Jobs

Build where you're strongest. All of our portfolio companies are hiring. We’d love to help facilitate a match.
companies
Jobs

Account Executive

Alexi

Alexi

Sales & Business Development
Toronto, ON, Canada
Posted on Oct 6, 2025

Alexi is transforming the legal industry through artificial intelligence, backed by $15M in Series A funding from leading investors Drive Capital and Draper Associates. As a fast-growing legal AI platform in Canada, we're revolutionizing how lawyers and litigation professionals work to achieve the best outcomes for their clients by automating complex legal tasks and workflows. Our AI-powered platform serves over 1,000 lawyers across leading law firms in the US and Canada. We've achieved rapid growth, doubling our customer base in 2024 alone, while increasing the engagement on the platform by 22x.

At Alexi, we believe that transforming the legal industry requires more than just innovative technology - it demands a culture of customer obsession, ownership, and continuous learning. We’re on a mission to transform legal work through AI.

The Role:

We're looking for an experienced Account Executive to drive new business growth in our mid-market law firm segment. You'll be responsible for the full sales cycle from prospecting to closing while serving as a trusted advisor to law firm leadership. This role involves strategic outreach to key decision makers at law firms, positioning Alexi's platform to solve their complex legal challenges.

The qualities of an ideal candidate are high ambition, strong work ethic, resourcefulness and creativity.

Responsibilities:

  • Drive new business growth across the mid-market law firm segment by identifying, prospecting, and closing new Alexi clients.
  • Strategically prospect to CIOs, Director of ITs, Knowledge Management and Innovation leaders, and partners.
  • Serve as a trusted advisor, deeply understanding client challenges and goals, and position the Alexi solution as means to drive measurable business impact.
  • Some travel required as you will be expected to attend industry conferences and meet with clients at their offices across the US and Canada.
  • Collaborate with product and marketing to share client feedback often in order to inform product development and marketing strategy.
  • Diligently track activity and deal status in CRM.

What You Bring:

  • 2 - 5 years of experience selling to mid-market or enterprise clients, with a preference towards the legal industry.
  • Familiarity with the legal industry and the landscape of legal technology solutions.
  • Exceptional communication and presentation skills, with the ability to build strong relationships, speak to diverse audiences, and influence decision-makers.
  • Demonstrated experience negotiating and closing technology or SaaS deals in the range of six-figures and higher.
  • Familiarity with AI & GenAI and its impact on the legal industry.
  • Bonus: Former practicing lawyer or obtained JD

If you feel you have the above skills and experience APPLY NOW and we will be in touch with all suitable candidates!