Virtual Remote Flight Dispatcher Jobs in Boston, MA

Catering delivery does not get a second chance. There are forty people in a conference room, a meeting that starts at noon, and one shot to get hot food through a loading dock, past a security desk, up a service elevator, and set up on a table. That is a fundamentally different problem than dropping a burrito at a doorstep, and the industry has never built for it. We orchestrate that last mile across the country every day, at a volume and complexity most people never see. The software to do it consistently well does not exist off the shelf.

We are looking for a Director of Product to define and own the Delivery & Fulfillment Intelligence Platform - the system of record and the system of intelligence for every delivery on our network. The scope runs the full lifecycle: demand and capacity planning, promise and lead-time calculation, routing and dispatch, in-flight risk detection and intervention, handoff and setup, and the learning loop that makes the next delivery better than the last. You will build on our multi-year re-platform investment, which gives you modern primitives to work from and leaves the delivery domain itself open to define. This role sits within the Platform domain, reports to the VP of Product Management for Platforms, and comes with a dedicated engineering, data, and data science team. You will work in close partnership with Supply Chain Operations, Delivery Partnerships, CX Product, and Restaurant Technology. There is far more to this than a job description can hold, and we will go deep in the interview.

What You'll Do:

• Define the vision, strategy, and multi-year roadmap for the Delivery & Fulfillment Intelligence Platform, holding a clear line: this platform owns the decision and the data; the experience teams own how that decision reaches customers, drivers, and restaurants.
• Define the delivery domain from first principles - the canonical event and state model, telemetry and history, and the governed contracts every other domain will build against.
• Develop key capabilities such as order risk assessment and proactive intervention, building- and address-level intelligence that compounds with every delivery, decomposed lead-time and promise accuracy, and dynamic routing and orchestration that re-dispatches in real time when conditions change.
• Build capabilities that don't come off a shelf - demand and capacity forecasting, and network optimization that allocates delivery supply against forecasted demand under real cost, coverage, and reliability constraints.
• Partner with the Data organization on the foundation all of it depends on: instrumenting the lifecycle, defining the metrics that matter (on-time performance, promise accuracy, straight-through rate), and standing up the learning loop that closes the gap between what we predict and what actually happens.
• Drive the hard architectural and commercial trade-offs: what we build versus what we buy (ETA services, optimization solvers, telematics), and what belongs in a model versus a solver versus a rule.
• Partner with Supply Chain Operations, Delivery Partnerships, and Finance to critically evaluate if and when it makes sense to insource all or part of delivery logistics - a whole market, a single service tier, or a hybrid where the operation is ours and the labor is contracted. Build the case from real data, keep supply type a platform configuration rather than a rewrite, and be equally prepared to conclude the answer is no.
• Represent this work at the executive level, bringing a point of view into the room rather than a menu of options, and holding the distinction between tactical wins this quarter and structural investments that compound over years.
• Hire, lead, and grow the product team around this platform. You will start hands-on and build out from there.
• Travel to Boston quarterly for planning cycles, architecture reviews, and business reviews. Have fun building logistics infrastructure for a delivery problem nobody else has bothered to solve properly.

What You Have:

• 10+ years of product management experience, including 3+ leading product managers, with deep grounding in platform, infrastructure, logistics, or marketplace operations products. This is a define-the-domain role, not an execute-the-roadmap role; you will set direction across an ambiguous, high-stakes space with significant autonomy.
• Experience hiring, developing, and retaining strong product managers - and the judgment to know when to coach and when to take the pen yourself. You are a builder who leads, not a manager who reviews.
• A demonstrated track record owning fulfillment, dispatch, logistics, or supply-chain intelligence products at meaningful scale - last-mile delivery, freight, field service, on-demand marketplaces, or comparable physical-operations businesses where software makes decisions that move vehicles and people.
• Real depth in at least two of: routing and dispatch optimization, ETA and travel-time prediction, demand and capacity forecasting, risk scoring and anomaly detection, or geospatial data systems.
• The judgment to know which problems actually need machine learning and which need a solver, a rules engine, or simply better data - and the discipline to argue for the cheaper answer. You have shipped ML-backed products in production and understand calibration, training/serving skew, offline versus online evaluation, and what it takes to operate a model that makes decisions with money attached.
• The ability to engage senior engineers as a peer on event-driven architecture: event schemas, state machines, idempotency, service boundaries, API contracts, and durable workflow orchestration. You can reason about where a capability should live and why, and you write specifications an engineer can build from.
• Experience in multi-sided marketplaces where the supply you depend on is neither employed nor directly controlled by you - and the practical instincts that come from working with third-party partner networks, SLAs, rate cards, and capacity commitments.
• Deep analytic ability. You build the metrics framework yourself, you find the data quality problems before anyone reports them to you, and you do not accept a number you cannot reconcile.
• A track record of influencing peers and executives without authority across product, engineering, data science, operations, and commercial teams - and the organizational discipline to run a multi-workstream program across several engineering teams simultaneously.
• Comfort operating in a business with real operational history: you can distinguish what should be rebuilt from what should be left alone, and you can sequence a multi-year platform build so that it delivers value long before it is finished.
• Experience within food delivery, restaurant technology, or B2B logistics is a plus.
• Ability to travel up to 5 days per quarter for Together Weeks, team gatherings and other events, when applicable.

The national total target cash compensation range for this position, including base salary and bonus target, is $229,000 - $321,000 annually.*

*Please note: Final offer amounts are determined by multiple factors, including prior experience, expertise and region & may vary from the amount above. This range does not represent additional compensation benefits (such as equity, 401K or medical, dental or vision insurance).