Cross-Sell Account Executive
Pearl
About Pearl
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.
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
Qualifications & 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
What We Offer
- Competitive base salary with uncapped commission
- 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