Head of Sales Development | Toronto (Remote)

Our client is a fast-growing, AI-native SaaS company that helps marketing teams figure out which creative is working and why. Now we’re building our first outbound function, and we need someone to own it.

The prospect

Everything that got them to our Series B came inbound: word of mouth, content, events, and the product itself. They have never had the need for a dedicated outbound motion. With our AI agent taking off, it’s time to build one.

You wouldn’t be starting from zero. They have a 700K-person CRM full of people who already know us, plus much of the infrastructure: personalization at scale, signal-based sequences, enrichment, RevOps support, and a properly segmented database. What’s missing is the person who pulls it together, decides where to point it, and owns the number.

You’ll start hands-on, prove what works, then hire and lead the team that scales it. If there are SDRs you’ve worked with who’d join you within a couple of phone calls, we want to hear about them.

What makes this role different

- A fun category. You’ll sell to marketers about ads and creative, about as far from dry B2B software as it gets.
- A warm-first database. They don’t have a list problem. They have a bandwidth problem and need reps who can own the accounts.
- Data nobody else has. They invest heavily in collecting paid, organic, and creator content, so you can open conversations with what a prospect’s competitors are running right now instead of a generic pitch.
- Fixed comp to start. Outbound is new here, so your first six months are fully fixed. Variable comp tied to the pipeline you build kicks in after that.
- AI as your headcount multiplier. No token limits.

What you’ll own

- The lists: who they target, in what order, and which signals move someone to the front of the line.
- The mediums: the right mix of email, phone, text, LinkedIn, events, and in-person for each segment,



whether you’re reaching the people running the ads or the leaders who own the budget.
- The messaging: the message, CTA, and offer for every segment.
- The number: getting them to predictable pipeline quickly.
- The team: recruiting SDRs (including people you’ve worked with before) and onboarding them into your system.

You might be a fit if you

- Have built this before: first sales development leader at a fast-growing B2B company, where you hired the team, wrote the playbook, and owned the pipeline. Today you’re likely a director, senior manager, or head of sales development.
- Know how to work warm pipeline and have turned event attendees, product activations, lost deals, and former customers into real meetings.
- Are AI-native, comfortable with Clay-style enrichment, signals, and automation, and have built workflows or agents that let one person do the work of a team.
- Are still great on the phone and can coach others to be.
- Have a bench of great SDRs who’d take your call.
- Understand the whole business, not just your part of the funnel.
- Have high agency: you don’t wait for perfect conditions or a finished playbook. You read the data honestly and move.

Bonus points

- Experience selling to marketers
- Running win-back programs for churned customers
- Building in-person culture among SDRs
- Running field or in-person programs (dinners, workshops, city events)
- Firsthand experience with the product

What you’ll get

- Competitive compensation and equity for all
- Health benefits from day one and a monthly health and wellness stipend
- A deeply AI-native culture where you’re encouraged to experiment with any tools you like
- A high-performers, low-egos team
- A well-funded Series B company with strong product-market fit
- Real impact: we’re still in startup mode, so your work shapes the product, the team, and the business
- An annual in-person company retreat

? Location: This role is fully remote, but candidates must be based in Toronto.

Interested? Apply or message me directly to learn more!

📌 Head of Sales Development - Martech (Series B) (Canada)
🏢 STA
📍 Canada