Director, Mid-Market Customer Success

G2•Chicago, IL

41d•Hybrid

About The Position

When you join G2, you're joining the team that helps businesses reach their peak potential by powering decisions and strategies with trusted insights from real software users. G2 is the world's largest and most trusted software marketplace. More than 100 million people annually - including employees at all Fortune 500 companies - use G2 to make smarter software decisions based on authentic peer reviews. Thousands of software and services companies of all sizes partner with G2 to build their reputation and grow their business - including Salesforce, HubSpot, Zoom, and Adobe. To learn more about where you go for software, visit www.g2.com and follow us on LinkedIn. As we continue on our growth journey, we are striving to be the most trusted data source in the age of AI for informing software buying decisions and go-to-market strategies. Does that sound exciting to you? Come join us as we try to reach our next PEAK! At G2, we have big goals, but we stay grounded in our PEAK (Performance + Entrepreneurship + Authenticity + Kindness) values. You'll be part of a value-driven, growing global community that climbs PEAKs together. We cheer for each other's successes, learn from our mistakes, and support and lean on one another during challenging times. With ambition and entrepreneurial spirit we push each other to take on challenging work, which will help us all to grow and learn. You will be part of a global, diverse team of smart, dedicated, and kind individuals - each with unique talents, aspirations, and life experiences. At the heart of our community and culture are our people-led ERGs, which celebrate and highlight the diverse identities of our global team. As an organization, we are intentional about our DEI and philanthropic work (like our G2 Gives program) because it encourages us all to be better people. G2's Customer Success organization operates with a product success mindset. Our directors lead teams that ensure customers fully adopt the G2 platform, activate usage across their organizations, and realize measurable value. This director role drives outcomes across a large book of business with responsibility for onboarding quality, feature utilization, review outcomes, retention performance, and customer advocacy. In this role, you'll be directly leading a team of 7-8 Customer Success Managers in our Mid-Market segment. This leader partners closely with our Mid-Market Account Management team to create connected coverage models and revenue aligned pod structures. The team operates at scale, averaging high logo volumes and a wide range of product maturity levels. The director will shape operating rhythms, deploy AI enabled workflows, and design scalable engagement strategies that improve customer output by measurable percentages. The role requires an operator who is comfortable experimenting with new technologies, managing complex cross functional issues, and elevating team performance through structured coaching, productivity programs, and clear execution frameworks.

Requirements

5 or more years in Customer Success or Account Management in a B2B SaaS environment with a track record of improving retention and product utilization.
2 or more years managing customer facing teams with at least ten direct reports or equivalent scale.
Experience leading teams supporting portfolios that exceed 250 customers or multiple millions of dollars in recurring revenue.
Proven ability to build operating cadences, dashboards, and forecasting models in Salesforce, Gainsight, or similar tools.
Demonstrated success using AI or automation in a customer facing setting resulting in measurable productivity or outcome improvements.
Strong consultative skills including discovery, data backed storytelling, and executive communication.
Ability to drive change across matrixed teams and navigate large scale customer challenges.

Responsibilities

Build a repeatable product success framework that increases activation, usage depth, and expansion readiness by measurable percentages across the customer base.
Define quarterly utilization targets and lead the team to drive adoption patterns that correlate with increased retention probability.
Partner with Product and Support to reduce friction across core workflows and surface top customer insights.
Lead a team of Customer Success Managers who support customers along the full adoption and value lifecycle.
Implement training and enablement programs that improve team productivity by at least 10 to 20% through process simplification and AI assisted workflows.
Design and refine pod structures that align account managers and customer success managers for multithreaded engagement.
Own core operating metrics including portfolio health, renewal forecast accuracy, onboarding throughput, and utilization coverage.
Drive the utilization of standard go-to-market tools such as Catalyst, Salesforce, Gong and various reporting standards and automation that enable real time health scoring, customer mapping, and renewal visibility.
Lead quarterly planning and capacity modeling to optimize portfolio distribution and workload balance.
Introduce new AI tools and workflows that increase CSM reach, reduce manual work, and scale personalized engagement to large segments.
Develop data backed experiments, document outcomes, and move successful pilots into full operational rollout.
Create adaptable AI use cases for onboarding, account insights, customer education, and in product decision support.
Represent Customer Success in executive level conversations related to retention, renewal risk, packaging, and customer experience improvements.
Partner with Support on complex escalations and help prioritize root cause resolutions.
Contribute to company level OKRs, particularly those tied to product performance, customer satisfaction, and operational efficiency.