Senior Manager, GTM Systems

HealthJoy•Chicago, IL

1h•Remote

About The Position

Let’s keep things simple: we are an unbelievably talented, hard-working, and compassionate team driving towards a mission that impacts every single one of us - even you! Healthcare benefits are complex, underutilized and a mystery for most users. We’re removing that complexity. Now more than ever, employers are adding value to their employees’ benefits like telemedicine and mental health services. HealthJoy’s industry-changing tech platform consolidates those benefits into a simplified benefits experience, saving users time and money. HealthJoy has garnered workplace awards for Inc.'s Fastest Growing Startups and Built In Chicago’s Best Places to Work while growing globally to nearly 400 team members. We’re continuing down the path of high growth and high impact, and this role is a key member of the Product Team making that happen. Your impact. HealthJoy is a leading innovator in the healthcare navigation industry, committed to transforming healthcare through cutting-edge technology solutions. Our mission is to improve patient outcomes, enhance healthcare efficiency, and drive innovation in the rapidly evolving healthcare landscape. We are seeking a dynamic and experienced thought leader to join our Revenue Operations team as Senior Manager, GTM Systems. This is a hands-on, senior-level role for a proactive problem-solver with 10+ years of experience who can own our Salesforce platform's configuration and user experience from end-to-end. You'll be responsible for the full lifecycle of our sales and go-to-market data, focusing on data integrity, user support, and delivering actionable insights through powerful declarative tools. This role is crucial for scaling our operations and using our data to drive strategic business decisions with HealthJoy leadership. Desired Outcomes: Architect a Seamless GTM Ecosystem: Act as the definitive owner and final authority for the Salesforce platform and our entire integrated stack (Rattle, DocuSign, Cirrus Insight, and billing/ICM tools). You will ensure these systems are harmonized and resilient, creating a "single source of truth" that allows the business to scale without technical friction. Pioneer an AI-Enabled Revenue Engine: Lead the strategic identification and implementation of "Agentic AI" opportunities (e.g., Agentforce, N8N, or custom LLM integrations). Your success will be defined by shifting the organization toward a self-service model, where automation handles the routine and your team is freed to focus on high-impact innovation. Drive Modernization to Eliminate "The Weeds": Proactively audit and overhaul manual, legacy processes—such as contract renewals and product refreshes—replacing them with automated, resilient solutions. You will be responsible for moving the organization from reactive troubleshooting to proactive system evolution. Function as a Strategic Liaison to FP&A and Leadership: Partner directly with the Director of FP&A to translate complex business requirements into a high-level technical roadmap. You will ensure that our systems are not just operational, but are strategically aligned with financial reporting needs and the broader go-to-market vision. Enablement, Compliance, and Instant Insights: Champion a culture of platform proficiency through strategic user training and rigorous security governance. You will own the permission architecture and compliance standards while delivering "insights at the fingertips"—a suite of real-time dashboards and high-fidelity reporting that empowers leadership to make proactive, data-driven decisions.

Requirements

10+ years of hands-on experience as a Salesforce Administrator.
Proven track record as the Subject Matter Expert (SME) for all things Salesforce, serving as the go-to resource for system configuration, customization and best practices.
Experience architecting, implementing, and maintaining CPQ solutions; Revenue Cloud Advanced experience a plus.
Strong experience designing, building, and managing integrations. including migrating data and processes from legacy software systems to Salesforce.
Demonstrated ability to evaluate integration tools, architect solutions, and ensure seamless data flow across platforms.
Adaptability: Prioritize and thrive in a fast-paced, ambiguous startup environment where priorities can shift quickly.
Proactive Problem-Solver: Don't wait to be told what to do; identify challenges, propose solutions and advocate for needed change.
Communication: Clearly articulate technical concepts to non-technical stakeholders and work effectively across departments.
Business Acumen: Demonstrates strong business acumen with the ability to think strategically, aligning team deliverables with broader business objectives and ensuring work directly supports organizational.
A forward-leaning mindset toward leveraging AI and machine learning to drive and optimize business outcomes. Experience with or a strong desire to learn Agentforce, N8N, or other agentic AI and automation platforms.

Responsibilities

Administer and configure a complex Salesforce platform, including custom objects, fields, workflows, and integrations, while leveraging Salesforce Flows, Lightning Web Components (LWCs), Apex, and other advanced platform capabilities.
Collaborate with Sales, Customer Success, Marketing, Finance, and Product teams to gather requirements and design scalable, maintainable solutions that effectively address business needs while enabling Salesforce best practices.
Ensure data quality and integrity through proactive, regular hygiene audits and updates.
Co-manage cross-functional implementations and the logic and connections of tools that integrate with Salesforce.
Own the end-to-end documentation strategy for Salesforce configurations and business processes.
Directly manage junior admin resources in Salesforce-related projects and day-to-day support.
Leverage new Salesforce features and best practices to drive continuous platform improvement.
Lead a tactical assessment of departmental priorities and resource allocation. Develop a data-driven recommendation for organizational design and process improvements to mitigate bottlenecks, maximize platform ROI, and accelerate the delivery of strategic business outcomes.