Senior Sales Executive, Transactional Practices - GLLF

Thomson Reuters • Toronto, ON

5d • Remote

About The Position

This position is open due to an existing vacancy to support our evolving business needs. We're seeking a Senior Sales Executive to drive new growth for our AI-enabled legal technology portfolio. This role is designed to strengthen relationships with transactional attorneys in large law firms and unlock powerful adoption across deal teams, practice groups, and firm-wide initiatives. You'll own end-to-end enterprise deal cycles with Global Large Law Firm (GLLF) clients, focusing on transactional practices (debt financing, M&A, and capital markets) while partnering closely with internal cross-functional teams to expand adoption through direct sales and practice group extension motions. You'll be expected to operate with high agency, build from the ground up, and help define the playbook for this team.

Requirements

• 4+ years of successful B2B software/SaaS sales experience with large law firms (particularly transactional practices), legal technology, or professional services technology solutions
• High-agency operator: you create clarity where there isn't any, develop creative solutions, and execute independently without waiting for perfect inputs
• Drive and resilience: genuine motivation to build something new, take on challenges, and push through ambiguity in a change-resistant industry
• Coachability: you seek feedback, learn quickly from experts, and are willing to try new methods—even when it challenges your defaults
• Relationship management & business development strength: proven ability to build long-term professional relationships, earn trust with senior law firm stakeholders, and maintain genuine curiosity about attorney workflows and firm challenges
• Communication and influence: ability to align internal teams and external buying committees around a shared vision and a mutual path to value
• Fluency in modern sales methodologies: MEDDICC/Challenger/Solutions Selling, mutual action plans, and value-based selling
• Workflow orientation: you can translate product capabilities into attorney outcomes—adoption plans, time savings, risk reduction, and measurable ROI—within diligence and transaction-heavy environments

Responsibilities

• Own full-cycle enterprise sales: prospecting, discovery, value mapping, business case development, multi-threading, negotiation, and close
• Build the segment from the ground up: create and execute a focused territory and account strategy for transactional practices within Global Large Law Firms; develop repeatable motions and messaging for this buyer set
• Engage senior stakeholders across transactional practices (e.g., Practice Group Leaders, Corporate/M&A Partners, deal team leaders, Innovation/Legal Ops Directors, Knowledge Management, and firm leadership) with compelling storytelling, tailored demos, and ROI-driven narratives
• Run structured opportunity plans: validate needs, align on success criteria, build mutual close plans, and drive complex deals to signature
• Become product fluent across solutions that support transactional and diligence-heavy workflows (e.g., CoCounsel and adjacent solutions used in due diligence, drafting/review, collaboration, and benchmarking including HighQ and Noetica); tailor demos to transactional attorney personas
• Create pipeline with disciplined outbound: execute targeted outreach, practice group mapping, and account-based campaigns to build durable pipeline across transactional practices
• Orchestrate internal resources (SEs, BDRs, marketing, enablement, legal, leadership) to progress multi-stakeholder opportunities and land/expand within accounts
• Drive internal alignment and influence: communicate learnings from the field, shape segment positioning, and influence product/enablement priorities to accelerate adoption
• Maintain forecasting rigor and CRM hygiene: accurate forecasting, consistent qualification (MEDDICC or similar), and strong opportunity documentation
• Consistent quota attainment: meet/exceed monthly, quarterly, and annual new business targets for the Global Large Law Firm segment
• Pipeline generation: build and sustain 3x quota pipeline through high-quality outbound, targeted campaigns, and partnership-driven sourcing
• Activity/coverage: maintain a strong customer-facing cadence (e.g., 10+ qualified customer meetings per week) and prioritize external momentum over internal overhead
• Messaging excellence: continuously refine segment-specific value messaging and competitive positioning as the market evolves
• Strategic rigor: maintain an actionable Territory Business Plan and account plans for top logos; document mutual close plans and next steps in CRM
• Builder mindset: contribute to and improve the GTM playbook—what works, what doesn't, and why—so the team scales faster

Benefits

• Flex My Way is a set of supportive workplace policies designed to help manage personal and professional responsibilities, whether caring for family, giving back to the community, or finding time to refresh and reset.
• Flexible work arrangements, including work from anywhere for up to 8 weeks per year
• Grow My Way programming and skills-first approach ensures you have the tools and knowledge to grow, lead, and thrive in an AI-enabled future.
• Comprehensive benefit plans to include flexible vacation, two company-wide Mental Health Days off, access to the Headspace app, retirement savings, tuition reimbursement, employee incentive programs, and resources for mental, physical, and financial wellbeing.
• Globally recognized, award-winning reputation for inclusion and belonging, flexibility, work-life balance, and more.
• Two paid volunteer days off annually and opportunities to get involved with pro-bono consulting projects and Environmental, Social, and Governance (ESG) initiatives.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed