Entry-Level Customer Success Representative

Calculum; Chicago (IL); Hybrid; USD 42,000 - 64,000; Full time

Benefits offered by this job

Hybrid work setup

Job summary

Calculum, a Chicago-based fintech company, is hiring an Entry-Level Customer Success Representative. You will support onboarding, enablement, and account growth across procurement and finance stakeholders.

The role offers hands-on experience in enterprise SaaS operations and data analytics, with hybrid work in Chicago. You’ll collaborate with Customer Success Managers to craft onboarding plans, prepare training materials, and curate knowledge resources, driving client adoption and measurable

Qualifications

• Pursuing or recent graduate with a degree in Finance, SCM, Business Analytics, Economics, or Communications.
• Interest in FinTech & operations with understanding of corporate finance, procurement, or business operations.
• Proficiency in Microsoft Excel (VLOOKUP/XLOOKUP) and Word/PowerPoint for executive presentations.
• Excellent written and verbal communication abilities with internal/external stakeholders.
• Collaborative, proactive, team-first mindset suited for a fast-paced startup.
• Highly organized with strong multitasking and project coordination; Location: Chicago, IL.

Responsibilities

• Assist CS Managers in onboarding plans, welcome packs, and governance frameworks.
• Prepare materials for platform training sessions and ADA demos for Procurement and Finance.
• Curate and maintain a library of playbooks, user guides, case studies, and demo materials.
• Track onboarding milestones, campaign dashboards, and value-realization metrics across accounts.
• Gather and synthesize client feedback for product and data science teams.
• Provide proactive operational support for follow-ups, meetings, and account reviews.

Skills

Analytical skills

Excel proficiency

Communication skills

Collaboration

Organization

Student/Graduate mindset

Education

Bachelor’s or Master’s degree

Tools

Excel

Job description

Entry-Level Customer Success Representative

Chicago (Hybrid)

Full Time

About Calculum

Calculum is a Miami-headquartered FinTech company that allows organizations to unlock millions in working capital and generate free cash flow by optimizing payment terms.

Calculum’s AI-powered platform, ADA, allows organizations to benchmark their payment terms against competitors and market standards. Companies can analyze all their suppliers in terms of payment terms, financials, sustainability, and ESG metrics, equipping category managers with the data needed to negotiate more favorable commercial terms. Calculum identifies on average over 10% in working capital benefits, positively impacting free cash flow that can be reinvested directly into business growth and sustainability programs.

Not every company seeks to disrupt a market, but that’s what we aim for at Calculum. We are changing how payment terms are negotiated with trading parties—and that requires advanced technology, industry expertise, and exceptional people. That’s where you come in.

Join Us as an Entry-Level Customer Success Representative: Your Impact Drives Our Success

Are you passionate about building client relationships, empowering enterprise teams, and shaping the future of FinTech and working capital management?

We are expanding our presence in Chicago and seeking an energetic, detail-oriented Entry-Level Customer Success Representative to join our team. In this role, you will work closely with our Customer Success Managers to support enterprise client onboarding, platform enablement, and account growth across major Procurement and Finance stakeholders.

This position offers hands-on experience in financial supply chain optimization, enterprise SaaS operations, corporate data analytics, and client-facing project management.

Impact & Responsbilities

• Client Onboarding & Enablement Support: Assist Customer Success Managers in crafting comprehensive onboarding plans, welcome packs, and stakeholder governance frameworks to set clients up for immediate success.
• Platform Demos & Training Prep: Help prepare materials for engaging platform training sessions and ADA demos, helping client teams in Procurement and Finance navigate benchmark insights and calculators.
• Content & Resource Curation: Help curate and maintain a library of best-practice playbooks, user guides, case studies, and demo materials to make it easy for clients to adopt platform features.
• Stakeholder & Campaign Tracking: Assist in tracking client onboarding milestones, active campaign dashboards, and value-realization metrics (cash flow generated, term extensions achieved) across client accounts.
• Data & Feedback Synthesis: Help gather and synthesize client feedback to share with our product and data science teams, ensuring we continuously improve the platform experience.
• Account Coordination: Act as a proactive operational support lead for client follow-ups, meeting preparation, and account reviews.

Skills & Qualifications

• Academic Background: Currently pursuing or a recent graduate with a Bachelor’s or Master’s degree in Finance, Supply Chain Management, Business Analytics, Economics, or Communications.
• Interest in FinTech & Operations: Strong curiosity and foundational understanding of corporate finance, technology, procurement, or business operations.
• Analytical Skills: Proficiency in Microsoft Excel (VLOOKUP/XLOOKUP, basic modeling) and Microsoft Word / PowerPoint for executive presentations.
• Communication Skills: Excellent written and verbal communication abilities, with a comfortable presence when interacting with internal and external stakeholders.
• Collaborative Ethos: High level of personal integrity, proactive initiative, and a team-first mindset built for a fast-paced startup environment.
• Organization: Highly organized with strong multitasking and project coordination abilities.
  Location: Based in or able to commute to Chicago, IL.

What’s In It For You?

• Career Acceleration: Fast-track your professional development with direct mentorship from senior leadership in FinTech, corporate finance, and customer success.
• Real Impact: See how your daily contributions directly drive client adoption, working capital optimization, and measurable financial value.
• Professional Growth: Hands-on exposure to enterprise SaaS workflows, AI analytics, and supply chain finance frameworks used by Fortune 500 companies.
• Dynamic Startup Environment: Experience life in a fast-moving, innovative startup where your ideas are valued and encouraged.
• Collaborative Culture: Join an ambitious, supportive team that celebrates wins, promotes mentorship, and values team success.
• Competitive Compensation & Flexible Hybrid Setup.