At a Glance
- Tasks: Lead the launch of an innovative AI Customer Success platform and drive customer engagement.
- Company: Join FutureSight, a venture studio empowering B2B SaaS startups with hands-on support.
- Benefits: Equity stake, initial funding, and access to a network of investors and advisors.
- Other info: Full-time commitment required; this is your chance to build something impactful.
- Why this job: Be at the forefront of AI innovation and shape the future of customer success.
- Qualifications: Experience in founding or scaling B2B SaaS ventures and strong leadership skills.
The predicted salary is between 135000 - 165000 $ per year.
FutureSight is seeking an experienced, visionary Founding CEO to lead our AI Customer Success opportunity. We are building the next evolution of Customer Success Management where every account gets proactive, intelligent engagement without relying on manual effort. Our platform analyzes product usage signals in real time, recommends the next best actions, and generates highly personalized outreach for CSM teams. The result? Higher revenue retention, predictable expansion, and clear insights leadership can actually act on.
As Founding CEO, you will:
- Win customers — Run pilots, shape pricing, and validate retention + expansion
- Build the product — Work with FutureSight's product/engineering pod to launch V1
- Raise capital — Lead the seed raise with our initial cheque
- Build your team — Hire your founding team and set the cultural foundation
About FutureSight: FutureSight is a venture studio that co-creates and invests in B2B SaaS and Vertical AI startups alongside exceptional entrepreneurs. We give founders an unfair advantage — pairing hands‑on studio support with early capital to reduce risk and increase the odds of success by 10x.
What We Bring:
- Validated problem — You will enter a venture with a proven market need 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:
- Founder‑level drive — You're motivated to co‑found a new venture as the CEO. With or without us, this is your calling
- Startup scrappiness — 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 or have been at a venture‑backed company
- Risk appetite and capacity — Read more on our post on the Entrepreneurial Risk Profile
- GTM chops — Proven success in B2B SaaS sales, marketing, and customer engagement
- Fundraising fluency — Able to craft investor narratives and close capital; well‑networked in fintech and early‑stage communities
- People leadership — Magnet for top talent; coach and culture carrier
- Bonus: Exposure to accounting/finance tools and processes or AI agents/LLMs
What You Can Expect:
- Daily active engagement with our team to launch initial product, achieve initial market traction and prepare for seed fundraise
- Full P/L ownership of the new entity
- A significant equity stake in the business
- This is a full‑time role; we are looking for someone to commit full‑time and exclusively to building and owning a new SaaS venture
Co-Founder & CEO in Winnipeg employer: FutureSight
Join a dynamic venture studio that fosters innovation and collaboration, where your vision as the Founding CEO will directly shape the future of AI in the multifamily property management sector. With a strong emphasis on employee growth, you will have access to significant equity stakes and the support of an experienced team, all within a culture that values creativity and strategic thinking. This is not just a job; it's an opportunity to lead a transformative project in a thriving industry.
