Remote Connectwise Jobs in Chicago, IL (NOW HIRING)

Are you looking for limitless career opportunities with a company that values growth, innovation, and teamwork? At Ntiva, we’re more than a Managed Services Provider, we’re a community dedicated to helping each other, our clients, and their businesses thrive both personally and professionally. Ntiva is a culture of people who are passionate about the work…and each other.

Our clients view us as an essential part of their teams, relying on us for strategic guidance, fast solutions to complex challenges, and proactive support. With strategic locations across the U.S. and leadership from our founder, Steven Freidkin, we’re on the front lines of a fast-paced industry, facing cybersecurity threats and rapid technology changes together.

If you thrive in a dynamic, supportive environment and enjoy going above and beyond, we’d love to meet you. Come explore one of our many opportunities and grow with us!

How you will make an impact

As the Account Manager (AM), you own the client relationship. This is the highest leverage seat in Client Success. Clients trust you to understand their business, connect their technology to where it is going, and make sure Ntiva delivers. You are not a messenger between the client and internal teams. You are the decision bearer in the room. The role is focused on four outcomes: clients who stay because risk was caught early, revenue that grows through disciplined roadmap execution and clean agreements, an expansion pipeline you qualified yourself, and time reclaimed from reactive work and spent on strategy instead.

Location and work expectations

• Hybrid role in the Chicagoland area, approximately 80% remote and 20% client visits. Allocation may fluctuate based on business needs.
• Must be able to travel by car to client locations, with a valid driver’s license and an insured vehicle.
• Monday through Friday, approximately 8am to 5pm CST.

What you will be doing

Own the relationship

• Own a defined book of business, generally $2M to $2.5M in annual recurring revenue across approximately 25 to 30 clients, sized by client tier mix and role level.
• Carry the relationship at the executive level. Show up prepared and on time, with an agenda and a written follow-up summary, and hold the room.
• Run escalations behind the scenes rather than in front of the client, communicate in the language of the client’s business rather than the ticketing system, and maintain a living map of each client’s decision maker, economic buyer, champions, and blockers.

Drive the strategy

• Understand how each client makes money, and translate their business objectives into a 12 to 24 month technology roadmap.
• Lead the prescribed engagement cadence for your book of business, including Service Reviews, Strategic Cadences, Technology Business Reviews, and Annual Reviews, leading with the client’s business context rather than a report on Ntiva activity.
• Position new services as answers to a problem you have already diagnosed, and qualify expansion opportunities before engaging solution architect or professional services time.
• Identify at-risk clients early using defined risk signals, and produce a written save plan before a contract conversation becomes necessary.

Own the commercials

• Read and reconcile a client invoice, and explain every line without escalating internally.
• Own renewals end to end: the right mix of services, a current agreement stack, migration off legacy SKUs, and statements of work precise enough that Onboarding can execute without chasing.
• Apply credit discipline as if the margin were your own, recognize when service recovery beats a credit, and use client profitability as an input to account strategy.
• Engage past due clients with clarity and speed, and own your part of accounts receivable tickets end to end with current notes.

Partner internally

• Know the services matrix and which team owns which work, including when to engage the solution architect, vCIO, IT Advisor, and Service Delivery, and when not to.
• Qualify work before engaging peer teams, hand off cleanly with confirmation of receipt and an explicit next step, respect peer team process rather than routing around it, and hold peer teams accountable respectfully through a defined path to a defined person.
• Bring client feedback back to Ntiva teams with the diagnostic work done and a solution proposed. Advocacy is not echo. Set client expectations early and hold the line, including saying no, and train clients on how to engage Ntiva.

Manage your capacity

• Manage your time so every client receives what they are entitled to, adhere to scheduled block time, and build the week around proactive work rather than inbox reaction.
• Delegate to the right team rather than carrying work by default, push clients toward self-service where it serves them well, and use approved AI tooling and published documentation for summaries, follow-up drafting, and routine reconciliation where appropriate.
• Work in ConnectWise Manage fluently across the AM workflow, keep ticket notes current so peer teams see movement without asking, and execute renewals, service additions, and decommissions per process.

