Cross-Sell Account Executive

Pearl is the global leader in AI solutions for the dental market. For dental offices and groups, Pearl delivers a full suite of patented image analysis tools that power better oral health and financial outcomes. Our work culture is collaborative and rewarding for self-driven, dynamic individuals keen to advance disruptive solutions revolutionizing a multi-billion dollar industry. Backed by top-tier venture capital partners, led by an executive team with deep industry experience and a proven record deploying AI solutions at scale, Pearl is a rapidly scaling SaaS business with a commanding hold on the growing worldwide market for dental AI.

We are seeking a results-driven Cross-Sell Account Executive to expand and grow revenue within our existing customer base. This role focuses on identifying expansion opportunities, running high-quality product demos, and closing incremental ARR by matching Pearl’s additional solutions to customer needs. The Cross-Sell AE will work closely with SDRs, Customer Success, and Sales Leadership to drive adoption across Pearl’s product portfolio while delivering an excellent customer experience.

• Own and grow revenue within an assigned book of existing Pearl customers through cross-sell and upgrade opportunities
• Conduct discovery to understand customer workflows, pain points, and business objectives
• Position and sell additional Pearl products by clearly articulating value, ROI, and clinical impact
• Run effective product demonstrations tailored to the customer’s current setup and growth goals
• Manage the full sales cycle for cross-sell opportunities from discovery through close
• Maintain accurate pipeline management, forecasting, and deal progression in Hub Spot
• Collaborate closely with SDRs on opportunity sourcing and with Customer Success on account context and handoffs
• Identify patterns, objections, and customer feedback to help refine messaging and sales playbooks
• Consistently meet or exceed monthly and quarterly revenue targets
• Report weekly, monthly, and quarterly results to sales leadership

• 1–3+ years of experience in a closing sales role such as Account Executive, Inside Sales, or similar (SaaS experience preferred)
• Proven ability to manage a pipeline and close revenue against a quota
• Strong discovery and consultative selling skills
• Confidence presenting and demoing software solutions over video
• Ability to clearly communicate value to both clinical and non-clinical stakeholders
• Highly organized, detail-oriented, and comfortable operating in a fast-paced startup environment
• Proficiency with CRM systems (Hub Spot preferred) and standard sales tools
• Self-motivated, coachable, and accountable with a strong ownership mindset

• Competitive base salary with uncapped commission
• Flexible work schedule with hybrid flexibility
• Ongoing training and professional development
• Opportunity to grow within a rapidly scaling AI company transforming dental care