Sr. AI Solutions Advisor at Switchboard in Canada, CA

Why Switchboard Exists

Every COO, CFO, and operating partner in middle market companies is being asked the same question right now: what's the AI plan?

Most of them are listening to pitches that don't fit how their business runs, calling for AI chatbots with a sparkle emoji, or being sold consulting decks priced to make a partner's quarter. They've never had less help figuring this out, and their needs are urgent.

We have spent two years building a company meant for this moment, and we are on our way to becoming the recognized leader serving our chosen markets.

Switchboard builds custom software, AI agents, and automated workflows for mid-market companies whose teams have become the glue between disconnected systems, manual processes, and spreadsheets. Switchboard helps teams regain productive time and delivers real, clear returns on investment.

The Role

As a profitable team growing largely on word-of-mouth and referrals, we’ve now laid the groundwork to launch our outbound sales role and accelerate pipeline development. Now, we’re ready to fill that seat. This role is for those who walk confidently into executive-level conversations and know how to clearly illustrate what working AI actually looks like inside of a business’ operations.

Most AI being deployed into middle market companies right now gets pitched in two ways: SaaS reps demoing chatbots bolted onto software the buyer gave up on years ago, and consultants closing six-figure "strategy engagements" that deliver slides rather than products. In this role, you’ll walk in next with something that actually works and show clients what enterprise-caliber AI looks like in their business.

You'll own the full sales cycle: hunting, qualifying inbound, running discovery, writing proposals, and closing deals and supporting expansion.

You'll focus on two buyer profiles: operations leaders at 100 to 1,000 person mid-market companies (COOs, CFOs, VPs of Ops), and PE firms bringing AI into their portfolio, from deal teams during diligence to operating partners working post-close.

Our engagements start with embedded discovery and prototyping where we get deep on how the client's business actually works and prove the highest-value AI opportunity on their real workflows. Your job is to land that first commitment, which we call a Jumpstart, and then set up the expansion into our longer-term retainer services that naturally follow. Conversion currently sits above 85%.

You'll work alongside our strategists and have the support of a shared BDR, report directly to Switchboard's CEO, and have the same AI tooling we use internally to move faster on your research, enrichment, scoping, and proposals.

What You'll Do

• Hunt and qualify. Build your own book through outbound, account research, and qualifying inbound. You aren't the type to wait for marketing to feed you.
• Run discovery that's actually useful. Our buyers are tired of generic AI pitches. You'll need to understand AI and technology deeply enough to operate like a peer, not pull pain points and talking points out of a template.
• Shape proposals. Craft ROI-driven outcomes, scoped against real problems, priced accordingly. You'll have scoping support where needed, but you own the deal.
• Close. Move deals from qualified to signed. Handle objections, navigate procurement, and get contracts over the line.
• Tee-up expansion. Stay close through Jumpstart delivery to set up the Deployment expansion. You don't deliver, but you don't disappear.

What Success Looks Like

• You're hitting quota on both Jumpstart entries and Deployment expansions.
• Most Jumpstarts you close convert to a Deployment engagement within 30 days of completion.
• Pipeline is organized, predictable, and growing quarter over quarter.
• Clients consistently describe conversations with you as "not what I expected from a sales call."
• You create a repeatable, scalable process that informs how we go to market across the organization.

Who We're Looking For

• 7+ years closing five- and six-figure B2B technology services or consulting deals. Bonus if you've sold custom software, AI or automation services, or consulting to ops-focused buyers.
• Credible with senior operators. You can sit across from a C-suite executive and have a real conversation about operations, systems, and where AI fits, without sounding like you read about it on LinkedIn last week. And your follow up written comms are easily understood and engaged with.
• Proven hunter. You're energized by net-new business and you know how to build pipeline from scratch.
• Comfortable with technical concepts. You don't write code, but have a genuine interest in tech & AI and you understand the difference between a workflow automation, an AI agent, and a custom platform, and where each may be of value for a client.
• AI-forward seller. You're comfortable leveraging AI for your own sales processes and working with an AI-powered GTM system.

What You'll Get

• A service that already works. We ship working software. You're not pitching a roadmap or a chatbot bolted onto software the buyer's been complaining about for five years. You're showing operators something they can see running on their real workflows.
• Personal AI fluency. You'll develop cutting-edge expertise in how AI actually gets deployed in real businesses, not just how it gets pitched.
• A seat where the playbook gets built. Direct line to the co-founders. You're not running plays someone else wrote. The early sellers shape the playbook, and that playbook carries their fingerprints & opportunities as we grow.
• Real support. A shared BDR for top-of-funnel, strategists for scoping, AI tooling that makes you faster on every part of the job, and go-to-market efforts that help fill the pipeline.
• At the frontier. AI is the conversation in every boardroom right now. You'll be selling into a market that's already convinced something needs to happen. They just need you to show them how.
• Compensation that reflects the role. Competitive base plus commission tied to closed business and expansion revenue. Real upside for someone who can build a book and close.
• Remote-first. Work anywhere in North America with at least 3 hours of PST overlap.
• Three weeks vacation to start, plus December company-wide shutdown and group extended health benefits.