How success is defined in this role

• CORE values. Care: outcomes over transactions, and a client who is struggling or unusually quiet is a signal to act on. Ownership: you are accountable from first engagement through renewal, including the fix that prevents a repeat. Responsiveness: you reply within a business day and update proactively. Empathy: you hear the concern before offering the solution.
• Four behaviors. Strategic Thinking: technology serves the client’s business goals, and you apply patterns across your portfolio. Proactive Engagement: you surface issues before they escalate and deliver value between formal touchpoints. Internal Advocacy: you represent client interests without damaging relationships with colleagues. Business Acumen: you speak credibly about money and protect both the relationship and Ntiva margin.

 You will be successful in this role if you have

• 2 to 5 years of client-facing or client services experience, preferably in the IT industry, and experience working with or for an IT Managed Service Provider (MSP).
• Commercial literacy. You can read an invoice or a contract, discuss renewals and pricing, and hold a conversation about money without needing someone else in the room.
• Credibility with executive stakeholders, and the ability to have hard conversations: setting expectations, delivering unwelcome news, and pushing back constructively.
• Operating fluency with technology. Engineering depth is not required, but you can discuss a client’s environment substantively and translate technical detail into business impact.
• A track record of getting results through cross-functional partners who do not report to you, and the judgment to diagnose before recommending.
• Disciplined organization and time management across a large portfolio, with a tactful, professional demeanor under pressure.
• Ability to communicate professionally in English, written and orally, including business correspondence, process documentation, and presenting to groups of managers, clients, and the public.

Bonus points for

• Bachelor’s degree (BA/BS) in business, IT, computer science, or a relevant field.
• Experience with ConnectWise or a similar service management system, familiarity with network, cloud, and security tooling, and demonstrated use of AI tooling to reduce administrative load.

Benefits and Perks

• Medical, Dental and Vision coverage for employeeand family 
• 401k + company-matched contributions 4% match on 5% contribution- no vesting period! (Employee and Company contribute after 90 days) 
• Group Term Life and Accidental Death and Dismemberment coverage (company provided) 
• Short-Term (voluntary enrollment) and Long-Term Disability coverage (company provided) 
• Health Savings Account (HSA) Options / PPO Options 
• Employee Assistance Program 
• Paid Time Off (PTO) + Volunteer Time Off (VTO) + 8Paid Holidays + 3 Floating Holidays 
• Education Reimbursement Program 
• Generous Employee Referral Program -cash bonus for successful referrals! 
• Dynamic Recognition and Rewards 
• Clear Promotion and Advancement Tracks 
• Work with Industry-Leading Talent  

The base pay range for this position is expected to be between $55,000 and $80,000 per year, plus a commission plan. The base pay offered may vary depending on multiple non-discriminatory factors including, but not limited to, market location, job-related knowledge, skills, and experience. The total compensation package for this position also includes medical benefits, 401(k) eligibility, and PTO. Additional details of participation in these benefit plans will be provided if an employee receives an offer of employment.

FLSA Status: Salaried, Exempt

Work Authorization Criteria 
Standard: We welcome applicants who are U.S. persons. At this time, we are unable to offer sponsorship or assume sponsorship of an employment visa.

Workspace Requirements and Remote Work Policy 
Team members must establish a dedicated safe workspace that is free from distractions, hazards, and that is secure from unauthorized access. This includes following Ntiva’s IT User and Security Policies that include but are not limited to password-protecting all equipment, keeping confidential and proprietary documents secure, refraining from using public Wi-Fi, having adequate arrangements in place to avoid significant interruptions from caregiving responsibilities during work hours (except in emergency situations with manager approval). Any remote work away from a team member’s normal expected dedicated safe workspace must be requested by team member, is subject to review by management, and must adhere to Ntiva policies and procedures.   
 
Our Commitment to a Diverse Workforce

 At Ntiva, we are committed to creating and maintaining a diverse, inclusive, and welcoming work environment for all employees and job applicants. We firmly believe that a diverse workforce fosters a wider range of perspectives, experiences, and ideas that lead to increased creativity, innovation, and problem-solving capabilities. As an equal opportunity employer, we actively seek to recruit and retain a diverse workforce that reflects the communities we serve. We prohibit discrimination of any kind, including but not limited to race, color, religion, gender, gender identity or expression, sexual orientation, marital status, national origin, age, hair length, protective hairstyles, organ donor status, disability, veteran status, or any other legally protected status and comply with all applicable laws governing nondiscrimination in employment. 
 
Application Deadline: The sooner you apply, the sooner we get to know you! Submit your resume today! Applications will be accepted until 8/07/2026.