Account Executive, Enterprise

Sliced Bread Ltd.; Toronto; Hybrid; CAD 100,000 - 150,000; Full time

Benefits offered by this job

Health benefits

Dental insurance

Vision insurance

Hybrid work environment

20 days off per year

Job summary

Clio, the global leader in legal AI technology, is seeking an Enterprise Account Executive in Toronto to drive growth with top law firms and corporate legal departments. You will manage complex, consultative sales cycles, deliver tailored product demonstrations, and lead negotiations from first contact to close.

You will collaborate with Solutions, Marketing, Product, and Customer Success to ensure a seamless buyer experience and a compelling value proposition.

Qualifications

• 5+ years' experience in B2B sales, with enterprise or mid-market focus.
• Proven track record of closing high-value deals (ARR $500k+).
• Excellent communication and presentation abilities across senior stakeholders.
• Ability to navigate complex sales cycles with multiple decision-makers.

Responsibilities

• Build and maintain relationships with key stakeholders and decision-makers.
• Lead product demonstrations addressing client needs to show Clio's value.
• Collaborate on tailored proposals and guide customers through solutions.
• Drive deals to close with cross-functional alignment and contractual negotiations.
• Maintain accurate records in HubSpot and provide regular forecasts.

Skills

Enterprise sales experience

C-level engagement

Negotiation

Relationship building

Pipeline management

Education

Bachelor's degree in business or related field

Tools

HubSpot

Job description

Clio is the global leader in legal AI technology, empowering legal professionals and law firms of every size to work smarter, faster, and more securely.

We are transforming the legal experience for all by bettering the lives of legal professionals while increasing access to justice .

Summary:

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What your team does

This is a high-impact Account Executive role at the forefront of redefining how the world’s most sophisticated legal teams work. You’ll be part of a team of AEs selling Clio’s category-defining AI and legal technology solutions to the most prestigious law firms and corporate legal departments in the country—driving change in an industry that’s ready for transformation. As an Enterprise Account Executive, you’ll have the opportunity to shape the company's growth and elevate execution.

Who you are

You are a proven account executive who thrives in complex, consultative enterprise environments. You know what it takes to navigate the legal market and command the room with senior partners, general counsel, and C-level executives.

What You'll Do

• Build and maintain strong relationships with key stakeholders and decision-makers.
• Serve as the primary point of contact throughout the sales process, fostering long‑term partnerships with clients.
• Prepare and deliver tailored sales presentations and product demonstrations that address specific client needs and use cases to convey the unique value proposition of the Clio platform.
• Collaborate with the Solutions team to create tailored proposals that align with client requirements.
• Guide clients through customized solution recommendations, ensuring proposals align with their business objectives.
• Lead contract negotiations to secure mutually beneficial agreements that meet both client needs and Clio's commercial goals.
• Drive deals to close by aligning with internal stakeholders to maintain compliance with company policies.
• Maintain accurate records of sales activities, client interactions, and deal progress in Hubspot.
• Develop and submit regular sales forecasts and pipeline updates for management review.
• Stay up-to-date with trends in the legal industry, particularly in case management and legal technology, to effectively position Clio's value in the market.
• Use competitor and market insights to strategically influence sales positioning and clientconversations.
• Work closely with marketing, product, and customer success teams to ensure a seamless buyer experience from initial engagement through to solution implementation, including the production of reusable video sales content.
• Act as a voice for client needs, providing feedback to internal teams to influence product development and client satisfaction initiatives.
• Participate in relevant professional networks and training to remain a trusted advisor for enterprise clients.
• Travel as needed (up to 25%) for client meetings, in‑person presentations, and relationship‑building activities at large law firms across North America

Who You are

• Demonstrated experience in developing client relationships, prospecting and negotiating complex and custom deals through to close.
• Skilled in managing complex, full sales cycles in an enterprise setting and navigating multiple stakeholders from large buying committees.
• 5+ years' experience in B2B sales, with proven success in a Mid‑Market or Enterprise Sales role, and with a strong track record of meeting or exceeding sales targets.
• Experience in closing new logo sales, preferably within the technology sector (but not essential), including high value ($500k+ ARR) contracts.
• Proficient with sales tools, and a master at pipeline and activity management.
• Exceptional communication, negotiation, and presentation abilities, able to convey complex ideas effectively across diverse channels.
• Proven team player who works well with cross‑functional teams to ensure client satisfaction and drive mutual success.
• Skilled in developing lasting client relationships, prospecting, and negotiating custom, high‑value deals.
• Highly driven, with a strong work ethic and a history of meeting and exceeding sales goals.
• Capable of working independently in fast‑paced, dynamic environments, and adept at prioritizing tasks effectively.
• Advanced ability to persuade, influence, and strategically plan sales activities to maximize results.
• Above all, we are hiring for experience, personality, and charisma – we you need to be able to develop strong relationships with our prospects by making the buyer journey fun and engaging.
• This is a new role.

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, Dublin and Sydney) to be in office minimum twice per week.
• 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 base salary range for this role is $100,000 to $150,000 CAD. with on‑target earnings (OTE) of $200,000 to $300,000 at 100% attainment. All commission eligible roles have a set base/variable pay mix depending on role, and are eligible for uncapped commissions. Variable compensation is not guaranteed and will depend on individual, team, or company performance. Initial placement within the range is informed by geographic region, experience, and skillset, with room to progress as impact and tenure grow. Final offer amounts will vary based on candidate profile.

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

We're a Human and High Performing AI company, meaning we use artificial intelligence to improve all of our operations. In recruitment, AI helps us streamline the process for greater efficiency. However, we've built our systems to ensure that a human always reviews AI‑generated output, and we never make automated hiring decisions.

Disclaimer: We only communicate with candidates through official @clio.com email addresses.