Co-Founder & CEO - AI Communication Agents for Freight & Logistics

Canada
Remote
Posted Oct 4, 2026
1 position

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Employment type: Full-time
Experience level: Lead · 10+ years
Posting language: English
Working hours: 40 hours per week
Location requirements: Country, Toronto, Ontario, Canada
Seniority: Executive

Job summary

Set HawkAI’s strategy and lead customer development, including refining its target market, pricing, positioning, and go-to-market approach, and converting pilots into paid engagements. Lead product development with FutureSight, raise seed capital, recruit the founding team, and establish the company’s culture.

Job details

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.

What you’ll do

Requirements

Candidates should have prior founding experience at a venture-backed company, a record of B2B SaaS go-to-market success, fundraising fluency, and the ability to attract and lead talent. Direct exposure to logistics, supply chain, freight, transportation, or enterprise software serving these industries is expected, along with familiarity with AI agents or large language models.