Senior Director, CTO Strategic Operations

Waystar • Louisville, KY

3d

About The Position

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. Stepping into a critical seat, you will take ownership of the operational rhythm of the department. You will lead critical initiatives across the Technology organization, provide leadership development to senior technology leaders, and ensure seamless communication and alignment across the organization.

Requirements

• 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
• 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
• 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

Nice To Haves

• Healthcare IT industry experience preferred

Responsibilities

• Strategic Advisory & Leadership Support
• Executive Communication & Presentation Development
• Meeting Orchestration & Facilitation
• Leadership Development & Coaching
• Cross-Functional Program Management
• Organizational Effectiveness

Benefits

• Competitive total rewards (base salary + bonus, if applicable)
• Customizable benefits package (3 medical plans with Health Saving Account company match)
• We offer generous paid time off for our non-exempt team members, starting with 3 weeks + 13 paid holidays, including 2 personal floating holidays. We also offer 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

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed
• Number of Employees: 1-10 employees