Head of Legal & Compliance

As the Director of Compliance, you will lead the evolution of Readymode’s Trust Infrastructure. You are responsible for ensuring our platform and our customers remain compliant with the complex, ever-changing landscape of telecommunications law (TCPA, TSR, STIR/SHAKEN). You are the central authority and strategic leader responsible for codifying trust and integrity across Readymode. This role is about more than oversight; you will be the operational expert ensuring our platform and our customers master the complex, ever-changing landscape of telecommunications law (TCPA, TSR, STIR/SHAKEN). You will lead the evolution of Readymode’s Trust Infrastructure by blending deep regulatory expertise with hands-on operational execution. This means developing robust policies, educating our internal teams from Sales to Product, and acting as a high-level advisor to our customers. Your goal is to transform compliance from a necessary hurdle into a competitive advantage and a business enabler. You will build scalable, proactive systems that protect our reputation and ensure Readymode remains the industry standard for responsible, high-performance dialling. Join us if you are ready to be the pivotal thought leader who embeds integrity across the entire customer lifecycle and sets the standard for responsible dialing technology. Key Responsibilities Develop, implement, and oversee our Compliance & GRC (Governance, Risk, and Compliance) program that meets or exceeds North American regulatory standards. Act as the primary expert on Canadian and US telecommunications laws (including TCPA, FCC/FTC regulations, and state-specific restrictions). Monitor changes in the landscape to proactively adjust company strategy. Maintain and manage the vetting of all customers to protect the integrity of the Readymode platform and ensure strict adherence to our Acceptable Use Policy. Develop and scale risk assessment processes. Identify potential vulnerabilities in the customer lifecycle and implement controls to mitigate legal and operational risks. Act as a thought leader in compliance for Readymode and partner with the Marketing team to produce high-value compliance content Empower the Readymode team, from Sales to Product, by translating complex regulations into actionable operational procedures. Ensure compliance is embedded from the first touchpoint to the end of the customer lifecycle. Build and maintain strong working relationships with regulatory authorities and industry groups. Maintain rigorous, audit-ready records of all compliance activities, customer reporting, and platform usage to ensure 100% transparency at all times. Partner with Engineering and Product teams to integrate compliance features (like state calling restrictions and DNC management) directly into the Readymode platform. Skills & Qualifications 8+ years of experience in Compliance, Legal, or Regulatory Affairs, preferably within the SaaS, Telecommunications, or FinTech sectors. Deep understanding of TCPA, TSR, STIR/SHAKEN, and DNC registries. Familiarity with data privacy frameworks (ie CCPA) is a significant asset. Proven ability to build a compliance function from the ground up in a high-growth environment. You know how to make compliance a "business enabler" rather than a bottleneck. Exceptional ability to communicate complex legal requirements to non-technical stakeholders and customers. Unwavering ethical standards and the ability to make difficult gatekeeper decisions to protect the company’s reputation. Bachelor’s degree in Law, Business, or a related field. A Juris Doctorate is preferred. Why Readymode? Make real impact – Shape our trajectory as we scale a profitable, established platform Report directly to the COO Clarity and structure – We run on EOS: clear priorities, defined accountability Talented team – Work with driven people who value execution and results Competitive package – Strong compensation including equity opportunity EOS Readymode runs on the Entrepreneurial Operating System (EOS), a proven framework that helps us maintain clarity, accountability, and alignment across the organization. As Director of Compliance, you'll work within this system to set quarterly Rocks, track weekly scorecard metrics, and participate in our structured meeting rhythms. Experience with EOS is a plus, but we're committed to supporting the right candidate in learning and thriving within this framework.