Strategic 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 from anywhere. 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 Fieldguide’s second Strategic Account Executive in Canada, you will play a pivotal role in expanding our presence across the region’s largest audit and advisory firms. This is a full-cycle strategic sales role focusing on driving net new revenue while shaping our global go-to-market approach for leading public accounting organizations.

You will drive a cross-functional, international sales strategy to penetrate key markets and build strong, value-based partnerships with senior stakeholders across Canada. By understanding each country’s market dynamics, priorities, and regulatory landscape, you’ll translate global strategy into local execution - delivering solutions that elevate efficiency, productivity, and the future of audit and advisory services.

This is an opportunity to help build the playbook for international growth and work directly with some of the world’s top Accounting firms while helping Fieldguide scale its global engine.

Reporting to our Sr. Director of Sales, this role is remote and based remotely in Canada.

What You’ll Do

• Drive strategy: Orchestrate account strategy across the region, landing international clients and ensuring alignment toward shared revenue goals.
• Own strategic accounts: Manage a targeted list of Canadian firms, overseeing the full sales cycle from prospecting to close.
• Drive revenue growth: Consistently achieve and exceed revenue targets and sales metrics across your global portfolio.
• Executive-level stakeholders: Manage, prepare, and partner effectively with senior executives, both external and internal.
• Market knowledge: Deep experience and knowledge of the Canadian market, including its business culture, buying dynamics, and competitive landscape
• Own complex project management: Coordinate stakeholders and deliverables across global accounts to advance large-scale opportunities.
• Build executive trust: Establish yourself as a trusted advisor with global decision-makers, aligning Fieldguide’s solutions to business needs and strategic objectives.
• Lead compelling engagements: Deliver executive-level presentations and solution walkthroughs that resonate across diverse stakeholders.
• Coordinate cross-functionally: Partner with Solutions, Finance, Product, and Marketing teams to deliver globally consistent yet locally relevant customer outcomes.
• Develop playbooks: Capture learnings and best practices to continuously refine Fieldguide’s enterprise and global sales processes.
• Represent Fieldguide globally: Attend key industry conferences and networking events to strengthen our global presence and open new opportunities.
• Travel up to 30% expected.

Who You Are

• 10+ years of sales experience as an Account Executive, with a focus on net new logos and account management with a proven track record exceeding quota and selling complex software solutions to key strategic accounts.
• Prior experience working for and/or selling directly to audit/advisory/assurance firms
• Strong executive presence and experience successfully selling to executives at large enterprise customers.
• Global strategist: Skilled at orchestrating multi-regional sales efforts, balancing global strategy with local execution.
• Able to manage complex, multi-threaded, highly technical 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 and coordinating the movement of multiple AE’s
• Team player who collaborates effectively across internal teams (Solutions, Finance, Product, Marketing, etc.)
• Motivated by building sales processes in a rapidly changing startup and being part of a team-oriented selling environment.

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
• 401k
• Wellness benefits starting on your first day
• Technology & Work from Home reimbursement
• Flexible work schedules