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Head Of Sales​/High Ticket Closer

Job in Chicago, Cook County, Illinois, 60601, USA
Listing for: My Virtual Mate
Full Time position
Listed on 2026-11-01
Job specializations:
  • Sales
    B2B Sales, Business Development, Sales Development Rep/SDR, Sales Representative
Salary/Wage Range or Industry Benchmark: 120000 - 210000 USD Yearly USD 120000.00 210000.00 YEAR
Job Description & How to Apply Below
Position: HEAD OF SALES/ HIGH TICKET CLOSER

We are looking for an experienced, results-driven sales professional to take ownership of the sales function, from prospecting and pipeline management to closing high-ticket deals and securing payments.

The business provides high-value services, including AI solutions, lead generation, client acquisition funnels, website development, and digital marketing solutions. Its clients range from small business owners to established companies.

With over a decade of agency experience, hundreds of case studies, and strong service delivery capabilities, the business has an established foundation for sales success. We are looking for a dedicated sales professional who can turn this foundation into consistent, measurable revenue growth.

Role Overview

This is a full-time, hands-on Head of Sales / High-Ticket Closer role combining B2B sales, business development, high-ticket closing, and pipeline management.

You will receive inbound leads and booked appointments while proactively developing the existing prospect database, reconnecting with previous leads, following up on stalled opportunities, and identifying upselling opportunities with past and existing clients.

You will own the complete sales process, from the initial conversation through to contract signing and payment collection.

Key Responsibilities

Close high-ticket B2B deals over Zoom and phone calls. Manage a consistent daily volume of sales calls, conversations, and follow-ups. Convert inbound inquiries and booked appointments into qualified opportunities and paying clients. Reactivate older leads, stalled opportunities, and prospects who previously attended appointments. Reconnect with former clients and identify upselling and cross-selling opportunities. Handle objections, negotiate effectively, communicate value, and secure buying decisions.

Manage proposals, contracts, and payment follow-ups through to completed sales. Maintain accurate CRM records, deal stages, follow-up tasks, and pipeline updates. Collaborate with the team to refine service offerings based on client feedback and sales performance. Take ownership of sales activity, pipeline performance, closed deals, and collected revenue.

Required Skills

Proven high-ticket B2B closing experience , preferably selling services to businesses or decision-makers. Demonstrated experience closing deals independently, rather than working exclusively in lead generation, appointment setting, or sales support. Strong understanding of B2B sales processes, including prospect qualification, discovery calls, objection handling, negotiation, and closing. Experience selling digital agency services, AI solutions, lead generation, marketing services, websites, or other related business solutions.

Native-level spoken and written English, with excellent communication and presentation skills. Confidence communicating directly with business owners, executives, and other decision-makers. Proven ability to follow up consistently, revive cold or stalled opportunities, and move prospects towards a buying decision. Ability to manage the full sales cycle, from the initial conversation through contract signing and payment collection. Strong CRM discipline, including pipeline tracking, maintaining accurate records, and scheduling follow-ups.

Self-motivation, accountability, and the ability to work independently without daily supervision. Availability for a full-time remote commitment, with flexibility to coordinate calls around prospect availability. Ability to provide measurable evidence of sales performance, such as revenue closed, deal values, close rates, or targets achieved.

Preferred Skills

Previous experience as a Head of Sales, Sales Manager, Senior Account Executive, or High-Ticket Closer. Experience working in a digital agency, AI agency, lead generation agency, marketing agency, or client acquisition business. Experience selling multiple services or bundled solutions, including AI automation, websites, funnels, paid advertising, and lead generation. An established track record of closing high-value B2B deals with small businesses, mid-market companies, or enterprise clients.

Experience generating new business through cold calling, outbound email, Linked In outreach, and database reactivation. Experience converting inbound appointments and managing a high-volume sales pipeline. Familiarity with CRM platforms, sales automation tools, and pipeline reporting systems. Experience identifying upselling, cross-selling, and recurring-revenue…

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