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Fieldguide is a venture-backed SaaS company (backed by Goldman Sachs Growth Equity, Bessemer Venture Partners, Y Combinator, and others) building AI-powered audit and advisory software for assurance practitioners in cybersecurity, privacy, and financial audit. The company is headquartered in San Francisco but operates as a remote-first organization.
As a full-cycle SMB Account Executive based in Canada, you will own a targeted account list of key SMB accounts and manage the complete sales cycle from prospecting through close. Your primary focus is converting net new business development opportunities with CPA firms across Canada, navigating complex, multithreaded sales motions.
You will take a consultative, partner-oriented approach, positioning Fieldguide as an AI partner rather than a vendor. Many target firms are family-owned and community-oriented, so you'll build authentic, trust-based relationships that respect their legacy while helping them embrace innovation. Through deep discovery and values-based selling, you'll help firms understand how Fieldguide's platform drives efficiency, modernization, and competitive differentiation.
Key responsibilities include: owning a targeted account list and full sales cycle; achieving and exceeding revenue targets; building trust-based relationships with decision-makers through thought leadership; developing and implementing sales strategies using MEDDICC methodology; collaborating cross-functionally with Solutions, Finance, Product, and Marketing teams; setting strategic direction to maximize market potential in your territory; presenting compelling solution walkthroughs; creating and executing account and territory plans; maintaining CRM diligence and forecasting accuracy; attending networking events and conferences; and up to 30% regional and national travel.
You will report to the Senior Manager, Sales.
REQUIREMENTS:
- Proven experience as an Account Executive with a track record of exceeding quota and closing net new logos
- Experience working for and/or selling directly to audit, advisory, or assurance firms (strongly preferred)
- Strong project management skills with ability to coordinate stakeholders and drive large, complex deals to completion
- Capacity to engage deeply and broadly across accounts—with executives, practitioners, and technical teams—to influence stakeholders and drive meaningful change
- Ability to independently manage complete sales cycles from prospecting through negotiation to close
- Experience managing complex, multithreaded sales processes involving multiple customer stakeholders from executives to day-to-day product users
- Team player who collaborates effectively across internal teams (Solutions, BDRs, Finance, Product, Marketing, Customer Success)
- Motivated by building sales processes in a rapidly changing startup environment, demonstrating adaptability, resourcefulness, and mentorship
