Summary:

We are currently seeking a Senior Director of Sales to lead and scale our largest sales segment, representing the high velocity, SMB space (1-4 users). Our ideal candidate will be located in Vancouver or Toronto. We’re open to a remote candidate across Canada for right person (travel to be expected).

Who you are:

This leader will oversee a dynamic team of 60+ sales professionals, including frontline managers and area directors, and will be instrumental in driving our next phase of growth. This role requires a strategic, forward-thinking sales leader with a proven track record of scaling large teams in high-growth SaaS environments, leveraging innovative sales strategies, including AI, programmatic selling, and partner channels.

As a 3rd line leader, you’ll report directly to the SVP of Sales and provide vision, direction, and operational oversight to ensure the team consistently achieves and exceeds sales goals. If you’re a sales leader who thrives in hyper-growth environments and can creatively approach market challenges, we want you on our team.

What you'll work on:

Strategic Leadership:

• Develop and implement a comprehensive sales strategy for the Velocity Sales segment, aligned with overall company goals.

• Identify and execute growth opportunities, including market activation, channel partnerships, affiliate sales, and AI-driven sales approaches.

• Lead the team in identifying untapped revenue streams, positioning the segment for exponential growth.

Team Development & Leadership:

• Lead, mentor, and develop a large, high-performing sales organization, including both frontline managers and senior sales leaders.

• Foster a culture of accountability, innovation, and continuous development across the team.

• Identify skill gaps and ensure robust succession planning through mentorship and training.

Sales Execution & Performance:

• Set, track, and optimize performance KPIs across the team to ensure alignment with growth objectives.

• Oversee accurate forecasting, pipeline management, and deal coaching to drive efficient sales operations and achieve revenue targets.

• Conduct weekly, monthly, and quarterly business reviews to ensure transparency, accountability, and continuous performance improvement.

Client & Stakeholder Engagement:

• Build and nurture strong relationships with key customers and partners, serving as an executive sponsor when necessary.

• Collaborate cross-functionally with marketing, product, and customer success teams to drive a cohesive customer experience and improve retention.

Market Analysis & Growth Opportunities:

• Analyze trends, market shifts, and competitive landscapes to anticipate challenges and seize opportunities for growth.

• Leverage AI and programmatic sales approaches to scale effectively while maintaining a personalized customer experience.

• Expand the segment into new markets and regions as the business grows.

Operational Excellence:

• Ensure sales processes, tools, and methodologies are effectively implemented and utilized to drive operational efficiency and success.

• Champion best practices in sales methodologies, forecasting accuracy, and territory planning to optimize performance across the segment.

What You Bring

• 10+ years of sales leadership experience, with at least 5 years managing large, SMB-focused sales teams in SaaS environments.

• Proven success in scaling sales organizations in hyper-growth SaaS companies, preferably with teams of 70+ people.

• Experience as a 3rd line leader, overseeing multiple layers of sales leadership.

• A strategic thinker with a track record of implementing creative, scalable growth strategies including AI integration, market activation, and outbound and partner-led sales approaches.

• Deep expertise in SMB sales, with an understanding of the micro SMB segment.

• Data-driven decision-maker with strong experience in forecasting, pipeline management, and performance analysis.

• Exceptional communication and relationship-building skills with internal and external stakeholders.

• A progressive mindset, eager to innovate and drive the sales org toward the future.

What you will find here:

Compensation is one of the main components of Clio’s Total Rewards Program. We have developed a series of programs and processes to ensure we are creating fair and competitive pay practices that form the foundation of our human and high-performing culture.

Some highlights of our Total Rewards program include:

• Competitive, equitable salary with top-tier health benefits, dental, and vision insurance

• Hybrid work environment, with expectation for local Clions (Vancouver, Calgary, Toronto, and Dublin) to be in office min. once per week on our Anchor Day.

• Flexible time off policy, with an encouraged 20 days off per year.

• $2000 annual counseling benefit

• RRSP matching and RESP contribution

• Clioversary recognition program with special acknowledgement at 3, 5, 7, and 10 years​​

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The full salary range* for this role is $171,700 to $214,700 to $257,700 CAD. and the full commission range is $114,400 to $143,100 to $171,800 CAD. The opportunity to earn commissions beyond the stated amounts are possible as commission earnings are uncapped.

Diversity, Inclusion, Belonging and Equity (DIBE) & Accessibility

Our team shows up as their authentic selves, and are united by our mission. We are dedicated to diversity, equity and inclusion. We pride ourselves in building and fostering an environment where our teams feel included, valued, and enabled to do the best work of their careers, wherever they choose to log in from. We believe that different perspectives, skills, backgrounds, and experiences result in higher-performing teams and better innovation. We are committed to equal employment and we encourage candidates from all backgrounds to apply.

Clio provides accessibility accommodations during the recruitment process. Should you require any accommodation, please let us know and we will work with you to meet your needs.

Learn more about our culture at clio.com/careers