Head of Legal & Compliance

Head of Legal & Compliance About the Role

As Head of Legal & Compliance, you will lead the evolution of Readymode’s Trust Infrastructure and serve as the company’s senior legal, compliance, and regulatory affairs leader.

This is a highly strategic and hands‑on role. You will be responsible for ensuring Readymode, our platform, and our customers operate within the complex and constantly evolving landscape of telecommunications law, including TCPA, TSR, FCC/FTC rules, state‑level calling restrictions, and DNC requirements.

You will also represent Readymode externally as our voice on compliance and regulatory matters. This includes building relationships with regulators, industry associations, policy groups, and other stakeholders, particularly in Washington, DC, where the future of outbound communications, telecom compliance, and consumer protection policy is actively being shaped.

Internally, you will partner cross‑functionally with Product, Engineering, Sales, Marketing, Customer Success, Support, and Executive Leadership to embed compliance into every stage of the customer lifecycle. You will help translate complex legal requirements into clear operating procedures, platform capabilities, customer education, and market‑facing compliance content.

This role is about more than risk management. The right candidate will help turn compliance into a competitive advantage for Readymode by building scalable systems, educating the market, protecting the integrity of our platform, and ensuring Readymode remains a trusted standard for responsible, high‑performance dialing technology.

You will also serve as the first point of contact for inbound legal matters, coordinating with external counsel as needed.

• Develop, implement, and oversee Readymode’s legal risk management, Compliance, and GRC program across North America.
• Serve as the internal authority on telecommunications compliance, including TCPA, TSR, FCC/FTC regulations, STIR/SHAKEN, DNC requirements, Canadian telecommunications rules, and state‑specific restrictions.
• Monitor regulatory, legislative, and enforcement developments and proactively adjust company strategy, policies, customer requirements, and platform controls.
• Maintain rigorous, audit‑ready records of compliance activities, customer reviews, platform usage, regulatory correspondence, customer reporting, and legal matters.
• Develop scalable risk assessment processes that identify vulnerabilities across the customer lifecycle and implement practical controls to mitigate legal, operational, and reputational risk.

• Represent Readymode externally with regulators, policymakers, industry associations, trade groups, and compliance-focused organizations.
• Act as Readymode’s voice in Washington, DC on key issues affecting outbound communications, dialing technology, consumer protection, telecom regulation, and responsible customer engagement.
• Build and maintain strong working relationships with relevant regulatory bodies, industry coalitions, standards groups, and public policy stakeholders.
• Help shape Readymode’s position on emerging regulatory issues and advocate for practical, responsible frameworks that support both consumer protection and legitimate business communication.
• Partner with Executive Leadership to brief the business on regulatory trends, enforcement activity, policy developments, and strategic risks.

• Own and continuously improve customer vetting, onboarding review, and ongoing monitoring processes to protect the integrity of the Readymode platform.
• Ensure customers adhere to Readymode’s Acceptable Use Policy, compliance standards, and responsible dialing expectations.
• Partner with Customer Success, Sales, Support, and Revenue teams to identify customer risk signals and intervene when necessary.
• Make difficult gatekeeper decisions when customer behaviour creates legal, regulatory, platform, or reputational risk.
• Develop escalation processes and enforcement playbooks for customer misuse, complaints, traceback inquiries, regulatory requests,…