Sign up to access all features of our service.
  • Job search
  • Favorites
  • Create a CV
    New
  • Salaries
  • Subscriptions

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

Full-time

FutureSight

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.

Vacancy posted 6 hours ago
Similar jobs that could be interesting for youBased on the Co-Founder & CEO - AI Communication Agents for Freight & Logistics in Toronto, ON vacancy
  •  ...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead a new AI-native reverse logistics orchestration venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. Reverse logistics — everything that happens after... 
    Suggested
    Full time
    Internship

    FutureSight

    Toronto, ON
    6 hours ago
  •  ...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Weli AI , a B2B WealthTech venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. Weli AI is an embedded intelligence layer for wealth advisors. It integrates... 
    Suggested
    Full time
    Internship

    FutureSight

    Toronto, ON
    6 hours ago
  •  ...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Crossfoot , an AI-native accounting agent platform. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. Crossfoot is agentic accounting for small-to-mid CPA... 
    Suggested
    Remplacement
    Full time
    Internship

    FutureSight

    Toronto, ON
    6 hours ago
  •  ...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Omnex , an AI-native operating system for multi-channel ecommerce sellers, currently in build at our studio. This is a co-founder partnership with meaningful founder equity, not a salaried executive role.... 
    Suggested
    Full time
    Internship

    FutureSight

    Toronto, ON
    6 hours ago
  • $50k - $300k per year

     ...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Reclaim , an AI-native denial management and revenue recovery venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. We are entering a $16B+ Total Addressable... 
    Suggested
    Full time
    Part time
    Internship

    FutureSight

    Toronto, ON
    6 hours ago
  •  ...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Maestro , an AI-native inventory-planning intelligence venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. Maestro is an autopilot planning intelligence... 
    Full time
    Internship
    Immediate start

    FutureSight

    Toronto, ON
    6 hours ago
  •  ...is seeking an experienced, visionary entrepreneur to co-found its next B2B AI venture with us. This is a co-founder partnership with meaningful founder equity, not a...  ...A true co-creation model in which you operate as CEO with FutureSight's cross-functional team as your partner... 
    Full time
    Internship

    FutureSight

    Toronto, ON
    6 hours ago
  •  ...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead InfluTracker , an AI-native content intelligence and publishing venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. InfluTracker is an AI-first content... 
    Full time
    Internship
    Immediate start
    10 hours per week

    FutureSight

    Toronto, ON
    6 hours ago
  • $150k per year

     ...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Concordance , an AI-native clinical documentation compliance venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. Concordance AI audits 100% of healthcare... 
    Full time
    Internship
    Manual labor

    FutureSight

    Toronto, ON
    6 hours ago
  •  ...opportunity to help define a new category at the intersection of applied AI, operational systems, and high-trust workflows. The Venture...  ..., and strong early market feedback. The Partnership The CEO co-founder is already in place and has completed extensive customer... 
    Full time

    FutureSight

    Toronto, ON
    6 hours ago
  •  ...marketing materials line by line, scanning communications for keywords, and reviewing trades and...  ...rules engine. We are building an explainable AI platform that reasons like a senior...  ...integrations. The Partnership The CEO co-founder is in place. The customer thesis... 
    Full time
    Internship

    FutureSight

    Toronto, ON
    6 hours ago
  •  ...delivery economics, and scalability. The teams that ship credible AI workers into trust-sensitive verticals in the next 18 months...  ...delivered through the same managed model. The Partnership The CEO co-founder is in place. The customer thesis is validated, design partners... 
    Full time
    Internship

    FutureSight

    Toronto, ON
    6 hours ago
  •  ...Opportunity FutureSight is seeking an applied AI builder to co-found and lead the technical direction...  ...from the ground up. This is a co-founder partnership with founder-level equity and...  ...from inception to exit. We are a team of founders, operators and designers with experience... 
    Full time
    Internship

    FutureSight

    Toronto, ON
    6 hours ago
  • $70.83k - $106.5k per year

     ...Manager, Freight Payables   Join Livingston and grow your career in the constantly changing...  ...payment matters, and support vendor / agent payment and remittance requirements....  ...coaching, and developing teams.  ~ Effective communication (oral & written) skills. Ability to... 
    Freight
    Long term contract
    Full time
    Flexible hours

    Livingston International

    Toronto, ON
    1 day ago
  • $30 - $50 per hour

     ...competitive advantage. Cresta’s unified AI platform combines conversational AI agents, real-time human agent augmentation...  ..., including United Airlines, Cox Communications, and Marriott, use Cresta to power...  ...the leading minds in AI today. Our CEO, Ping Wu , founded and led Google... 
    Internship
    Work at office

    Cresta

    Toronto, ON
    15 days ago
  • $30 - $50 per hour

     ...competitive advantage. Cresta’s unified AI platform combines conversational AI agents, real-time human agent augmentation...  ..., including United Airlines, Cox Communications, and Marriott, use Cresta to power...  ...the leading minds in AI today. Our CEO, Ping Wu , founded and led Google... 
    Hourly pay
    Internship
    Work at office
    Local area

