Senior Director, Mid Market & Public Sector Sales

Clio - Cloud-Based Legal Technology; Toronto; Hybrid; CAD 188,000 - 284,000; Full time

Job summary

A leading company in legal technology is seeking a Senior Director for Mid-Market & Public Sector Sales to drive growth and lead a high-performing sales team. This role offers a competitive salary, flexible work environment, and a commitment to diversity and inclusion.

Benefits

Competitive salary with health benefits

Hybrid work environment

Flexible time off policy

$2000 annual counseling benefit

RRSP matching and RESP contribution

Clioversary recognition program

Qualifications

• 10+ years of SaaS sales leadership experience.
• Proven success in scaling Mid-Market and Upmarket sales teams.
• Experience in the legal vertical preferred.

Responsibilities

• Lead and mentor a high-performing Mid-Market sales team.
• Develop and execute strategies for pipeline growth.
• Establish disciplined forecasting and pipeline management.

Skills

Sales Leadership

Strategic Planning

Operational Discipline

Market Activation Strategies

Cross-Functional Collaboration

Job description

Senior Director, Mid Market & Public Sector Sales

Join to apply for the Senior Director, Mid Market & Public Sector Sales role at Clio - Cloud-Based Legal Technology

Senior Director, Mid Market & Public Sector Sales

3 weeks ago Be among the first 25 applicants

Join to apply for the Senior Director, Mid Market & Public Sector Sales role at Clio - Cloud-Based Legal Technology

Clio is more than just a tech company–we are a global leader that is transforming the legal experience for all by bettering the lives of legal professionals while increasing access to justice.

Summary:
We are currently seeking a Senior Director, Mid-Market & Public Sector Sales to join Clio’s Sales Leadership Team. This role can be based in Vancouver or Toronto, or remotely across Canada or the U.S. Travel to be expected.

Who you are:
We are looking for a strategic and operationally rigorous sales leader to drive Clio’s rapidly growing Mid-Market segment. The ideal candidate will have deep expertise in Mid-Market and Upmarket SaaS sales, a proven ability to scale teams, and experience in the legal vertical (government experience is a plus). This leader will bring a structured approach to sales execution, ensuring strong pipeline generation, forecasting accuracy, and cross-functional alignment to accelerate growth. Additionally, this leader will play a critical role in market activation, leveraging BDRs, channel partnerships, and creative GTM strategies to drive revenue.

What you’ll work on:

• Team Leadership & Development: Lead and mentor a high-performing Mid-Market sales team, ensuring managers and reps are well-equipped to exceed revenue goals. Foster a culture of accountability, performance, and continuous improvement within the team. Implement scalable processes for talent development, career progression, and succession planning.

• Pipeline Generation & Market Activation: Develop and execute creative strategies to drive pipeline growth, including optimizing BDR contributions and activating channel partners. Partner with Marketing to refine messaging, target accounts, and demand generation strategies that fuel Mid-Market expansion. Identify and test new GTM motions to accelerate sales cycles and improve conversion rates.

• Operational Excellence & Forecasting: Establish and enforce a disciplined forecasting and pipeline management process, ensuring high predictability and accuracy. Use data-driven insights to drive operational improvements and optimize sales performance. Ensure consistent execution of Clio’s sales methodology, coaching managers and reps on best practices.

• Cross-Functional Collaboration: Work closely with Post-Sales, Product, and Revenue Operations to align on GTM strategy, product roadmap priorities, and customer success initiatives. Influence pricing, packaging, and sales enablement programs to maximize effectiveness in the Mid-Market segment. Serve as the voice of Mid-Market customers, advocating for their needs across internal teams.

What you bring:

• 10+ years of SaaS sales leadership experience, with 5+ years in second or third-line leadership roles.
• Proven success in scaling Mid-Market and Upmarket sales teams within high-growth SaaS companies.
• Experience in the legal vertical preferred, with government sales experience as a plus.
• Strong operational discipline, with a track record of holding teams accountable to accurate forecasting and pipeline rigor.
• Ability to build and execute creative market activation strategies, leveraging BDRs, channel partnerships, and outbound efforts.
• Exceptional ability to collaborate cross-functionally, driving alignment with post-sales, product, revenue operations, and marketing teams.
• An agile, adaptable mindset, thriving in a fast-paced environment where rapid iteration and learning are key.

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 minimum 2 days per week on our Anchor Days.
• 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

The full salary range* for this role is $188,800 to $236,000 to $283,200 CAD and the full commission range is $125,800 to $157,300 to $188,800 CAD. The opportunity to earn commissions beyond the stated amounts are possible as commission earnings are uncapped.

We aim to hire all candidates between the minimum and the midpoint of the full salary range. We reserve the midpoint to the maximum of the salary band for internal employees who demonstrate sustained high performance and impact at Clio. The final offer amount for this role will be dependent on individual experience and skillset of the candidate. Please note there are a separate set of salary bands for other regions based on local currency.

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