Geared toward experienced sales leaders comfortable with consultative selling and AI workflow integration, with a preference for candidates who have worked in audit, advisory, or assurance firms and can thrive in a remote, high-growth environment.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Fieldguide via Ashby
About Us
Fieldguide is establishing a new state of trust for global commerce and capital markets by augmenting the work of assurance and audit practitioners with AI agents. The value we bring firms: Expertise, amplified. We are based in San Francisco and have raised over $125M+ in venture funding from top Silicon Valley investors to accomplish our ambitious vision, including Goldman Sachs, Bessemer Venture Partners, 8VC, Floodgate, Y Combinator, Justin Kan, Elad Gil, and more.
We are the leading transformation partner for agentic audit and advisory with more than 50% of the top 100 CPA firms as customers, including several Big 4, and an industry-leading NPS to match. We save up to 75% of time on manual tasks and unlock over 4x capacity for audit practitioners, helping provide the work-life balance that is rare in the profession. Fieldguide's trajectory matches where later-stage vertical AI leaders were at this point in their journey, and you'd be joining early enough to have a meaningful impact.
Fieldguide values diversity, both in backgrounds and in experiences to help build the future of audit and advisory. We are deliberate in preserving a winning culture with our FFLOWI values - Fearless, Fast, Lovable, Owners, Win-Win, Inclusive - providing space for teammates to do their career’s best work through a tightly knit support network.
If you want to shape the most important shift in how commerce and capital markets establish trust, alongside world-class teammates, Fieldguide would love to build with you.
About the Role
Fieldguide is building the AI platform that will define the future of audit and advisory, and we’re looking for a Senior Manager, Mid-Market Sales to lead the team driving that vision. This is a high-impact, high-visibility role where you’ll own the performance and development of a team of Mid-Market Account Executives, while helping shape how we scale a core segment of our business. You’ll coach your team to meet and exceed revenue goals and help shape our sales strategy, processes, and high-performing culture. By championing a values-based selling approach, you’ll ensure the team is aligned with our mission to improve the efficiency and productivity of audit and advisory services.
You’ll be close to the deals, close to the team, and close to leadership. If you’re energized by building (reps, process, pipeline), this is the role for you.
This is a remote role located in the United States and reports to our VP, Sales. 30% travel required.
What You’ll Do
- Lead, coach, and support a team of Account Executives, ensuring they meet individual and team goals across pipeline generation, sales activity, and revenue performance.
- Help your team build relationships with key decision-makers at top audit and advisory firms by coaching them on how to understand business needs and tailor solutions accordingly.
- Review and guide deal strategies throughout the sales cycle, from prospecting to close.
- Partner cross-functionally with teams including Solutions, Finance, Marketing, and Product to ensure your team is equipped to deliver an excellent customer experience.
- Monitor key sales metrics and use data to guide coaching conversations, forecast revenue, and optimize team performance.
- Coach team to build deep industry knowledge and a point of view on the profession’s future, equipping them to lead credible, strategic executive conversations with prospects.
- Play a key role in refining our sales playbook, improving onboarding, and scaling best practices across the sales team.
- Lead and train your team on MEDDICC, using it to guide deal strategy, sharpen qualification, and forecast with precision.
- Represent Fieldguide at networking events and conferences, and help your team uncover new opportunities through relationship building.
- Up to 30% travel is required
Who You Are
- 2+ years of experience managing a sales team, ideally in a high-growth enterprise B2B SaaS environment.
- 5+ years of experience in a closing role, with a strong track record of exceeding quota and closing complex 6-figure deals with enterprise accounts.
- 1+ years experience working for and/or selling to audit, advisory, or assurance firms.
- Comfortable leading multi-threaded, highly consultative sales processes that involve multiple stakeholder levels, from executives to end users.
- Experienced in hiring, onboarding, and developing sales talent.
- Motivated by building repeatable processes in a startup environment and creating a collaborative, high-performing sales culture.
- AI-Native: You've built and used repeatable AI workflows (agents, prompts, automations, or tools) as part of your core work, and can point to specific outputs you've improved.
- Comfortable with Ambiguity: You move forward and deliver strong work even without all the answers. You've built a process, framework, or plan from scratch with no existing template, and can describe the specific structure you created to bring clarity to an unclear situation.
- Adaptable: Priorities shift and you recalibrate quickly. You've navigated a significant mid-cycle shift (tooling change, reorg, changing priorities, scope change) and can show how you adjusted your approach without losing momentum on active work.
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:
- Comprehensive health coverage (medical, vision, dental), plus life and disability insurance
- Equity stock options
- Paid public holidays, flexible PTO and flexible work schedules
- 401(k) plan through Human Interest
- Wellness benefits
- Technology and work from home reimbursement
- Paid parental leave
Source: Fieldguide careers (Ashby)