Account Executive - Mid Market

Evolo AI•Toronto, ON

About The Position

WHY EVOLO No buyer should need a seller to understand what they’re buying. Yet for every complex product, that’s still how it works: the real answers sit behind a sales call with someone paid to close you. GPTs didn’t fix it; they only help buyers who already know what to ask, and most don’t. Evolo is buyer-side AI: companies put their best guided journey directly in the buyer’s hands, 24/7, at the buyer’s pace, zero pressure to commit. The company shapes the narrative. The buyer commands the journey. And every journey produces the data asset no CRM has ever held: first-party, declared intent, compounding with every interaction. This isn’t a thesis anymore. We’ve crossed the hardest line in enterprise AI, from pilot to production. Four major financial institutions run Evolo inside their sales workflows today, and all four have expanded and extended their partnerships. Three more are onboarding. We’re backed by Portage and Golden Ventures, and we expect the second half of this year to be our steepest curve yet. We are shaping a new category: AI for product & offer education to 2x conversion. And it is forming right now, and so is the team that will own it. This is a founding-team seat: the people we hire this year are shaping the growth foundation of Evolo, the product, the culture, the standards everything after gets built on. Your seat: you’ll own Evolo’s mid-market sales motion end to end, from the first outbound call to an insurance broker or wealth manager to a signed deployment they expand. ABOUT THE ROLE As a Founding Mid-Market Account Executive at Evolo, you will be the first rep building our mid-market sales motion from scratch, selling directly to insurance brokers, wealth managers, and similar regulated financial services firms who move faster than Evolo’s large-FI enterprise buyers but still expect a seller who understands compliance and complex products. You will run the full cycle yourself, prospecting, discovery, demo, and close, with no inherited playbook and no SDR team handing you pipeline. In this role, you will leverage your experience closing mid-market SaaS deals to build the outbound motion, sales process, and ideal customer profile that Evolo’s mid-market segment runs on going forward. You will work directly with the founders to translate what you learn in the field into pricing, messaging, and product priorities, setting the standard every mid-market rep hired after you will follow.

Requirements

Track record of quota attainment as a full-cycle B2B SaaS account executive, closing deals without inherited pipeline or an SDR team behind you
Experience selling to regulated or compliance-sensitive buyers such as insurance brokers, wealth managers, or financial services firms, translating complex product value into terms they trust
Comfort running a fast, multi-stakeholder sales cycle, moving a deal from first call to signature in weeks rather than quarters
Outbound prospecting discipline, building your own pipeline against a defined ideal customer profile rather than working inbound leads
CRM and sales-tooling fluency such as Salesforce or HubSpot, keeping pipeline and forecasting accurate without an operations team behind you
Consultative discovery skills that surface a buyer’s real workflow and budget owner, not just their stated pain point
Startup instincts over enterprise-process instincts, since there is no ramp deck, marketing engine, or sales floor to lean on here

Responsibilities

Own the full mid-market sales cycle end to end, from outbound prospecting through discovery, demo, negotiation, and close
Build and refine Evolo’s mid-market ideal customer profile, targeting insurance brokers, wealth managers, and similar regulated firms
Generate your own pipeline through outbound prospecting, since there is no SDR team or inbound engine to hand you leads yet
Partner with the founders to shape pricing, packaging, and messaging based on what mid-market buyers actually respond to
Stand up the CRM, forecasting, and sales process that every mid-market rep hired after you will run on
Coordinate with product and engineering to translate field feedback into the roadmap, ensuring Evolo builds what mid-market buyers need next
Represent Evolo at industry events and broker and advisor networks, building the relationships that turn into pipeline over time

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