Compensation - $125K base and $125K bonus - $250K

Quota - $1M top - 50 accounts

THE CHANCE

A global enterprise software organization is hiring a Strategic Account Executive to own and grow a portfolio of 50-100 enterprise accounts across Ontario. This is the highest-complexity, highest-value individual contributor role on the team - a distinct tier above the other reps in the group, carrying a $1M quota against their $600-700K. The mandate is expansion-led - roughly 60% cross-sell and upsell into an installed base, with a meaningful 40% net new logo component.

You will sell into Corporate Legal departments and General Counsel offices, and into adjacent functions including Finance, IT, and Procurement. The portfolio spans a mature suite of legal research, matter management, workflow, and AI-assisted solutions used daily by in-house legal teams. The role operates at C-Suite and Board level and requires an enterprise seller who can run long, multi-threaded buying cycles alongside fast transactional deals - often simultaneously.

THE ROLE

Reportin g To Sales Manager, reporting into the VP Sales Manager’s S tyleLeads by example; empowering and empath etic

Team A small team of quota-carrying reps, the majority of whom are currently overachieving. This is the only 'Strategic' seat on the team - a distinct tier above the other reps, who carry $600-700K quotas. Accounts 50-100 enterprise accounts across Ontario - Banking, Insurance, Retail, and Telco verticals

Mix60% expansion (cross-sell / upsell) | 40% net new logoDeal Sizes$15-20K transactional | $2-3M strategic

Close Rate 25-30%

Buyers - Corporate Legal departments and General Counsel offices, plus adjacent functions including Finance, IT, and Procurement - operating at C-Suite and Board level

Travel 10-20%, within region





Working ModelHybrid - a blend of in-office and home. Most clients are located downtown, so the expectation is to be in the office or with clients a few days a week.

RESPONSIBILITIES

- Develop and execute multi-year account strategies for enterprise Corporate Legal customers, focused on ARR expansion and net revenue retention (NRR)
- Engage and influence C-Suite and Board-level stakeholders, positioning the organization as a strategic partner across Legal, Operations, Finance, IT, and executive leadership
- Lead complex, multi-threaded sales cycles - navigating large organizations with multiple stakeholders and extended buying timelines
- Drive insight-led, consultative conversations that uncover deep business needs and align tailored, high-value solutions
- Build and progress a robust pipeline of both transactional and long-cycle strategic opportunities
- Orchestrate cross-functional account teams - pre-sales, product specialists, customer success, and leadership - to deliver cohesive, high-impact engagements
- Identify and execute expansion opportunities within accounts, increasing solution adoption, depth, and long-term customer value
- Leverage Salesforce, Gong, LinkedIn, and AI tools to manage pipeline, track contacts, and drive proactive outbound activity
- Provide accurate forecasting and strategic account insight to sales stewardship

WHAT THEY’R

- FOR10+ years of enterprise software sales experience,



with a proven track record managing complex, high-value accounts and exceeding quotaDemonstrated ability to sell into Corporate Legal, General Counsel, and executive-level buyers - ideally into large enterprise accounts such as banks or financial institutionsLegal tech background strongly preferred; someone who has passed the bar and moved into technology is a compelling profileStrong multi-threading ability - can navigate org charts, build champions, and manage complex internal buying groups
- Proactive, outbound hunter mentality - this is not a role for someone who waits on leads
- Consultative and solution-oriented: understand the pain, then map the solution
- Formal sales methodology training an asset (Sandler, MEDDIC, Challenger, Miller Heiman)
- Proficiency in Salesforce, Gong, LinkedIn, MS Office, and AI-assisted selling toolsAn LL.B or legal background is considered a strong differentiator

WHY THIS ROLE

- A long-established brand with deep institutional trust - clients rely on the platform for content, research, security, and ecosystem cohesion in a single environment
- A genuine content moat: the flagship research and workflow products are embedded in how enterprise legal teams work day to day, which underwrites the expansion motion
- Strategic transformation underway - new sales leadership is actively moving the team toward a proactive, modern selling culture with empowered reps
- The only 'Strategic' AE seat on the team: $1M quota and true enterprise scope against $600-700K for every other rep in the group
- Hybrid working model, strong benefits, mental health days, tuition reimbursement, volunteer days, and global ESG programs
- A large, stable, global employer with a credible platform and real internal career progression

📌 Strategic Account Executive (Toronto)
🏢 Fathom Talent Group
📍 Toronto