Account Executive at SiftMed — St. John's Tech Job

Who Are We?

As a group of passionate technology developers, successful entrepreneurs, and industry experts, SiftMed is scaling quickly. We build AI processing software that organizes, categorizes, and analyzes medical files - helping teams find facts in medical data that can change lives.

Our buyers sit inside claims and legal organizations where medical records are the bottleneck - and where a faster, more accurate review changes outcomes for real people. We're adding an Account Executive to carry that story into the market across the US and Canada, and to turn it into closed business.

What Do We Offer?

We work hard, but we don't take ourselves too seriously. You'll have a seat at the table, real ownership, and the ability to make a visible impact across the business. We care deeply about building an inclusive, diverse, and equitable workplace.

Who Are You?

You're a full-cycle seller who is equally comfortable cold-opening a regional carrier and navigating a procurement, security, and legal review at a national one. You've sold into insurance - ideally P&C - and you know how claims organizations actually buy: who has the pain, who has the budget, who can quietly kill a deal.

You've done this at a startup, so you know the job isn't just closing. It's figuring out which segments respond, writing your own sequences when there's no playbook yet, and telling the product team what you keep hearing on calls. You don't wait for leads to show up, and you don't ignore the ones that do.

You're direct, organized, and honest about your pipeline - including the deals that aren't real. You bring curiosity about how AI is changing claims and legal work, and you can explain it to a skeptical buyer without overselling.

What You Will Be Doing

Own Full-Cycle Sales Across the US and Canada

Own the full cycle - prospect, qualify, discover, demo, business case, negotiate, and close - across insurance and legal buyers in both markets.
Sell a mix of deal sizes: land with regional carriers and firms, and run longer, multi-stakeholder cycles with larger enterprise accounts.
Navigate procurement, security review, and privacy diligence, coordinating internal resources to keep deals moving.
Build and defend accurate forecasts, and keep Salesforce current enough that the number means something.

Build Pipeline - Outbound and Inbound

Self-source a meaningful share of your pipeline through targeted outbound into named accounts within our ICP.
Work marketing-sourced and BDR-sourced leads with speed and rigour, and close the loop on what converts.
Work conferences, webinars, and association partnerships as pipeline sources, not just attendance.
Partner with Marketing on messaging, sequences, and ICP refinement based on what you hear in live conversations.

Run Discovery That Earns the Deal

Run structured discovery that surfaces real economic pain - review time, cost per file, accuracy, capacity, and turnaround.
Build business cases and ROI narratives that hold up in front of finance and operations leaders.
Multi-thread across claims, legal, operations, IT, and procurement so deals don't hinge on one champion.
Deliver tailored demos that connect SiftMed's output to the buyer's specific workflow.

Be a Source of Market Signal

Bring competitive, pricing, and objection intelligence back to the team, consistently and specifically.
Feed product and marketing the patterns you're seeing across segments and geographies.
Support a clean handoff to Customer Success so what you sold is what gets delivered.

AI Fluency + Application

At SiftMed, AI is at the core of what we build. We need someone who doesn't just understand AI as a buzzword - you live it.

You use AI tools in your daily workflow - account research, call prep, follow-up, proposal drafting, and pipeline analysis.
You can speak credibly about how AI works in a regulated, high-stakes context, and address accuracy, privacy, and trust objections head-on.
You're excited to experiment with new AI-enabled sales tools and bring back what works.
You stay current on how AI is changing claims and legal workflows, and can separate hype from practical application.

Here Are Our Prerequisites

4 - 8 years of full-cycle B2B SaaS sales experience, with a consistent record of hitting or beating quota.
Sold into insurance - P&C strongly preferred - with a working understanding of how claims organizations operate and buy.
Startup experience - you've sold in an environment where the playbook, the category, and sometimes the product were still being built.
Genuine outbound ability - you can build pipeline from a cold list, not just work what's handed to you.
Comfortable with complex, multi-stakeholder cycles - including procurement, security, and privacy review.
Disciplined in CRM and forecasting - Salesforce hygiene and honest pipeline calls.
Demonstrated use of AI tools in your sales workflow - research, outreach, or productivity.

It Would Be Great If You Have Experience In

Selling into P&C carriers, TPAs, or plaintiff and defence law firms.
Healthtech, legaltech, or other regulated industries with privacy and security scrutiny.
Selling into both US and Canadian markets, and knowing where the buying differs.
Document-heavy or workflow automation software sold to operations and claims teams.
Building a territory or segment from scratch, including your own outbound motion.
Working closely with Marketing on ICP definition, messaging, and campaign feedback loops.

What Success Looks Like

First 90 Days

You can run discovery and demo independently, and speak credibly to claims and legal workflows.
A named-account target list is built for both US and Canadian markets, with outbound running against it.
Qualified pipeline is being created from both self-sourced and marketing-sourced activity.
Your first deals are progressing with forecasts that hold up to scrutiny.

First 12 Months

You're consistently hitting quota with a healthy mix of mid-market and enterprise deals.
Self-sourced pipeline is a reliable, repeatable part of your number - not an occasional spike.
You've closed business in both the US and Canada and can articulate what's different about each.
Your feedback has measurably sharpened ICP, messaging, and the sales playbook for the reps who come after you.