Enterprise Account Executive

Clio; Toronto; Hybrid; CAD 120,000 - 180,000; Full time

Benefits offered by this job

Hybrid model

Equitable compensation

Company equity

RRSP-matching in Canada

Wellness programs

Volunteer time off

RESP contribution

Job summary

Clio is seeking an Enterprise Account Executive in Toronto to lead complex, multi-stakeholder sales engagements with the world’s most prestigious law firms and corporate legal departments. You will drive strategic opportunities, deliver tailored demonstrations, and guide negotiations to close mutually beneficial agreements.

In this role, you will collaborate with cross-functional teams, maintain active pipelines in HubSpot, and travel up to 25% to meet clients across North America.

Qualifications

• 5+ years of B2B enterprise sales experience.
• Proven track record of meeting or exceeding sales targets.
• Experience selling technology solutions to large law firms or corporate legal departments is a plus.

Responsibilities

• Manage complex, multi-stakeholder enterprise sales cycles.
• Build relationships with senior partners, general counsel, and C-level executives.
• Deliver tailored proposals and product demonstrations to address client needs.
• Lead contract negotiations to close high-value deals.
• Collaborate with marketing, product, and customer success to ensure a seamless buyer journey.

Skills

Enterprise sales

B2B sales

Negotiation

Pipeline management

Stakeholder management

Presentation

Tools

HubSpot

Job description

• 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
• 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

Benefits

• Specialized learning and development programs and access to an in-house performance coach
• Equitable compensation for your contributions, regardless of gender, race, or any other identifying factor
• Access to pay transparency on all of our global roles
• Company equity for applicable employees
• RRSP-matching in Canada, 401k in the US, and pension plans in Ireland
• Hybrid model – striking the right balance between the benefits of in person connectivity that in office brings, and the flexibility of remote
• Flexible paid time off (4-week minimum with opportunities for personalization based on individual needs and achievements)
• Parental leave options for birthing and non-birthing parents
• A $500 contribution to your child’s RESP
• Various health, dental, and vision benefits for you and your family, including an Employee and Family Assistance Program
• Virtual and In-person Wellness Programs to support mental and physical health
• Paid time for volunteering through our Clio Gives program
• $2000 annual counseling benefit for CAD Clions

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 executivesSkilled in managing complex, full sales cycles in an enterprise setting and navigating multiple stakeholders from large buying committeesProven team player who works well with cross-functional teams to ensure client satisfaction and drive mutual successSkilled in developing lasting client relationships, prospecting, and negotiating custom, high-value dealsAdvanced ability to persuade, influence, and strategically plan sales activities to maximize resultsDemonstrated experience in developing client relationships, prospecting and negotiating complex and custom deals through to closeAbove 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 engagingProficient with sales tools, and a master at pipeline and activity management5+ 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 targetsExperience in closing new logo sales, preferably within the technology sector (but not essential), including high value ($500k+ ARR) contractsCapable of working independently in fast-paced, dynamic environments, and adept at prioritizing tasks effectivelyHighly driven, with a strong work ethic and a history of meeting and exceeding sales goalsExceptional communication, negotiation, and presentation abilities, able to convey complex ideas effectively across diverse channels