Head of Operations

Lever Middleware Test Company; Chicago (IL); On-site; USD 150,000 - 210,000; Full time

Job summary

Carol's Club is seeking a Head of Operations in Chicago to lead and optimize internal functions across Sales, Customer Success, Marketing, and Finance. You’ll implement operating rhythms, KPIs, and scalable processes to accelerate growth and improve time-to-value.

The role requires 8–12+ years in operations, strong executive collaboration, and proven leadership. A Bachelor’s degree is required, MBA is a plus; experience with Salesforce, HubSpot, and Looker is preferred.

Qualifications

• 8–12+ years of experience in business operations, revenue operations, or strategy roles in SaaS, tech-enabled services, or startup environments.
• Proven success leading operations through periods of rapid growth or transformation.
• Familiarity with scaling business systems and tools such as Salesforce, HubSpot, Asana, NetSuite, Gainsight, Looker or similar platforms.
• Exceptional cross-functional collaboration and communication skills; experience influencing at the executive level.
• Strong analytical orientation with experience building, managing, and interpreting operational dashboards.
• Demonstrated leadership capabilities in building high-performing teams and scalable processes.
• Bachelor’s degree required; MBA or related graduate degree is a plus.

Responsibilities

• Lead and optimize internal operations, ensuring seamless coordination across Sales, Customer Success, Marketing, and Finance functions.
• Build and own operating rhythms and KPIs across departments—establishing accountability frameworks and reporting mechanisms that enable scale.
• Drive process improvement initiatives, systems integrations, and automation efforts to reduce inefficiency and improve time-to-value across teams.
• Collaborate closely with Revenue and Customer teams to optimize lifecycle execution, renewal management, and GTM effectiveness.
• Serve as strategic partner to the CEO and executive team, enabling data-informed decision-making through strong business intelligence and analytics.
• Support budgeting, forecasting, and headcount planning processes in partnership with Finance.
• Manage key vendors, tools, and technology platforms that support internal operations (CRM, project management, support, and ERP systems).
• Hire, lead, and mentor a growing Ops team; foster a culture of ownership, curiosity, and continuous improvement.

Skills

Cross-functional collaboration

Executive stakeholder management

Analytics & dashboards

Team leadership

Education

Bachelor's degree

MBA or related graduate degree

Tools

Salesforce

HubSpot

Asana

NetSuite

Gainsight

Looker

Job description

At Carol's Club, we revolutionize career coaching by leveraging our retained executive search expertise and insider hiring insights to deliver unmatched, results-driven strategies. Unlike generic programs, our no-nonsense approach focuses on what decision-makers truly value, empowering leaders to stand out, be recognized, and amplify their internal and external brand equity while maximizing their earning potential.

Through tailored solutions—such as interview coaching from retained search experts who know what hiring managers and companies need and want to hear, resume and LinkedIn optimization, and precision preparation—we help you navigate today’s evolving employment market with confidence. At Carol's Club, we don’t just guide your career, we ignite it, ensuring you achieve sustainable growth and secure impactful opportunities for years to come.

Key Responsibilities

• Lead and optimize internal operations, ensuring seamless coordination across Sales, Customer Success, Marketing, and Finance functions.
• Build and own operating rhythms and KPIs across departments—establishing accountability frameworks and reporting mechanisms that enable scale.
• Drive process improvement initiatives, systems integrations, and automation efforts to reduce inefficiency and improve time-to-value across teams.
• Collaborate closely with Revenue and Customer teams to optimize lifecycle execution, renewal management, and GTM effectiveness.
• Serve as strategic partner to the CEO and executive team, enabling data-informed decision-making through strong business intelligence and analytics.
• Support budgeting, forecasting, and headcount planning processes in partnership with Finance.
• Manage key vendors, tools, and technology platforms that support internal operations (CRM, project management, support, and ERP systems).
• Hire, lead, and mentor a growing Ops team; foster a culture of ownership, curiosity, and continuous improvement.

Key Qualifications

• 8–12+ years of experience in business operations, revenue operations, or strategy roles in SaaS, tech-enabled services, or startup environments.
• Proven success leading operations through periods of rapid growth or transformation.
• Familiarity with scaling business systems and tools (e.g., Salesforce, HubSpot, Asana, NetSuite, Gainsight, Looker, or similar platforms).
• Exceptional cross-functional collaboration and communication skills; experienced in influencing at the executive level.
• Strong analytical orientation with comfort building, managing, and interpreting operational dashboards.
• Demonstrated leadership capabilities in building high-performing teams and scalable processes.
• Bachelor’s degree required; MBA or related graduate degree is a plus.

Competencies

• Builder’s mindset with attention to detail and a relentless drive for improvement.
• Balances strategy with execution—comfortable in both the weeds and the boardroom.
• High EQ, low ego—able to inspire teams while holding them to high standards.
• Operates with urgency, transparency, and integrity.

Pay is biweekly

This is a job description taken off a random Head of Operations posting on LinkedIn :)