Enterprise Account Executive

Wisedocs is a fast-growing, venture-backed AI platform that transforms how insurance companies analyze claims. With ~$20M USD raised, 100+ team members globally, and 90+ customers across North America and Australia, we’re doubling revenue year over year. 

Founded by experts who’ve experienced the claims process firsthand, Wisedocs combines deep domain knowledge with next-gen AI trained on 100M+ documents. Our platform turns complex medical records into clear, structured insights—backed by expert human oversight. 

Join a mission-driven team building intelligent products that cut through complexity, accelerate decision-making, and make a real impact when it matters most.  

Role Summary 

We are searching for our next Enterprise Account Executive. The ideal candidate has experience selling to national carriers and law firms, experiencing building outbound pipeline, and a deep understanding of sales methodologies. 

In this role, you will be focused on our Enterprise segment, supporting customers through our Enterprise Sales Cycle. You are comfortable managing multiple stakeholders, understand all aspects of an Enterprise Cycle from multi-threading to security and compliance, and you have a proven track record of closing 6-7 figure deals.  

You have experience running an outbound and inbound cycle simultaneously and are able to manage your time to keep your pipeline healthy and growing. You are driven and are able to work self-directed and at a fast pace.  While this role is an individual contributor role, you are seen in your organization as a leader, and have the tenacity, experience and wisdom to coach your peers. 
 
Ontario based candidates: The position is a hybrid model with 20% travel within Canada and the US 

What you'll be doing: 

• Running a full lifecycle of an opportunity, from sourcing all the way through to close.   

• Running discovery calls, demos, and negotiation calls.   

• Building a pipeline of opportunities and researching, engaging and qualifying prospective customers through calling, emailing, networking, social media and in person  

• Collaborate closely with our Customer Success organization to ensure a smooth hand off from sales to onboarding for our clients   

• Work cross functionally with teams including product and operations to provide consistent client and market feedback to the organization.   

• Travel nationally and to the US to attend Conferences and other events  

• Other duties as assigned 

What Experience We Need 

• 10+ years' experience in an Enterprise Sales Role selling SaaS solutions. 

• Experience selling Insurtech solutions 

• You’ve been trained and follow a sales methodology (Sandler, Challenger, etc...) 

• You are technically competent and are comfortable running a product demonstration 

• You have a consistent track record of achieving quota. We are only looking for a top performer  

• Previous experience in the Insurance is desirable 

• Experience or understanding of Sales Tools, including Hubspot, SalesLoft, Zoominfo etc...   

• You have a successful track record owning the full sales cycling including prospecting to build your own pipeline, through opportunity development and closing. 

• Comfortable attending events and travelling nationally   

• Very personable and comfortable striking up a conversation (including cold calling), and building relationships  

• A go-getter and an entrepreneurial spirit 

• High level of professionalism  

• Excellent verbal and written communication skills  

• Strong organization and time management skills   

What We Offer 

• Flexible hybrid environment with the option to collaborate in-person at our Toronto HQ. 

• Modern employee benefits, including health and dental coverage  

• Competitive compensation, with valuable stock options, as we’re still a young company growing very quickly.   

• An opportunity to develop very rapidly in your career. We can offer you a super-immersive learning environment, and when you thrive there, you will have the opportunity to rapidly develop this opportunity into senior practitioner or management opportunities as you choose.   

• Access to a learning and professional development fund to help you level up your career while you’re working with us. We hope to be an incredible step up in your career if you decide to come and work with us.   

• Company events   

• Generous Paid Time Off   

• Paid Sick Days   

• Casual Dress code   

• Employee Referral Bonus   

• Tuition Assistance   

• Plus, many other Recognition Programs!   

Recruitment Journey at Wisedocs   

We're excited to meet you and explore the possibilities together!  At Wisedocs, honesty is one of our core values. Our Recruitment process is transparent to ensure you are set up for success:    

• Round 1 – People & Culture Chat: 20–30 min conversation about your background, goals, and the role.  

• Round 2 – Interview with the Enablement Manager: Deep dive into your experience and problem-solving approach. (30 min) 

• Round 3 – Presentation Interview with the SVP of Customer Success and Enterprise Account Executive (45 mins) 

• Round 4 – Interview with our COO: Learn about the Wisedocs Vision and how you’ll make an impact. 

Compensation 

The total on-target earnings (OTE) range for this position is $275,000 - $300,000 CAD. This range reflects the full growth journey within the role — from building and developing skills early on, to becoming highly proficient and ultimately achieving excellence. Where an offer lands within the range is based on your experience, skills, and impact, which we assess throughout the hiring process.  
We’re committed to fair and transparent pay and ongoing career development. If your expectations fall outside this range but you’re excited about the role, we still encourage you to apply.  

Note: We use AI-powered tools alongside human review to support a fair, inclusive, and efficient hiring process, helping us work smarter and create better experiences for our customers and team. 

This posting is for current and future opportunities at Wisedocs. Even if there isn’t an immediate opening, we’re always excited to meet great people. If your experience lines up, we encourage you to apply — we’ll reach out when a role opens that’s a good fit. 

*Wisedocs AI is an equal opportunity employer and are committed to providing employment accommodation in accordance with AODA. If you require an accommodation, please notify us and we will work with you to meet your needs.