Senior Account Executive

ClearRisk Inc.; San Juan de Terranova; Remote; CAD 120,000 - 180,000; Full time

Benefits offered by this job

OTE plan

Stock options

Health plan

Paid time off

Remote work flexibility

Job summary

ClearRisk Inc. is seeking a Senior Account Executive in St. John’s, NL or remote to own a territory, prospect aggressively, and close multi-stakeholder SaaS deals. You’ll report to the CRO and partner with a lean team to drive growth across North America.

You will lead discovery, run demos, build ROI models, and manage the full sales cycle while traveling within Canada and the US as needed. If you’re entrepreneurial and customer-focused, join us to shape our sales playbook and own your success.

Qualifications

• 5–10 years of complex B2B SaaS sales experience in a quota-carrying closing role.
• Proven success closing multi-stakeholder deals with long sales cycles and executive or economic buyers.
• Hands-on experience building business cases or ROI models and running mutual action plans

Responsibilities

• Hunt and build your territory: build and run a territory plan and decide where to focus.
• Self-source at least 50% of your pipeline through multi-channel prospecting, including phone, email, LinkedIn, events, referrals and partners.
• Run the full sales cycle: own discovery, demos and proposals to close deals.
• Map the full buying group early and engage all stakeholders to understand motivators and needs.
• Build mutual action plans with your prospects and coordinate teams for execution.

Skills

Territory planning

Self-sourcing pipeline

Prospecting

Solution selling

CRM proficiency

Negotiation

SaaS sales

Communication

Education

Post-secondary education

Tools

Salesforce

LinkedIn Navigator

Job description

St. John’s, NL or Remote · Full-time, Permanent · Reports to the Chief Revenue Officer

Some sellers want a territory handed to them, a full pipeline waiting and a large team doing the

groundwork. This role isn’t for them. We’re looking for a Senior Account Executive who hunts, builds

and closes: someone who treats a territory like their own business and is energized by the ownership,

pace and impact that come with a smaller company.

About ClearRisk

ClearRisk is a rapidly scaling SaaS company. We are searching for a driven individual to join our sales

team as a Senior Account Executive. Reporting to the Chief Revenue Officer, the ideal candidate is an

entrepreneur at heart, has a passion for building external relationships, driving sales and all the benefits

and challenges that go along with that!

ClearRisk empowers our customers by optimizing risk and improving safety for their employees and the general public. We keep people from harm and help our customers be more successful. Our cloud-based claims and risk management solutions provide customers with a suite of tools and insights built for industries such as municipalities, utilities, real estate/property groups, manufacturers, retailers and more. Our solutions lower insurance and risk management costs while giving meaningful data insights that drive business growth.

You’ll have strong team support and a proven, mature SaaS solution that’s currently in-use within over

350 organizations in North America providing documented results.

Why This Role

• Build your own book. You’ll own a territory and the strategy to win it. At least half of your pipeline will come from your own prospecting, with the rest from inbound demand, events and partners.
• Shape the playbook. You’ll work directly with our CRO, and your input on targeting, messaging and process will influence how ClearRisk sells.
• Support where it matters. A subject matter expert with deep risk management experience joins select discovery calls and demos. Our BDR team follows up on inbound and event leads. We’re investing in paid demand generation, a new website launching early 2027 and an active events calendar, and our security and implementation teams back you through every deal.
• The honest version. We don’t have layers of BDRs, sales engineers and enablement staff. You’ll run your own discovery, demos and proposals, and coordinate the people around you to get deals done. If that sounds like freedom rather than a burden, keep reading.

The Sale

Our buyers manage real risk: people, property, fleets, claims and insurance programs. A risk or insurance leader is usually the champion, with IT, procurement, department leaders and senior executives (VP through CFO or CEO) involved in the decision. Sales cycles run three to twelve months, and some deals go through formal procurement. Many buyers are purchasing this kind of software for the first time, so they rely on you to guide them through the process.

What You’ll Do

Hunt and build your territory

• Build and run a territory plan: segment and prioritize accounts by fit and timing and decide where
• Self-source at least 50% of your pipeline through multi-channel prospecting, including phone, email, LinkedIn, events, referrals and partners.
• Use buying signals such as leadership changes, rising insurance costs and new budget cycles to reach the right people at the right time.
• Turn conferences and industry events into meetings and qualified opportunities.
• Open doors with senior leaders, not just end users.

Run the full sales cycle

• Own every stage from first conversation to signed contract, including discovery, demos and proposals.
• Map the full buying group early: champion, influencers, technical evaluators, procurement, decision makers and economic buyer. Know who signs, who can block and what each person needs.
• Engage every stakeholder to understand what motivates them, both for their organization and for them personally.
• Build business cases and ROI models with your champion that stand up in front of finance and executive leadership.
• Build mutual action plans with your prospects and use them to keep both sides accountable to dates, decisions and next steps.
• Navigate formal procurement, including RFPs, by coordinating internal contributors while staying accountable for the outcome.
• Coordinate the people who help you win, including our subject matter experts, security, product and implementation teams, and external partners.

Operate like an owner

• Qualify rigorously, focus your time on deals that will close and walk away from poor fits early.
• Deliver on monthly, quarterly and annual pipeline and revenue targets, as well as pipeline velocity and win rate.
• Keep your CRM clean and current (next steps, risks, close dates) and forecast accurately.
• Share customer and competitive insight with our Product team to inform the roadmap.
• Hand off smoothly to Implementation and Customer Success, and support expansion opportunities where you can help.
• Travel within Canada and the US as required, typically eight to nine trips per year.

Who You Are

• A hunter. Building pipeline from nothing energizes you. You don’t wait for leads.
• Autonomous. Give you a territory and a target, and you’ll build the plan and run it. You get
• Strategic. You think about where to play and how to win before you act, in your territory, in each account and in every deal.
• Extremely organized. Your pipeline, follow-up and forecast are always in order.
• Focused on deals that close. You qualify hard and protect your time.
• Trusted by buyers. You close with empathy and honesty. We don’t push customers into bad-fit solutions; we’d rather earn long-term trust than a short-term win.
• Entrepreneurial. You want the ownership, pace and visibility of a smaller company, and you run your pipeline like your own business.

What You Bring

Required

• Post-secondary education, ideally in business, marketing, economics or a technical field.
• 5–10 years of complex B2B SaaS sales experience in a quota-carrying closing role.
• A consistent record of meeting or exceeding quota, with a significant share of your pipeline selfsourced.
• Proven success closing multi-stakeholder deals with long sales cycles and executive or economic buyers.
• Hands-on experience building business cases or ROI models and running mutual action plans or a
• Strong discovery, demo and presentation skills, and excellent written and verbal communication.
• Proficiency with Salesforce or a comparable CRM.
• Ability to travel within Canada and the US as required.

Nice to have

• Experience selling to public sector organizations or managing formal procurement such as RFPs.
• A background in insurance, risk management, safety or claims, or experience selling insurance or risk software.

What We Offer

• A structured OTE plan, which we’ll walk through in detail during the interview process so you can see exactly how you’ll succeed.
• A structured onboarding and ramp program with clear milestones to track your progress.
• Stock options, a robust health plan and paid time off.
• The flexibility to work from our St. John’s office or remotely.
• A culture of openness, transparency and idea generation, where we keep it real.