Mid-Market SaaS Account Executive - Full-Cycle Close

Waitwhile; Chicago (IL); On-site; USD 80,000 - 100,000; Full time

Benefits offered by this job

Health, dental and vision insurance..

Unlimited Paid Time Off

401K with company match

Health Savings Accounts

Flexible Spending Accounts

Disability Insurance

Life Insurance

Tuition Reimbursement

Voluntary Wellness Program

Employee Discounts

Community involvement

CliftonStrengths coaching

Job summary

Waitwhile, a fast-growing SaaS company in Chicago, is seeking a Mid-Market Account Executive to expand our footprint and bring the platform to more businesses. You’ll own the full sales cycle, targeting $30K–$150K ARR deals, and collaborate with BDRs, Marketing, CS, and Sales Engineering to build pipeline and demonstrate value.

Ideal candidates have 4–6+ years of B2B SaaS sales experience, a track record of closing Mid‑Market or upper‑SMB, and strong consultative selling skills.

Qualifications

• 4–6+ years of B2B SaaS sales experience.
• Proven track record closing Mid‑Market or upper‑SMB deals.
• Strong consultative and value‑based selling skills.
• Excellent communication, presentation, negotiation, and storytelling.
• Experience navigating complex buying processes with multiple stakeholders.
• Ability to translate customer needs into clear business value.
• Independent pipeline ownership in a fast-moving environment.

Responsibilities

• Own the full sales cycle from prospecting to close for Mid-Market deals.
• Build pipeline with inbound and outbound activity with BDRs and Marketing.
• Lead tailored demos connecting Waitwhile’s capabilities to customer needs.
• Negotiate and close deals delivering long-term value.
• Collaborate cross-functionally with Sales, Marketing, RevOps, Product, CS.
• Track opportunities and forecast in HubSpot.

Skills

SaaS sales

Mid-Market deals

Sales targets

Value-based selling

Communication skills

Negotiation

Storytelling

Complex sales cycles

Pipeline ownership

Education

Bachelor’s degree or equivalent

Tools

HubSpot

ZoomInfo

Chorus

Notion

Job description

Waitwhile, a fast-growing SaaS company in Chicago, is seeking a Mid-Market Account Executive to expand our footprint and bring the platform to more businesses. You’ll own the full sales cycle, targeting $30K–$150K ARR deals, and collaborate with BDRs, Marketing, CS, and Sales Engineering to build pipeline and demonstrate value.

Ideal candidates have 4–6+ years of B2B SaaS sales experience, a track record of closing Mid‑Market or upper‑SMB, and strong consultative selling skills.