Director, Engineering Operations & Strategy

Klaviyo•Boston, MA

About The Position

At Klaviyo, the Office of the CTO translates technology strategy into execution at scale. This is a unique role—and we won’t sugarcoat it: the challenges are significant. The reward? Deep ownership, measurable impact, and growth that’s anything but ordinary. If you’re motivated by solving hard problems and working directly with the CTO to build what lasts, this role is for you. You will be the CTO’s force multiplier . You’ll run the engineering operating cadence, drive strategic planning and resource allocation, and partner on mission‑critical programs across platform, data, product, and security. In high‑stakes moments, you will bring crisp judgment, structured thinking, and an executive narrative that moves decisions forward. You’ll model Klaviyo’s values— Drivers wanted, Move fast, no shortcuts, Be meticulous in your craft, Win together —and keep AI at the center of how work gets done. What success looks like in the first 6–12 months? A predictable CTO operating system that clarifies priorities and accelerates decisions within engineering and with partner functions; visible progress on key technical projects and programs, and strong relationships at all levels of the organization.

Requirements

Technical Operator: Seasoned technical leader (8–12+ years) with experience in Chief of Staff, Engineering Strategy, Engineering Operations, or Technical Engineering roles, ideally having supported CTO- or VP-level R&D organizations in high-growth software environments.
Technical Fluency & Problem Solver: Technically fluent, able to discuss architecture and platform trade-offs, linking them to reliability, velocity, and cost. Solves hard problems under pressure, seeks feedback, and learns quickly. High EQ and strong judgment.
Operationally Rigorous & Metrics-Driven: Operationally rigorous and metrics-driven, establishing clear cadences, dashboards, and KPIs for goal-to-delivery. Expertise in OKRs, SLOs, Throughput/Lead Time, headcount plan vs. actuals, and hub ratios.
Strategic Workforce Planner: Expert in engineering org design, capacity planning, headcount management, and budget adherence. Deep understanding of hub ratios, healthy spans & layers, career architecture alignment, and translating technical needs to headcount.
Exceptional Communicator & Influencer: Exceptional communicator with executive presence. Crafts compelling narratives and influences C-level stakeholders and teams at all levels (Product, Eng, Data, Security, Finance, People).
AI-Forward & Innovative: AI-forward, with experience experimenting with AI. Eager to learn and responsibly explore new AI tools for efficiency for self and Engineering organizations.
Meticulous Attention to Detail: Willing to roll up your sleeves and take on any task — from high-level strategy to everyday operational details. Proactive in identifying and solving issues, maintaining the highest quality and consistency even while juggling multiple priorities.
Dynamic & Impactful Leader: Fast-moving, analytical, and structured thinker. Brings order to ambiguity, makes swift, high-quality decisions. Strong, organized leadership, raising the bar on accountability, ownership, urgency, and impact.
Resilient & Mission-Driven: Exhibits grit and determination, resilient to change and context switching. Committed to the organization's mission and values, energized by building for customers at scale.

Nice To Haves

Experience designing platform/infrastructure or developer productivity orgs; familiarity with measuring developer velocity, reliability (SLOs), and cost‑of‑serve.
Background in B2B SaaS or product‑led organizations.

Responsibilities

Be an extension of the CTO — Prep materials and briefings for key decisions and forums; act as proxy in select engagements with clear guardrails.
Operationalize CTO priorities — Translate strategic initiatives into execution by coordinating multi-quarter, cross-functional efforts focused on reliability, productivity, data quality, and cost efficiency, ensuring teams are aligned and accountable for measurable impact.
Proactively surface and solve problems — Create clarity from ambiguity; identify risks early; propose structured options and trade‑offs; keep work moving with urgency. Be a clarity creator.
Run the operating cadence — Drive annual/quarterly planning and OKRs along with Product Ops and Business Ops, planning for Engineering and technical initiatives, weekly staff, technical reviews, and follow‑through; publish crisp inputs/outputs and "what’s decided" artifacts.
Translate roadmaps into resource plans — Partner with Recruiting, Finance, People, and Engineering Leadership to own capacity planning end-to-end. Forecast and reconcile headcount against technical roadmap and budget; and assist in translating approved plans into role charters and structured hiring.
Craft internal and external narratives — Build Board/SLT updates, All‑Hands content, and executive briefs that translate technical choices into customer and business impact.
Institutionalize operational excellence — Make incident/postmortem, risk, and dependency mechanisms visible and durable; raise accountability, ownership, intensity, and impact across R&D.
Put AI at the center — Transform workflows by putting AI at the center, building smarter systems and ways of working from the ground up.

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