Sr. Director of Business Applications & Systems

You are the guardian of our source of truth. Alice runs on a stack of 25+ interconnected SaaS tools, Salesforce, HubSpot, NetSuite, Workato, Gong, Outreach, IronClad, Okta, and more, and when that stack misfires, every team in the company feels it. Your job is to make sure it doesn’t. But ownership isn’t just maintenance. As we scale our GenAI capabilities across the company, the quality of our core systems becomes the foundation everything else is built on. You’ll be the one who ensures that when our GenAI Builder, our RevOps team, or our Finance team needs data, it’s clean, current, and accessible. You’re not a systems administrator. You’re the person who decides alongside with the business opener what the core stack looks like, how it grows, and how to build our agentic layer on top of it. You’ll manage a small team alongside a curated bench of specialized freelancers and subcontractors for deep technical work, and you’ll be the escalation point when things break. You report directly to the CFO. What You’ll Own Core Stack Administration • Own the full tech stack: GTM (Salesforce, HubSpot, Outreach, Gong, ZoomInfo, Seismic), Finance (NetSuite, Stripe, Mesh, Opstream, Dokka, Expensify), Operations (JIRA, Notion, IronClad), and Infrastructure (Okta, Workato, Slack, Google Analytics) some of the tools will be co owned with IT • Ensure data integrity, system reliability, user access governance, and documentation across all platforms • Manage vendor relationships, license renewals, and cost optimization across the portfolio Integration Layer • Own all integrations, with Workato as the primary orchestration platform • Maintain and improve existing integrations • Rationalize complex workflows; eliminate automations that create more problems than they solve • Provide the GenAI Builder with clean, reliable data pipelines as a foundation for AI solutions External Resource Management • Build and maintain a bench of freelancers for deep technical work (SFDC development, NetSuite implementation, Workato orchestration) • Define scopes, manage delivery, and QA external work, you are accountable for outcomes, not just delegation • Know when to build internally vs. bring in external expertise, and make that call quickly, be responsible for the team’s capacity Internal Support Model • Define the internal support model: who handles what, how tier-1 is routed to team members or vendors, and when to escalate • Act as the escalation point when something requires system-level judgment, not the first line of response • Build documentation and runbooks that reduce dependency on any single person GenAI Enablement • Serve as the systems layer that enables GenAI adoption across the company, ensuring that AI builders can connect to reliable, well-structured data • Evaluate and onboard new AI-adjacent tooling into the stack with proper governance • Work closely with the GenAI Builder to ensure integrations and data quality support agentic workflows Business Data Infrastructure & Data Layer • Design and own the architecture of our business data layer: a centralized data store (e.g. BigQuery, Snowflake, or equivalent) fed by our core source systems, Salesforce, HubSpot, NetSuite, HRIS, and others • Define and enforce data governance for the business data layer: what data is included, how it is structured, who has access, and how freshness is maintained, strictly business-oriented data (CRM, finance, HR, operations), not product telemetry or customer content • Ensure the data layer is structured for GenAI consumption: well-documented schemas, consistent naming conventions, and access patterns that allow the GenAI Builder and AI tools to query reliably without going directly to production source systems • Partner with relevant stakeholders to define the data entities and metrics that need to be available in the layer, and ensure the layer evolves to meet new analytical and AI use cases What Success Looks Like in Year One • All core integrations are documented, stable, and monitored with clear escalation paths • The data flowing through our systems is reliable enough to serve as a foundation for AI-powered workflows • A curated bench of trusted external resources is operating on defined scopes with clear accountability alongside an internal team • The internal support model is running without this role being the first line of response • A governed business data layer is live and operational: core source systems (Salesforce, HubSpot, NetSuite, HRIS) are syncing reliably into the data store, schemas are documented, and the GenAI Builder can query data without going to production systems directly • Every team feels like the stack is working for them, not the other way around