Kyle E.

I lead regulated (HIPAA/SOC2/HITRUST) technology initiatives and product companies through their next stage—where the way you’ve been operating won’t get you where you need to go. Sometimes that’s a founder-led startup that needs operational maturity to close enterprise deals. Sometimes it’s a major initiative that needs to move faster without breaking governance. The scale varies. The discipline is the same. At this stage, teams usually don’t need a full COO or operational CTO. They need an operating partner to own execution and stabilize delivery. I make the operating structure fit the work—building it, fixing it, tuning it, or working within it—and I deliver through it. How I Do It Cross-functional delivery leadership from sales to support. Planning, roadmap, and cash flow alignment. Transparency and compliance—OKRs, KPIs, SOC 2, HIPAA. Vendor selection, negotiation, and management. Procurement and outsourcing transitions. Client onboarding and B2B operational processes. Scale without hidden risk. Senior leadership without FTE commitment. Clean handoff to internal teams or a roadmap for when to build internally. I work across the delivery ecosystem—coordinating with HR, finance, and legal so execution doesn't stall waiting on another function. The shape depends on what you need. Let's talk. Why Me • I've seen both sides break: Startup chaos with no structure. Enterprise bureaucracy that slows everything down. I know what "just enough" looks like—and how to build it without overbuilding. • Built for regulated environments: Led operational maturity at a healthcare AI startup—HITRUST certification, SOC 2 readiness, $60M enterprise pipeline enabled. Compliance is easier to build early than bolt on later. • Enterprise transformation at scale: Delivered $50M+ provider data platform across 34 Blue plans. Ran executive workgroups, served as Release Train Engineer, led multi-million dollar procurements. I know how large organizations actually work—and where they get stuck. • Cross-functional fluency: Product management, engineering coordination, infrastructure and security setup, data governance, B2B client onboarding, vendor negotiations, outsourcing transitions. I work across functions so execution doesn't stall. • Ownership, not oversight: I don't manage from slides. I stay close to the work, own outcomes, and tell you what's actually happening. • Effective at different altitudes: Equally comfortable leading executive steering committees and ensuring technology teams are delivering value. I don't write code—I make sure the people who do are set up to deliver. I can establish an SDLC and ensure it's followed, or make sure infrastructure and security deployments follow an approved architecture. The Role I Play I'm not a fractional CTO, COO, or CSO. I operate across those boundaries—building the connective tissue between functions and making organizations ready for what's next. For startups, that means building the operational foundation for scale—structure that enables growth without slowing it down. Landing that first enterprise client. Minimizing pain as sales increase. Demonstrating viability to the next round's investors. For enterprises, that means tuning the system for transformation—speed without breaking what works—to deliver the benefits promised by your transformation strategy. I build the company the leadership team will step into—or the program the organization can sustain after I'm gone. How I Work Engagement model: I work on retainer, project-based, or milestone-based engagements depending on what fits. I'm not looking for a full-time role—I'm looking for ownership of outcomes. For early-stage companies, I'm open to flexible arrangements including equity participation or performance-based bonuses—depending on fit and scope. Team: I embed solo, working directly with a sponsor or leadership team. I work with your existing staff and can lead recommendation and selection of additional vendors or team members as needed. Governance and compliance: I've operated inside enterprise PMOs and built SOC 2/HIPAA compliance at startups. I can integrate with your existing structure or help you build one—I'll adapt to your process or introduce only what you need. Pace: I move fast when the situation calls for it and deliberately when it doesn't. I've seen startup speed and enterprise rigor—I know when each matters and how to coach teams to adapt. Working relationship: I stay close to the work—typically one or two levels from the people doing it. I'll tell you what's actually happening, not what's easy to hear. I expect access to decision-makers and clarity on authority. If you need operational maturity to close enterprise deals or have a major initiative that needs to move faster without breaking governance, let's start with a brief conversation. Message me with what you're building, where execution is stalling, and what success needs to look like.