Entrepreneur in Residence (Future CEO / Founder) - Customer Success AI

FutureSight Inc.; Canada; Remote; CAD 80,000 - 150,000; Full time

Job summary

An innovative venture studio is seeking a dynamic co-founder to lead the development of a groundbreaking Customer Success Management platform. This role offers the unique opportunity to own the product roadmap, build a talented team, and engage in early commercial pilots. With a focus on leveraging AI to enhance customer engagement, you'll be at the forefront of transforming how businesses retain and expand their customer base. As a key player in this venture, you'll have significant equity ownership and hands-on support from a world-class team, making this an exciting opportunity for entrepreneurial spirits ready to make a substantial impact.

Benefits

Significant equity ownership

Venture studio support in various areas

Qualifications

• Experience in building or being early at a venture-backed SaaS company.
• Proven success in customer success or revenue operations.

Responsibilities

• Own the product roadmap and deepen customer discovery.
• Lead the team to build and ship the MVP.
• Run commercial pilots and iterate on pricing.

Skills

Customer Success

Revenue Operations

Enterprise SaaS Sales

Fundraising

Leadership

AI & Data Analysis

Tools

Gainsight

Totango

Catalyst

Job description

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 exceptional entrepreneurs, providing proven playbooks, hands-on functional expertise, and the capital necessary to transition from whiteboard to seed and beyond.

The Venture: Automating Customer Success Management

FutureSight 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.

What We Bring to the Table

• Validated problem & early market pull — We’ve interviewed dozens of CS, RevOps, and sales leaders and secured pilot interest.
• Studio bench strength — Designers, engineers, growth marketers, and fundraising pros are embedded from Day 1.
• Capital commitment — Initial funding for early hires and building the MVP with potential for follow-on funding.

What You’ll Do

• Own the thesis & roadmap – Deepen customer discovery, refine the wedge, and translate insights into a crisp GTM plan.
• Build the product & team – Work with FutureSight’s product/engineering pod to ship V1, then hire your core team.
• Run early commercial pilots – Land lighthouse customers, iterate pricing/positioning, and prove retention + expansion impact.
• Raise external capital – Lead the next round with our support, telling a data-backed growth story.
• Operate as CEO – Set culture, own P&L, report to the Board, and scale the venture.

You Bring

• Founder-level drive — You’ve built (or been early at) a venture-backed SaaS company and love zero-to-one chaos.
• GTM chops — Proven success in customer success, revenue operations, or enterprise SaaS sales.
• AI & data curiosity — Comfort turning messy product-usage and CRM data into user-facing value.
• Fund-raising fluency — Able to craft investor narratives and close capital.
• People leadership — Magnet for top talent; coach and culture carrier.

Nice-to-Haves

• Prior work with CS tooling (Gainsight, Totango, Catalyst, etc.).
• Exposure to LLMs, agents, or predictive analytics.
• Network in B2B SaaS (Series A–C) customer-success or RevOps communities.

What You Can Expect

• Significant equity (founder-level ownership) plus stipend.
• Hands-on venture studio 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 behind you—apply with your résumé + LinkedIn and tell us (briefly) why you’re the right founder.

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