Drips

Manage full enterprise sales cycle for national accounts, build and convert a 7-figure pipeline, lead complex multi-stakeholder sales, and develop long-term strategic partnerships with senior decision-makers. | 5-10+ years enterprise sales experience, proven quota achievement, ability to close 6-7 figure deals, strong executive communication, and willingness to travel 50%+. | Account Executive – National Accounts Location: Remote | United States Reports To: VP of Sales Type: Full Time | High Drive | High Impact | Quota-Carrying About Drips Drips is a fast-growing, tech-enabled managed service transforming how organizations engage their customers at scale. Our engagement platform delivers measurable outcomes across the customer journey, helping national, regional, and local enterprises improve acquisition, retention, satisfaction, and operational efficiency. We work in direct collaboration with our customers to drive business outcomes, improve experiences, and create meaningful impact making Drips an indispensable partner in today’s value-driven landscape. Job Overview We are seeking a top-performing Account Executive with experience selling complex, six- and seven-figure enterprise deals. You are commercially driven, operationally sharp, and thrive in consultative sales cycles that require creativity, discipline, and persistence. This is a hunter role—you’ll be responsible for penetrating national accounts across multiple verticals, developing new opportunities, guiding them through a structured enterprise sales process, and closing deals that deliver long-term value for our customers. Responsibilities Own the full enterprise sales cycle from prospecting to close for net-new national accounts. Build, manage, and convert a 7-figure pipeline within assigned target accounts. Lead complex, multi-stakeholder sales motions focused on ROI, outcomes, and long-term strategic partnerships. Develop and deepen relationships with C-Suite and VP-level decision-makers across functions such as Operations, Finance, Digital Strategy, and Customer Experience. Lead strategic deal orchestration and account planning across multi-stakeholder buying committees. Maintain high standards of CRM hygiene, account planning, and disciplined follow-through. Partner cross-functionally with marketing, product marketing, product, and client services teams to ensure alignment and execution. Champion Drips’ Voice-of-Customer program and drive client OKR’s Willingness to travel 50%+ for national account coverage What You Bring 5–10+ years of successful enterprise sales experience with a proven track record of quota achievement. Demonstrated ability to close 6 to 7-figure, multi-year deals. Strong ability to navigate matrixed organizations and influence senior decision-makers. Established executive acumen, communication skills, credibility, and follow-through. Hunger to learn, curiosity to ask better questions, and resilience in a fast-moving, high-growth environment. Commitment to a high-performance culture built on accountability, discipline, and integrity. Experience working with organizations undergoing digital transformation in customer engagement Preferred Qualifications: Experience in the Property & Casualty (P&C) or Education markets. Why Join Us? Category-defining company solving meaningful problems at scale. Opportunity to partner with leading national enterprises on initiatives that matter. A sales career with purpose, impact, and growth. High-performance culture and value-driven teams. Competitive base + commission structure. Unlimited PTO

Analyze AI customer interaction data, refine training datasets, optimize AI models, and collaborate with cross-functional teams to improve AI-driven conversations. | Bachelor's degree or equivalent experience in data-related fields, strong analytical skills, experience with data tools like Excel or SQL, attention to detail, critical thinking, and communication skills. | Drips – AI Data Analyst Drips revolutionizes customer engagement with Conversations as a Service (CaaS), delivering scalable, authentic, and data-driven dialogues. As an AI Data Analyst, you will play a critical role in shaping the performance and accuracy of AI-powered conversational systems by analyzing model outputs, refining data pipelines, and ensuring the continuous improvement of AI-driven interactions. In a world where customer engagement depends on precise, effective AI, Drips differentiates itself by leveraging high-quality data to power meaningful, human-like conversations. Your role will focus on assessing model launch success, curating clean and structured datasets for AI training, and identifying trends to enhance system performance. By applying analytical rigor, strategic problem-solving, and a passion for AI, you will help optimize Drips’ AI models to drive engagement, compliance, and customer satisfaction. This is an entry-level position that blends data analysis, model evaluation, and cross-functional collaboration to enhance AI effectiveness while maintaining the