Co-Founder & CTO, AI B2B Startup

FutureSight

$150K — $250K *
US-AnywhereRemote in Canada
Enterprise Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5-7 years in a technical leadership role, ideally in a startup or B2B SaaS environment
  • Proven experience in AI execution, particularly with LLMs and agentic workflows
  • Strong technical leadership skills with the ability to scale engineering teams
  • Previous co-founding experience or a significant role at a venture-backed company
  • GTM instincts and ability to translate customer needs into actionable product strategies
  • Demonstrated ability to attract top engineering talent and foster a positive culture

Responsibilities

  • Own the technical vision by defining the architecture, AI strategy, and long-term platform roadmap
  • Collaborate with product and engineering teams to build and ship Version 1 of the product
  • Run pilot programs with lighthouse customers to validate product positioning and retention strategies
  • Design the tech stack for scalability, extensibility, and best security practices for Customer Success
  • Support seed fundraising efforts with compelling product narratives and traction evidence
  • Build and lead a high-performing engineering organization as the company scales

Benefits

  • Access to pre-seed funding for initial hires and MVP development
  • Embedded team of designers, engineers, and marketers from Day 1
  • Proven market need backed by early adopter interest and momentum to scale
Full Job Description
FutureSight is hiring an experienced and visionary Founding CTO for a new B2B SaaS company reimagining Customer Success through AI. This venture is building the next stage of Customer Success Management by proactively engaging every account to retain, expand, and delight. The platform monitors usage signals, surfaces next-best actions, and generates hyper-personalized outreach-unlocking higher revenue retention, net-new expansion, and leadership-ready insights for customer teams.

We're aiming to launch in Q3 2025.

The idea is validated, early adopters are lining up, and the studio team is ready to build with you.
As Founding CTO, You Will:
  • Own the technical vision - Define architecture, AI approach, and long-term platform strategy
  • Build the product - Partner with FutureSight's product/engineering team to ship V1
  • Run Pilots - Land lighthouse customers, iterate pricing/positioning, andvalidate retention + expansion
  • Scale the tech stack - Design for scale, extensibility, and CS security best practices
  • Raise capital - Support the seed round with a strong product narrative and traction
  • Build your team - Hire and lead the engineering org as the company grows
About FutureSight

FutureSight is a leading venture studio 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 team including:
  • John Carbrey - 4x founder, bootstrapped to $100M ARR
  • Joshua Auslander - Seasoned CFO and strategic advisor with $200M aggregate exits
  • Kevin Nguyen - Product leader with 0 → 1 SaaS scale-up experience
  • Alan Smith - Globally recognized early stage validation expert, 24 products launched, an exit, 5M+ books sold
  • Prathna Ramesh - Early-stage investor and capital strategy advisor


What We Bring to the Table
  • Validated problem & early market pull - You will enter a venture with a proven market need, early adopter interest, and strong momentum toward building and scaling
  • Studio bench strength - Designers, engineers, growth marketers, and fundraising pros are embedded from Day 1
  • Capital commitment - Initial pre-seed funding for early hires and building the MVP with potential for follow-on funding, and access to our investor and advisor network


What You Bring to the Table
  • Founder-level drive - You're motivated to co-found a new venture as the CTO. With or without us, this is your calling.
  • Startup scrappiness - You know what you're signing up for. You're familiar with the scrappiness of owning something from start to finish
  • Previous founding experience - You have co-founded a product company or B2B SaaS venture, have been at a venture-backed company, or have equivalent intrapreneurial experience
  • Risk appetite and capacity - Read more on our post on the Entrepreneurial Risk Profile
  • AI execution - Proven ability to ship LLM/agentic workflows into production
  • Technical leadership - You've scaled teams and aligned tech strategy with GTM
  • GTM instincts - Proven ability to engage customers, translate needs into product, and drive adoption through early sales, business development, and go-to-market execution
  • People leadership - Attracts top talent and builds a strong engineering culture

Bonus:
  • Experience with CS tooling (Gainsight, Catalyst, etc.)
  • Fundraising fluency and ability to craft investor narratives and close capital
  • Network in B2B SaaS/RevOps communities
What You Can Expect

Daily active engagement with our team to launch initial product, achieve initial market traction, and prepare for seed fundraise.

Ready to Build?

If this opportunity speaks to you, let's talk. Send us your resume and LinkedIn-and tell us briefly why you think we'd be a great match.

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

Similar Jobs

More Jobs at FutureSight

More Enterprise Technology Jobs

Find similar Co-Founder & CTO, AI B2B Startup jobs: