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Director of Client Operations - Cloud

Thinkahead

Chicago, Illinois Hybrid permanent

Posted: February 26, 2026

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Quick Summary

AHEAD provides cloud infrastructure and delivery services to enterprises, focusing on delivering digital transformation solutions. The Director of Client Operations is responsible for overseeing client operations, managing client relationships, and ensuring successful project delivery.

Job Description

AHEAD builds platforms for digital business. By weaving together advances in cloud infrastructure, automation and analytics, and software delivery, we help enterprises deliver on the promise of digital transformation.

At AHEAD, we prioritize creating a culture of belonging, where all perspectives and voices are represented, valued, respected, and heard. We create spaces to empower everyone to speak up, make change, and drive the culture at AHEAD.

We are an equal opportunity employer, and do not discriminate based on an individual's race, national origin, color, gender, gender identity, gender expression, sexual orientation, religion, age, disability, marital status, or any other protected characteristic under applicable law, whether actual or perceived.

We embrace all candidates that will contribute to the diversification and enrichment of ideas and perspectives at AHEAD.

The Director of Client Operations – Cloud will oversee the operational execution, governance, and scalability of AHEAD’s Cloud business.

This role is a strategic leadership position designed for an operator who thrives in ambiguity and is excited to define the processes, governance, and operating model that will power AHEAD’s next phase of Cloud growth. The Director will play a critical role in shaping how Cloud business is transacted, billed, booked, and supported at scale.

This role is responsible for demystifying Cloud operations and translating complex partner programs, funding mechanisms, deal structures, and booking paths into repeatable, compliant, and scalable processes. This leader will achieve results by evaluating and organizing processes, data, and workflow which helps optimize business outcomes. They will need to work cross-functionally driving efficiencies to help AHEAD scale its operations.

As a people leader, this Director will manage and grow a global team of Client Operations professionals across the U.S. and India, initially leading a team of approximately five direct reports with expected growth as the Cloud business scales. This role serves as a strategic partner to Sales, Finance, Services, and Executive Leadership, ensuring Cloud transactions are executed accurately, efficiently, and in alignment with company policies and partner program requirements.

This role has fiduciary responsibility to the business and must ensure AHEAD’s financial success by acting as a steward of Cloud transactions from pre-sale through post-sale. The Director must possess strong financial and operational acumen, with a deep understanding of Cloud partner programs, deal registrations, funding, quoting, booking, invoicing, and post-sale issue resolution.


Responsibilities:
• Oversee the day-to-day activities and operations of a Cloud-focused team across U.S. and India-based teams
• Lead teams through high-volume, time-sensitive periods including month-end, quarter-end, and year-end close
• Recruit, onboard, develop, and retain top Cloud operations talent as the business scales
• Establish and monitor KPIs to assess team performance, transaction quality, cycle times, and compliance
• Coach team members to deepen their understanding of Cloud business models, partner programs, and their impact on financial outcomes
• Foster a high-performance, collaborative, and accountable team culture across geographies
• Serve as the operational subject-matter expert for Cloud partner programs, including program requirements, deal registrations, funding mechanisms, incentives, and compliance obligations
• Define and operationalize Cloud booking strategies that align with partner program requirements, company policies, and financial objectives
• Design, implement, and scale Cloud-specific operational processes, procedures, and reporting
• Ensure accurate interpretation and execution of Cloud partner agreements, program rules, and financial structures
• Partner with Finance to ensure Cloud transactions align with accounting principles, revenue recognition rules, and margin expectations
• Own Cloud billing and subscription-based operational models, including consumption-based, term-based, and hybrid billing structures
• Establish governance and controls around subscription lifecycle management, including provisioning, renewals, expansions, amendments, cancellations, and terminations
• Ensure accurate booking paths for Cloud transactions, including marketplace and direct partner motions, while minimizing revenue leakage and cash exposure
• Lead investigation and resolution of complex Cloud billing discrepancies, usage variances, pricing issues, and partner funding impacts
• Design scalable processes and reporting to support recurring revenue models, subscription forecasting, and deferred revenue management
• Act as a strategic partner to Sales and Sales Leadership to enable efficient Cloud deal execution while protecting the business
• Manage and resolve escalations related to Cloud opportunity management, quoting, booking, invoicing discrepancies, funding, and post-sale issues
• Support post-sale program management, including investigation and resolution of invoice discrepancies, funding shortfalls, and partner issues
• Maintain regular cadence with Sales Leadership regarding pipeline health, deal structure considerations, and Cloud-specific risks
• Review Cloud sales programs and non-standard transactions to identify and mitigate financial, compliance, and revenue recognition risks
• Partner with Sales, Finance, Cloud partners, and customers to resolve issues impacting order accuracy, revenue recognition, and cash flow
• Present metric-driven reporting and insights to leadership to support decision-making and continuous improvement
• Ensure Cloud operational practices support scalability, audit readiness, and financial integrity


Qualifications:
• 5+ years of Operations or Sales Support in the Technology industry
• 5+ years of direct people management
• 3+ years of exposure to Cloud product sales or operations (i.e: Amazon, Google, or Microsoft)
• Bachelor’s degree, Advanced degree in Business, Economics, Finance or Operations or Professional Certification such as Project Management Professional (PMP) or Lean Six Sigma.
• Strong people leadership skills, including coaching, performance management, and talent development
• Executive presence with the ability to influence cross-functional stakeholders
• Deep operational and financial acumen with strong understanding of revenue recognition and accounting principles
• Strong analytical, reporting, and problem-solving skills
• Ability to operate effectively in a fast-paced, high-transaction sales environment
• Experience transacting business with international vendors and teams
• Salesforce experience required; Office 365 proficiency
• Strong organizational, communication, and presentation skills
• Continuous improvement mindset with the ability to scale processes as the business grows


Why AHEAD:

Through our daily work and internal groups like Moving Women AHEAD and RISE AHEAD, we value and benefit from diversity of people, ideas, experience, and everything in between.

We fuel growth by stacking our office with top-notch technologies in a multi-million-dollar lab, by encouraging cross department training and development, sponsoring certifications and credentials for continued learning.

USA Employment Benefits include:
- Medical, Dental, and Vision Insurance
- 401(k)
- Paid company holidays
- Paid time off
- Paid parental and caregiver leave
- Plus more! See benefits https://www.aheadbenefits.com/ for additional details.

The compensation range indicated in this posting reflects the On-Target Earnings (“OTE”) for this role, which includes a base salary and any applicable target bonus amount. This OTE range may vary based on the candidate’s relevant experience, qualifications, and geographic location.

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