Senior Director, CTO Strategic Operations

Overview Waystar provides market‑leading technology that simplifies and unifies healthcare payments. Our cloud‑based platform helps healthcare providers focus on what matters most: their patients. We are a mission‑driven organization operating at the intersection of healthcare, finance, and technology, processing billions of transactions annually. The Senior Director of CTO Operations serves as a strategic partner, trusted counsel to, and force multiplier for the Technology organization. This is not an administrative role; it requires executive experience, strategic thinking, and the ability to be the organizational glue across the technology organization. You will take ownership of the operational rhythm of the department, lead critical initiatives across the Technology organization, provide leadership development to senior technology leaders, and ensure seamless communication and alignment across the organization. Responsibilities Strategic Advisory & Leadership Support Serve as a trusted advisor and thought partner to the CTO and leadership team on strategic initiatives, organizational challenges, and leadership decisions. Provide candid feedback on leadership approach, communication strategies, and executive decision‑making. Act as a sounding board for new ideas, helping to refine and pressure‑test concepts before broader implementation. Support the CTO and leadership team in working through complex organizational and strategic challenges. Executive Communication & Presentation Development Design, develop, and produce executive‑level presentations for Board of Directors meetings. Create comprehensive business review decks for CEO and senior leadership audiences. Develop compelling presentations for leadership conferences and strategic planning sessions. Ensure all executive communications to the Technology organization reflect strategic priorities and organizational messaging. Meeting Orchestration & Facilitation Organize, prepare agendas for, and facilitate weekly senior leadership Technology staff meetings, ensuring productive outcomes and clear action items. Choose and drive content that aligns with strategic messaging priorities for weekly technology organization all‑hands meeting. Ensure meeting cadences support organizational alignment, transparency, and rapid decision‑making. Leadership Development & Coaching Provide daily coaching on organizational challenges, staff management issues, and leadership effectiveness. Foster a culture of innovation, psychological safety, metric‑based decision‑making, and high velocity. Guide VP’s on strategies to influence the CTO and executive leadership more effectively. Support leadership development across the technology organization through mentorship and counsel. Cross‑Functional Program Management Lead complex, cross‑functional initiatives requiring coordination across multiple departments. Serve as liaison between the technology organization and other business units to ensure alignment and collaboration. Be a vocal conscience for reflection on the cross‑functional consequences of the Technology department’s strategy. Organizational Effectiveness Identify opportunities to improve technology organization effectiveness, processes, and culture. Drive implementation of organizational initiatives and change management efforts. Monitor departmental health metrics and provide insights to senior leadership team. Qualifications Experience 15+ years of progressive leadership experience, with significant time in executive or senior management roles. Extensive background leading organizations in technology or related industries. A technical degree (CS/Engineering) or equivalent technical fluency is highly valued – you must be able to “speak engineer” and understand technical use cases in the Healthcare IT market space. Previous experience in Chief of Staff, VP Engineering/CTO, VP Operations/COO or similar strategic leadership role strongly preferred. Healthcare IT industry experience preferred. Skills & Competencies Exceptional strategic thinking and business acumen with the ability to see around corners and anticipate organizational needs. Possess the courage and psychological safety to constructively coach senior technology leaders on strategic and operational risks in their organizations. An uncanny ability to distill complex, ambiguous problems into clear, actionable frameworks. Outstanding executive communication skills, both written and verbal, with experience presenting to C‑suite and Board‑level audiences. Advanced presentation development skills with the ability to distill complex information into clear, compelling narratives. Proven ability to influence without authority and build credibility with senior leaders. Strong coaching and mentoring capabilities with a track record of developing high‑performing leaders. Expert facilitation skills with the ability to drive productive discussions and consensus among senior stakeholders. Excellent project and program management skills with the ability to drive results across organizational boundaries. High emotional intelligence with the ability to provide candid, constructive feedback to executives. Demonstrated ability to maintain confidentiality and exercise sound judgment in sensitive situations. Personal attributes: comfortable operating in ambiguity and managing competing priorities, strong executive presence with gravitas to engage peer executives across the organization, diplomatic approach with the ability to navigate complex organizational dynamics – the ability to influence without direct authority, results‑oriented with focus on driving meaningful organizational outcomes. Benefits Competitive total rewards (base salary + bonus, if applicable). Customizable benefits package (3 medical plans with Health Saving Account company match). Generous paid time off for our non‑exempt team members, starting with 3 weeks + 13 paid holidays, including 2 personal floating holidays; flexible time off for our exempt team members + 13 paid holidays. Paid parental leave (including maternity + paternity leave). Education assistance opportunities and free LinkedIn Learning access. Free mental health and family planning programs, including adoption assistance and fertility support. 401(K) program with company match. Pet insurance. Employee resource groups. Equal Employment Opportunity Statement Waystar is proud to be an equal opportunity workplace. We celebrate, value, and support diversity and inclusion. Qualified applicants will receive consideration for employment without regard to race, color, religion, age, sex, national origin, disability status, genetics, marital status, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws. This applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training. #J-18808-Ljbffr Waystar, Inc