Co-Founder & CEO - AI Communication Agents for Freight & Logistics (Chicago)

The Opportunity

FutureSight is seeking a Co-Founder & CEO to lead HawkAI, an enterprise AI venture for US logistics brokerages, carriers, and warehouse operators. This is a co-founder partnership with meaningful founder equity, not a salaried executive role.

HawkAI deploys always-on, multi-channel AI workers that autonomously manage high-volume freight communications across calls, texts, and emails, integrating directly with core freight systems including TMS, load boards, and broker/carrier databases. The platform handles track-and-trace calls, appointment scheduling, carrier rate negotiation, proof-of-delivery capture, and shipment status updates end-to-end — autonomously resolving 90%+ of routine communications and escalating only exceptions to human staff. Rather than another point tool layered on top of existing systems, HawkAI is designed to operate as the always-on communication layer for logistics teams, enabling them to focus on exceptions and value-driving work.

We are now seeking the founder to lead the venture from here.

Market Context

• The US logistics BPO market for outsourced communications is approximately $26B, representing a major automation opportunity in a labour-intensive industry
• Approximately 150,000 US freight forwarders, 3PLs, and warehouses form the target market, with tiered subscription pricing yielding a $1.5B annual TAM
• Mid-sized US brokerages handle thousands of daily calls, with staff unable to answer or follow up on every transaction, contributing to OTIF (On Time/In Full) penalties and costly delays
• Early customers deploying AI communication assistants report approximately 33% lower operating costs and significantly faster call resolution
• AI supply chain software is growing at approximately 23% CAGR globally from 2025–2031, with North America seeing 30–45% annual growth in AI-driven logistics spend

About FutureSight

FutureSight is a leading venture builder that co-creates world-class software companies with values-driven entrepreneurs from inception to exit. We are a team of founders, operators and designers with experience successfully bringing software to market at scale.

You’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow‑on capital), and Johnny Tong (0‑to‑1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth.

The Partnership

• Founder equity with meaningful ownership from inception
• Pre‑seed capital committed by FutureSight for early hires and MVP development, with potential for follow‑on funding
• Venture building resources, including embedded design, engineering, growth, and fundraising support from day one
• Investor and advisor network across vertical AI and early‑stage capital markets
• A true co‑creation model in which you operate as CEO with FutureSight's cross‑functional team as your partner

What you'll own

As Co-Founder & CEO, you will set the venture's direction and lead its execution.

• Strategy — Refine the ICP, pricing model, and product positioning across freight brokerages, 3PLs, carriers, and warehouse operators
• Customer Development — Lead pilots with mid-sized to enterprise freight brokerages, convert them to paid engagements, and build the go‑to‑market motion targeting Heads of Logistics, Supply Chain, and Operations
• Product — Partner with the FutureSight product and engineering team to ship V1 and iterate on user feedback, with a focus on TMS and load board integrations, conversational AI quality, and autonomous workflow execution
• Capital — Lead the seed raise, supported by FutureSight's network and traction
• Team — Recruit and lead the founding team, and establish the cultural foundation of the company

Co-Founder Profile

• Previous founding experience at a venture‑backed company
• Demonstrated success in B2B SaaS go‑to‑market, including sales and customer engagement
• Fundraising fluency, with the ability to develop investor narratives and close capital
• Proven ability to attract, develop, and retain top talent
• Clear‑eyed understanding of the risks and demands of co‑founding a venture‑backed company
• Direct exposure to logistics, supply chain, freight brokerage, transportation, or B2B enterprise software serving these industries, with familiarity in AI agents/LLMs

How to Apply

Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate.

FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.