Remote
SaaS
himalayas
About this role
Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages.
While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles!As an Account Executive SMB Firms at Caseware, your goal will be to drive new, upsell and cross-sell sales of Caseware’sproduct suite with a focus on small and medium-sized clients within our US market.
Your role will be focused on sales within the firm market segment and will be primarily selling our OnPoint suite of products to small firms and sole proprietors. This is a massive opportunity because our research is showing 100,000+ sole proprietors in the US market alone, and with our recent strategic partnership with we expect huge support in marketing.
We are going through a build-up of our Sales organization, and you will be a founding member of the future of Sales Operations at Caseware. If are a Sales Professional with a hunter-mentality and going after new business is something that inspires you, we want to hear from you! (This role will be 50/50 split between inbound & outbound activities).
This role would be perfect for you if you are success-driven, achievement-oriented, love sales, and believe in performance rewards for exceeding sales goals.
This role is remote and is open to all candidates who reside and are eligible to work in US (preferably on the East coast).❗Note, a successful candidate will work in North American time zones - EST, MT, PST (The time zone is TBD depending on the territory assigned).
What you will be doing: Using prospecting solutions like ZoomInfo and LinkedIn to generate leads within a defined territory and region. Using sales and marketing assets to create email campaigns Given a list of contacts generated by marketing as well as existing inbound leads, contact
Tools & Tech Stack
Commission Structure
Base Salary
Not disclosed — ask in interview
Commission
Structure not specified
OTE
$,
Split
50/50
Ramp Period
Not mentioned — clarify timeline
Selling Motion
Sales Cycle
SMB / Transactional
Under 1 month, high-velocity closing
Prospecting
Hybrid
Mix of inbound leads and outbound prospecting
Buyer Persona
C-Suite
Selling to executive decision-makers
Requirements at a Glance
Typical Day — Account Executive
Estimates based on role type and selling motion — actual may vary by company.
Role Signals
Green Flags
Warm leads provided
Location flexibility
SaaS — Interview Intel
Typical Sales Cycle
30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)
Common Buyer Objections
- "We're locked into a contract with [competitor]"
- "We built something in-house already"
- "We don't have budget until next quarter"
- "Our team won't adopt another tool"
Key Industry Metrics
Hot Topics to Reference
- • AI-native product disruption
- • PLG vs sales-led motion debate
- • Vertical SaaS consolidation
- • Usage-based pricing models
Use these insights to speak the buyer's language in interviews.
Tags
Walk me through your discovery process.
Template questionHow do you handle a prospect who goes silent mid-deal?
Template questionTell me about your largest closed deal and the sales cycle.
Template questionHow do you build business cases for stakeholders?
Template questionDescribe a deal you lost and what you learned.
Template questionThis Account Executive position at CaseWare involves managing the full sales cycle from prospecting through close.
SaaS sales roles typically involve consultative selling with longer deal cycles.
This remote-friendly role provides geographic flexibility while maintaining access to a SaaS market.
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