Chief of Staff to the CTO

Description

The company runs a network for trade that uses AI to help governments and businesses make global supply chains more resilient and secure while goods keep moving.

This is a chief of staff role for the CTO and the leadership of Product, Engineering, and Implementation. You act as an extension of the CTO, pick up context across all workstreams, make prioritization decisions, and run the operations of a technical organization that delivers to commercial and government customers worldwide.

You also manage the business side of the Product and Engineering organization: its operating rhythm, budget, and headcount planning, working with Finance and the People team. You will build and lead the program management office, a group of technical program managers who run cross-functional programs and customer deliveries.

The role carries real operational ownership and sound judgment, keeping technical functions aligned with company strategy and governance. Where compensation, leveling, org design, and budget are involved, you apply the frameworks owned by the People CoE and Finance. You work as the CTO's counterpart to those functions, not as a separate source of authority.

Responsibilities

• Lead or staff the highest-priority initiatives that Product and Engineering leadership identifies.
• Run the operating rhythm: plan and facilitate staff meetings, roadmap and portfolio reviews, metrics reviews, and leadership offsites, then record and share the decisions.
• Build and lead a team of technical program managers. Hire and develop them, set the standard for the function, and decide which TPMs sit within teams and which are shared.
• Own the portfolio view of active programs and customer deliveries, including intake and prioritization. Set delivery standards for planning, status, risk and dependency tracking, launch readiness, and government contract reporting, and build the tooling that shows delivery health.
• Find where priorities clash across Product, Engineering, Implementation, and the public and private sector delivery efforts, and drive those conflicts to a decision.
• Decide what reaches the CTO, in what format, and which issues to escalate or settle at a lower level.
• Write board and all-hands material and internal updates for Product and Engineering that reflect the organization's actual state.
• Work with the People CoE to run headcount planning, org design, and leveling and compensation within Product and Engineering. Apply the central frameworks, track where the org is over or under capacity, and act as the CTO's single contact for the People team.
• Own the Product and Engineering budget and spending against the plan Finance sets. Track burn, explain variance, model headcount and vendor trade-offs, and act as the CTO's contact for FP&A. Co-own success metrics with FP&A so they tie to business levers for growth and capital deployment.

Requirements

• About 10 years in product management, technical program or portfolio management, strategy, business operations, or another role with real operational ownership rather than coordination.
• A track record of running several parallel workstreams and competing stakeholders where ownership is unclear, and keeping all of them moving.
• Experience building or running a PMO or program portfolio, including intake, prioritization, and delivery tracking processes that teams actually follow.
• Experience managing and growing a team, ideally of program or project managers. You have hired, coached, and given direct feedback, and built a team people want to join.
• Enough technical understanding to discuss APIs, infrastructure, deployment, and architecture at a conceptual level with a platform engineer, and to read a design doc and challenge it. You are not a coder.
• Financial and operational skill: managing a budget, explaining variance, and weighing headcount and spend trade-offs.
• Comfort with org design and workforce planning as a partner to the People function. You are a strong thought partner without running that function.
• Ability to influence engineers, PMs, and go-to-market leads through trust, clear framing, and good timing, not by citing the CTO.
• Very precise work: clear systems others can follow, strong first drafts, and async updates that need little editing.
• Nice to have: experience delivering programs under government contracts, including milestones, deliverables, and compliance reporting.
• Nice to have: experience building production systems with LLMs, agents, evals, or retrieval.
• Nice to have: experience using engineering metrics such as DORA or SPACE to improve how a team works.
• Nice to have: background in trade, supply chain, compliance, or work with government customers.
• The role is based in Brooklyn, NY, USA, with hybrid flexibility. Candidates must live within commuting distance of the Williamsburg, Brooklyn office.

Conditions

Base salary range: $235,000-$285,000 per year. The final offer depends on factors such as experience, education, training, critical skills, and business needs.

Most full-time offers include equity, which counts toward total compensation. The role also includes either a discretionary bonus or a variable compensation plan.

The recruiter can share more detail on pay and benefits during the hiring process.

The company is an equal opportunity employer.

Benefits

• Flexible time off with no fixed allowance.
• Paid parental leave: 14 weeks for non-birthing, adoptive, and foster parents, and up to 26 weeks for birthing parents, paid at 100% of base salary.
• Medical, vision, and dental coverage. The high deductible health plan is fully paid by the employer for employees, with an employer contribution to an HSA. A flexible spending account is also available.
• Life, short-term and long-term disability, and AD&D insurance at no cost to you.
• 401(k) with Fidelity.
• Pre-tax commuter benefits for transit or parking.
• Free premium Calm subscription for meditation, sleep, and mindfulness.
• Pet insurance through Wishbone, and/or a Total Pet vet and telehealth discount plan.
• Free confidential employee assistance program.
• Dependent care FSA for pre-tax childcare savings.