Drips

Reviewing and responding to customer messages, auditing chat data, and supporting training and testing activities. | Strong attention to detail, excellent communication skills, experience with auditing or training, and reliable internet access. | Customer Experience Chatroom Operator (Full-Time) (Remote) About the Role: Drips is seeking dedicated and detail-oriented individuals to join our remote team as a Customer Experience Chatroom Operator. This full-time position plays a critical role in ensuring seamless, high-quality interactions with consumers through our AI-driven conversational SMS platform. This role focuses on handling sensitive and enterprise-level conversations. Additionally, operators in this role will assist with auditing chatroom data, providing training, and supporting client demo testing. Every day, Drips powers millions of automated, humanized conversations for our clients, but automation isn’t always enough. When our AI encounters uncertainty in a consumer response, you and your teammates step in to interpret and respond to messages appropriately, ensuring an optimal customer experience. Your accuracy is critical—your responses help train and improve our AI model while ensuring a positive customer interaction. Full-time: 40 hours per week Shifts: This role is staffed from 8 AM – 12 AM EST. Work from home with remote training conducted via Zoom Key Responsibilities: Review and respond to inbound text messages using pre-set canned responses. Enhance canned responses to add context and a human touch. (Example: If a user says they’re sick, you might add: “Sorry to hear that!”) Handle enterprise-level and sensitive conversations with professionalism and discretion. Audit chatroom data for accuracy, compliance, and AI training improvements. Assist in training new chatroom operators and sharing best practices. Support client user acceptance testing (UAT) by evaluating and providing feedback on chat interactions. Balance efficiency with high-quality responses to maintain low wait times and minimize backlog. Maintain a high level of response quality—interactions are evaluated using a 1-4 rating scale for accuracy and effectiveness. What We’re Looking For: Exceptional attention to detail and commitment to accuracy. Strong typing skills (no 'hunt and peck' typing). Excellent grammar, spelling, and logical reasoning skills. Ability to interpret user intent when messages contain typos, slang, or ambiguous phrasing. Clear and professional written communication. Reliable and responsible for adhering to a designated schedule. Ability to handle and analyze sensitive customer interactions. Experience with auditing and training is a plus. Access to a stable and secure private internet connection (company computer provided). If you’re a detail-oriented, tech-savvy communicator who thrives in a fast-paced environment, we’d love to have you on our team! Apply today!

