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Cypress HCM

Regional Sales Manager (Chicago)

Cypress HCM, Chicago, Illinois, United States

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Position Overview We’re seeking a driven, value-focused sales professional to join our team. The ideal candidate has 5+ years of SaaS sales experience and a strong background in Construction Tech. This is a mission‑critical role that will significantly influence our long‑term growth by helping construction builders adopt the industry’s leading planning and scheduling platform in your assigned region. This position reports to the Head of Sales and offers flexibility to work remotely within your strategic market.

Key Responsibilities

Prospecting & Outreach: Identify and develop new opportunities within our ideal customer profile, educating prospects on how our collaborative, easy‑to‑use planning platform can transform their business.

Market Ownership: Conduct face‑to‑face and virtual meetings to deeply understand customer challenges, goals, and needs.

Product Expertise: Lead tailored product demos and partner with Solutions Engineering for more customized presentations.

Team Performance: Consistently meet and exceed quota goals while contributing to collective team success.

Value‑Based Selling: Sell effectively to multiple stakeholders, differentiate against competitors, negotiate confidently, and close deals with a clear focus on value.

Customer Partnership: Work closely with sales engineering and customer success teams to deliver a best‑in‑class customer experience.

Cross‑Functional Collaboration: Partner with solutions engineering, customer success, and business development teams to drive strong customer outcomes.

Qualifications

Experience: 5+ years in full‑cycle SaaS sales with a proven ability to source, develop, and close strategic deals.

Startup Readiness: Comfortable operating in a fast‑paced, entrepreneurial environment with a builder’s mindset.

Prospecting Skills: Hunter mentality with a proactive, results‑oriented approach to creating new pipeline.

Performance Track Record: Consistent history of exceeding quotas while maintaining integrity and customer focus.

Communication: Exceptional written and verbal communication skills, with the ability to uncover needs and clearly present business value to both technical and non‑technical audiences.

Mindset: A strong mix of curiosity, ambition, resilience, optimism, and a value‑driven approach.

Collaboration: Excellent interpersonal skills and experience working effectively across teams, especially with solutions engineering and customer success.

Job Details

Seniority level: Mid‑Senior level

Employment type: Full‑time

Industries: Appliances, Electrical, and Electronics Manufacturing, Industrial Machinery Manufacturing

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