Account Executive – Cross-Sell

Jobtailor; San Diego (CA); On-site; USD 90,000 - 130,000; Full time

Job summary

Jobtailor in San Diego is seeking an experienced Account Executive to own full-cycle SaaS sales, from outbound prospecting to closing. You will lead high-volume product demos, qualify opportunities, and shepherd deals through pricing and negotiations.

Collaboration with Account Managers and Customer Success will ensure a seamless customer journey and strong revenue growth. The role emphasizes outbound pipeline generation, tailored demos, and data-driven pipeline hygiene to hit quarterly quotas

Qualifications

• 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, multiple product demos daily, without sacrificing quality or personalization.
• Strong outbound instincts; must generate own pipeline, not just inbound leads.
• Excellent verbal and written communication, translating AI product features into business value for law firms.

Responsibilities

• Own the hand-raiser queue and run product demos for inbound expansion leads across new product offerings.
• Build outbound pipeline through proactive outreach into 2,500+ accounts, using product usage data and history.
• Deliver tailored product demos highlighting AI products for each account's needs.
• Manage qualification, demo, proposal, pricing, negotiation, and close.
• Coordinate with Account Managers and Customer Success for context, health signals, warm introductions, and issue routing.

Skills

Full-Cycle Closing

SaaS Sales

Pipeline Management

Product Demo Delivery

CRM Proficiency

Tools

CRM Software

Job description

• Own the hand-raiser queue and run product demos for every inbound expansion lead across new product offerings.
• Build outbound pipeline through proactive outreach into the 2,500+ account base, using product usage data and account history.
• Deliver tailored product demos positioning the right AI products for each account's needs.
• Manage qualification, demo, proposal, pricing, negotiation, and close.
• Coordinate with Account Managers and Customer Success for account context, health signals, warm introductions, and issue routing.
• Maintain fluency in the product roadmap and pricing models and translate them into customer-facing value.
• Maintain accurate CRM pipeline and report on demos booked, show rate, win rate, and MRR closed against quota.
• Feed customer feedback, objections, and competitive insights to product and GTM teams.
• Escalate customer concerns to Customer Success to protect relationships and customer experience.

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; 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 and close partnership with Account Management and Customer Success.

Core Competencies

Demonstrates expertise in full-cycle sales processes, including product demonstrations, negotiation, and closing in a SaaS environment. Proficient in managing customer relationships and translating technical product features into business value.

Highest-signal resume keywords

• Full-Cycle Closing Experience
• SaaS Sales Expertise
• Pipeline Management
• Product Demo Delivery
• CRM Proficiency

Hard Skills

• Sales Pipeline Management
• Product Demonstration
• Negotiation Skills
• Proposal Development
• Pricing Strategy
• Account Qualification
• Forecasting
• Customer Feedback Analysis
• Competitive Insights Gathering
• AI Product Knowledge

Soft Skills

• Excellent Communication
• Collaborative Style
• Outbound Sales Instincts
• Personalization Skills
• Customer Relationship Management

Industry Keywords

• SaaS
• Account Executive
• Expansion Sales
• Customer Success
• Product Roadmap

Tools & Technologies

• CRM Software