Remote SMB Account Executive, Canada

About Us
Fieldguide is establishing a new state of trust for global commerce and capital markets through automating and streamlining the work of assurance and audit practitioners specifically within cybersecurity, privacy, and financial audit. Put simply, we build software for the people who enable trust between businesses.

We’re based in San Francisco, CA, but built as a remote-first company that enables you to do your best work. We’re backed by top investors including Growth Equity at Goldman Sachs Alternatives, Bessemer Venture Partners, 8VC, Floodgate, Y Combinator, DNX Ventures, Global Founders Capital, Justin Kan, Elad Gil, and more.

We value diversity — in backgrounds and in experiences. We need people from all backgrounds and walks of life to help build the future of audit and advisory. Fieldguide’s team is inclusive, driven, humble and supportive. We are deliberate and self-reflective about the kind of team and culture that we are building, seeking teammates that are not only strong in their own aptitudes but care deeply about supporting each other’s growth.

As an early stage start-up employee, you’ll have the opportunity to build out the future of business trust. We make audit practitioners’ lives easier by bringing together up to 50% of their work and giving them better work-life balance. If you share our values and enthusiasm for building a great culture and product, you will find a home at Fieldguide.

About the Role:

As a full cycle SMB Account Executive, you will be responsible for selling Fieldguide’s AI Advisory & Audit Cloud solutions as we expand into new territories this coming year. Your main responsibilities will be prospecting, identifying, and converting new business development opportunities for net new SMB accounts. This role will require working closely with CPA firms in Canada, where you will navigate a complex, multithreaded sales motion.

By taking a consultative, partner-oriented approach, you will guide firms as they undergo a significant technology shift in the industry—positioning Fieldguide not just as a vendor, but as a true AI partner. In the SMB space, where many firms are family-owned and deeply community-oriented, you will build authentic, trust-based relationships that respect their legacy while helping them embrace innovation. Through deep discovery and values-based selling, you will help these firms understand how Fieldguide’s platform can drive efficiency, modernization, and competitive differentiation, ultimately redefining the future of audit and advisory services.

This position will report to the Senior Manager, Sales and will be remote in Canada.

What You’ll Do:

• Own a targeted account list of key SMB accounts, overseeing the full sales cycle from prospecting to close.

• Achieve and exceed revenue targets and key sales metrics.

• Build strong, trust-based relationships with key decision-makers by providing thought leadership, understanding their business needs, and aligning Fieldguide’s solutions accordingly.

• Develop and implement sales strategies aligned to goals and targets by leveraging the MEDDICC sales methodology.

• Collaborate cross-functionally with teams including Solutions, Finance, Product, and Marketing to ensure customer needs and expectations are met throughout the sales process.

• Set strategic direction to maximize market potential within your assigned territory through effective planning and execution.

• Present compelling solution walkthroughs to prospects using insights uncovered during discovery.

• Own the creation, ideation, and execution of key account and territory plans.

• Maintain CRM diligence, forecasting accuracy, and clear communication with internal stakeholders related to your territory.

• Attend networking events and conferences to build relationships that generate new business opportunities.

• Up to 30% regional and national travel.

About You:

• Experience as an Account Executive, with a focus on net new logos and a proven track record of exceeding quota.

• Experience working for and/or selling directly to audit, advisory, or assurance firms is strongly preferred.

• Strong project management skills, with the ability to coordinate stakeholders and drive large, complex deals across the finish line.

• Capacity to engage deeply and broadly across an account—executives, practitioners, and technical teams—to influence stakeholders and drive meaningful change.

• Able to manage complex, multithreaded sales processes involving customer stakeholders from executives to day-to-day product users.

• Experience independently managing a complete sales cycle from prospecting to negotiation to close.

• Team player who collaborates effectively across internal teams (Solutions, BDRs, Finance, Product, Marketing, Customer Success, etc.).

• Motivated by building sales processes in a rapidly changing startup and being part of a team-oriented selling environment, demonstrating adaptability, resourcefulness, and mentorship.

More about Fieldguide:

Fieldguide is a values-based company. Our values are:

• Fearless – Inspire & break down seemingly impossible walls.

• Fast – Launch fast with excellence, iterate to perfection.

• Lovable – Deliver happiness & 11 star experiences.

• Owners – Execute & run the business with ownership.

• Win-win – Create mutual value & earn trust for life.

• Inclusive – Scale the best ideas with inclusive teams.

Some of our benefits include:

• Competitive compensation packages with meaningful ownership

• Flexible PTO

• Wellness benefits starting on your first day

• Technology & Work from Home reimbursement

• Flexible work schedules

Jobicy JobID: 154969