Hire the Best High-Ticket Closing Freelancers in Chicago, IL

$125K+ closed solo on a $2.5K offer, in just a few short months. 50+ deals. 40%+ close rate. So I know how to build the entire front end of a sales system. Ranked top percentile of 120K+ experienced closers on Closerscored. Back to back salesman of the year at JRM, while also breaking multiple records (highest gross month and year). I close every day on high-volume inbound, which means I see what's working right now. Not theory from a course, not a framework from 2022. I bring that pattern recognition to founders who are leaving money on the table somewhere in their funnel. Two ways I work with founders: 1. Call Audits & Sales Teardowns — Send me your team's recorded calls and current pitch. You get a Loom walkthrough with specific fixes: openers, discovery gaps, objection handling, closing language, follow-up. 2. Full-Stack Sales Breakdown — A full front end breakdown. From building quality lead list, speed to lead, scripts, qualifying and closing. What I need from you: A real offer with proof of concept. If it's converted a few times, I can find what's broken and scale what's working.

I operate at the intersection of revenue generation, account management, client success, and sales operations, with over $5M+ in collected revenue across digital marketing, SaaS, e-commerce, CPG, coaching, financial services, and real estate-related offers. My background is heavily rooted in startup and high-growth environments where I’ve been responsible for far more than just closing deals. I’ve helped companies build pipeline, refine messaging, improve sales processes, increase retention, develop SOPs, train teams, and create scalable systems around revenue generation. I’m strongest in roles where I can combine: - consultative sales - operational thinking - strategic communication - and relationship management to help businesses grow efficiently. ━━━━━━━━━━━━━━━ ✅ Full-Cycle Account Executive & Revenue Growth ━━━━━━━━━━━━━━━ I’ve sold offers ranging from $4K to $54K+ across both B2B and B2C environments while managing the full customer journey from prospecting and discovery through onboarding, retention, and expansion. Experience includes: • Outbound prospecting & pipeline generation • Discovery, demos, and strategic sales conversations • Proposal development & negotiation • Client onboarding & retention • Upsell and expansion strategy • CRM pipeline management & forecasting • Relationship-based closing I’m comfortable operating in both inbound-heavy and outbound-heavy environments and have experience working directly with founders, operators, investors, and executive stakeholders. ━━━━━━━━━━━━━━━ ✅ Startup, GTM & Sales Operations Experience ━━━━━━━━━━━━━━━ Beyond direct sales, I’ve also contributed heavily to: • Sales process development • SOP creation • CRM organization • Messaging refinement • Objection handling frameworks • Call review & rep coaching • Sales training & onboarding • Pipeline and follow-up systems I naturally think like an operator, not just a rep. ━━━━━━━━━━━━━━━ ✅ Digital Marketing & Client Success ━━━━━━━━━━━━━━━ At Pixel Penguin Media, I work directly with clients and internal media buying teams to align marketing performance with business outcomes. This includes: • Meta + Google Ads strategy conversations • Funnel and conversion analysis • Client communication & retention • Revenue-focused growth planning • Managing expectations and long-term relationships ━━━━━━━━━━━━━━━ ✅ CPG, SaaS & Consultative Sales ━━━━━━━━━━━━━━━ At Opply, I closed $860K+ in contracted deals through outbound prospecting and relationship-driven sales. This included: • Mid-market & enterprise outreach • Strategic procurement conversations • Cash flow & operational efficiency positioning • Long-cycle relationship management • Industry partnerships and trade show networking ━━━━━━━━━━━━━━━ ✅ Leadership & Team Building ━━━━━━━━━━━━━━━ • Built and led a team of 15+ agents in insurance • Generated $300K+ in revenue within first few months • Experience onboarding, coaching, and improving rep performance • Comfortable helping companies build repeatable sales infrastructure ━━━━━━━━━━━━━━━ What I Do Best ━━━━━━━━━━━━━━━ • Build trust quickly with prospects and clients • Lead high-level consultative conversations • Translate complex offers into simple value propositions • Improve sales processes and customer experience • Balance revenue generation with long-term retention • Operate effectively in fast-moving startup environments If you're looking for someone who can contribute beyond just taking calls and can help drive revenue, improve process, and strengthen client relationships at the same time, I’d be happy to connect.

I'm a professional sales closer. I have been selling remotely via zoom and phone for over 10 years. I have worked for companies such as JP Morgan, AON Hewitt and Assurance. The past 4 years I have worked in high-ticket sales as a top producing closer. I use KPI's to increase performance and I consistently close in 30-50% range depending on the product. I am an expert native American English speaker. I have a mortgage license, series 6, 63 and Insurance licenses in 26 states. My home office is set up with dual monitors and high speed internet.