highest standards of accuracy and compliance. Responsibilities:AI Data Analysis & Intent Modeling • Analyze AI-powered customer interactions across multiple client use cases and calls to action, ensuring AI models accurately interpret consumer intent. • Structure and refine training datasets to improve AI decision-making, ensuring the system adapts to real-world language and evolving consumer behaviors. Model Optimization & Continuous Improvement • Leverage insights from AI Quality Analysts and other stakeholders to refine AI intent models, response selection, and decision pathways. • Implement updates to conversational AI based on reported misclassifications, engagement drop-offs, and areas of confusion identified through quality monitoring. • Work closely with engineering and product teams to test and deploy AI model updates efficiently and accurately. Data Curation & Annotation • Create annotation guidelines and frameworks that standardize how AI training data is labeled and utilized. • Identify gaps or inconsistencies in existing training data, implementing strategies to enhance dataset quality and AI adaptability. Collaboration & Cross-Team Support • Work with AI Quality Analysts to interpret findings from conversation audits and translate them into actionable AI model adjustments. • Partner with product, engineering, and data science teams to refine AI decision-making and conversational flow. Who You Are You are a critical thinker with a keen analytical mindset, capable of dissecting complex data to uncover patterns and drive improvements. You thrive in problem-solving environments, where precision and adaptability are key to optimizing AI models. You have a strong attention to detail, ensuring that AI-driven conversations accurately reflect consumer intent across diverse industries and use cases. You excel at translating data into action, using insights from quality monitoring to refine AI performance and enhance user engagement. You’re comfortable working with large datasets, structuring clean training data, and collaborating across teams to fine-tune AI decision-making. If you enjoy solving challenges, working with cutting-edge AI technology, and making data-driven improvements, this role is for you. Qualifications • Bachelor’s degree in Data Science, Analytics, Computer Science, Linguistics, Mathematics, or a related field (or equivalent 1+ years practical experience). • Strong analytical skills with the ability to interpret data, identify trends, and make data-driven recommendations. • Basic experience with data manipulation tools such as Excel, SQL, Python, or similar (experience with AI training data is a plus). • Attention to detail and the ability to recognize patterns and inconsistencies in language, data, and AI model behavior. • Critical thinking skills to assess AI performance and make informed adjustments based on quality findings. • Strong communication skills to collaborate with cross-functional teams and translate data insights into actionable improvements. • Ability to learn and adapt in a fast-paced AI-driven environment with evolving technologies and methodologies. • Experience with AI models, NLP, or conversational AI (preferred but not required). Applicant Instructions: To be considered for the AI Data Analyst position, all applicants must submit a cover letter along with their resume. The cover letter should address the following requirements: • Highlight two or more of the following skillsets, with specific examples: • Experience analyzing customer interaction data (e.g., chat, SMS, or email) to identify trends, improve AI intent recognition, or enhance model performance. • Familiarity with AI-driven tools or platforms, such as ChatGPT, Copilot, Grok, or similar technologies, and how you have used them for data analysis, AI training, or model evaluation. • Data analysis expertise, including experience structuring datasets, generating reports, or identifying patterns using tools like Power BI, Excel, SQL, Tableau, or other data visualization software. • Ability to interpret and apply quality findings from AI models to refine intent mapping, improve AI responses, and optimize system performance. • Experience working with large datasets to train AI models, improve data accuracy, or support automation in a customer engagement or AI development setting. • Proven ability to manage multiple priorities in a fast-paced, analytical environment, demonstrating problem-solving skills and adaptability. • Write the cover letter with a tone that demonstrates enthusiasm for the role and your passion for AI-powered customer engagement. Include how your background aligns with Drips' mission to transform customer interactions. • Mention which Drips Core Value (available on our website) resonates most with you and explain why. • Keep your cover letter under 250 words. Failure to follow these instructions may result in your application being disqualified. We value attention to detail and clear communication, so make sure your application reflects these qualities!