensure consistent growth.
• Build long-term relationships with clients.

Skills

Sales leadership

Customer relationship management

Negotiation skills

Financial acumen

Team development

Education

Bachelor’s degree in Business, Marketing, or related field

Master’s degree

Tools

HubSpot CRM

Salesforce

Job description

Portfolio+ is a leading Canadian financial technology company that provides innovative wealth management and investment software solutions to banks, credit unions, and financial institutions across the country. With more than 30 years of industry experience, Portfolio+ offers a robust suite of portfolio management systems that support registered and non-registered investments, GICs, mutual funds, and equity products.

Headquartered in Ontario, Portfolio+ delivers scalable, cloud-based platforms designed to enhance operational efficiency, meet regulatory compliance, and improve the client experience. The company is recognized for its secure, reliable, and future-ready technology, trusted by financial institutions to manage billions in assets.

Portfolio+ fosters a collaborative and inclusive workplace culture, with a strong focus on innovation, professional growth, and delivering high-impact solutions to the evolving financial services sector.

Key Responsibilities

Strategic Leadership

• Define and execute the overarching sales strategy, methodology, and closure plans while aligning to business objectives.
• Develop and implement a strategic sales plan to achieve annual revenue and bookings targets, ensuring growth and customer expansion.
• Collaborate with leadership to establish competitive pricing models that maximize revenue and market competitiveness.

Sales Operations

• Manage and grow the sales pipeline, ensuring a consistent flow of qualified opportunities to meet future revenue goals.
• Track and forecast sales performance, providing regular updates and actionable insights to management.
• Oversee contract negotiations and, where applicable, lead direct negotiations with clients.
• Develop and execute personal sales plans, ensuring individual sales targets are met alongside team goals.
• Drive both team-wide and individual efforts to close deals, expand customer relationships, and achieve overall revenue objectives.
• Oversee and manage the HubSpot CRM to ensure accurate tracking of sales activities, customer interactions, and pipeline management, optimizing the platform for efficient team collaboration and data-driven decision-making.

Customer Success & Engagement

• Build and nurture long-term client relationships to enhance retention and lifetime value.
• Develop and implement comprehensive account plans that include communication strategies, engagement approaches, and retention initiatives.
• Deliver compelling presentations that showcase Portfolio+’s value proposition to clients and industry audiences.
• Serve as a brand ambassador, representing Portfolio+’s values, mission, and vision across internal and external platforms.
• Identify and participate in relevant industry events and conferences to build brand awareness and expand networks.

Team Leadership & Development

• Recruit, onboard, and develop high-performing sales professionals.
• Foster a culture of accountability, collaboration, and continuous improvement.
• Provide mentorship, coaching, and performance evaluation to support team and individual development.
• Equip the sales team with the tools, training, and resources needed for success.
• Define, measure, and optimize KPIs to track and improve performance across the team.

Market Analysis & Collaboration

• Continuously monitor industry trends, competitor activities, and market dynamics to inform strategy.
• Collaborate with the marketing team to create effective sales enablement tools and campaigns.
• Act as a liaison between sales, marketing, and revenue operations to ensure alignment.

Ideal Candidate Profile

The ideal candidate for the Head of Sales at Portfolio+ is a strategic and results-driven sales leader with a proven track record of driving revenue growth in the financial technology or enterprise SaaS space. They bring deep experience building and leading high-performing sales teams, developing and executing go-to-market strategies, and cultivating strong relationships with financial institutions across Canada and beyond.

A strong understanding of the sales cycle for complex B2B solutions, ideally in regulated industries, is essential. The successful candidate is both a hands-on builder and a collaborative team player, with a passion for customer success, a data-informed approach to decision-making, and the ability to thrive in a fast-paced, entrepreneurial environment. They are excited by the opportunity to scale a growing company, contribute to its strategic direction, and help shape the future of banking technology.

Requirements

• A Bachelor’s degree in Business, Marketing, Sales, or a related field. A Master’s degree with additional leadership certifications will be an asset.
• Minimum of 10 years of progressive experience in sales, business development, or account management within the financial services industry. Experience working in agile environments will be an asset.
• Proven track record of consistently meeting and exceeding sales targets in complex enterprise accounts.
• Strong business and financial acumen, with the ability to engage and sell effectively at the executive level.
• Excellent negotiation and communication skills, with the ability to tailor messaging for diverse audiences.
• Demonstrated ability to coach, mentor, and inspire high-performing sales teams.
• Growth-oriented mindset with a commitment to ongoing personal and professional development.
• Extensive experience in B2B enterprise software sales, including complex software and system integrations.
• Proven ability to craft and position compelling value propositions for cloud-based solutions at a strategic level.
• Adept at understanding customer needs and delivering tailored solutions that build long-term strategic partnerships.
• Strong analytical skills to assess performance metrics, evaluate customer data, and optimize sales strategies.
• Proficient in CRM platforms (e.g., HubSpot, Salesforce) and data-driven tools to enhance team performance and decision-making.
• Solid understanding of the regulatory landscape related to open banking, including GDPR, PSD2, and other compliance frameworks.
• Skilled at balancing client advocacy with alignment to broader organizational sales goals.
• Collaborative team player who contributes to a positive, inclusive, and high-performing work environment.
• Self-motivated, adaptable, and self-aware in dynamic and evolving business environments.

How to Apply

If you are interested in pursuing this exciting opportunity, please apply online here. For more information or if you have questions, please contact Bola Moradeyo [e-mail]

Diversity and Accessibility Statement

Portfolio+ is committed to being an organization where diversity and different perspectives are valued. They strive to be an organization that is inclusive, supportive, and reflective of the communities and organizations they serve and encourage applications from candidates who identify as part of a traditionally marginalized community.

KBRS will provide support in its recruitment processes to applicants with disabilities, including accommodation that considers an applicant’s accessibility needs. If you require accommodation to participate as a candidate in the recruitment process, please contact [e-mail], or communicate your needs to our team.