Head of Strategic Initiatives

Ready is seeking a strategic, commercially-minded leader to identify and build the next major sources of enterprise value for the company. As Head of Strategic Initiatives, you will work across the executive team, Product, Revenue, Partnerships, and Programs to turn emerging opportunities into scalable businesses—from developing the thesis and validating the market to shaping the offering, building the go-to-market motion, and securing lighthouse customers. This is a hands-on builder role for someone who thrives in ambiguity and is energized by creating the playbook, not simply executing one. About your role at Ready ⚡ 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. A bit about you 🥇 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 About what you get… 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 Equal Employment Opportunity At Ready, we believe that the best ideas come from people with different backgrounds, experiences, and perspectives. We are committed to creating an inclusive workplace where everyone has the opportunity to do their best work. Ready is proud to be an Equal Opportunity Employer. We make all employment decisions based on qualifications, merit, and business needs, and do not discriminate on the basis of race, color, religion, creed, sex, sexual orientation, gender identity or expression, pregnancy, national origin, ancestry, age, disability, genetic information, veteran or military status, marital status, or any other status protected by applicable law. If you need a reasonable accommodation during the hiring process, please let us know — we're happy to work with you to ensure an accessible and equitable experience.