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Pilothouse Digital

Sales Executive

Canada

Pay: A base salary of $50,000-70,000 CAD.
Job type: Full-time
Experience: 2–4 years of experience in sales, business development, partnerships, account management, or another revenue-generating role.
Posting language: English
Posted: Oct 1, 2026

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Original job description

The Opportunity

Pilothouse is redefining what an agency can look like after performance marketing.

We’re looking for a commercially driven salesperson to help qualified eCommerce brands understand how Pilothouse can support their next stage of growth.

You’ll guide prospects through our sales process, from initial qualification and discovery through proposal development and close. You’ll work closely with Pilothouse’s growth leaders and internal specialists to understand each prospect’s business, identify where we may be able to help, and build confidence in the right solution.

You do not need to arrive as an expert in performance marketing or eCommerce. We’re looking for someone with strong sales fundamentals, intellectual curiosity, and the ability to learn a complex offering. We’ll provide the industry knowledge, tools, and support needed to build your credibility over time.

Every business has another growth lever. Your job is to ask the right questions, understand what is getting in the way, and help prospective partners see a path forward with Pilothouse.

About Pilothouse

Pilothouse is an Integrated Growth Agency that partners with eCommerce brands approaching or exceeding the $10M growth inflection point.

Rather than selling individual advertising channels, we help ambitious brands identify and execute their next growth lever through our Scaling Growth System. This framework brings brand, creative, media, retention, and measurement together into one coordinated growth system.

Our partner company, DTC Media, generates a steady pipeline of qualified opportunities through podcasts, newsletters, communities, and in-person events. This allows our growth team to spend more time understanding business challenges and building the right solutions, and less time relying exclusively on cold prospecting.

Who This Role Is For

This role is well suited to someone who has developed solid sales fundamentals and is ready to take on a more consultative, complex sales environment.

You may not yet know everything about eCommerce, performance marketing, or agency services. What matters is that you can build trust, ask thoughtful questions, manage a disciplined sales process, and learn quickly.

You’re likely someone who:

Has experience managing prospects through a structured sales process.
Can confidently lead discovery calls and uncover business needs.
Knows how to build relationships without relying on a scripted or overly transactional approach.
Is curious about how companies grow and wants to develop greater commercial and eCommerce fluency.
Can communicate clearly with founders, marketing leaders, and other senior stakeholders.
Is comfortable receiving coaching and involving subject-matter experts when a conversation becomes more technical.
Is organized and self-accountable, maintains accurate CRM records, and follows through consistently.
Naturally looks for ways to use AI, automation, and better systems to improve their work.
Is motivated by targets and commission while still caring about finding the right fit for the client.

What You’ll Do

Manage Qualified Opportunities

Respond to qualified inbound opportunities, assess fit, and guide prospects through Pilothouse’s sales process.

Lead Discovery Conversations

Ask thoughtful questions to understand the prospect’s business, priorities, challenges, current marketing approach, and reasons for considering a new partner.

Develop Proposals

Partner with Pilothouse leaders and subject-matter experts to shape recommendations, develop proposals, and communicate the value of working with Pilothouse.

Advance and Close New Business

Maintain momentum across opportunities, navigate objections, coordinate decision-makers, negotiate commercial terms within established parameters, and close new partnerships.

Build Trusted Relationships

Develop credibility with founders and marketing leaders through preparation, strong communication, curiosity, and consistent follow-through.

Maintain Pipeline Discipline

Keep CRM information accurate and current, manage follow-up cadences, identify stalled opportunities, and maintain reliable visibility into pipeline health and expected outcomes.

Support Targeted Prospecting

Contribute to focused outbound activity, event follow-up, referrals, and strategic account outreach when additional pipeline development is required.

Improve the Sales Process

Identify practical ways to improve sales materials, workflows, automation, reporting, qualification, and prospect follow-up.

Coordinate Strong Handoffs

Work closely with growth, marketing, and delivery teams to ensure new clients experience a clear and well-organized transition from sales into onboarding.

