• Oversee a multi-location operation with up to 100 company drivers • Focus on P&L, asset management, safety, customer service, and driver onboarding • Handle management of tractor maintenance, compliance, and service delivery • Track operational performance including on-time pick-up and delivery, volume, and empty miles • Ensure driver recruiting and retention meets established fleet size goals

About Us Fieldguide is the AI-native platform for audit and advisory — the place where practitioners and agents work together to deliver higher quality work, faster, and with better client outcomes. Over 50 of the top 100 accounting and consulting firms trust Fieldguide to accelerate growth, improve quality, and transform the way audit and advisory work gets done. We're rooted in San Francisco, CA, but built as a remote-friendly, global company. We're backed by top investors including Growth Equity at Goldman Sachs Alternatives, Bessemer Venture Partners, 8VC, Floodgate, and Y Combinator. 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 we are building, seeking teammates who are not only strong in their own aptitudes but care deeply about supporting each other's growth. If you share our values and enthusiasm for building a great culture and product, you will find a home at Fieldguide. About the Role Fieldguide is an AI-native platform built for audit, advisory, and assurance workflows. Our customers are sophisticated accounting and advisory firms that operate in highly regulated environments, maintain long-term vendor relationships, and respond to renewal motions that are consultative and value-based. We're growing fast, and retention and expansion are core to the business. Reporting to the VP of Sales, this is a build-and-run role. There's no team to inherit and no playbook to follow. You'll own the full renewal lifecycle across our customer base — from first conversation through contract execution — while building the processes, systems, and frameworks that scale with the business. As the function grows, you'll have the opportunity to hire and develop a team of Renewals Specialists. The right person for this role has done the IC work, is ready to own outcomes rather than advise on them, and has the commercial instincts and credibility to build a renewals motion at a fast-moving Series C company. What You'll Do Own the Renewal Motion - Manage the full renewal lifecycle for all accounts: outreach, risk triage, negotiation, and close - Maintain a rolling 90-120 day renewal forecast; report weekly on pipeline health, risk, and expected outcomes - Develop a data-driven renewal strategy for each account before entering any negotiation, factoring in customer health, usage trends, stakeholder dynamics, and risk - Lead commercial negotiations directly with customers, including executive-level conversations on multi-year and at-risk accounts - Drive price increases, multi-year structures, and expansion identification at contract renewal - Work closely with CSEs to identify churn signals early and build mitigation strategies - Maintain clean renewal data and pipeline hygiene in HubSpot Build the Renewals Function - Build the renewals playbook from scratch: outreach cadences, escalation frameworks, negotiation guidelines, and segment-specific engagement models - Own the KPI framework for renewals — anchor it in leading indicators like MAU/WAU and consumption pacing, not just trailing metrics like GRR and NRR; establish the reporting cadence with Finance and CS leadership — this role shapes what the function measures - Design tiered engagement models across Strategic, Enterprise, Mid-Market, and SMB customer segments - Partner with Finance on Available-to-Renew (ATR) tracking and integration into the ARR forecast - Implement AI-assisted workflows for health scoring, churn risk flagging, and renewal automation where appropriate - Be the go-to resource on renewals best practices internally, setting the standard for how Fieldguide approaches retention and expansion Drive Cross-Functional Alignment - Represent renewal risk in deal reviews, QBRs, and exec-level revenue conversations - Partner with CSMs on health scores and churn signals — as part of the same team, this is a tight loop, not a handoff - Work with Product to access and interpret usage data (MAU/WAU, entitlement pacing, feature adoption) and translate it into renewal risk signals and customer conversations - Work with Finance on cohort analysis, GRR/NRR attribution, and retention economics - Coordinate with Legal and Deal Desk on non-standard contract structures - Feed customer signals back to Product and GTM leadership: usage trends, objections, competitive pressure, value realization About You - You have 7+ years in SaaS renewals, customer success, or commercial account management, with a track record of personally owning and hitting GRR/NRR targets - You've built a renewals function or motion from scratch — you wrote your own playbooks; you didn't inherit them - You're a strong commercial negotiator, comfortable leading high-stakes conversations at the CFO or executive level - You're analytically fluent: you can build a renewal forecast, segment a book of business by risk, and present cohort-level retention performance to leadership - You're CRM-proficient; HubSpot is strongly preferred, Salesforce is acceptable - You're an effective cross-functional operator who builds credibility through rigor and follow-through, able to influence Sales, Finance, and Legal without direct authority - You're ready to manage a small team; prior people management experience is preferred but not required for the right candidate - You're comfortable in a fast-moving environment where the playbook is still being written Bonus Points - Background in audit, accounting, or professional services, or experience selling to those firms — Fieldguide's customers are sophisticated practitioners, and knowing how they buy, budget, and evaluate software matters - Experience in AI-native SaaS or with AI workflow tools (health scoring, churn prediction, automated renewal triggers) - Experience scaling a renewals function through a Series B or C inflection point 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 - Loveable — Deliver happiness & 11-star experiences - Owners — Execute and run the business with ownership - Win-win — Create mutual value and earn trust for life - Inclusive — Scale the best ideas with inclusive teams Some of our benefits include: - Competitive compensation packages with meaningful equity ownership - Flexible PTO - Wellness benefits, including a bundle of free therapy sessions - Stock options - Technology and work-from-home reimbursement - Company offsites

