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, energetic 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

📌 Enterprise Account Executive (Winnipeg)
🏢 Clio
📍 Winnipeg