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Salary: USD 65,000 - 130,000 / annual
Lawmatics is building a dedicated growth motion within its existing customer base of 2,500+ law firms. The company is seeking a Cross-Sell Account Executive to drive expansion revenue by introducing new product offerings to current customers and converting interest into recurring revenue.
This is a full-cycle sales role that sits at the intersection of sales and customer success. You will own inbound expansion opportunities while running proactive outreach into the customer base to generate new opportunities. Every conversation starts from an existing relationship, not a cold prospect.
Key responsibilities include:
- Managing the inbound hand-raiser queue: running product demos for every expansion lead across new product offerings
- Building outbound pipeline through proactive outreach cadences into the 2,500+ account base, using product usage data and account history to identify expansion opportunities
- Delivering high-impact, tailored product demos that position AI products for each account's stage, usage pattern, and business need
- Owning opportunities end-to-end: qualification, demo, proposal, pricing, negotiation, and close
- Cross-functional partnership with Account Managers and Customer Success for account context, warm introductions, and issue routing
- Maintaining deep fluency in product roadmap and pricing models, translating features into clear customer value
- Tracking pipeline accuracy in CRM and reporting on demos booked, show rate, win rate, and MRR closed against quota
- Surfacing field intelligence (customer feedback, objections, competitive insights) to product and GTM teams
- Escalating customer concerns with urgency to Customer Success to protect relationships and customer experience
This is a high-volume, fast-cycle role with a demo-heavy calendar. You will run multiple product demos daily, manage your own pipeline end-to-end, and be measured on new monthly recurring revenue (MRR) generated from cross-sell and upsell.
Requirements:
- 2+ years of full-cycle closing experience in a SaaS Account Executive, upsell, or expansion role
- Track record of managing high-volume, short sales cycles with strong pipeline discipline
- Comfort with a demo-heavy calendar and multiple product demos daily without losing quality or personalization
- Strong outbound instincts; ability to generate your own pipeline, not just work inbound leads
- Excellent verbal and written communication; ability to translate technical AI product features into clear business value for law firm owners and staff
- Rigorous CRM hygiene and forecasting habits
- Collaborative style and ability to work closely with Account Management and Customer Success
- Experience selling into legal tech, practice management, or CRM software is a plus but not required
