Pilothouse Digital · 3 weeks ago
Sales Executive
Canada
Full-time
Remote
Entry, Mid Level
CA$120K/yr - CA$150K/yrPilothouse 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.
Advertising
Hiring Manager
Jennifer Aggio
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
Qualification
Required
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
Preferred
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
Pilothouse Digital
Pilothouse Digital is digital marketing & advertising based company.
Founded in 2019
51-200 employees
Funding
Current Stage
Growth StageLeadership Team
Jeffrey Shannon
Co-Founder
Company data provided by crunchbase