Monitor, troubleshoot, and support cloud-based integrations and workflows, ensuring data accuracy and incident resolution. | Experience with Azure, APIs, FTP/SFTP, and incident management in a support or operations environment. | Software Technical Support Specialist 1 Role Overview The Software Technical Support Specialist 1 is responsible for monitoring, triaging, and resolving production issues across Drips’ core systems, with a focus on Azure Logic Apps, FTP-based integrations, and billing/data workflows. This role serves as the first line of defense for production-impacting incidents, ensuring data accuracy, prompt incident response, and clear communication with internal stakeholders. You will partner closely with Engineering, QA, and Production teams to investigate system alerts, diagnose integration or configuration problems, and document both the issue and the resolution path for future reuse. This role closely works with the Drips implementation team, helping implement client programs accurately, swiftly and at volume. This role sits at the intersection point for all Drips operations. This is an ideal role for someone who enjoys technical troubleshooting, structured processes, and continuous improvement. This is a remote role within Drips’ Production department. While the schedule is generally flexible, candidates who are able to work a second-shift (afternoon/evening) schedule are strongly preferred to provide coverage for later-day production monitoring and incident response. Key Responsibilities Monitor and Support Systems Proactively monitor system health, alerts, and integrations in Azure (Logic Apps, related services) and other monitoring tools. Identify anomalies or failures in near real time and ensure appropriate escalation to internal teams when needed. Help refine monitoring thresholds, alerting rules, and dashboards as the environment evolves. Troubleshoot Technical Issues Diagnose and resolve software, configuration, and integration issues across Azure Logic Apps, FTP/SFTP connections, APIs, and related workflows. Perform structured root-cause analysis on incidents, including reviewing logs, API responses, and configuration history. Recommend and implement repeatable fixes and guardrails to prevent recurrence. Integration & Workflow Management Oversee Logic App and FTP integrations, ensuring reliable and accurate data flow between Drips and third-party systems. Validate data mapping, file formats, and connection settings align with expected configurations. Support billing and data integration workflows, helping to identify where data is missing, malformed, or misrouted. Act as a key stakeholder in the client implementation process, working collaborative with integration specialists, helping solution and implement new client integrations Incident Response Serve as the first point of contact for billing processor failures and other production-impacting incidents. Quickly assess severity and customer impact; initiate appropriate escalation paths and communication. Track incidents from detection through resolution, ensuring proper closure and documentation. Cross-Functional Collaboration Work closely with Engineering, QA, Production, and Client-facing teams to identify, document, and resolve system defects or recurring failure patterns. Translate complex technical issues into clear, concise language for both technical and non-technical stakeholders. Participate in process-improvement and automation initiatives related to monitoring, alerting, and support workflows. Documentation & Knowledge Management Create and update tickets in Azure DevOps (or equivalent tools), ensuring each issue is fully documented from initial report through resolution. Maintain internal knowledge base articles for recurring issues, standard operating procedures, and runbooks. Contribute to training and troubleshooting materials for internal stakeholders. Data Accuracy & Reporting Update system data from third-party sources where needed, ensuring integrity, compliance, and consistency across systems. Identify trends in recurring technical issues and provide structured reporting and insight to leadership. Support the development of monitoring and incident dashboards for visibility into failures, response times, and remediation outcomes. Required Skills & Experience Professional experience: Typically 2–5 years in a technical support, production support, systems operations, or similar role in a software/SaaS environment. Cloud & Integration Technologies Proficiency with Microsoft Azure, especially Logic Apps and related DevOps/monitoring tooling is required. Working understanding of FTP/SFTP integrations, APIs, and network connectivity troubleshooting (timeouts, DNS, authentication, credential issues, etc.). Data & Analysis Familiarity with SQL and Excel for investigating data issues, validating assumptions, and supporting ad-hoc analysis. Comfort reading and interpreting error logs, API responses, and system health metrics. Problem-Solving & Execution Strong analytical and problem-solving skills with high attention to detail and data accuracy. Ability to manage multiple incidents and workstreams simultaneously in a high-volume, time-sensitive environment. Communication & Collaboration Effective written and verbal communication skills, including the ability to distill complex technical issues into clear documentation for broader audiences. Demonstrated success working cross-functionally with Engineering, QA, and Operations/Production teams. Mindset & Work Style Process-driven, with a focus on root cause analysis, repeatable procedures, and identifying opportunities for automation and improvement. Organized, reliable, and comfortable working with structured ticket queues, SLAs, and documented workflows. Preferred Qualifications Education: Bachelor’s degree in Computer Science, Information Systems, Engineering, or a related technical field preferred but not required. Experience working with: Production support for billing, payment processors, or other financial/transactional systems. High-volume, integration-heavy environments where data moves between multiple internal and external systems. Incident management, ITSM, or DevOps tools (e.g., Azure DevOps, Jira, ClickUp) for structured tracking and collaboration. Exposure to or interest in: Building or refining monitoring and alerting strategies for cloud-based applications. Automation of routine operational tasks and incident workflows. Drips Core Values & How This Role Embodies Them At Drips, our work is grounded in a set of core values that shape how we show up for our clients, our teammates, and our product: Lean, Improve, Happiness, Team, Passion, and Curiosity. The Software Technical Support Specialist 1 role is expected to live these values in day-to-day work. Lean – Saves cycles for clients and teammates by using data, clear processes, and automation to solve problems efficiently. You focus on accurate triage, right-sized solutions, and thoughtful prioritization of incidents and requests. Improve – Treats every incident and failure as a chance to get better. You look for root causes (not just symptoms), contribute to better monitoring and workflows, and help turn lessons learned into updated runbooks, SOPs, and tooling. Happiness – Brings solutions, not just complaints. You communicate clearly and calmly under pressure, focus on unblocking others, and help create a support experience that builds trust with internal teams and clients. Team – Works with (not around) other departments to get to the right answer. You collaborate closely with Production, Engineering, QA, Client Success, and others, share context openly, and respect the priorities and workloads of partners across Drips. Passion – Cares deeply about the quality and stability of our systems. You take ownership of your queues and projects, lean into complex issues, and look for ways to go beyond “good enough” in monitoring, triage, and follow-through and implementations. Curiosity – Asks “why” and “what if” when something breaks or doesn’t behave as expected. You thoughtfully strive to understand support requests to deliver deeper value beyond the surface level. You dig into logs and data, learn from subject-matter experts, and use each new scenario to broaden your understanding of Drips’ platform and clients. Living these values is a key part of success in this role and in the Production organization more broadly. Compensation & Career Path This role sits within Drips’ Software Technical Support job family and is part of a defined growth path based on experience, scope, and impact. About Drips Drips is the founder of Conversations as a Service, and helps organizations orchestrate large-scale, 1:1 conversations at critical moments in the customer journey, enabling more personalized and effective outreach across channels. By combining technology, thoughtful design, and data-driven insights, Drips supports clients in driving engagement, conversions, and long-term customer relationships. As part of the Production organization, this role is central to ensuring that Drips’ systems are reliable, accurate, and ready to support those conversations at scale. Equal Opportunity Drips is an equal opportunity employer. We are committed to building a diverse and inclusive team and do not discriminate on the basis of race, religion, color, national origin, gender, gender identity or expression, sexual orientation, age, disability, veteran status, or any other protected characteristic. We welcome applicants from all backgrounds and experiences who are excited about the role and our mission.

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!