Strategic Account Executive

STRATEGIC ACCOUNT EXECUTIVE Confidential Search • Toronto, ON• Enterprise Legal Technology FATHOM TALENT Executive Search & Talent Advisory location - Toronto - Hybrid Compensation - $125K base and $125K bonus - $250K Quota - $1M top - 50 accounts THE OPPORTUNITY 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 Reporting To Sales Manager, reporting into the VP Sales Manager’s StyleLeads by example; empowering and empathetic 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.Accounts50–100 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 Sales Cycles -1–2 months transactional | 6–18 months 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 Travel10–20%, 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 leadershipLead 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 engagementsIdentify 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 activityProvide accurate forecasting and strategic account insight to sales leadership WHAT THEY’RE LOOKING 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

Develop and execute multi-year account strategies to drive ARR expansion and net revenue retention within a portfolio of 50-100 enterprise accounts. Lead complex, multi-threaded sales cycles targeting C-Suite and Board-level stakeholders across Legal, Finance, and IT functions.

Requires over 10 years of enterprise software sales experience with a proven track record in legal tech or selling to General Counsel. A legal background or LL.B is strongly preferred, along with proficiency in modern sales methodologies and tools like Salesforce and Gong.

• Mental health days • Tuition reimbursement • Volunteer days • Global ESG programs

Identified from the job description. Confirm important requirements above.

• Enterprise Software Sales
• Strategic Account Management
• C-Suite Engagement
• Cross-selling
• Upselling
• Multi-threaded Sales Cycles
• Consultative Selling
• Pipeline Management
• Forecasting
• Salesforce
• Gong
• LinkedIn
• Legal Technology
• Account Strategy
• Outbound Prospecting

• Sales
• Software
• Legal
• Technology
• Management & Leadership

Minimum education

Master’s degree

Minimum experience

10+ years

Apply by

Sep 7, 2026

Posting language

English

Working hours

40 hours per week

Seniority

Mid-Senior level

Application method

Direct apply is available