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 Sep 15, 2025
Job Description
Sailes is the market-leading, authentic, AI for Sales on Autopilot for the Fortune 500+. Our patent-pending, personality driven AI autonomously completes every step of the sales prospecting process - from research and discovery to data enrichment, intelligent interaction, objection handling, and social media engagement - hands-free.
Beyond sales enablement agents, our Sailebots are a true Digital Labor solution that multiplies the power of world class AEs by 16X.
Sailes is Sales with AI and we’re looking for a dynamic and proven renaissance AE to serve on a select team within our organization.
Overview:
As an Independent Account Executive, you will have the opportunity to sell cutting edge AI from wherever you are. You will work closely with the Head of Sales to acquire new customers. You will be responsible for managing the entire sales process—from prospecting to closing deals—while leveraging your expertise to drive revenue growth.
This role is a 1099 contract position, offering flexibility while expecting a high degree of ownership and accountability. Compensation will be 100% performance-based with full autonomy, unlimited earning potential and double the industry standard commission.
Key Responsibilities:
- Utilize your own prospecting strategies, alongside a Sailebot, to identify and engage potential clients.
- Conduct discovery calls to understand business challenges and align Sailes' solutions with client needs.
- Present and demonstrate how Sailes provides tailored solutions to drive meaningful outcomes for prospects.
- Negotiate contracts ranging from five to high-six figures in annual value.
- Consistently meet or exceed revenue targets while building a strong sales pipeline.
- Provide insights and feedback to marketing and product teams to refine Sailes' offerings.
- Operate with a high level of autonomy, bringing strategic thinking and problem-solving skills to every engagement.
Requirements & Qualifications:
- Minimum of 3-5 years of full-cycle sales experience.
- Demonstrated success selling disruptive, complex solutions to mid-sized and enterprise organizations.
- Strong ability to navigate 3-9 month sales cycles with significant contract values.
- Expertise in sales technology and go-to-market strategies.
- Excellent communication skills, with the ability to translate abstract value into tangible business outcomes.
- Proven ability to manage pipelines, negotiate effectively, and build long-term client relationships.
- Self-starter mentality with the ability to operate independently and drive results.
- Preferred: Proximity to NYC for occasional in-person meetings.