Partnering with visionary founders to build iconic companies in the central U.S.
Lewis & Clark Ventures is an early stage venture firm managed by former founders and operators. We invest in late seed through Series B companies between the coasts.
Independent Account Executive
Sailes
Sales & Business Development
United States
Posted on Feb 20, 2026
The Sailes Residency: A Fellowship for Elite, AI-Powered Sellers
Sailes | Remote | Contract | Performance-Based
Sailes is the Intelligent Prospecting System trusted by Fortune 500+ teams and recognized as one of the fastest-growing AI companies on the Inc. 5000. Our autonomous AI completes the entire prospecting process — from research to enrichment, engagement, intelligent interaction, follow-up, qualification, and learning, hands-free.
- For AE’s it’s a personal prospecting companion with 16X the output.
- For Executive Leadership, it’s the prospecting system of record that prospects, learns, and reports.
Now, we’re launching The Sailes Residency: A selective, six-month fellowship for top-tier Account Executives who want to redefine the future of selling with AI and Machine Learning.
This is not a traditional sales role.
It’s an invitation to join a high-performance cohort of independent sellers operating with cutting-edge AI, unlimited autonomy, and the opportunity to earn at the very top of the profession.
Overview
As a Sailes Resident (Independent AE), you will:
- Sell breakthrough Machine Learning technology from anywhere as part of a dedicated team
- Join a competitive, collaborative cohort of elite sellers
- Run full-cycle deals supported by your own Sailebot®
- Earn 2x industry-standard commissions on any deal you close and shared commission for any deal your team closes.
- Operate as a contractor with full flexibility
- Receive consideration for a full-time role at Sailes upon completion of the Residency
This program is built for proven sellers who thrive with autonomy, think strategically, and are hungry to apply ML and AI as a true force multiplier.
What You’ll Do
- Actively engage and collaborate with the team across all channels (email, Slack, meetings)
- Combine your personal prospecting style with a dedicated AI instance to build and engage pipeline
- Conduct high-quality discovery meetings that frames Sailes’ Intelligent Prospecting System in an executive language
- Lead 2-3 weekly demos
- Manage 2-4 month enterprise sales cycles and high-value negotiations
- Close contracts ranging from $50K to high six-figures
- Maintain a strong, disciplined pipeline
- Provide insights that sharpen Sailes’ GTM strategy along with product feedback to improve our system.
- Operate with extreme agency, accountability, and creative problem-solving
What We’re Looking For
- 3+ years of full-cycle sales experience
- Proven success selling disruptive or complex SaaS solutions
- Experience working mid-market and enterprise deals
- Ability to steer multi-stakeholder, high-value contracts
- Strong command of sales tech and modern GTM motions
- Exceptional storytelling, communication, and executive-presence skills
- Strong pipeline and deal-management discipline
- A proactive, competitive, resourceful mindset
- Bonus: proximity to NYC for optional in-person sessions and office access
Why Join the Sailes Residency
- Beyond a job, this is an invitation to join a network of your peers as part of a flagship cohort shaping the future of AI-powered selling.
- Earn outsized commissions with zero cap
- Master AI-driven outbound and Digital Labor workflows while earning resume assets and AI for Sales credentials
- Partner directly with Sailes leadership
- Open a pathway to a full-time role post residency
How to Apply
If you’re a top performer who wants to create the future of sales and join a selective, high-impact fellowship, we’d love to meet you.
Apply now to join The Sailes Residency. Shape the future of intelligent GTM.