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.

What You’ll Own

Legal, Compliance & GRC Leadership

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.

Regulatory Affairs, Industry Engagement & DC Representation

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.

Customer Vetting, Platform Integrity & Acceptable Use

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, and other compliance events.

Customer Education & Market-Facing Compliance Enablement

Partner with Marketing, Customer Success, Sales, and Product Marketing to create high-value compliance content for customers and prospects.
Develop practical customer-facing resources such as compliance guides, webinars, playbooks, policy explainers, onboarding materials, FAQs, and best-practice documentation.
Help customer-facing teams confidently explain Readymode’s compliance posture, platform controls, and responsible use expectations.
Act as a senior advisor to strategic customers on compliance-related questions, responsible platform usage, and evolving regulatory requirements.
Translate complex regulatory obligations into clear, actionable guidance that customers can understand and operationalize.

Internal Enablement & Cross-Functional Leadership

Educate and empower internal teams across Sales, Customer Success, Support, Product, Engineering, Marketing, and Leadership.
Convert complex legal and regulatory requirements into simple operating procedures, training materials, scripts, approval workflows, and product requirements.
Partner with Product and Engineering to integrate compliance features directly into the Readymode platform, including state calling restrictions, DNC management, consent workflows, customer controls, reporting, and audit capabilities.
Collaborate with Sales and Customer Success to ensure compliance is embedded from first customer touchpoint through onboarding, adoption, renewal, and expansion.
Provide practical, business-minded guidance that enables growth while protecting the company.

Legal Intake & Outside Counsel Management

Serve as the primary intake point for inbound legal matters, including contract reviews, vendor agreements, regulatory correspondence, customer disputes, litigation holds, subpoenas, and other legal inquiries.
Triage legal issues and coordinate with external counsel where specialized advice or formal legal representation is required.
Manage outside counsel relationships to ensure efficient, practical, and cost-effective legal support.
Support contract review processes and help identify recurring legal or commercial risks that should be addressed through templates, policies, or operational controls.

Skills & Qualifications

8+ years of experience in Legal, Compliance, Regulatory Affairs, GRC, or a related function, ideally within SaaS, telecommunications, fintech, contact center technology, adtech, or another regulated technology environment.
Deep understanding of TCPA, TSR, FCC/FTC regulations, STIR/SHAKEN, DNC registries, consent requirements, outbound calling rules, and related telecommunications compliance frameworks.
Familiarity with Canadian telecommunications regulation and data privacy frameworks such as CCPA/CPRA is a strong asset.
Experience engaging with regulators, trade associations, policy groups, or industry coalitions is strongly preferred.
Ability to represent a company externally with professionalism, credibility, and sound judgment.
Proven ability to build or scale a compliance function in a high-growth environment.
Strong business judgment with the ability to make compliance a business enabler rather than a bottleneck.
Exceptional communication skills, with the ability to translate complex legal and regulatory concepts for executives, technical teams, customer-facing teams, and customers.
Experience creating or supporting customer-facing compliance education, thought leadership, training, webinars, guides, or policy content.
Strong cross-functional leadership skills and the ability to influence Product, Engineering, Sales, Marketing, Customer Success, and Executive teams.
Experience managing inbound legal matters, contract review, regulatory correspondence, litigation holds, and outside counsel relationships.
Unwavering ethical standards and the ability to make difficult decisions that protect the company’s reputation and platform integrity.
Bachelor’s degree in Law, Business, Public Policy, Regulatory Affairs, or a related field.
Juris Doctorate strongly preferred, particularly for candidates without equivalent in-house legal or regulatory leadership experience.

What Success Looks Like

Readymode has a clear, scalable legal and compliance operating model.
Customer vetting, monitoring, escalation, and enforcement processes are consistent, documented, and audit-ready.
Compliance is embedded into the product roadmap and customer lifecycle.
Sales, Customer Success, Support, Marketing, Product, and Engineering teams understand how to operationalize compliance in their day-to-day work.
Customers have access to clear, practical compliance education that helps them use Readymode responsibly.
Readymode is viewed externally as a credible, responsible voice in outbound communications and telecom compliance.
Regulatory and legal risks are identified early, communicated clearly, and managed proactively.
Compliance becomes a competitive advantage and a core part of Readymode’s market positioning.

Why Readymode?

Make real impact: Shape the trajectory of a profitable, established, high-growth platform.
Own a broad mandate: Lead both legal and compliance, with direct influence on risk posture, product strategy, customer trust, and industry positioning.
Be our external voice: Represent Readymode with regulators, policymakers, industry groups, and the broader compliance community.
Partner with the business: Work directly with Executive Leadership and cross-functional teams to make compliance practical, scalable, and commercially valuable.
Report directly to the COO.
Clarity and structure: We run on EOS, with clear priorities, defined accountability, quarterly Rocks, and weekly scorecard metrics.
Talented team: Work with driven people who value execution, ownership, and results.
Competitive package: Strong compensation, including equity opportunity.

EOS at Readymode

Readymode runs on the Entrepreneurial Operating System, a proven framework that helps us maintain clarity, accountability, and alignment across the organization.

As Head of Legal & Compliance, you will work within this system to set quarterly Rocks, track weekly scorecard metrics, and participate in structured meeting rhythms. Experience with EOS is a plus, but we are committed to supporting the right candidate in learning and thriving within this framework.

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