Head of Strategic Initiatives

About the Role

Partner with the CEO and executive team to identify, evaluate, and prioritize Ready's highest-value strategic opportunities. Own strategic initiatives from thesis through commercialization, including the business case, market strategy, commercial model, and execution plan. Identify and develop new markets, customer segments, use cases, and business models where Ready has a differentiated right to win. Build go-to-market motions for emerging opportunities in partnership with Product, Revenue, Partnerships, and Programs. Originate and advance high-value opportunities, including statewide, enterprise, and complex multi-stakeholder agreements. Develop lighthouse customers and partners that validate new markets, offerings, and commercial models. Translate market and customer needs into scalable product opportunities in partnership with Product. Build repeatable playbooks around successful initiatives and transition proven motions into Ready's core teams for scale. Measure success through value created, including strategic revenue, pipeline, market expansion, customer adoption, and long-term enterprise value.

Requirements

• Proven senior leadership experience across strategy, go-to-market, business development, product, or enterprise technology.
• Track record of turning ambiguous opportunities into executable strategies and measurable business outcomes.
• Strong commercial instincts with experience developing new markets, offerings, GTM motions, and complex enterprise opportunities.
• Ability to move fluidly between market strategy, customer discovery, product, financial analysis, and commercial execution.
• Strong executive presence and experience building relationships with senior customers, partners, and internal leaders.
• Ability to influence and execute across functions without relying on direct organizational authority.
• Exceptional analytical, problem-solving, written, and verbal communication skills.
• A builder mentality and comfort operating with significant autonomy in environments where the playbook does not yet exist.
• Experience with government, critical infrastructure, telecommunications, utilities, broadband, or other regulated markets is a plus.

About Ready

• Creative problem solvers approaching a legacy industry with a new point of view
• Humble but ambitious, knowledgeable but curious, persistent but not obnoxious
• Concise and effective in written and spoken communication
• Comfortable working remotely with some travel
• One team, one dream

Benefits

• Competitive salary plus meaningful equity upside
• Meaningful executive-level equity participation
• Competitive and expanding benefits for employees and dependents
• 100% remote work with travel as needed
• Teamwide retreats 1–2x per year
• The opportunity to play a defining role in building Ready's next major sources of enterprise value