Cross-Sell Account Executive

Lawmatics • San Diego, CA

5d • $65,000 - $130,000

About The Position

Lawmatics is building a dedicated growth motion inside its existing customer base of over 2,500 law firms. This role is for a full-cycle seller focused on introducing new products to current customers and converting interest into expansion revenue. The Cross-Sell Account Executive will manage inbound expansion opportunities and conduct proactive outbound outreach to generate new opportunities within the existing customer base. This position requires a blend of sales and customer success skills, as conversations will stem from existing relationships. The role is characterized by high volume, fast cycles, and full ownership, involving daily demos, end-to-end pipeline management, and a focus on generating new monthly recurring revenue (MRR) from cross-sell and upsell activities.

Requirements

• 2+ years of full-cycle closing experience in a SaaS Account Executive, upsell, or expansion role.
• A track record of managing high-volume, short sales cycles with strong pipeline discipline.
• Comfort with a demo-heavy calendar, multiple product demos daily, without losing quality or personalization.
• Strong outbound instincts: this role is part hunter, part farmer, and requires generating your own pipeline, not just working inbound leads.
• Excellent verbal and written communication, with the ability to translate technical AI product features into clear business value for law firm owners and staff.
• Rigorous CRM hygiene and forecasting habits.
• A collaborative style: this role only works well in close partnership with Account Management and Customer Success.

Nice To Haves

• Experience selling into legal tech, practice management, or CRM software is a plus, not a requirement.

Responsibilities

• Own the hand-raiser queue: Run product demos for every inbound expansion lead across new product offerings.
• Build outbound pipeline: Run proactive outreach cadences into the 2,500+ account base, using product usage data and account history to identify and prioritize the best-fit expansion opportunities.
• Deliver high-impact product demos: Deliver a consistent cadence of tailored product demos, positioning the right AI products for each account's stage, usage pattern, and business need.
• Own opportunities through close: Manage qualification, demo, proposal, pricing, negotiation, and close.
• Partner cross-functionally: Coordinate closely with Account Managers and Customer Success for account context, health signals, and warm introductions, and route non-expansion issues back to the right team.
• Stay current on product and pricing: Maintain deep fluency in the product roadmap, including new products and pricing models as they launch, and translate that into clear customer-facing value.
• Track and report on your funnel: Maintain accurate pipeline in CRM and report on demos booked, show rate, win rate, and MRR closed against quota.
• Surface field intelligence: Feed customer feedback, objections, and competitive insights back to product and GTM teams to sharpen positioning and pricing.
• Escalate customer concerns with urgency: If a current customer surfaces a concern or issue during a demo or outreach, loop in Customer Success immediately so it gets resolved fast, protecting the relationship and the customer experience ahead of any expansion conversation.

What This Job Offers

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