Senior Account Executive

Roots Automation is seeking a high-energy Account Executive to join our growing Sales team and help shape the future of how businesses use AI to drive speed, accuracy, and scale.

We’re building cutting-edge infrastructure that powers real-time document processing, custom model deployment, and multimodal intelligence, bringing AI from research to production in one of the world’s most critical and fast-moving markets. Our platform automates complex insurance workflows with over 98% accuracy, enabling carriers and brokers to achieve results in weeks instead of months.

About the Role

As an Account Executive at Roots Automation, you’ll own the full sales cycle from prospect to close, selling our AI-first, industry-aware AI Agents to enterprise organizations. You’ll partner closely with internal leaders and Fortune 1000 executives to identify opportunities, drive consultative discussions, and deliver tangible business outcomes.

This role is ideal for someone who’s driven, extroverted, and consultative by nature, someone who thrives on building relationships, understanding customer pain points, and closing meaningful deals.

We move fast, value action over bureaucracy, and are looking for someone eager to make an immediate impact.

Key Responsibilities

• Own the full sales cycle: from prospecting and discovery through negotiation and close.

• Drive consultative, value-based sales, articulate complex solutions in simple, outcome-driven terms.

• Develop authoritative knowledge of Roots’ Digital Coworker platform and demonstrate its value to prospects.

• Engage C-suite and VP-level decision makers in ROI-focused conversations that align AI automation to business goals.

• Manage a fast-paced pipeline through outbound prospecting, marketing-qualified leads, and networking.

• Meeting or exceeding revenue targets, maintaining accurate forecasts, and CRM hygiene (Salesforce).

• Collaborate cross-functional with marketing and process engineering teams to tailor solutions and materials.

• Represent Roots at industry events and trade shows, serving as a brand ambassador.

Position Requirements

• 5+ years of B2B SaaS or enterprise technology sales experience (required).

• Proven track record of closing deals with C-suite executives and managing 6-month or shorter sales cycles.

• Strong consultative and strategic selling skills, you’re naturally curious and thrive on understanding business problems.

• Exceptional soft skills and emotional intelligence; able to connect authentically and effectively.

• Comfortable operating in fast-moving, entrepreneurial environments with evolving processes.

• High integrity and competitive drive. You’re hungry to win and motivated by impact.

• Skilled at navigating complex organizations and building multi-threaded relationships.

• Experience with CRM systems (preferably Salesforce) and pipeline management best practices.

• Excellent written and verbal communication skills.

• East Coast or Midwest-based (New York strongly preferred).

Who You Are

• Consultative by instinct. You don’t just sell products; you diagnose problems and deliver outcomes.

• Tenacious and self-motivated. You push through challenges and find creative ways to win.

• Personable and energetic. You build trust quickly and bring enthusiasm to every interaction.

• Seasoned, not managerial. You’ve got depth of experience but want to keep closing deals, not manage teams.

Roots is building agentic AI to transform insurance.

We’re trusted by 3 of the Top 5 P&C insurance carriers and 3 of the Top 10 brokers, and we’ve built InsurGPT™, the most advanced Generative AI model trained on proprietary, insurance-specific data. It reads, reasons, and infers like a human, with purpose-built models tuned for real-world performance and precision.

Roots has raised $44M from top-tier investors including Harbert Growth Partners, MissionOG, and Liberty Mutual Strategic Ventures. We’re growing fast, tackling massive industry challenges, and shaping the future of AI in one of the world’s largest markets.

Join a world-class team building multimodal AI systems, shipping production-grade models, and redefining what’s possible through collaboration, speed, and curiosity.

Final offer amounts are determined by multiple factors, including experience and expertise, and may vary from the amounts listed above.

Roots Automation is an Equal Opportunity Employer. All applicants will be considered for employment without attention to race, color, religion, sexual orientation, gender identity, national origin, veteran or disability status. Roots Automation is a progressive and open-minded workplace where we do not tolerate discrimination or harassment in any form. If you are smart, passionate and good at what you do, come as you are.

Roots Automation is also committed to providing reasonable accommodations to individuals with disabilities throughout the application process and employment. If you need assistance or an accommodation, please contact us for more information.