Senior Sales Executive at Pilothouse Digital – Alberta | Jobyssey

The Opportunity

Pilothouse is redefining what agencies look like after performance marketing.
You'll work directly with Pilothouse's leaders to help grow the sales engine of one of North America's leading eCommerce growth agencies.
Your primary focus will be guiding qualified prospects through Growth Discovery, developing proposals, and closing new partnerships. Along the way, you'll help improve the sales systems and processes that support the team.
This isn't a role for someone who simply wants to sell agency services.
Every business has another growth lever. Your job is to help founders find it.

About Pilothouse

Pilothouse is an Integrated Growth Agency that partners with ecommerce brands at the $10M+ inflection point.

Rather than selling advertising channels, we help ambitious brands identify and execute their next growth lever through our Scaling Growth System - a framework that integrates brand, creative, media, retention, and measurement into a single growth system.

Our partner company, DTC Media, generates a steady pipeline of qualified opportunities through podcasts, newsletters, and in-person events, allowing our growth team to spend more time solving business problems and less time prospecting.

Who this role is for

This role requires genuine business and eCommerce fluency. The consultative pitch is P&L-centric, speaking to contribution margin, LTV, creative challenges, and incrementality, so the ideal candidate has the ability to hold a credible business conversation with a founder or marketing leader. We’ll be screening for that fluency first, ahead of raw sales-volume experience.

You're energized by understanding why companies grow, not simply how to close deals.
You enjoy learning about how businesses grow.
You naturally adopt AI and automation to improve every part of your sales process.
You can comfortably discuss contribution margin, customer acquisition, cash flow, retention, pricing strategy, and incrementality with a founder, and know when to ask thoughtful questions instead of pretending to know the answer.
You’re organized and self-accountable. You keep a clean CRM and hit cadence without being chased.

Nice to haves

Agency or DTC operating experience.
Familiarity with advertising platforms (Meta, Google, Amazon, Klaviyo, Triple Whale, etc).
Experience building or running sales automations and reporting.

Areas of Accountability

Own the Growth Discovery Process: Guide prospects from first conversation through Growth Discovery, identifying strategic opportunities and building conviction around Pilothouse's recommendations.
Revenue Growth & Target Achievement: Consistently meet and exceed monthly revenue targets by closing high-value deals and expanding business relationships across both channels.
Build Relationships: Become a trusted advisor to founders and senior marketing leaders.
Inbound Lead Qualification & Conversion: Quickly assess inbound leads, determine fit, and guide prospects through the sales process to maximize conversion rates.
Client Relationship Development: Build strong relationships with both outbound prospects and inbound leads, effectively communicating the company's value proposition and how services meet their needs.
Outbound Sales & Lead Generation: Proactively identify and engage potential clients through cold outreach, networking, and strategic prospecting to drive new business opportunities.
Collaboration & Reporting: Work closely with internal teams (including marketing and delivery) to ensure seamless handoffs post-sale and alignment with company objectives, providing regular insights on pipeline health, lead trends, and performance.

Objectives

Consistently achieve monthly revenue targets.
Maintain forecast-quality CRM data.
Improve conversion rates across the commercial funnel.
Expand the sales operating system through AI and automation.

What success looks like (first 90 days)

A documented, repeatable exploratory-call and qualification playbook in use.
Progression from shadowing live calls to supervised solo calls, with exploratory-to-audit conversion benchmarked against the current operators and trending toward that baseline.
At least one sales-to-onboarding integration improvement live, with delivery confirming better handoff experience.
At least one automation or reporting project shipped with sales operations.
Demonstrates business credibility with prospective founders by independently leading Growth Discovery conversations.
Success in this role comes from asking better questions than anyone else in the room.

Qualifications

Education & Experience:

Experience selling complex, consultative solutions to founders or senior operators.
4+ years of experience in outbound sales, inbound sales, partnerships, or business development.
Proven track record of consistently meeting or exceeding revenue targets across both channels.
Experience using CRM tools (Salesforce, HubSpot, Pipedrive) and sales automation tools.

Skills & Abilities:

Strong sales acumen with excellent qualification, negotiation, and closing skills.
Exceptional communication and relationship-building abilities.
Self-motivated, results-driven, and capable of managing a fast-paced sales cycle.
Ability to collaborate effectively across teams to drive business growth and enhance lead conversion strategies.

Compensation

We believe exceptional commercial talent should share directly in the value they create. Compensation includes a competitive base salary, uncapped commission, and the opportunity to grow alongside the business.

$70,000 - $100,0000 CAD base + commission

Reports To: VP of Growth

Direct Reports: None

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