Entrepreneur in Residence (Future CEO / Founder) - Customer Success AI 2 weeks ago Be among the first 25 applicants

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About FutureSight

FutureSight is a venture studio that co-creates and funds world-class B2B AI software companies from Day 1. Our team of repeat founders, operators, product leaders, and investors collaborates closely with entrepreneurs, providing proven playbooks, hands-on expertise, and capital to support startups from inception through growth.

The Venture: Automating Customer Success Management

FutureSight aims to revolutionize Customer Success Management by proactively engaging customers to retain, expand, and delight. Our platform monitors usage signals, suggests next-best actions, and generates personalized outreach, leading to higher retention, expansion, and strategic insights.

What We Bring To The Table

Validated problem & early market interest with pilot engagements

Embedded team of designers, engineers, marketers, and fundraisers

Initial funding to build MVP and hire early team members

What You'll Do

Own the thesis & roadmap: deepen customer discovery, refine target market, and develop GTM strategy

Build the product & team: collaborate with product/engineering teams to ship V1 and then hire core team members

Run early pilots: secure lighthouse customers, iterate on pricing and positioning,



demonstrate retention and expansion impact

Raise external capital: lead next funding round with data-backed growth stories

Operate as CEO: set company culture, manage P&L;, report to the Board, and scale the venture

Requirements

You Bring

Founder-level drive: experience building or being early at a venture-backed SaaS company

GTM expertise: success in customer success, revenue operations, or enterprise SaaS sales

AI & data curiosity: ability to turn product usage and CRM data into value

Fundraising skills: craft investor narratives and close funding

People leadership: attract top talent, coach, and foster company culture

Nice-to-Haves

Experience with CS tools (Gainsight, Totango, Catalyst, etc.)

Knowledge of LLMs, agents, or predictive analytics

Network in B2B SaaS (Series A-C) customer success or RevOps communities

Perks

What You Can Expect

Significant equity (founder-level ownership) plus stipend

Hands-on support in product, design, growth, talent, finance, and fundraising

Ready to Build?

If automating proactive customer success excites you and you want a world-class co-founder team, apply with your résumé + LinkedIn and tell us why you're the right founder.

FutureSight values diversity, equity, and inclusion and welcomes applicants from all backgrounds.

📌 Entrepreneur in Residence (Future CEO / Founder) - Customer Success AI (Winnipeg)
🏢 FutureSight
📍 Winnipeg