Head of Commercial

Lydia.ai; Toronto; Hybrid; CAD 120,000 - 160,000; Full time

Job summary

Lydia.ai is seeking a Head of Commercial to build ORCA’s go-to-market strategy from the ground up. You will lead the effort to identify customer segments, establish pricing, and create sales processes for SMB and mid-market clients.

The ideal candidate will have over 8 years of experience in commercial leadership and a proven ability to develop and implement strategies that drive growth. This is a unique opportunity to bring a new AI platform to market, creating the necessary materials and processes.

Qualifications

• 8+ years of experience in commercial leadership or related fields.
• Experience in building sales or growth functions from scratch.
• Proven track record of owning revenue targets.

Responsibilities

• Build ORCA’s go-to-market strategy for SMB and mid-market customers.
• Define commercial positioning, pricing, and sales motion.
• Create sales and marketing materials at each funnel stage.

Skills

Commercial leadership

GTM strategy

SaaS growth

Enterprise sales

Business development

Job description

Lydia AI - ORCA

Lydia AI is building ORCA, an agentic AI platform that helps businesses research, analyze, and present complex information using AI‑powered workflows. ORCA is designed for work that requires expert‑level research, judgment, and decision‑making to move forward. It helps teams turn fragmented information, manual analysis, and complex business questions into structured, decision‑ready outputs. Use cases include market intelligence, financial research, loan origination, and other workflows where businesses need to move from research to action faster.

The Opportunity

This is an opportunity to define how ORCA goes from early traction to a scalable commercial business. The right person will help decide where we win first, how customers discover value, how we convert demand into revenue, and how we build a repeatable GTM engine across segments.

We are looking for someone who is excited by the blank page: a commercial leader who can create the strategy, materials, processes, and discipline needed to bring a new AI platform to market.

The Role

We are hiring a Head of Commercial to build ORCA’s go‑to‑market engine from the ground up. This is not a role for someone to simply manage an existing pipeline. We are looking for someone who can build the commercial machine: identify the right customer segments, sharpen the use cases, define the positioning, build the sales funnel, create the materials, own revenue targets, and establish the operating discipline needed to scale. The initial focus will be on building a scalable GTM motion for SMB and mid‑market customers, while creating the foundation to support larger enterprise opportunities over time.

Key Responsibilities

• Build ORCA’s GTM strategy, starting with SMB and mid‑market customers.
• Identify the highest‑potential customer segments and use cases for early adoption.
• Define ORCA’s commercial positioning, packaging, pricing, and sales motion.
• Build the sales funnel from the ground up, including lead generation, qualification, conversion, onboarding, expansion, and retention.
• Create the sales and marketing materials needed at each stage of the funnel, including pitch decks, demo narratives, landing page messaging, use case briefs, proposal templates, ROI narratives, and objection handling.
• Own pipeline generation, revenue targets, forecasting, and commercial reporting.
• Carry quota and directly close early customers.
• Build operating discipline around CRM, funnel metrics, customer activation, conversion rates, sales cycle length, and account expansion.
• Work closely with leadership and product teams to translate customer feedback into sharper messaging, better packaging, and stronger product‑market fit.
• Lay the foundation for future sales, growth, partnerships, and customer success hires.

What We’re Looking For

• 8+ years of experience in commercial leadership, GTM strategy, product‑led growth, SaaS growth, enterprise sales, or business development.
• Proven experience building a sales, growth, or commercial function from the ground up.
• Experience carrying quota or owning revenue targets.
• Strong understanding of how to bring SaaS, AI, automation, data, fintech, retail tech, or enterprise software products to market.
• Ability to create commercial assets from scratch, including sales decks, messaging, pricing models, onboarding flows, proposals, and funnel materials.
• Strong judgment on how to simplify a complex AI product into clear, high‑value customer use cases.
• Experience selling to or building relationships with SMBs, mid‑market companies, retailers, financial institutions, insurers, lenders, fintechs, or consumer‑facing businesses.
• Product‑led growth experience is a strong plus.