--- title: 'Deployments / Operations at Fleetline' canonical: 'https://feeny.ai/job/deployments-operations-fleetline-new-york-6nsdjwz5pjqv' type: 'job' last_seen: '2026-09-10' --- # Deployments / Operations at Fleetline - **Company:** Fleetline - **Location:** New York, NY - **Compensation:** $110k–$135k - **Employment:** full-time - **Work type:** onsite - **Posted:** 2026-06-12 - **Last confirmed live:** 2026-09-10 - **Apply:** https://jobs.ashbyhq.com/fleetline/6db47e4e-a79f-4b55-8046-12a7706bd176 ## Job description Fleetline writes optimization algorithms for enterprise trucking fleets. We work with some of the largest fleets in the country and are rapidly scaling our operations. About us: - Scaled from 0 to $Xm in signed contracts in under eight months - Lean team of 12 based in New York City; everyone deeply cares about the company’s mission, our clients, and each other. That care translates into high standards, close relationships, and intensity. - Backed by a large seed round from top investors like BoxGroup, Base10, and more. About deployments: - A strong deployment strategist will have the ability to lead an industrial organization through one of the largest digital transformations it has gone through in decades. This requires a few key traits: - Ethos. There are three main components that make up ethos in this context: - The ability to learn quickly; you’ll quickly gain credibility with our clients if you deeply understand transportation and logistics and the idiosyncrasies of their operations. This requires someone who can learn vast amounts of new information about a complex industry and specific corporations on the fly. - Strong communication skills - Authority; being able to speak with conviction and confidence is critical in winning the trust of management at enterprise fleets, and, correspondingly, helping lead the deployment of new technology. - Strategic thinking: Each fleet has noticeably different operations, and, as such, the deployments are rarely consistent. Being able to figure out the best organizational structure and workflows to propose to each fleet based on their particular circumstances requires a strong strategic mind. - Organization; deployment strategists will manage multiple large clients at once. - Scrappiness; being willing to do whatever it takes to push the deployment, team, and product forward, irregardless of how sexy/interesting it might be. We’re looking for people who can in the short-term execute deployments at a high-level, and in the long-term help shape the playbook for how we deploy our software with clients and recruit a team that can execute that playbook. Outside of deployments: Our ideal candidate has the desire to wear many hats based on priorities. A few examples are: - Recruiting - recruiting engineers and future operations team members. - Product Management - triage issues and come up with product lines based on experiences being on the ground with clients. - Sales/GTM - helping scale our revenue function If you have any questions, please email veer@fleetline.ai ## About Fleetline ## Company Overview - **One-liner**: Fleetline builds a complete-context algorithmic load planner powered by a combination of advanced optimization and large language models (LLMs) to automate dispatch for mid-to-large-sized trucking fleets. - **Entity Type**: Private (startup; Y Combinator Summer 2025 batch) - **Headquarters**: New York, NY, USA - **Founded**: 2025 - **Founders**: Saurav Kumar and Veer Juneja ## Core Business - **Primary industry**: Logistics / Supply Chain Technology (Trucking Fleet Management) - **Target customers**: B2B – mid to large-sized trucking fleets (dispatchers, planners, fleet managers) - **Mission or purpose**: Turn complex fleet planning from a headache into a fleet’s largest competitive advantage by automating the hard work so humans can focus on the rest. ## Products & Services - **Fleetline AI Load Planner**: A SaaS platform that combines traditional optimization algorithms with LLMs to simulate billions of possible weekly schedules and select the optimal one. Key features include: - **Predictive Events**: Forecast delays, breakdowns, and Hours-of-Service (HOS) violations. - **AI Assistant**: A ChatGPT-like interface trained on fleet history and TMS data for instant operational context. - **Aggregated Loadboard**: Unifies brokers, public boards, and customer freight into a single view. - **Contract & Spot Freight Optimization**: Assigns contract loads optimally and dynamically fills gaps with spot loads. - **Customer Demand Forecasting**: Helps manage capacity and schedule ahead. - **Performance Analytics**: Dashboards for network health, profitability, and planning tradeoffs. - **White Glove Customization**: Onsite training and custom planning logic tailored to each fleet’s constraints. ## Market Standing - **Valuation/Market Cap**: Not disclosed - **Key Metric**: Total Funding – Y Combinator-backed (Summer 2025 batch; amount not publicly disclosed; typical YC investment is $500k) - **Notable Investors/Partners**: Y Combinator (primary partner: Jared Friedman) - **Growth Signals**: Founded in 2025, already working with large fleets in California and in talks with others across the country. Team size of 11 (as of Summer 2025). Open roles for Founding Engineer and Founding Algorithm Developer indicate early-stage hiring momentum. ## Competitive Advantages - **LLM + Optimization Hybrid**: Unlike traditional rigid algorithms, Fleetline’s models can adapt to soft preferences and real-world exceptions (e.g., a driver needing to leave early) via natural language prompts. - **Complete Context**: Simulates billions of permutations across contract freight, spot market, driver constraints, and real-time events – all in one system. - **Rapid Onboarding**: Claims to go from first call to optimized planning in two months, including historical simulation to estimate ROI before signing. - **White Glove Service**: Hands-on, in-person training and custom algorithm calibration for each fleet. ## Strategic Focus - Automate the entire dispatch planning workflow for mid-to-large fleets, replacing manual, siloed tools. - Expand from contract freight optimization into real-time spot market matching and predictive analytics. - Build a defensible data moat by capturing fleet-specific constraints and driver preferences through LLM interaction. ## Why Work Here - **Early-stage impact**: As a founding engineer or algorithm developer, you’ll shape the core product from the ground up. - **Compensation**: Competitive salary ($130K–$190K) plus meaningful equity (0.40%–1.00%) for early hires. - **Location**: Based in New York, NY – office/onsite with in-person training culture (hybrid/remote policy not explicitly stated but likely in-office for close collaboration). - **Team**: Small, tight-knit team of 11 with founders who have prior experience at Meta, Nvidia, and as previous founders (Blast AI). - **Tech stack**: Working at the intersection of AI/LLMs, optimization algorithms, and logistics – a high-impact domain. - **Culture**: Emphasis on first principles thinking, adaptability, and solving a hard real-world problem. Open to new grads (as noted on YC job postings). ## Sources 1. [fleetline.ai](https://www.fleetline.ai/) 2. [Y Combinator](https://www.ycombinator.com/companies/fleetline) 3. [jobs.ashbyhq.com/fleetline](https://jobs.ashbyhq.com/fleetline) 4. [fleetlineai.com/careers](https://fleetlineai.com/careers) ## Other roles at Fleetline - [Founding Algorithm Developer](https://feeny.ai/job/founding-algorithm-developer-fleetline-new-york-zhj3ygpfgzk3) — New York, NY - [Founding Engineer](https://feeny.ai/job/founding-engineer-fleetline-new-york-4002cd20gchh) — New York, NY