Head of Customer Success — Construction Growth

Jobba Trade Technologies, Inc.; Chicago (IL); On-site; USD 150,000 - 230,000; Full time

Job summary

Jobba Trade Technologies, Inc. is seeking an ambitious Director of Customer Success to lead our post-sales strategy, own onboarding, retention, and expansion for construction industry partners.

You will work directly with key clients, shape a world-class CS engine, and ensure rapid time-to-value as we scale. As a strategic Player-Coach, you will hire and mentor a high-performing team, build processes, data frameworks and playbooks, establish executive sponsorship with C-suite stakeholders, and

Qualifications

• 8+ years in Customer Success, Account Management, or Client Services within B2B SaaS, with 3+ years leading or managing team members.
• Growth-stage experience scaling CS function through ARR expansion.
• Metrics-driven mindset with impact on NRR, churn, and adoption metrics.
• Player-Coach mentality: strategic thinker who can also engage directly with clients.
• Industry expertise in construction, real estate tech, field service, or complex workflow automation software.

Responsibilities

• Drive Retention & Revenue Growth: Own key metrics including NRR, GRR, and Expansion ARR; partner with Sales for upsell/cross-sell opportunities.
• Build & Scale the CS Engine: Design a repeatable customer lifecycle framework from onboarding to renewal.
• Champion Construction Adoption: Understand construction workflows and build adoption strategies for deep software usage.
• Build & Mentor the Team: Hire, coach, and lead a high-performing CS team with accountability and data-backed execution.
• Build C-Suite & Field Relationships: Act as executive sponsor for high-value accounts and secure long-term partnerships.
• Leverage Modern CS Tech & Data: Implement CS platforms, playbooks, and predictive health scoring to identify churn risks.
• Cross-Functional Collaboration: Partner with Product and Sales to feed customer insights into the roadmap.

Job description

Jobba Trade Technologies, Inc. is seeking an ambitious Director of Customer Success to lead our post-sales strategy, own onboarding, retention, and expansion for construction industry partners.

You will work directly with key clients, shape a world-class CS engine, and ensure rapid time-to-value as we scale. As a strategic Player-Coach, you will hire and mentor a high-performing team, build processes, data frameworks and playbooks, establish executive sponsorship with C-suite stakeholders, and