Drips

Lead an integration team and oversee client integration delivery, strategy, documentation, and escalation of complex compliance-sensitive projects. | Requires 5–8 years in technical implementations or SaaS delivery, 2 years of direct team management, APIs, webhooks, Azure Logic Apps, and a bachelor’s degree. | About Drips Conversations that click. Drips delivers two-way conversations that get responses, drive action, and lead to real outcomes. Instead of one-way outreach — texts, alerts, and calls people didn't ask for — Drips asks a question, and the response is what moves people to action and drives results for the organizations we serve. Across healthcare, insurance, education, and financial services, Drips teams work continuously to help clients get results where it counts: care gaps closed, medications refilled, enrollments completed, and more. W e don't chase metrics — we deliver outcomes, backed by nearly a billion regulated-industry conversations and ten years of zero compliance violations. Drips' focus on empowering enterprises to drive real, meaningful conversations with consumers has sparked rapid growth since the company was founded in 2016. W e are well funded and looking to accelerate the next era of growth and expansion of our team. We're more than just a high-growth company — we're a community . Even though we work remotely , we've fostered a one-of-a-kind work environment by embracing our core values: Lean, Improve, Happiness, Team, Passion, and Curiosity . If you want to love the productyou work on, solve hard problems, and grow your career — we want to talk with you! Job Overview The Integrations Manager / Team Lead owns Drips' integrations function end to end: the technical delivery of client integrations (APIs, webhooks, FTP/SFTP , Azure Logic Apps) across onboarding and production support, and the people leadership of the team that delivers them. This is the first dedicated people-management role for Integrations at Drips — the Manager will build and grow a team of Integration Project Managers/Specialists, set the technical and process standards the team works to, and remain hands-on for the highest-complexity or compliance-sensitive client integrations (e.g., HIP AA/Medicaid-adjacent, enterprise EA migrations). The role reports to the VP of Operations and partners closely with Engineering, Production, Client Success, and QA to ensure integrations are delivered on time, with data integrity , and with documentation standards that support scale. Duties / Responsibilities Team Leadership & People Management Build, lead, and mentor a team of Integration Project Managers/Specialists, including hiring, onboarding, and career development. Set clear goals and expectations for direct reports; conduct regular 1:1s and performance reviews. Allocate team resources and capacity across competing client implementations based on priority and complexity . Foster a culture of accountability , ownership, and continuous improvement within the team. Integration Strategy & Program Ownership Own the integration strategy and roadmap for Drips, aligned to broader Operations objectives. Define and track KPIs such as integration cycle time, first-time launch success rate, UAT defect rates, and post-launch client-reported issues. Partner with Product and Engineering to prioritize tooling and platform improvements that increase integration capability and scale. Design and refine repeatable, documented integration processes, including intake and prioritization workflows. Technical Delivery Oversight Oversee integration delivery across APIs, webhooks, FTP/SFTP connections, Azure Logic Apps, and billing/data workflows. Serve as the escalation point for complex, high-risk, or compliance-sensitive integrations (e.g., HIP AA-adjacent, enterprise migrations). Ensure documentation standards — data mapping specs, API documentation, testing/acceptance criteria — are maintained consistently across the team. Validate data mappings, authentication methods, and system configurations for high- complexity engagements. Cross-Functional Collaboration Partner with Client Success, Production, Engineering, and QA to ensure integrations align with platform standards and client expectations. Represent the Integrations function in cross-departmental planning and process discussions. Coordinate cross-functional resolution of integration-related incidents and risks. Reporting & Executive Visibility Report on team performance, project/portfolio status, and risk exposure to the VP of Operations. Build and maintain dashboards (e.g., Tableau, DCC dashboards) that provide visibility into integration health, throughput, and risk. Create and maintain the reporting and tooling that give leadership visibility into integration throughput, risk, and capacity as Drips' client base and integration volume scale. Skills & Qualifications 5–8 years of experience in integration project management, technical implementations, or SaaS