Manager / Sr. Manager, Technical Operations

About this role

About Spark Advisors

We're building healthcare tech for a system that desperately needs it.

Each year, millions of Americans deal with confusing changes to their Medicare plans that impact their prescriptions, access to care, and pocketbooks. These aren’t just inconveniences – they are potentially life-altering changes that leave seniors medically and financially vulnerable.

Independent Medicare advisors play a crucial role in guiding seniors through this complexity and helping them find the right coverage for their needs. But their ability to be effective healthcare advocates has long been hamstrung by broken tools and outdated systems.

Spark is fixing that. We’re the fastest-growing Medicare platform in the country, combining AI, an industry-leading CRM, and client services to transform how 10,000+ brokers acquire, enroll, and support clients in their local communities.

Join a talent-dense team from Square, Ramp, Yext, Oscar, and Cedar — backed by Primary Ventures and Viewpoint Ventures — that is serious about building technology to expand access to quality healthcare. We offer remote work, sabbaticals, company retreats, and other generous benefits that earned us recognition as one of Inc. Magazine’s Best Workplaces of 2025

Healthcare is overdue for innovation. Let’s redefine what its future looks like — together.

Summary Spark Advisors is building the technology backbone for a modern Medicare distribution platform — supporting thousands of independent agents with compliant, AI-augmented tools. We're looking for a hands-on leader to own Technical Operations: the intersection of IT, security, DevOps, and infrastructure that keeps our AWS-native platform reliable, compliant, and secure as we scale. This is a foundational hire. You'll be the first dedicated owner of this domain, building out policy, tooling, and a team as appropriate, while working shoulder-to-shoulder with engineering leadership on a live, regulated production environment. You'll report directly to the CTO and have significant influence over how the function is structured and staffed. AI is core to how we operate, not a side initiative. We expect this function to run lean by design — using AI agents and tooling to extend what a small team can own, from infrastructure and security operations to how the broader org works day to day. You'll be expected to bring a point of view on where AI genuinely replaces manual toil versus where it adds risk, and to build the function with that judgment baked in from day one. What You'll Do AI-Enabled Operations

Apply AI/agentic tooling to DevOps and infrastructure work; automated remediation, anomaly detection, capacity and cost optimization, and agent-assisted incident response and runbook execution

Apply AI to InfoSec; AI-assisted log/alert triage, compliance evidence collection, vulnerability prioritization, and phishing/threat detection — while maintaining human sign-off on anything security-critical

Drive org-wide AI enablement for technical operations: evaluate and roll out agentic tooling to support the broader organization

Set guardrails for safe AI adoption in a regulated environment — data handling, auditability, and model/tool vetting — so speed doesn't come at the cost of compliance

DevOps & Infrastructure

Own the reliability, scalability, and cost-efficiency of our AWS-native infrastructure (Lambda, Step Functions, Kinesis, Connect, Bedrock, and related services)

Drive CI/CD maturity, infrastructure-as-code practices (SAM/CloudFormation/Terraform), and environment consistency across dev/staging/prod

Own observability: logging, monitoring, alerting, and incident response processes; drive down MTTR

Manage on-call rotations and runbooks; be a calm, decisive presence during incidents

Information Security & Compliance

Own the security posture of a HIPAA- and CMS-regulated platform: policies, controls, risk assessments, and audit readiness

Lead SOC 2 / HIPAA compliance programs, vendor security reviews, and incident response

Partner with engineering on secure-by-default practices (secrets management, least-privilege IAM, PHI handling, encryption at rest/in transit)

Own security awareness training and access governance across the company

IT Operations

Manage corporate IT: employee onboarding/offboarding, endpoint management, SSO/identity (Okta or similar), device security, and helpdesk support

Own vendor and SaaS management, including procurement, licensing, and access reviews

Build scalable, self-serve IT processes appropriate for our headcount

Leadership & Cross-Functional Partnership

Build and lead a small, high-leverage team as the function grows — hire well, and know when not to hire, favoring automation and good tooling over headcount

Partner closely with the VP of Engineering, Data Engineering, and Product on shared infrastructure needs

Represent technical operations to the board, auditors, and enterprise customers/partners when needed

Set and report on operational KPIs; uptime, deployment frequency, MTTR, security findings closure rate

What We're Looking For

5+ years in a technical operations, DevOps, infrastructure, or security leadership role, ideally with 2+ years managing people or leading cross-functional initiatives

Deep hands-on experience with AWS; IAM, networking, serverless, and container services

Direct experience with security compliance frameworks (SOC 2, HIPAA, ISO 27001) — you've been through an audit, not just read about one

Strong infrastructure-as-code and CI/CD chops

Experience operating in a regulated or high-stakes environment such as healthcare, fintech, insurance is a strong plus

A builder's mindset: comfortable with ambiguity, allergic to unnecessary process, and biased toward reversible, incremental decisions

Excellent judgment under pressure — you're often the person who is calm when something breaks in production

Clear communicator who can translate technical risk into business terms for non-technical…