Enterprise SAAS Account Executive

SimplePin; Canada; Remote; CAD 200,000 - 250,000; Full time

Job summary

Join a forward-thinking company on a mission to transform the insurance industry through digital innovation. As an Enterprise Account Executive, you will drive the full sales cycle, engaging with influential players and showcasing a premium product that streamlines financial workflows. This role offers the chance to make a significant impact in a $1.3 trillion industry while working in a dynamic, remote-first environment. If you thrive in fast-paced settings and are eager to build relationships, this is the opportunity for you. Help shape the future of fintech and unlock new revenue streams for clients.

Benefits

Competitive Compensation

Performance-based Commission

Remote Work Flexibility

Professional Development Opportunities

Qualifications

• 3-5 years of success in B2B SaaS sales, preferably in fintech or insurance.
• Strong communicator with proven ability to exceed sales targets.

Responsibilities

• Own your pipeline: Prospect and qualify new leads in the insurance sector.
• Lead demos and negotiations through to close.

Skills

B2B SaaS Sales

Relationship Building

Consultative Selling

CRM Tools (HubSpot, Salesforce)

Communication Skills

Tools

HubSpot

Salesforce

Job description

Enterprise Account Executive – Help Modernize Insurance FinTech

About SimplePin

We’re on a mission to simplify the complicated. At SimplePin, we’re transforming the insurance industry by making financial workflows faster, easier, and fully digital. Agencies, Carriers, and MGAs use our platform to eliminate friction, save time, and unlock new revenue—and we’re just getting started.

The Role

We’re growing fast and looking for our next Enterprise Sales Executive to help us bring modern fintech to one of the biggest and oldest industries out there. You’ll drive the full sales cycle—prospecting, pitching, and closing deals with some of the most influential players in insurance. If you’re someone who loves building relationships, thrives in a fast-moving environment, and gets a buzz from winning, we’d love to talk.

Why You’ll Love It Here

• Competitive Compensation – Base with a performance-based commission structure designed to reward results with six-figure earnings.
• Level Up – Sell a premium product to large enterprise clients and sharpen your skills on complex deals
• Make an Impact – Help bring digital transformation to a $1.3 trillion industry
• Startup Energy – Work with smart, motivated teammates who want to build something meaningful

What You’ll Do

• Own your pipeline: Prospect and qualify new leads across key insurance segments
• Sell consultatively: Understand pain points and position SimplePin as a must-have solution
• Drive the deal: Lead demos, proposals, and negotiations through to close
• Collaborate: Partner with marketing and customer success to deliver value at every stage
• Crush your quota: Track your progress and stay sharp using tools like HubSpot

What We’re Looking For

• 3–5 years of success in B2B SaaS sales (bonus points for fintech, payments, or insurance experience)
• Strong communicator and relationship builder—you’re great with people and thrive in conversations
• Proven ability to hit or exceed targets and drive results
• Curious, coachable, and hungry to learn
• Comfortable working independently in a remote-first team
• Experience with CRM tools like HubSpot or Salesforce

Extra Credit If You’ve:

• Sold into insurance agencies, carriers, or MGAs
• Worked with complex buying cycles or large deal sizes

Let’s Build Something Great Together

If you’re looking to grow fast, earn big, and be part of a team that’s changing the game in insurance fintech, we want to meet you.

Apply now!

Seniority level

• Seniority level

  Mid-Senior level

Employment type

• Employment type

  Full-time

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