delivery environments, including 2+ years directly managing a team. Proven people leadership: hiring, coaching, performance management, and career development for technical staff . Strong technical fluency with APIs, FTP/SFTP integrations, webhooks, authentication methods, and network connectivity troubleshooting. Proficiency with Microsoft Azure, particularly Azure Logic Apps and related monitoring/DevOps tooling. Experience building repeatable implementation processes, documentation frameworks, and intake/prioritization workflows. Familiarity with SQL and Excel for validating integration outputs and troubleshooting data discrepancies. Exceptional written and verbal communication; able to lead client-f acing technical discussions and translate technical detail for executive audiences. Experience with structured tracking tools such as ClickUp, Jira, or Azure DevOps. Bachelor's degree in Computer Science, Information Systems, Engineering, or related field preferred but not required. Hands-on, keyboard-level comfort with the work itself — able to dig into APIs, logs, configurations, and data mappings directly , not just manage through others, especially for complex or escalated integrations. Preferred Qualifications Experience in telephony/SMS, T CP A/HIP AA-adjacent, or other regulated-data integration environments. Experience with billing processors or financial transaction systems. Exposure to DevOps practices and CI/CD deployment environments. Experience building dashboards or reporting frameworks for operational visibility (e.g., Tableau). Prior experience managing managers or team leads, not just individual contributors. Cover Letter Requirements Please include a brief cover letter describing your experience leading technical integration teams, managing client-facing escalations, and working with APIs, webhooks, or FTP/SFTP integrations in a regulated or compliance-sensitive industry. 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 Integrations Manager / Team Lead is expected to live these values in day-to-day work. Lean – Saves cycles for the team and for clients by building repeatable integration processes, clear documentation, and automation instead of one-off fixes. Improve – Treats every escalation and defect as a chance to strengthen the integration framework; looks for root cause, not just the symptom, and turns lessons learned into updated playbooks and tooling. Happiness – Builds a team environment where Integration Project Managers/Specialists feel supported, coached, and set up to do their best work. Team – Partners openly with Engineering, Production, Client Success, and QA; takes ownership of integration outcomes rather than pointing to other teams. Passion – Brings energy and pride to solving hard, client-f acing technical problems and to growing the Integrations function as Drips scales. Curiosity – Asks questions, digs into how systems actually behave, and stays current on integration technologies and practices that could improve Drips' platform.

Lead Solutions Consulting team to convert market opportunities into signed business and manage operational infrastructure and KPIs. | 8-12 years in product strategy or solutions consulting with 2-3 years team management and a bachelor's degree in business or related field. | Director of Market Solutions Position Summary: We are seeking an analytical and hands-on Director of Go-to-Market Strategy & Solutions Consulting to bridge the gap between what Drips could build, what Drips should sell, and the team that helps capture it. This role sits within Market Solutions and carries two connected halves of one mandate: defining and sizing market opportunities before they ever reach Product's roadmap or Sales' pitch deck, and leading the Solutions Consulting team that turns qualified opportunities into scoped, signed, executable business. The ideal candidate will not only lead market and competitive analysis but will build the operational infrastructure, team KPIs, coverage models, and reporting, needed to measure whether the opportunities identified are actually being captured. If you are passionate about market strategy, energized by building and running a team, and enjoy working at the intersection of product, commercialization, and pre-sales execution, this role is for you. Who You Are: This role is for someone who gets real satisfaction from figuring out what's true about a market before anyone else does, and who wants the responsibility of building a team that can prove it. You think in evidence, not hunches, and you're the kind of person who'd rather sit with an unanswered question than settle for the first plausible answer. You are comfortable holding ambiguity and bringing structure to questions nobody has answered yet. You carry two different kinds of authority comfortably. When you don't have the title to back an idea, you earn the room through the quality of your thinking. When you do have the authority, over a team, a