Role Description Cardiff’s growth depends on the strength of its client relationships. As a Portfolio Manager, you are the anchor of that relationship, the person our clients trust to guide them through renewals, capitalize on new funding opportunities, and ensure their long-term success with Cardiff. This is not a passive account maintenance role. It is a revenue-generating, relationship-first position that sits at the intersection of sales, strategy, and service. The work you do directly impacts client retention, portfolio performance, and Cardiff’s continued expansion across diverse industries nationwide. Cardiff is looking for a proactive Portfolio Manager to oversee and expand a dedicated book of active clients. In this capacity, you will: - Cultivate enduring partnerships - Recognize strategic opportunities for renewal or upsells - Act as the central liaison across the entire client journey We are searching for a consultative professional who excels in high-velocity settings, demonstrates superior relationship oversight, and possesses a documented history of accelerating revenue within established accounts. Qualifications - Minimum of 2 years within customer success, account management, or revenue-generating renewal functions - Background in fintech, commercial lending, or merchant cash advance ecosystems - Demonstrated success in overseeing client portfolios and exceeding established financial objectives - Exceptional aptitude for persuasive communication, professional negotiation, and long-term relationship cultivation - Disciplined organizational skills with a mastery of high-velocity time management Requirements - Drive recurring revenue growth through disciplined renewal management, proactive risk mitigation, and precise forecasting - Complete onboarding and develop a working understanding of Cardiff’s products, funding criteria, and renewal process - Shadow senior team members and review existing client accounts to understand portfolio composition and relationship history - Get up to speed on Salesforce CRM workflows, internal tools, and cross-functional team processes - Establish initial contact with key accounts and begin building rapport with existing clients - Take full ownership of your assigned book of business and begin managing active renewal conversations independently - Build and maintain an accurate renewal pipeline in Salesforce, with reliable forecasting of upcoming opportunities - Identify upsell and capital expansion opportunities within the existing portfolio and begin converting them - Conduct initial business reviews with priority accounts and establish a cadence for ongoing client engagement - Consistently meet or exceed monthly renewal and revenue targets - Operate with full independence across your portfolio, proactively identifying at-risk accounts and taking corrective action before churn occurs - Deliver regular portfolio health analysis with forward-looking insights to leadership on retention trends and growth opportunities - Be recognized as a trusted strategic partner by your clients Benefits - Comprehensive medical, dental, and vision coverage - 401(k) retirement framework to ensure long-term financial security - Flexible Paid Time Off (PTO) and observed holidays to promote sustainable performance and balance - Remote-first flexibility complemented by strategic home office infrastructure support

• Serve as a trusted advisor to Regional Sales Directors and District Sales Managers, diagnosing performance gaps across skills, mindset, process, and tools. • Translate business priorities into targeted capability‑building strategies aligned to growth drivers (new business acquisition, menu expansion, competitive displacement). • Partner with Global Commercial Education to shape the annual capability roadmap grounded in field insights. • Design and deploy role‑specific capability journeys that build proficiency over time—not one‑off trainings. • Focus on high‑impact commercial capabilities, including: Strategic account planning & opportunity management, Clinical and economic value selling, Competitive differentiation & objection handling, Deal strategy & advanced negotiation, Territory & time optimization. • Conduct regular field rides and side‑by‑side coaching with Sales Specialists and District Managers. • Strengthen frontline manager effectiveness by coaching them on how to coach and embedding consistent coaching frameworks. • Use Salesforce (Summit), PowerBI, and other tools to diagnose performance trends, identify skill gaps, and measure capability impact. • Lead enablement strategy for APOC product launches, ensuring the field is clinically credible, commercially confident, and competitively equipped. • Apply modern learning principles (adult learning, microlearning, digital enablement) to create engaging, scalable solutions.