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FutureSight

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

Canada

Job type: Full-time
Posting language: English
Posted: Oct 1, 2026

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Original job description

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.

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More about this job

Responsibilities

Set HawkAI’s strategy and lead customer development, including running pilots with freight brokerages, converting them to paid engagements, and building the go-to-market motion. Partner with FutureSight to develop and iterate on the product, lead fundraising, recruit the founding team, and establish the company’s culture.

Requirements

Candidates should have previous venture-backed founding experience, a record of B2B SaaS go-to-market success, fundraising capability, and the ability to attract and retain talent. Direct exposure to logistics, supply chain, freight brokerage, transportation, or enterprise software serving these industries is sought, along with familiarity with AI agents or LLMs.

Skills

Venture Founding
B2B SaaS Go-to-Market
Sales
Customer Development
Fundraising
Investor Relations
Talent Recruitment
Team Leadership
Logistics
Supply Chain
Freight Brokerage
Enterprise Software
AI Agents
Product Strategy
Pricing Strategy
Customer Engagement

Benefits

Founder Equity
Pre-Seed Capital
Venture-Building Resources
Design, Engineering, Growth, and Fundraising Support
Investor and Advisor Network

Visa sponsorship

Not detected in the job text

Hiring contact

John Carbrey

Keywords

HawkAI
Artificial Intelligence
AI Agents
Large Language Models
Freight Logistics
Logistics Brokerages
Freight Forwarders
Third-Party Logistics
Carriers
Warehouse Operators
Load Boards
Broker and Carrier Databases
Track and Trace
Appointment Scheduling
Carrier Rate Negotiation
Proof of Delivery
Shipment Status Updates
Autonomous Workflows
Conversational AI
B2B SaaS
Go-to-Market Strategy
Customer Development
Enterprise Sales
Product Strategy
Pricing
Fundraising
Seed Funding
Customer Pilots
Venture Building

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