quota, how the work gets done, you use it fully. You'd rather build the process yourself than wait for someone to hand it to you, and you'd rather own an outcome than just advise on one. What actually drives you is watching something travel the whole distance: a read on the market that becomes a business case, a business case that becomes a team's mandate, and a team that closes the gap between what's possible and what's real. You're not satisfied being the person with the good idea; you want to be the person who builds what makes it true. Key Responsibilities: Own Market and Competitive Intelligence: Maintain a current view of the competitive landscape and broader market trends, and turn findings into point-of-view documents that inform roadmap and positioning decisions. Build Strategic Recommendations: Pick up signals from sales calls, Solutions Consulting, Customer Success, and product roadmap conversations, research open strategic questions such as new capability areas and potential partner opportunities, and bring forward a clear recommendation, not just a summary of options. Size and Assess Product Opportunities: Partner with Product and Engineering leadership to evaluate incoming capability ideas, sizing the market (TAM/SAM/SOM) and assessing strategic fit, without owning execution, delivery, or the final call. Draft Commercial Briefs: Prepare Commercial Briefs, structured recommendations on what to commercialize and why, for the early 'Assess' stage of Drips' go-to-market process, and present them to the cross-functional leadership group that reviews and prioritizes new ideas. Translate Capabilities Into Sellable Packages: Define the use case behind new capabilities and work with subject matter experts across targeted industries to establish the ideal client profile, then build repeatable frameworks and playbooks that can be reapplied as Drips expands into new verticals. Lead the Solutions Consulting Team: Hire, coach, and manage a team of Solution Consultants who take qualified opportunities from discovery through proposal delivery, ensuring the team has the skills, coverage, and support to do that work well. Elevate the Team's Operating Infrastructure: Build on the existing KPIs, SLAs, quota structure, and coverage model for Solutions Consulting, sharpening and scaling them so the department can keep growing without outgrowing its own process. Drive Alignment Post-Decision: Once direction is set, help communicate and align Product, Sales, Solutions Consulting, and Marketing around it. Qualifications: Bachelor's degree in business, marketing, or a related field, or equivalent experience. 8 to 12 years of experience in product strategy, product management, solutions consulting, sales engineering, or a hybrid strategy/pre-sales role, ideally in B2B SaaS, including at least 2 to 3 years directly managing or mentoring a team. Experience working in or selling into healthcare, insurance, education, or another highly regulated industry, or a demonstrated ability to ramp quickly in a regulated market. Demonstrated experience turning market or competitive research into an actual business case or roadmap recommendation, not just a research summary. Experience building or maturing operational infrastructure for a team, such as KPIs, SLAs, coverage models, or quota structures, including experience scaling systems that already exist as a team grows. Ability to identify risks in a potential opportunity and outline mitigation plans, not just build the case for pursuing it. Comfort both establishing new process where none exists yet, on the market strategy side of this role, and maturing and scaling existing process as a team grows, on the Solutions Consulting side. Comfort operating without formal authority on strategic recommendations, paired with full ownership and accountability for team management and operations. Strong written and verbal communication skills, including comfort presenting analysis and recommendations directly to senior leadership. Comfort communicating directly with clients. This role leads a team that works face-to-face with Drips' clients, and should be just as comfortable stepping into a client conversation as presenting internally. Working knowledge of market-sizing frameworks (TAM/SAM/SOM) and competitive analysis methods. Experience partnering closely with Product and Engineering teams without owning execution is a plus. Familiarity with generative AI tools to enhance and automate workflows, such as research synthesis, reporting, or drafting, is a plus. Applicant Instructions: All applicants are asked to submit a cover letter alongside their resume that contains the following details: Include two or more of the Key Responsibilities listed above that you have direct experience with and feel confident discussing. Mention the Drips core value (available on our website) you embody the most. Include your salary requirements or range. Keep the cover letter under 250 words.