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Head of Sales

Sybill AI, Inc.

Job Overview

Location

Remote

Job Type

Full-time

Full Job Description

📋 Description

• Sybill AI is at the forefront of revolutionizing the sales landscape, empowering Business-to-Business (B2B) Account Executives (AEs) to reclaim their time and maximize their impact. We understand that traditional sales roles are bogged down by administrative tasks, with AEs spending a mere 1.5 hours a day on crucial customer calls, while the rest is consumed by back-office drudgery. Sybill is engineered to automate this inefficiency, liberating sales professionals to concentrate on their core strengths: building meaningful relationships and closing deals. Our innovative platform goes beyond simple meeting note-taking; Sybill intelligently generates and manages to-do lists derived from both calls and emails, and then actively assists in auto-executing these tasks using advanced AI capabilities. This encompasses a wide range of critical sales activities, including updating Customer Relationship Management (CRM) systems, crafting and sending personalized follow-up emails, scheduling subsequent meetings, conducting in-depth research, customizing essential sales collateral such as presentations, one-pagers, and Requests for Proposals (RFPs), and much more. Ultimately, Sybill empowers AEs to achieve significantly more while expending less effort, with the ambitious vision of enabling an AE to close 200% more revenue.
• We have secured $15 million in funding to bring this vision of the future sales assistant to life. With a rapidly growing base of over 750 satisfied customers, an impressive 70% of our revenue is generated through word-of-mouth referrals, a testament to the power of our Product-Led Growth (PLG) offering. Our team is small but exceptionally mighty, comprising some of the sharpest and most driven minds in the industry, all collaborating towards a common goal. We leverage a sophisticated combination of proprietary AI models and foundational Large Language Models (LLMs) to power our agentic technology, ensuring the delivery of highly accurate and impactful results.
• The ideal candidate for Sybill thrives on a culture of continuous progress and simplicity. We seek individuals who value speed and efficiency over perfection, who possess the ability to cut through complexity, maintain a sharp focus on what truly matters, and consistently raise the bar in their daily work. A deep commitment to achieving tangible outcomes is paramount; candidates must be driven by real results – not just effort or activity – for our users, the business, and the team. Collaboration is key; we foster an environment where team members share successes, readily offer support, and understand that collective success is the only true measure of achievement. We encourage open and honest communication, the courage to address difficult topics directly, and a genuine openness to learning from every experience, both wins and mistakes. Challenges are not viewed as deterrents but as catalysts for creative problem-solving and innovation.
• As the Head of Sales at Sybill, you will be instrumental in owning and driving revenue growth across our mid-market and enterprise customer segments. This pivotal role demands the design, execution, and continuous optimization of our sales strategy. Importantly, this is not a people management position; you will lead from the front, acting as a high-performing individual contributor who thrives on execution, experimentation, and delivering measurable impact. You will personally engage in key deals, refine our sales messaging and positioning through direct, real-world feedback, and collaborate cross-functionally to shape the overarching strategy for how Sybill is sold, scaled, and adopted within client organizations. You will operate as a player-coach, embodying the spirit of a founder-level operator who builds robust, repeatable sales systems through hands-on experience, continuous learning, and iterative refinement. Your contributions will be critical in defining how Sybill's cutting-edge AI technology transforms the very nature of how sales professionals operate.
• Your responsibilities will encompass owning the entire sales funnel, from initial prospecting and qualification through to negotiation and successful closing, with a focus on mid-market and enterprise accounts. You will be responsible for designing and iteratively improving Sybill's go-to-market approach, meticulously optimizing messaging, discovery processes, and overall deal cycles. A consistent track record of exceeding targets is expected, underpinned by a rigorous, metrics-driven methodology for forecasting and pipeline management. You will forge strong partnerships with the founders, marketing, product, and customer success teams to ensure alignment of our go-to-market strategy, accelerate deal velocity, and identify emerging market opportunities. A key aspect of this role involves leveraging AI tools, including Sybill itself, on a daily basis to dramatically scale your personal productivity, prospect with greater intelligence, and close deals more efficiently. Furthermore, you will serve as the internal voice of the customer, providing invaluable, real-time insights that shape product direction and refine our market positioning.

🎯 Requirements

• Minimum of 4 years of experience in a closing sales role, with at least 2 years specifically within SaaS sales.
• Proven track record of tenacity in winning deals, adept at multithreading, transforming challenges into opportunities, and overcoming obstacles.
• Demonstrated comfort navigating uncertainty and ambiguity, with a proactive approach to making strategic decisions and a willingness to engage at any level to drive results.
• Passion for the potential of AI in sales, evidenced by active usage of AI tools such as ChatGPT.
• High horsepower, strong problem-solving skills, adeptness at frequent context switching, effective management of multiple concurrent projects with expansive ownership, and ruthless prioritization.
• Exceptional presentation and communication skills.
• A demonstrable growth mindset, characterized by rapid learning, constant iteration, and proactive adaptation to market and competitive shifts.
• Honesty, transparency, and a collaborative spirit, with a willingness to embrace giving and receiving direct feedback for continuous improvement.

🏖️ Benefits

• Competitive compensation package including salary and performance-based incentives.
• Comprehensive health, dental, and vision insurance.
• Significant equity stake, offering the opportunity for substantial long-term financial growth.
• Opportunities for rapid professional growth and autonomy within an early-stage, high-impact environment.
• Flexible Paid Time Off (PTO) policy, recognizing the importance of work-life balance and rejuvenation.
• Annual company offsite events for strategic planning, collaboration, and team building.
• Remote-friendly work environment with flexible hours to support deal closing efforts.

Skills & Technologies

REST

Remote

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Sybill AI, Inc.

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About Sybill AI, Inc.

Sybill AI is a company focused on revolutionizing business operations through artificial intelligence. They provide an AI-powered platform designed to automate complex workflows, enhance decision-making, and unlock hidden insights within enterprise data. Their solutions aim to streamline processes across various departments, including finance, sales, and operations, by leveraging advanced machine learning and natural language processing. Sybill AI's technology helps businesses to improve efficiency, reduce costs, and gain a competitive edge by transforming raw data into actionable intelligence. The platform is built for scalability and integration, enabling seamless adoption within existing business infrastructures to drive digital transformation and operational excellence.

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