Sales & Marketing Technology Lead

Sales & Marketing Technology Lead (Mid-to-Senior) We are looking for a mid-to-senior level Sales & Marketing Technology Lead to take ownership of our entire sales and marketing tech ecosystem—not just HubSpot. This role goes beyond administration and into architecture, integration, and strategic execution. You will be responsible for building and optimizing the operational backbone that powers our go-to-market teams, ensuring all systems, tools, and data flows are aligned, scalable, and efficient. As Skyline continues to grow through acquisitions, you will play a critical role in integrating new businesses and standardizing processes across the organization. Key Responsibilities Tech Stack Ownership & Governance Own and manage the full Sales & Marketing tech stack (HubSpot, AccuLynx, CallRail, Airtable, n8n, and others) Audit current tools and workflows to identify inefficiencies and opportunities for optimization Manage vendor relationships and lead the evaluation and implementation of new technologies across teams Workflow Architecture & Automation Design, build, and maintain scalable workflows to automate lead routing, sales handoffs, lead scoring, and internal notifications Reduce manual processes and improve operational efficiency across marketing and sales functions CRM & Data Architecture (HubSpot + Beyond) Act as the primary owner of HubSpot while ensuring seamless integration with the broader tech stack Maintain CRM integrity as the source of truth by managing data structure, deduplication, and reporting accuracy Build and optimize email drip campaigns and lead nurturing sequences aligned with the customer journey M&A Integration & Data Migration Lead the technical onboarding of newly acquired companies into the existing systems Own CRM data migration, property mapping, and pipeline standardization across brands Clean and reconcile legacy data to ensure consistency and usability from day one Integrations & Systems Connectivity Design and manage integrations across platforms using tools like Zapier, APIs, webhooks, and low-code automation tools Ensure real-time, reliable data flow between systems to support decision-making and reporting Project Management & Execution Own tech-driven projects end-to-end—from scoping and planning to execution and optimization Troubleshoot system issues and remove operational bottlenecks across the tech stack Act as the bridge between business needs and technical implementation The Ideal Candidate Tech-Savvy Operator 3–6+ years of experience managing HubSpot and/or similar CRM/MarTech platforms Comfortable quickly learning and optimizing new tools beyond HubSpot Systems Thinker Strong understanding of workflows, integrations, APIs, and data architecture Thinks in logic (if/then), and understands how systems impact the full funnel M&A & Data Mindset Experience with data migrations, onboarding new business…