Vertical Sales Director

Jobgether; Canada; Remote; CAD 140,000 - 230,000; Full time

Benefits offered by this job

Remote work

Competitive compensation

Health & retirement benefits

Paid time off

Career development

Leadership opportunities

International environment

Growth opportunities

Inclusive recruitment

Job summary

Jobgether is partnering with a partner company to fill a senior leadership role based in Canada. The Vertical Sales Director leads North American enterprise sales for AI-powered SaaS financial software, owning the full cycle from prospecting to close and building a high-performing remote team.

You will formulate regional growth plans, manage forecasts, and collaborate with internal stakeholders to align sales with broader business goals.

Qualifications

• Minimum 5 years in a sales leadership role overseeing full-cycle enterprise sales.
• Proven track record selling SaaS financial software to enterprise customers.
• Experience selling to C-level executives and senior stakeholders.
• Experience building and guiding high-performing sales teams.

Responsibilities

• Define and execute North America sales strategy across industry verticals.
• Lead full enterprise sales cycle from initial meetings to signed agreements.
• Identify strategic prospects, build account plans, and maintain a strong pipeline.
• Recruit, coach, and retain top-performing sales professionals.
• Provide coaching and performance management to drive results.

Skills

Enterprise sales

C-level engagement

Team leadership

Forecasting & pipeline

Negotiation & closing

Strategic account planning

Education

Bachelor's degree or equivalent

Master's degree preferred

Job description

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Vertical Sales Director based in Canada.

Join an international AI-driven software organization focused on transforming enterprise financial operations and accelerating business growth. As Vertical Sales Director for North America, you will lead regional sales strategy, drive enterprise customer acquisition, and expand revenue across key industry verticals. You will take ownership of the full sales cycle, from developing new opportunities and engaging senior decision-makers to negotiating and closing strategic deals. A key part of your mission will be building, developing, and retaining a high-performing sales team while establishing repeatable sales processes and a strong pipeline. Working closely with internal stakeholders, you will help shape regional expansion plans, strengthen customer relationships, and maintain a deep understanding of market trends. This is an exciting opportunity for an entrepreneurial sales leader who thrives in a fast-paced environment and wants to make a measurable impact on the growth of innovative AI-powered SaaS solutions.

Accountabilities

• Define and execute sales strategies across North America, adapting approaches to different industry verticals and regional market opportunities.
• Lead the full enterprise sales cycle, converting initial meetings into qualified opportunities, managing complex negotiations, and securing long-term customer agreements.
• Drive new business acquisition and revenue growth by identifying strategic prospects, developing account plans, and building a sustainable pipeline.
• Recruit, develop, motivate, and retain a high-performing sales team capable of achieving ambitious commercial objectives.
• Provide ongoing coaching, training, and performance support to help sales representatives improve their skills and consistently deliver results.
• Establish and maintain accurate weekly and monthly sales forecasts, pipeline reporting, and performance tracking to support effective decision-making.
• Implement repeatable sales methodologies and processes that improve execution, conversion rates, and overall team productivity.
• Build relationships with C-level executives and other senior decision-makers, communicating business value and positioning solutions around customer needs.
• Maintain a strong understanding of target industries, financial software markets, competitive dynamics, and evolving customer requirements.
• Collaborate with internal teams to align sales priorities, share market insights, improve customer outcomes, and support broader business objectives.
• Contribute to the development of regional growth plans and help establish a successful presence in new markets.

Requirements

• At least five years of experience in a sales leadership role, with responsibility for managing full-cycle sales processes.
• A strong and consistent track record of success in enterprise sales, particularly in acquiring new customers and achieving revenue targets.
• Experience selling financial software solutions in a SaaS environment; experience with Order-to-Cash (O2C) software is a significant advantage.
• Demonstrated ability to develop and execute structured, repeatable sales strategies and methodologies.
• Proven experience selling complex solutions to C-level executives and other senior enterprise stakeholders.
• Experience recruiting, developing, and leading high-performing new business sales teams in fast-paced environments.
• Strong pipeline management, sales forecasting, and performance analysis capabilities.
• An entrepreneurial mindset, with a strong focus on customer value, business development, and building new growth opportunities.
• A proactive, self-motivated approach and the ability to take ownership of regional sales performance.
• Excellent communication, negotiation, relationship-building, and leadership skills.
• Ability to collaborate effectively with cross-functional teams and align sales execution with organizational goals.
• A bachelor's degree or equivalent relevant professional experience; a master's degree is preferred.
• Ability to work effectively in a remote, international environment and adapt to evolving market conditions.

Benefits

• Remote work: Fully remote position with the flexibility to work from home.
• Competitive compensation: Salary package designed to attract experienced sales leadership talent.
• Health and wellness: Medical coverage, life insurance, retirement plan matching, and additional wellness programs.
• Paid time off: Competitive paid vacation and company holidays, in addition to applicable public holidays.
• Career development: Learning opportunities, mentorship programs, and support for professional advancement.
• Leadership opportunities: The chance to build and develop a sales team while shaping regional commercial growth.
• International environment: Opportunity to collaborate with colleagues and customers across different regions and cultures.
• Growth and innovation: The opportunity to contribute to the expansion of AI-powered enterprise software solutions in a dynamic market.
• Inclusive workplace: A commitment to providing a welcoming and accessible recruitment experience, with accommodations available during the hiring process.