Account Executive

Elective

Vancouver, BC

Elective is a Vancouver-based Series A fintech that builds the lending infrastructure for the online education industry: flexible payment options at checkout for courses, coaching programs, and digital learning communities, with Elective carrying the risk. The company is five years old, founder-led, and profitable.

To date, Elective has supported over 100,000 customers funding their education across North America, all underwritten, funded, and serviced through a platform Elective built from the ground up.

The company is now investing in dedicated sales leadership for the first time. To date, growth has been driven entirely by the CEO. This is the first Account Executive seat at the company. You’re not joining a sales org to optimize it. You’re helping to build one from the ground up, on top of a profitable platform with proven unit economics and a merchant base that expands predictably once activated.

The person in this role partners directly with the CEO, owns the full merchant lifecycle from first contact through first transaction, and helps drive the next phase of revenue growth.

This is a foundational hire. You’ll help define what sales looks like at Elective - the process, the playbook, the operating rhythm. The role grows as the function does, with a clear path to sales leadership for the person who builds it well.

The person who thrives here is energized by hunting, owns their deals end-to-end, and holds themselves accountable to merchants being live and transacting - not just signed.

What you’ll be doing

- Building and owning the pipeline. You’ll qualify and close inbound merchants while proactively building your outbound motion in parallel. The inbound pipeline gives you a running start - but the expectation is that you’re hunting too, not waiting for leads to come to you.

- Running the full sales cycle. Discovery, structuring proposals with Risk and Underwriting, negotiation, close. You’ll develop a repeatable motion and refine it as you learn what works.

- Owning activation accountability, not just signatures.



Your job isn’t done at close. You stay accountable for getting merchants to their first transaction — monitoring progress, diagnosing what’s blocking them, and applying relationship leverage to get them live.

Customer

Care handles the onboarding, training, and education. You step in when a merchant has the knowledge and isn’t moving.

- Working cross-functionally on deal structure. You’ll collaborate with Risk to get merchant programs underwritten and approved. You understand the terms well enough to have an informed conversation with a merchant about their offer — and you don’t treat internal review as a blocker you work around.

- Building the playbook as you go. You’re the first person in this seat. You’re documenting what works — objection handling, qualification criteria, outreach sequences, handoff processes. You’re building the foundation the next hire stands on.

- Driving expansion through QBRs. Once merchants are live and transacting, you’ll run periodic business reviews with our highest value accounts to identify program changes and new volume opportunities.

- Partnering directly with the CEO. You’ll have direct access to the CEO and a short feedback loop. You’ll bring pipeline visibility, deal context, and market intelligence into a weekly operating cadence.

Your first 90 days

- Within 30 days, you’ll have fully ramped on the product, the merchant profile, and the existing pipeline. You’ll have your first deals moving.

- Within 60 days, you’ll have closed your first few merchants and have a clear view of what’s working and what isn’t in the sales motion.

- Within 90 days, you’ll have multiple accounts live and transacting,



and a rough first draft of the playbook you’re building.

What you bring

- 3+ years in a full-cycle sales role, ideally at a fast-moving startup or fintech company. A track record of closing — you’ve owned a deal from outbound to signed contract, not just one part of the funnel.

- Hunger over pedigree. You’re motivated by upside, ownership, and building something from the ground up.

- Accountability for outcomes. You measure yourself on activated, transacting merchants — not meetings booked or contracts signed.

- Strong commercial instincts. You can hold a deal-level conversation with a business owner about program structure and trade-offs, and connect Elective’s value to their business and revenue.

- Comfort with ambiguity. There’s no SDR handing you leads, no RevOps team pulling reports, no playbook to inherit. You ramp through doing, not through being taught. You bring the answer to the room, not the question.

- Clear, direct communication. You can run a discovery conversation that moves a merchant from curious to convinced. Your follow-ups are specific and advance the deal — not check-ins for the sake of checking in. You can summarize a complex deal situation in two sentences so the CEO can make a decision without a meeting. Internally and externally, you write and speak with precision.

- Operator mindset. You treat Customer Care, Risk, Finance, and Compliance as partners, not obstacles. You understand that a signed merchant on bad terms is worse than no merchant at all.

- Hands-on with contemporary tools. HubSpot or equivalent CRM, outbound sequencing, and AI tools you’ve actually formed strong opinions on.

- Domain experience in fintech, payments, BNPL, lending, or vertical SaaS into online education or the creator economy is a nice-to-have, not a must-have. Adaptability matters more.

The details

Compensation: $155,000 - $205,000 OTE

Location: Vancouver, BC. Hybrid, minimum three days per week in office.

Reporting line: Co-Founder and CEO

📌 Account Executive (Vancouver)
🏢 BoldHouse Executive Search
📍 Vancouver