Director of Accounting & Client Services

About Cartera Consultants Cartera Consultants is a Chicago-based outsourced accounting firm providing end-to-end financial management services to small and mid-sized businesses nationwide. We serve as the internal accounting team for our clients — handling everything from day-to-day bookkeeping to CFO-level advisory, financial reporting, budgeting, forecasting, and operational KPIs. We specialize heavily in restaurant accounting and also serve clients in real estate, professional services, media, management companies, and holding companies. Our model is à la carte and highly scalable — we grow alongside our clients, from single-location startups to multi-unit operators. Our team includes U.S.-based accounting professionals across two Chicago offices. We leverage tools including QuickBooks Online, QuickBooks Desktop, Restaurant365, Ottimate/PlateIQ, Bill.com, and a wide range of payroll and POS platforms. The Opportunity Cartera Consultants is in an active growth phase — expanding our client base, deepening our service offerings, and building the internal infrastructure to support that growth. We are looking for a senior accounting leader to help us scale: someone who can own quality control, lead and develop the team, and serve as the primary point of accountability for client deliverables while we continue to grow. This is a role for someone who wants to be part of building something — not just managing the status quo. For the right person, there is significant long-term opportunity within the firm. What You'll Own Serve as the firm's senior technical accounting authority — reviewing and signing off on all client financials, reconciliations, and reporting packages Lead, mentor, and develop a team of staff and senior accountants and AP specialists Manage client relationships at the CFO/Controller level, including financial reviews, strategic conversations, and escalation resolution Oversee weekly and monthly operational reporting deliverables including cash flow, labor reports, COGS, budgets, and KPI dashboards Establish and enforce firm-wide quality control standards and review processes Drive onboarding of new clients — scoping, setup, systems integration, and team assignment Collaborate with the Managing Partner on firm strategy, service expansion, and client retention Support recruiting, training, and performance management of accounting staff Step in as a working manager when needed — this is a hands-on role, especially in the near term What Success Looks Like in Your First 90 Days You have taken over primary review responsibility for client financials — firm leadership is no longer the final checkpoint Financials are going out on time with fewer revisions, escalations, and corrections after delivery You have identified inconsistencies across client accounts and put standards in place to address them The team is more confident, more consistent, and has a clear point of accountability above them You have a firm grasp on each client's complexity, nuances, and reporting cadence Client relationships at the Controller/CFO level feel stable and well-managed What Your Day to Day Looks Like Reviewing reconciliations, journal entries, financial statements, and reporting packages across multiple client engagements before they go out the door Catching and correcting GL issues, classification errors, and inconsistencies — accuracy is non-negotiable Leading and coaching a team of staff and senior accountants and AP specialists across varying client complexity Managing close deadlines across multiple clients simultaneously without dropping the ball Fielding complex accounting questions from the team and serving as the go-to technical resource Communicating directly with clients at the Controller or CFO level — reviewing financials, explaining variances, and providing strategic context Continuously improving internal workflows and review processes to increase efficiency as the firm grows This is not a back-office-only role — you are client-facing, team-leading, and technically hands-on all at once What We're Looking For CPA required 7+ years of progressive accounting experience; public accounting or client services background strongly preferred Deep technical accounting proficiency — you can spot an error, explain the journal entry, and coach someone through it Experience managing a team and owning client relationships Proficiency in QuickBooks Online (QBO) required; Restaurant365, Bill.com, or Ottimate/PlateIQ experience a strong plus Restaurant or multi-unit industry experience highly desirable Strong communicator — able to translate financial data into clear, plain-language insights for non-financial clients Self-directed, highly organized, and comfortable owning outcomes in a fast-paced environment Entrepreneurial mindset — you see this as building something, not just filling a seat Compensation & Benefits Competitive base salary commensurate with experience ($110,000 – $140,000) Performance-based bonus Significant long-term growth opportunity within the firm for the right candidate In-office role based in Chicago, IL near O'Hare Airport Professional development and continuing education support Collaborative, low-bureaucracy environment where your work directly shapes the firm Why Join Cartera? You won't be a cog in a machine here. Cartera is growing, and this role sits at the center of that growth. You'll have real ownership over the quality and direction of our client work, a direct line to firm leadership, and the opportunity to grow with us in a meaningful way. If you're a strong technical accountant who also knows how to lead people and serve clients — and you're ready to stop being underutilized — we'd like to talk. Pay: $110,000.00 - $140,000.00 per year Benefits: 401(k) 401(k) matching Dental insurance Health insurance Paid time off Vision insurance License/Certification: CPA (Preferred) Work Location: In person