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TaxGrit
Head of SalesTaxGrit • Winnipeg, Canada
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Head of Sales

Head of Sales

TaxGrit • Winnipeg, Canada
6 days ago
Job type
  • Full-time
Job description
TaxGrit is the AI native tax practice management platform for Canadian CPA firms. We handle T1 and T2 filing workflows, client onboarding, document collection, e signatures, and firm wide automation in a single platform, replacing the legacy stack of TaxDome, TaxCycle, and Canopy.

About the role We are hiring our first sales leader. You will own TaxGrit's commercial motion end to end: GTM strategy, outbound playbook, founder led to founder assisted transition, SDR onboarding and management, pricing conversations, discovery, demos, and close. You will partner directly with the founder during the moment TaxGrit moves from challenger to default choice in Canadian accounting tech.

What you'll own

The TaxGrit GTM playbook from cold prospect to closed customer

Hiring, onboarding, and managing the SDR team and growing the commercial team through 2027

Pipeline forecasting, quota setting, and revenue reporting to the founder

Discovery, demo, and closing motion design and refinement

Pricing, packaging, and competitive positioning against TaxDome, Canopy, and TaxCycle

Account expansion playbook for multi seat firms and mid market accounts

What we're looking for

10 to 15 years in B2B SaaS sales, with 5+ years carrying or leading a revenue quota

Demonstrated experience scaling early stage SaaS revenue (Seed to Series B stage)

Track record of building and managing high performing sales teams

Vertical SaaS background preferred: tax, accounting, legal, healthcare, fintech, or similar regulated B2B

Strong founder partnership instincts, comfortable operating in ambiguity

Familiarity with Canadian SMB and mid market sales motions

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Head of Sales • Winnipeg, Canada

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