Director of Client Success at Lyra Technology Group in Naperville, IL

Lyra Technology Group is seeking a Director of Client Success for one of its operating companies. The Director of Client Success is the post-sale owner of client retention and revenue expansion, where client value means the measurable return a client gets not just from their technology investment but from the partnership itself. That value lives in how effectively the MSP translates a client's business goals, risk tolerance, and operational challenges into technology decisions that move them forward. This role blends technical fluency with executive-level relationship management: the person in this seat earns the trust of clients as a strategic advisor, runs a disciplined roadmap and business review motion, and converts that trust into measurable MRR and NRR growth. Unlike a traditional account manager, this is not a coordination or escalation role. Unlike a salesperson, the lever is not prospecting; it is deepening the value clients already receive and identifying what they should be investing in next. Beyond their own book of business, the Director of Client Success owns the processes and standards that make client success repeatable: building them where they do not exist and improving them where they do.

You will own…

Client Relationships and Advisory Presence

• Serve as the face of the company for client value: the person clients call when they want to think through a business challenge, not just a technology problem.
• Build and sustain trusted advisor relationships with client executives and key stakeholders, maintaining an active in-person presence including regular on-site visits and travel as needed.
• Stay current on the industries, compliance environments, and business pressures your clients operate in, so your recommendations are grounded in their reality, not generic best practice.
• Maintain a clear view of client health across your book: flag at-risk accounts early, develop recovery plans, and escalate where needed.

Technology Fluency and Recommendations

• Translate technology recommendations into business terms: quantify risk, articulate ROI, and connect infrastructure decisions to client outcomes rather than specs.
• Serve as a credible voice in technical discussions without being the engineer in the room, with working knowledge of endpoint protection, identity and access management, backup and disaster recovery, Microsoft 365 and Azure, network infrastructure, compliance frameworks such as HIPAA, CMMC, SOC 2, and CIS Controls, and cybersecurity insurance requirements.
• Lead hardware lifecycle conversations with clients, including refresh planning, end-of-life risk, and the real cost of deferring investment.
• Lead AI strategy conversations with clients, helping them identify where AI can create measurable value in their business, and translate those conversations into prioritized roadmap items.

Retention and Growth

• Own net revenue retention for an assigned book of business, including renewals, expansion, and churn prevention.
• Run a disciplined business review cadence with every client, focused on forward-looking strategy rather than operational recaps, and build technology roadmaps that align client business goals with a prioritized plan for the next 12 to 36 months.
• Identify upsell and cross-sell opportunities through proactive roadmap and planning conversations, not reactive quoting, and maintain a pipeline that gives the delivery team a consistent backlog to pull from.
• Drive AI revenue as a core growth lever, identifying opportunities to introduce AI-enabled tools and services that create measurable client value and building that into the expansion pipeline.

Practice Development

• Translate how client success should work into documented standards, repeatable cadences, and tracking systems that hold the team accountable and scale with the business.
• Improve how accounts are segmented, how reviews are structured, how health is measured, and how risk is flagged.
• Track KPIs including QBR completion, upsell pipeline, expansion results, churn, client health scores, and AI-attached revenue, and provide regular feedback to leadership on trends, service gaps, and opportunities.

Leading and Managing the Team

• Set clear expectations for what strong performance looks like in every post-sale seat and hold the team accountable to defined KPIs including QBR completion, upsell pipeline, NRR outcomes, and results in AI strategy and AI revenue.
• Run a consistent one-on-one and team cadence that gives direct reports the direction and feedback they need to perform without requiring constant escalation.
• Coach to outcomes: when someone is underperforming, identify whether the gap is skill, process, or prioritization and address it directly.
• Own hiring and onboarding for the team, and develop internal talent with intention rather than waiting for roles to open.

Our ideal Director of Client Success has the following qualifications:

• 5+ years of experience in account management, client success, or a comparable B2B client-facing role, with at least some of that experience in an MSP or IT services.
• Demonstrated track record of owning and growing a book of business: retaining clients, expanding revenue, and managing renewals with accountability for outcomes.
• Ability to hold strategic, forward-looking conversations with C-suite and executive stakeholders, not just operational or service conversations.
• Comfortable leading upsell discussions that are advisory in nature: the goal is to recommend what genuinely fits, not to push transactions.
• Experience building or improving operational processes within a team or department: translating how work gets done into documented standards, establishing systems that ensure consistency, and defining the metrics that measure whether it is working.
• Working knowledge of technology roadmapping, business reviews, and white space analysis. Direct experience with tools like ScalePad Lifecycle Insights, MyITProcess or similar is a plus.
• Proficiency with HubSpot or comparable CRM. ConnectWise or PSA experience preferred.
• Strong organizational discipline across a multi-client portfolio: you manage cadences, follow through consistently, and do not drop details.
• A proactive disposition: you identify risk before it becomes churn and find opportunity before clients ask.

The targeted base compensation for this role is $110,000-$120,000 with variable compensation. This role operates out of Naperville, IL in a hybrid model and includes regular in-person client meetings.

If you are a post-sale leader who builds trust face to face, knows how to turn client relationships into long-term partnerships, and wants to build something, not just manage it, we would like to talk.