Job Overview
Location
Chicago, Illinois, USA
Job Type
Full-time
Category
Chief of Staff
Date Posted
February 24, 2026
Full Job Description
📋 Description
- • Ensono is seeking a highly strategic and results-oriented Chief of Staff to partner directly with the SVP of New Logo Sales. This pivotal role is designed to be a force multiplier, empowering the sales organization to achieve and exceed its growth objectives. You will be instrumental in shaping and executing the strategy for acquiring new logos, focusing on optimizing seller performance, driving pipeline progression, and ensuring seamless cross-functional alignment. Your primary mission will be to translate the SVP's vision into actionable programs and initiatives that yield measurable outcomes, directly impacting Ensono's market expansion and revenue growth.
- • As a key strategic advisor, you will deeply engage with the SVP to refine and articulate the overarching strategy for new logo acquisition. This involves a critical analysis of the ideal client profile (ICP), ensuring it is clearly defined, communicated, and consistently applied across the entire sales team. You will lead the development and refinement of this ICP, working collaboratively to identify target markets, understand customer needs, and equip sellers with the insights and tools necessary to effectively engage and convert these prospects.
- • A significant aspect of your role will be program development and execution. You will conceptualize, design, and implement programs specifically tailored to support the goals of the New Logo Sales organization. These programs will have a strong emphasis on seller enablement, providing them with the training, resources, and support needed to enhance their skills, improve their effectiveness, and ultimately drive more deals to closure. You will be responsible for defining success metrics for these programs and rigorously tracking their impact on key performance indicators.
- • Communication is paramount in this role. You will be responsible for creating and executing comprehensive communication strategies that ensure consistent, frequent, and impactful messaging reaches the New Logo Sales team and all relevant stakeholders. This includes managing internal communications, ensuring alignment across departments, and providing clear updates on strategic initiatives, program progress, and performance. You will also coordinate communications for a geographically diverse sales team, ensuring everyone is informed and aligned, regardless of their location.
- • You will play a crucial role in the operational cadence of the sales organization. This includes coordinating and supporting critical processes such as programmatic reviews, budgeting, sales planning, and forecasting. Your involvement will ensure these processes are efficient, data-driven, and aligned with strategic objectives, providing the SVP with the insights needed for informed decision-making.
- • Mentoring and leadership development are integral to your responsibilities. You will mentor sales leaders and individual sellers, fostering a culture of collaboration and continuous improvement. By building leadership capabilities within the team, you will empower them to navigate complex sales cycles and drive greater success. This includes enhancing cross-functional collaboration, breaking down silos, and ensuring a unified approach to client engagement.
- • Building and maintaining strong relationships with other departments is essential for success. You will act as a bridge between the New Logo Sales team and other critical functions such as Marketing, Product, Finance, and Operations. By fostering these relationships, you will ensure seamless communication and effective program strategies that support the sales organization's objectives and contribute to overall business success.
- • Partnering with HR, you will contribute to the development and execution of talent strategies specifically for the sales organization. This includes initiatives focused on career development, specialized sales training, and employee engagement, ensuring that the sales team is motivated, skilled, and aligned with Ensono's values and goals.
- • You will be tasked with identifying, structuring, and driving multiple strategic programs simultaneously. This requires exceptional project management skills to oversee complex initiatives from conception through completion, ensuring they are delivered on time and within scope, and that they deliver the intended business impact.
- • You will be responsible for analyzing sales performance and engagement data. By translating complex data into actionable insights, you will identify trends, pinpoint areas for improvement, and recommend strategies to accelerate pipeline progression and increase deal closure rates. This data-driven approach will be critical in optimizing sales efforts.
- • In certain instances, you may be required to manage relationships with strategic partners, ensuring these collaborations effectively support the New Logo Sales organization's goals and contribute to broader business objectives.
- • Finally, you will develop and manage meeting strategies, including crafting agendas, preparing compelling presentations, and diligently following up on action items. This ensures that meetings are productive, focused, and lead to tangible progress on key initiatives.
🎯 Requirements
- • 5–8 years of management experience.
- • Experience working within an IT sales or operations environment.
- • Proven ability to coordinate and lead internal resources to achieve key milestones.
- • Strong project management skills; able to structure, manage, and coordinate multiple projects and processes.
- • Excellent communication and presentation skills, with the ability to deliver clear, organized, and impactful presentations.
- • Ability to build strong business relationships across all levels of the organization.
🏖️ Benefits
- • Unlimited Paid Days Off
- • Three health plan options
- • 401k with company match
- • Eligibility for dental, vision, short and long-term disability, life and AD&D coverage, and flexible spending accounts
- • Family Forming Benefit including fertility coverage and adoption/surrogacy reimbursement
- • Paid childbearing and paternal leave
- • Education Reimbursement, Student Loan Assistance or 529 College Funding
- • Sabbatical leave
- • Wellness program
- • Flexible work schedule
Skills & Technologies
Senior
Remote
About Ensono Holdings LLC
Ensono Holdings LLC is a hybrid IT services provider that designs, manages, and optimizes mainframe, cloud, and infrastructure environments for large enterprises. The company delivers 24x7 support, application modernization, data center outsourcing, and advisory services across AWS, Azure, and private cloud platforms. Serving Fortune 500 clients in finance, retail, insurance, and government, Ensono combines certified engineering talent with proprietary automation and analytics to reduce operational risk and cost. Headquartered outside Chicago, Illinois, it operates global delivery centers in the United States, United Kingdom, and India, ensuring resilient, scalable, and secure technology operations for mission-critical workloads.
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