Cross-Sell Account Executive

Pearl is the global leader in AI solutions for the dental market, seeking a results-driven Cross-Sell Account Executive to expand and grow revenue within their existing customer base. This role focuses on identifying expansion opportunities, conducting product demos, and closing additional revenue by aligning Pearl’s solutions with customer needs. Responsibilities 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 HubSpot 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 Skills 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 (HubSpot preferred) and standard sales tools Self-motivated, coachable, and accountable with a strong ownership mindset Intellectual Agility: A strong desire to learn and apply AI-driven solutions to everyday operational challenges, with a comfort level in iterating quickly and pivoting based on new information Automation-First Instincts: Experience looking at repetitive, high-friction tasks and actively experimenting with new tools to solve them at scale SaaS experience preferred HubSpot preferred Benefits Comprehensive health benefits package Flexible work schedule with hybrid flexibility Ongoing training and professional development Opportunity to grow within a rapidly scaling AI company transforming dental care Company Overview Pearl is the global leader in dental AI, powering diagnosis, care, and practice performance for doctors and clinics in 120+ countries. It was founded in 2019, and is headquartered in West Hollywood, California, USA, with a workforce of 51-200 employees. Its website is