Head of Mid Market Sales

Accountabilities

Sales Leadership and Team Development: Lead, manage, and develop the Mid Market sales organization across the Americas, initially overseeing three sales managers, with planned growth to four. Build a high-performing team by recruiting, coaching, mentoring, and developing managers and account executives.
Revenue and Performance Management: Take ownership of regional revenue targets and overall sales performance. Translate business objectives into actionable sales strategies, establish clear priorities, and ensure consistent execution across the organization.
Sales Strategy and Execution: Develop and implement effective sales programs that improve performance across market segments. Establish scalable processes, strengthen sales execution, and ensure the organization is positioned to achieve ambitious year-over-year growth objectives.
Pipeline Generation and Optimization: Drive sustainable pipeline generation strategies and maintain healthy pipeline coverage. Introduce programs and best practices that improve lead generation, conversion rates, forecasting accuracy, and overall sales productivity.
Market Expansion: Identify opportunities to expand the serviceable addressable market by targeting new industries, customer segments, and product opportunities. Help establish a clear growth strategy to support the organization's ambition of reaching more than $200 million in annual recurring revenue by 2027.
Multi-Product Sales Strategy: Develop effective approaches for selling a growing portfolio of products, increasing cross-selling and expansion opportunities, and positioning solutions against established competitors in replacement and consolidation sales cycles.
Cross-Functional Collaboration: Partner closely with Revenue Operations, Marketing, Product, and other commercial leaders to align go-to-market initiatives, improve operational efficiency, and support the organization's broader growth strategy.
Business Performance Analysis: Evaluate regional performance, identify business challenges, and use data-driven insights to determine the most impactful opportunities for improvement. Go beyond forecasting and reporting by actively implementing initiatives that accelerate growth.
Sales Excellence and Customer Experience: Promote a collaborative, customer-focused sales culture built around deep product knowledge, industry expertise, and a strong understanding of talent acquisition challenges.
Organizational Development: Establish a culture of accountability, continuous learning, clear communication, and high-quality execution while supporting career progression and leadership development within the sales organization.
Requirements
Extensive experience as a second-line sales leader within a high-growth B2B SaaS organization, ideally with a business generating at least $100 million in annual recurring revenue.
Proven experience managing sales managers and leading multi-layered sales organizations, rather than exclusively managing individual contributors.
Demonstrated success recruiting, developing, and retaining high-performing sales managers and account executives, with the ability to make effective performance management decisions when necessary.
Strong experience leading a sales-led Mid Market go-to-market strategy, ideally targeting businesses with approximately 100 to 1,000 employees.
A successful track record of achieving ambitious revenue targets and driving sustainable year-over-year growth in competitive SaaS markets.
In-depth understanding of modern pipeline generation strategies, including pipeline coverage, demand generation programs, sales productivity, and forecasting practices.
Experience developing sales strategies for multi-product platforms, including competitive replacement opportunities, product expansion, and complex sales cycles.
Strong commercial and strategic thinking, with the ability to assess business performance, identify growth opportunities, and translate insights into practical initiatives.
Excellent leadership and coaching skills, with the ability to empower managers, build accountability, and develop a culture of high performance.
Outstanding collaboration and relationship-building abilities, particularly when working with senior stakeholders and cross-functional teams.
Strong communication and change management skills, with the ability to influence stakeholders, implement operational improvements, and drive organizational alignment.
A proactive, ownership-oriented mindset, with a focus on creating measurable business impact rather than simply monitoring forecasts and reporting results.
A customer-centric approach and genuine interest in developing deep expertise in SaaS products and the talent acquisition technology industry.
Benefits
Competitive Compensation: Annual on-target earnings for Canadian candidates ranging from CA$352,000 to CA$418,500, structured with a 50/50 base salary and commission split.
Equity Participation: Opportunity to receive company equity, allowing employees to participate in long-term business growth.
Commission Structure: Performance-based commission offering significant earning potential linked to sales results.
Unlimited Paid Time Off: Flexible vacation policy, with four weeks of annual time off recommended and actively encouraged.
Family Leave: Twelve weeks of fully paid family leave currently available to eligible US employees, with plans to expand coverage internationally as circumstances allow.
Remote-First Environment: Flexibility to work remotely from Canada or the United States.
Equipment and Workspace Budget: Generous budget for professional equipment, software, and office furniture to create a productive working environment.
Learning and Development: Monthly education allowance of $100, with additional support for higher-cost learning opportunities, such as conferences, subject to manager approval.
Long-Term Equity Flexibility: Ten-year exercise window for stock options, providing greater flexibility when making decisions about equity after leaving the organization.
Career Development: Opportunities to grow professionally within an expanding organization, with a strong emphasis on leadership development, coaching, and internal progression.
Collaborative Culture: An environment that prioritizes thoughtful communication, high-quality work, teamwork, accountability, and sustainable long-term success.
Meaningful Impact: The opportunity to shape a growing sales organization, influence go-to-market strategy, and contribute directly to ambitious business expansion plans.