// Open Role at Sierra Studio
Stealth AI Startup
For the past three years, we’ve been building AI systems. We’ve watched a pattern emerge across the SaaS landscape: companies know they need to become AI-native, they have roadmaps full of commitments, and they’re watching the category shift in real time. These companies are busy with existing customers and their lengthy roadmap. They can’t route the resources to keep up. The gap between ambition and execution is widening.
We’ve built something to close the gap. After six months of development and a live pilot generating real results, we’re ready to bring it to market.
The Opportunity
This is a CEO role at an early-stage, stealth AI startup. The company is being incubated by a venture studio with deep technical roots and a strong network. You won’t be starting from zero. You’ll have a working MVP, a live pilot customer, two technical co-founders, and an ecosystem of genuinely great people behind you.
In year one, you are the sales motion. Your job is to find the next customers, build relationships with heads of product and engineering at B2B SaaS companies, close deals, and develop the playbook from the ground up.
You’ll own GTM strategy and refine the ICP as you learn what it takes to win. As you prove what works, you’ll build the team and function around it.
We are open to a variety of backgrounds. We have two profiles that we think may be particularly strong fits for the role:
The Operator. You’ve sold software or tooling to SaaS companies before, ideally early stage. You’ve built ARR from 0 to 1. You’re comfortable personally carrying the relationships, closing deals, figuring out what resonates. You know the kinds of companies we’re selling to, and you might already know some of the next customers. You thrive without infrastructure around you and you don’t wait for permission to move.
The VC Turned Founder. You’ve spent time on the investing side, you understand what early-stage companies need to win, and you’re ready to operate. You have the network, the market intuition, and the hunger to build something yourself. You can tap into networks or channels of customers based on your existing relationships.
Either way, you bring:
Leadership and a mentality centered in service;
Strong relationship building and maintenance, with enough charisma to impress but genuine honesty and direct communication;
A bias to action — you move fast and figure it out;
Comfort with ambiguity — you don’t need a playbook to get started;
Resilience — you can handle long, big projects and stay motivated;
An ownership mentality — this is your company to build.
The team. We have a high bar. This is true for capability as well as for character. The people you’ll work with are technically strong, emotionally intelligent, and genuinely kind. It’s something we protect.
The backing. You’ll have access to the resources, network, and PMF insight of a venture studio that has been building in AI for years. Many critical pieces are already assembled: working product, a live pilot, and a technical team that has already done some of the hard parts. Your assignment is to join something that's already in motion with strong backing.
The upside. The experience and learning opportunity of a lifetime. With salary ($100-250k) and meaningful equity (5-12%), negotiated case by case depending on experience, fit, and needs.
If this sounds like you, we’d love to hear from you.