The RoleLawmatics is building a dedicated growth motion inside our existing customer base of 2,500+ law firms. As we continue to expand our product offering to help law firms, we need a full-cycle seller focused entirely on introducing these products to current customers and converting interest into expansion revenue.
The Cross-Sell Account Executive takes ownership of inbound expansion opportunities and pairs that with proactive outbound into the customer base to generate new opportunities. This role sits at the intersection of sales and customer success: every conversation starts from an existing relationship, not a cold prospect, and success depends on knowing the product and the account equally well.
This is a high-volume, fast-cycle, full-ownership sales role. You will run demos daily, manage your own pipeline end to end, and be measured on new monthly recurring revenue (MRR) generated from cross-sell and upsell.
What You'll Do- 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 You'll Bring- 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.
- Experience selling into legal tech, practice management, or CRM software is a plus, not a requirement.
- 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.
San Diego pay range
$65,000-$130,000 USD
