Head of Operations

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Job Title Head of Operations

Location Remote

Time Zone Core Hours: 10:00 AM – 3:00 PM Central Time (CT)

Role Overview We are looking for a Head of Operations to own the operating engine of a fast-growing professional services firm. This role sits at the intersection of sales execution, client delivery, and team performance. You will be the second-in-command reporting directly to the Owner, with authority and accountability across the full business—responsible for driving MRR growth, protecting client retention, and building the operational infrastructure that makes results repeatable at scale.

Key Responsibilities

• Design and own the operating system that connects sales, onboarding, delivery, and retention into one cohesive engine

• Lead a distributed global team across time zones, setting weekly priorities and holding contractors and employees accountable to results

• Own new MRR targets: coordinate SDR activity, manage an outsourced sales team, and close new business personally where needed

• Build an MRR-first model: define packaging, pricing minimums, and scope controls that reduce churn and rework

• Run weekly sales and ops cadences, maintain a live scorecard, and deliver monthly KPI reviews to the Owner

• Strengthen client onboarding, communication standards, and escalation protocols to protect a 95%+ retention target

• Manage capacity planning, contractor coverage, and scheduling to prevent delivery bottlenecks during growth

• Own rolling 13-week cash flow tracking and flag risks proactively

• Build and maintain SOPs, templates, and checklists so the team can execute consistently without heroics

• Track and improve key metrics: MRR health, close rates, on-time delivery, rework rates, and labor cost as % of revenue

Required Qualifications

• Demonstrated experience building a services firm from early stage to $1–$5M in recurring revenue

• Proven track record owning both the revenue side (sales, pricing, pipeline) and the delivery side (staffing, retention, client experience)

• Hands-on experience selling and delivering monthly recurring services: bookkeeping, accounting/CAS, fractional CFO, IT managed services, or similar

• Experience improving client retention through structured onboarding, expectation management, and proactive escalation

• Experience managing distributed or global teams, including contractors, across multiple time zones

• Data-driven operator: you run weekly scorecards and make decisions with numbers, not gut feel

• Must have prior remote work experience, be proficient with remote collaboration tools (Slack, Zoom, ClickUp, Google Workspace, or similar), and have ideally worked with US or UK-based companies. Applications without this experience will not be considered.

Preferred Qualifications

• Experience selling into small-to-mid-sized B2B service or SaaS companies

• Background building referral and partner programs with accountants, attorneys, lenders, or financial advisors

• Preference for lean, low-overhead environments where ownership is real and results speak for themselves

Tools & Technology

• Slack

• ClickUp

• Google Workspace

• Google Meet / Zoom

• QuickBooks Online (QBO)

• Canopy

• UltraTax

Please NOTE It is crucial that you complete the application form in full. As part of the application process, you will be required to record a video. If your application is successful, you will receive an email confirming next steps—the video is the first step of the interview process. If you do not record a video, we will not be able to consider you for ANY open roles.

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