Director of Customer Success (Chicago)

About the Role

We build workflow software tailored specifically for the construction industry. We are seeking an ambitious, results-driven Director of Customer Success to lead our post-sales strategy, build a world-class CS engine, and ensure our construction partners achieve rapid value from our software. As a strategic Player-Coach, you will own customer onboarding, retention, and expansion. You will work directly with key clients while building the processes, data frameworks, and team needed to scale.

Key Responsibilities

• Drive Retention & Revenue Growth: Own key metrics including Net Revenue Retention (NRR), Gross Retention (GRR), and Expansion ARR. Partner with Sales to identify upselling and cross-selling opportunities.
• Build & Scale the CS Engine: Design a repeatable customer lifecycle framework—from initial onboarding and time-to-value (TTV) optimization to renewal and advocacy.
• Champion Construction Adoption: Understand the unique workflows of construction teams (from executives in the office to crews in the field) and build adoption strategies that ensure deep software usage.
• Build & Mentor the Team: Hire, coach, and lead a high-performing CS team, fostering a culture of accountability, empathy, and data-backed execution.
• Build C-Suite & Field Relationships: Act as an executive sponsor for high-value accounts, building strong relationships with key stakeholders to secure long-term partnerships.
• Leverage Modern CS Tech & Data: Implement CS platforms, automated playbooks, and predictive health scoring to proactively identify churn risks and operational efficiencies.
• Cross-Functional Collaboration: Partner closely with Product and Sales to feed customer insights back into the product roadmap and ensure seamless customer handoffs.

What We’re Looking For

• Track Record: 8+ years in Customer Success, Account Management, or Client Services within B2B SaaS, with 3+ years leading or managing team members.
• Growth Stage Experience: Experience scaling a CS function through rapid ARR expansion (e.g., $5M to $15M+ ARR).
• Metrics-Driven Mindset: Proven ability to impact NRR, churn reduction, and adoption metrics through data and playbooks.
• Player-Coach Mentality: You thrive on setting high-level strategy, but you're equally excited to roll up your sleeves, hop on a client call, or solve a workflow problem directly.
• Industry Expertise (Strong Plus): Direct experience with construction, real estate tech, field service, or complex workflow automation software.

Why Join Us?

• Direct impact on company strategy and top-line growth as we scale to $10M ARR and beyond.
• Competitive compensation package (Base + Bonus/Equity + Benefits).
• Collaborative, fast-paced environment solving real-world challenges for the construction industry.