
Chief of Staff, CTO
Posted Aug 8

Posted Aug 8
This is a fully remote position, open to applicants in Spain.
β’ Oversee the engineering leadership cadence, which includes director-level syncs, agendas, documented decisions, and follow-through.
β’ Manage the quarterly OKR and QBR cycles, focusing on objective updates, follow-ups, issue escalation, and preparation for reviews.
β’ Keep an up-to-date record of leadership decisions and commitments, ensuring they are followed through to completion.
β’ Identify any stalled or unassigned cross-team tasks and assign clear ownership.
β’ Coordinate special projects through chartering, planning, tracking, and transitioning to permanent owners.
β’ Create concise, decision-ready presentations and materials for the CTO, executive team, and board-level stakeholders.
β’ Guide delegated decisions to completion by means of documentation, escalation, and communication.
β’ Standardize planning, tracking, and communication rituals and templates for engineering leadership.
β’ Collaborate with teams across Product, Data/Analytics, BizOps, Finance, Legal, and IT on initiatives, procurement, contracts, and budgeting.
β’ Actively utilize AI in daily operations and seek opportunities to implement AI within the function.
β’ Establish an operational cadence, identify unassigned initiatives, take charge of the OKR/QBR loop, and set performance benchmarks within the first 90 days.
β’ Proven experience in managing the operating system of an engineering organization, likely as a TPM lead, head of engineering operations, or similar role.
β’ Proven track record in managing cadence, planning, and cross-team coordination on an organizational scale.
β’ Demonstrated capability in driving ambiguous, multi-team initiatives through influence without direct authority.
β’ History of transforming complex information into clear, decisive executive-level documentation.
β’ Ability to establish robust operating systems and follow-up mechanisms.
β’ Capability to collaborate effectively with engineers, engineering managers, and directors while gaining their trust.
β’ Sufficient technical fluency to engage in technical discussions and coordinate efforts without being the technical authority.
β’ Proficient in English at a C1+ level.
β’ Proficient in Russian for both internal and external technical communications.
β’ Nice to have: prior experience as Chief of Staff, Engineering Operations, or TPM lead reporting to engineering leadership.
β’ Nice to have: experience enhancing operational efficiency in engineering organizations with over 100 employees, including automation and AI tools.
β’ Nice to have: experience in procurement, vendor contracting, or budgeting.
β’ Nice to have: familiarity with nonprofit technology or payments domain.
β’ Nice to have: knowledge of Node.js/NestJS, React, MongoDB, ClickHouse, Kafka, Cloudflare, PCI DSS 4.0.1, SOC 2 Type II, and ISO 27001.
β’ Private medical insurance for the employee and their family.
β’ 23 paid vacation days annually.
β’ 11 paid public holidays each year.
β’ 5 company-paid sick leave days.
β’ English language learning courses.
β’ Opportunities for relevant professional development.
β’ Access to gym or swimming pool facilities.
β’ Home Office Setup Assistance: the company provides support for purchasing furniture (such as an office chair, desk, and monitor) and other items to create a comfortable workspace.
β’ Co-working options available.
β’ Flexibility for remote work.
Weflow | getweflow.com
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The Cigna Group
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