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About the Role

Our client is seeking a results-driven Digital Sales Account Executive to support and grow relationships within its existing mid-market customer base. In this role, you will manage a portfolio of approximately 300 to 500 customer accounts, uncover new business opportunities, and help customers solve operational challenges using our client's cloud-based accounting ecosystem. You will own the complete sales cycle, including prospecting within existing accounts, conducting discovery calls, delivering product demonstrations, negotiating agreements, and closing business. This is an excellent opportunity for an experienced B2B sales professional to join a growing team and gain valuable experience within a leading technology organization.

Responsibilities

Manage and grow a portfolio of approximately 300 to 500 existing mid-market customer accounts.
Identify upsell, cross-sell, and account expansion opportunities within the client's existing customer base.
Conduct approximately 25 outbound calls per day, supported by consistent email and digital outreach.
Lead the complete sales process, including account research, discovery, product demonstrations, objection handling, negotiation, and closing.
Develop a strong understanding of mid-market accounting best practices and industry-specific business needs.
Identify gaps in customer processes and align appropriate solutions from the client's small business ecosystem.
Build relationships and manage communication with multiple stakeholders throughout the sales cycle.
Maintain an accurate and well-organized sales pipeline.
Consistently update customer, activity, opportunity, and forecasting information within applicable business systems.
Use tools such as Gong, Outreach, and AI-enabled productivity platforms to improve sales effectiveness.
Collaborate cross-functionally with marketing, business development, customer success, and other internal teams.
Provide actionable feedback to internal stakeholders to improve customer experiences and team operations.
Demonstrate a customer-first mindset and operate with integrity in every interaction.

Requirements

At least four years of B2B sales experience, ideally within a SaaS, fintech, technology, or cloud-based solutions environment.
Experience managing and growing existing customer accounts.
Demonstrated success in an end-to-end sales role, including discovery, demonstrations, solution selling, negotiation, and closing.
Strong pipeline management and sales forecasting capabilities.
Ability to assess pipeline health, identify gaps, and create an action plan to achieve sales targets.
Excellent verbal and written communication skills.
Strong time management, organization, and attention to detail.
A proven ability to uncover customer challenges and connect those needs to relevant business solutions.
Experience selling to mid-market customers.
Experience using consultative sales methodologies such as SPIN Selling, Challenger, or Solution Selling.
Familiarity with Gong, Outreach, CRM platforms, and AI-supported productivity tools.
Experience managing a high-volume account portfolio.
Experience in accounting technology, financial services, fintech, or small-business solutions.

Skills

Gong
Outreach
CRM platforms
AI-supported productivity tools
SPIN Selling
Challenger
Solution Selling

Location

Downtown Toronto

Work Type

Hybrid
Contract

Experience Level

At least four years of B2B sales experience

Salary/Compensations

$27 - $31/hr

About the Company

We’re a leading provider of business and technology services. We accelerate business transformation for our customers. Our expertise in strategy, design, execution and operations unlocks business value through a range of solutions. We’re a team of 80,000 strong, working with over 6,000 customers, including 80% of the Fortune 500 across North America, Europe and Asia, who partner with us for our scale, full-stack capabilities and speed. We’re strategic thinkers, hands-on collaborators, helping customers capitalize on change and master the momentum of technology. We’re building tomorrow by delivering business outcomes and making positive impacts in our global communities. TEKsystems and TEKsystems Global Services are Allegis Group companies. Learn more at TEKsystems.com.

Equal Opportunity

The company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.
Pursuant to the San Francisco Fair Chance Ordinance, for all positions located in the city and county of San Francisco, we will consider for employment qualified applicants with arrest and conviction records.
We may use Artificial Intelligence (AI) to support parts of our hiring process, including sourcing, screening, and evaluating candidates. AI helps assess applications and qualifications, but final decisions are made by our hiring team. By applying, you acknowledge and agree that your application may be reviewed using AI tools.