Areas of Accountability

Qualified pipeline progression and conversion.
Monthly and quarterly new-business revenue.
Discovery-call quality and opportunity qualification.
Proposal development and follow-through.
CRM accuracy and forecast reliability.
Sales-cycle momentum and next-step discipline.
Client experience throughout the sales process.
Effective handoff of closed business to delivery.
Continued development of eCommerce and commercial fluency.

Objectives

Consistently work toward monthly and quarterly revenue targets.
Convert qualified opportunities into strong-fit Pilothouse partnerships.
Maintain accurate, forecast-quality CRM data.
Improve conversion rates across assigned stages of the commercial funnel.
Develop the business and eCommerce knowledge needed to lead increasingly sophisticated sales conversations.
Contribute to a more consistent and scalable sales operating system.

What Success Looks Like in the First 90 Days

Develops a strong working understanding of Pilothouse’s services, ideal client profile, sales process, and value proposition.
Progresses from shadowing calls to independently leading qualification and discovery conversations.
Consistently captures business needs, decision criteria, risks, stakeholders, and next steps in the CRM.
Begins managing a defined pipeline of qualified opportunities with appropriate coaching and support.
Builds proposals in partnership with internal leaders and subject-matter experts.
Demonstrates strong follow-up, organization, and sales-process discipline.
Establishes credibility with prospective clients through thoughtful questions, preparation, and clear communication.
Contributes at least one practical improvement to sales follow-up, reporting, automation, or handoff.
Shows measurable progress toward the expected conversion and revenue benchmarks for the role.

Qualifications

Experience

2–4 years of experience in sales, business development, partnerships, account management, or another revenue-generating role.
Experience leading discovery conversations and managing opportunities through multiple stages of a sales process.
Demonstrated ability to work toward and achieve individual or team revenue targets.
Experience using a CRM such as HubSpot, Salesforce, or Pipedrive.
Experience selling services or complex solutions is an asset, but not required.
Agency, SaaS, eCommerce, media, or professional-services experience is an asset, but not required.

Skills and Abilities

Strong discovery, relationship-building, and follow-up skills.
Clear and confident written and verbal communication.
Ability to understand business needs and connect them to a proposed solution.
Comfortable discussing pricing and navigating common sales objections.
Organized and able to manage multiple opportunities in a fast-moving environment.
Coachable, curious, and motivated to build new industry knowledge.
Comfortable collaborating with technical or subject-matter experts.
Self-motivated, target-oriented, and accountable for results.
Interested in using AI, automation, and data to improve sales effectiveness.

Compensation

This role includes:

A base salary of $50,000-70,000 CAD.
An uncapped commission plan.
The opportunity to take on increasingly complex opportunities and grow alongside Pilothouse’s commercial organization.

Success in this role comes from strong sales fundamentals, genuine curiosity, and asking better questions than anyone else in the room.

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More about this job

Responsibilities

Manage qualified sales opportunities from discovery through proposal, negotiation, and close, while building trusted relationships with founders and marketing leaders. Maintain accurate CRM records and pipeline forecasts, collaborate with internal specialists, improve sales processes, and coordinate smooth handoffs to delivery teams.

Requirements

Candidates should have 2–4 years of experience in sales, business development, partnerships, account management, or another revenue-generating role, including experience managing opportunities and working toward revenue targets. Strong discovery, communication, organization, CRM, follow-up, and relationship-building skills are required; experience in complex services, agencies, SaaS, eCommerce, media, or professional services is an asset but not required.

Skills

Sales
Business Development
Discovery
Relationship Building
Opportunity Qualification
Proposal Development
Negotiation
Objection Handling
Pipeline Management
CRM Management
Forecasting
Communication
Client Handoffs
Process Improvement
AI And Automation
eCommerce

Visa sponsorship

Not detected in the job text

Keywords

Sales
Business Development
eCommerce
Performance Marketing
Integrated Growth Agency
Scaling Growth System
Brand
Creative
Media
Retention
Measurement
Qualified Pipeline
Discovery Calls
Opportunity Qualification
Proposal Development
Revenue Targets
CRM
HubSpot
Salesforce
Pipedrive
Pipeline Forecasting
Sales Process
Commercial Terms
Objection Handling
Strategic Account Outreach
AI
Automation
Data
Client Onboarding
DTC Media

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