Director of Operations

About Watchmen Logistics Watchmen Logistics is building the best tech-forward third-party transportation provider in the world, and we're hiring the leader who helps us get there. We're a freight brokerage operating as an authorized agent of Trinity Logistics. We run on modern, AI-driven technology instead of spreadsheets and phone tag, so our people spend their time where it matters: solving problems for customers and carriers. One rule sits above everything else: the customer comes first. Every load, every update, every call back. Technology is how we scale that standard, not a replacement for it. The Role The Director of Operations is the CEO's right hand: the person who owns day-to-day execution so the business runs at a high standard whether or not the founder is in the room. You'll lead our operations and dispatch team, protect the customer experience on every shipment, and turn what works into repeatable systems. This is a hands-on leadership role. You'll be solving a late truck at 6 a.m. and planning how we double volume next year. Reports to: CEO. This is a remote, full-time role. What You'll Own Customer service excellence Own service quality across every account: on-time pickup and delivery, proactive updates, fast issue resolution. Be the escalation point when something goes wrong, and make sure customers hear about problems from us first. Build relationships with key shippers and turn good service into more freight. Operations and team leadership Lead, coach and hold accountable the dispatch and operations team. Set daily, weekly and monthly operating rhythms: load reviews, exception handling, performance huddles. Hire, onboard and develop talent as we grow. Raise the bar with every hire. Carrier network Strengthen carrier sourcing, vetting and relationships so we cover freight reliably at the right margin. Enforce carrier compliance and safety standards on every load. Technology and process Champion our technology stack and drive full adoption across the team. Spot manual work and bottlenecks, then work with the CEO to automate or redesign them. Write and maintain the playbooks (SOPs) that let us scale without losing quality. Performance and growth Track and report the numbers that matter: on-time %, tender acceptance, margin per load, claims, customer retention. Act as the CEO's operating partner on priorities, special projects and growth initiatives. Who You Are Character first. We hire for who you are, then train for what you know. Integrity without exception. You tell the truth, especially when it's bad news. You do what you said you'd do. High engine. You bring energy every day and outwork the problem in front of you. Urgency. A delayed load is a customer's problem right now, and you treat it that way. Leadership. People follow you because you set the standard, own the outcome and develop others. Ownership. No "that's not my job." You find the problem, fix it, then fix the system that caused it. Composure. Calm, clear decisions when the phones are ringing and three things are breaking at once. Coachable. You want direct feedback and get better fast. Experience 3+ years in logistics, freight brokerage, 3PL or transportation operations (or a strong record of leading high-performance teams in another fast-paced field). Experience leading, coaching or managing a team. Comfortable with technology. You pick up new systems quickly and push others to use them well. Strong communicator in writing and on the phone with customers, carriers and your team. Willing to work the hours freight demands, including early mornings and the occasional after-hours issue. Bonus Points Former college athlete, military service, or another high-performance team environment. Background in freight brokerage sales or carrier sales. Experience with a TMS, load boards (DAT, Truckstop) and carrier-vetting tools. You've helped a small, fast-growing company scale. What Success Looks Like First 30 days: You know every key customer, carrier and …

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