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

FutureSight; Canada; On-site; CAD 100,000 - 150,000; Full time

Benefits offered by this job

Significant equity

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

Job summary

Join a leading venture studio as an Entrepreneur in Residence to revolutionize Customer Success Management with AI. You'll lead product development, secure funding, and shape company culture, all while working with a world-class co-founder team. If you're driven and passionate about automating customer success, this is your chance to make a significant impact.

Qualifications

• Experience building or being early at a venture-backed SaaS company.
• Success in customer success, revenue operations, or enterprise SaaS sales.

Responsibilities

• Own the thesis & roadmap: deepen customer discovery and develop GTM strategy.
• Collaborate with product/engineering teams to ship V1 and hire core team members.
• Lead next funding round with data-backed growth stories.

Skills

GTM expertise

AI & data curiosity

People leadership

Tools

Gainsight

Totango

Catalyst

Job description

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

2 weeks ago Be among the first 25 applicants

Get AI-powered advice on this job and more exclusive features.

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

Benefits

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.