    Cresta

    Toronto, ON
    17 days ago
  • $108k - $158k per year

     ...Senior Manager, AI and Innovation Communications Our purpose at Thomson Reuters is to Inform the Way Forward. Together with the professionals and institutions we serve, we help uphold the rule of law, turn the wheels of commerce, catch bad actors, report the facts, and... 
    Full time
    For contractors
    Work at office
    Local area
    Flexible hours
    Shift work
    2 days per week
    3 days per week

    Thomson Reuters

    Toronto, ON
    17 hours ago
  •  ...seeking a Personal Assistant to the CEO. About This Role  This role supports our CEO and founder directly. The majority of this...  .... That means managing the logistics of his family life, running...  ...professional correspondence and communications.  ~ Support with... 
    Full time
    Flexible hours

    Dokainish & Company

    Toronto, ON
    22 days ago
  •  ...center. Our platform combines the best of AI and human intelligence to help contact centers...  ...the prestigious Stanford AI lab, Cresta's co-founder and chairman is Sebastian Thrun , the...  ..., and more. Our leadership also includes CEO, Ping Wu , the co-founder of Google Contact... 
    Remote job
    Work at office
    Local area
    Work from home
    Home office

    Cresta

    Toronto, ON
    more than 2 months ago
  •  ...better, more human customer experiences with AI. We are primarily an in-person company...  ...upholding them in everything we do. Our co-founders are Bret Taylor and Clay Bavor . Bret...  ...Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the... 
    Full time
    Flexible hours

    sierra

    Toronto, ON
    14 hours ago
  •  ...’re funded and supported by Canada’s top leaders including the founders of Wealthsimple, Shopify, Ada, MindBeacon and many more. We are...  ...technology, marketing, and finance. - Regularly partner and communicate with SV and relevant investors and/or Board of Directors. - Create... 

    simpleventures

    Toronto, ON
    14 days ago
  • $138.5k - $173k per year

     ...Manager, Integrated Marketing - Co-Marketing leads DoorDash...  ...external stakeholders, proactively communicating campaign performance,...  ...impact. Have experience using AI tools within your day to day (...  ...consumers. We are a technology and logistics company that started by enabling... 
    Full time
    Local area

    DoorDash Canada

    Toronto, ON
    14 hours ago
  • $100k - $115k per year

     ...About the Job : We are seeking a skilled Conversational AI Engineer to be a core contributor in designing building testing and deploying...  ...: Build and maintain conversational flows within the chosen Agent platform (e.g. Dialogflow CX Playbooks) including creating intents... 
    Permanent employment
    Full time
    Work at office
    Local area

    INFOYA

    Toronto, ON
    17 hours ago
  •  ...Description Job Opportunity: Marketing Co-ordinator Role Overview Company...  ...range of marketing functions, including communications, advertising, branding, digital marketing...  ...pricing, and market opportunities.  Event Logistics: Plan and support meetings, trade shows,... 
    Permanent employment
    Full time
    Work at office
    Immediate start

    Oomple

    Toronto, ON
    1 day ago
  • $70k - $100k per year

     ...execution systems, practical AI adoption, faster decision-making...  ...Partner to support the CEO and Executive Team from our Toronto...  ...coordination, recruiting flow, executive communication, and operating rhythm. The...  ...comfortable working in a founder-led, fast-moving environment.... 
    Long term contract
    Full time
    For contractors
    Work at office
    Monday to friday

    Big Viking Games

    Toronto, ON
    15 days ago
  • $140k - $260k per year

     ...provider dedicated to the advancement of AI agents and web-based applications. By developing...  ...developer ergonomics and API design. Communication: Exceptional technical writing skills and...  ...Screening: A 30-minute introductory call with a Co-Founder. # Leadership Interview: A... 
    Full time
    Internship
    Work at office

    MLabs

    Toronto, ON
    14 days ago
  • $85 per hour

     ...Mercor connects elite creative and technical talent with leading AI research labs. Headquartered in San Francisco, our investors include...  ..., and Jack Dorsey . Position: Security Engineer (Coding Agent Experience) Type: Contract Compensation: $85/hour... 
    Remote job
    Contract work
    Summer work

    Mercor

    Toronto, ON
    15 days ago
  • $85 per hour

     ...Mercor connects elite creative and technical talent with leading AI research labs. Headquartered in San Francisco, our investors include...  ..., and Jack Dorsey . Position: Backend Engineer (Coding Agent Experience) Type: Contract Compensation: $85/hour... 
    Remote job
    Contract work
    Summer work

    Mercor

    Toronto, ON
    19 days ago
  •  ...Purpose of the Job We are looking for a Staff AI Platform & Agent Runtime Engineer to build the foundation for enterprise-scale AI and agent execution at EQ Bank. In this role, you will architect and operate the platform that powers our next generation of AI agents from... 
    Full time

    eqbank

    Toronto, ON
    5 days ago
  •  ...explore, design, and implement AI strategies that are secure, scalable...  ...tell us it's not. This is a CEO and product person rolled into...  ...— you close. Deploy AI and agents as core infrastructure in...  ...Are Proven experience as a founder, CEO, or product leader who shipped... 
    Full time
    For contractors
    Remote work

    Human Agency

    Toronto, ON
    3 days ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Co-Founder & CEO - AI Communication Agents for Freight & Logistics. Be the first to apply!