[Remote] Sales Executive

Note: The job is a remote job and is open to candidates in USA. Pilothouse Digital is a company focused on connecting agency founders and leaders through a private, vetted network. They are seeking a Membership Advisor who will own the full sales motion, proactively identify qualified agency founders, and ensure that only the right members join the network.

Responsibilities

• Proactively identify and reach out to qualified agency founders via LinkedIn and other channels
• Generate and manage your own pipeline, keeping conversations moving and organized
• Lead advisory-style interview calls that evaluate fit, challenge assumptions, and clearly communicate the value of Agency
• Handle follow-up and objections with confidence and clarity
• Close aligned founders and turn away misaligned ones without hesitation
• Consistently drive 3-5 successful closes per week
• Share patterns, objections, and insights from conversations to help refine outreach, positioning, and messaging
• Lead generation and outbound outreach
• Pipeline quality and momentum
• Member advisory calls and interview process
• Close rate and weekly targets
• Clear signal back to the team on who is and is not a fit
• Feedback that helps sharpen how Agency grows

Skills

• You have experience in sales, outreach, or lead generation, ideally in agencies, B2B SaaS, or membership-based businesses
• You enjoy starting conversations and are comfortable with cold outreach when done thoughtfully
• You are relentless in follow-up without being pushy
• You can manage multiple conversations at once and keep details straight
• You understand agency economics and founder psychology
• You ask better questions than you pitch
• You believe bringing in the wrong person does real damage
• You've sold to agency founders or C-suite executives
• You've worked with or sold memberships for premium networks
• You bring an existing network in the agency or marketing ecosystem

Benefits

• Paid vacation days
• Benefits through Sun Life after completion of 90 day probationary period

Company Overview