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Customer Sales and Support Lead | Work from Home

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60601, USA
Listing for: Spoke
Remote/Work from Home position
Listed on 2026-06-20
Job specializations:
  • Sales
    Customer Success Mgr./ CSM, Sales Development Rep/SDR, Inside Sales, Client Relationship Manager
Salary/Wage Range or Industry Benchmark: 60000 - 80000 USD Yearly USD 60000.00 80000.00 YEAR
Job Description & How to Apply Below

About the Company

A leading group transportation platform revolutionizing how people move together. While the app handles real-time hailing, the Event Trips division specializes in high-touch, pre-scheduled, hourly van reservations for weddings, corporate events, and large-scale social gatherings. A fast-growing company looking for a high-energy, results-driven professional to own the sales-to-execution lifecycle of these premium experiences and help scale the Event Trips business.

The Role

As the Customer Sales & Support Lead, you are the primary driver of sales success and operational excellence for Event Trips. You will own the full quote-to-confirmation process while delivering seamless live operations support during active events. This is a sales-first role with clear operational accountability — you convert leads, lock in bookings, manage drivers, and ensure every trip launches flawlessly with post-booking support.

Critical

Focus

Your core mandate is rapid response times and booking conversion. Once a trip is confirmed, all post-booking changes, cancellations, refunds, reporting, and ongoing support are your responsibility to ensure a seamless customer experience. You are to be laser-focused on new business, itinerary creation, quotes, driver acceptance, and live event execution.

Roughly 75% Sales & Booking | 10% Live Operations & Client Success | 5% Process Optimization

Key Responsibilities Sales & Booking Excellence (~75%)
  • Respond to customer inbound requests via web forms, email, and phone — as quickly as possible, converting leads into confirmed Event Trips bookings via email, texts, and calls. Every new inquiry requires both an email and a text upon initial response.
  • Gather critical trip details (dates, precise pickup/drop-off points, vehicle requirements, special requests) and create accurate, competitive quotes accounting for hourly rates, deadhead time, and waiting intervals.
  • Build professional itineraries and proposals that win business and set clear expectations.
  • Aggressively follow up on open quotes to drive conversions and hit response-time SLAs.
  • Optimize CRM: manage the full lead lifecycle, build sequences and templates, eliminate leakage, and maximize booking volume.
  • Develop and refine pricing strategies, communication playbooks, and quote templates to improve win rates and protect margins.
  • Coordinate driver acceptance, vehicle assignment, and scheduling to lock in bookings and prepare for flawless execution.
Live Operations & Client Success (~10%)
  • Act as Mission Control during active events: provide real-time updates to staff, customers, and drivers via Slack, text, and phone.
  • Monitor live trips, anticipate disruptions (delays, route issues, driver challenges), ensure driver acceptance of dispatched trips, and coordinate rapid solutions to maintain service quality.
  • Deliver white-glove, proactive support throughout the event window to ensure every client receives a 5-star experience.
  • Manage post-event billing for added hours, refunds, and ensure positive customer support.
Process Optimization & Response Time (~5%)
  • Identify bottlenecks in the quote-to-trip workflow and recommend improvements that boost efficiency and conversion by lowering response times.
  • Enforce strict handoff protocols: once a booking is confirmed, route all subsequent changes, cancellations, refunds, and support requests to the appropriate team.
  • Maintain a clear lead queue to ensure every inquiry is first in line to receive a response.
What You’ll Bring
  • 2–4+ years in high-volume sales, logistics coordination, premium customer success, or operations roles — transportation, events, hospitality, or marketplace environments strongly preferred
  • Exceptional verbal and written communication skills with a sales-oriented, customer-first mindset
  • High proficiency in Hub Spot — sequences, templates, workflows, reporting, and pipeline management
  • Strong understanding of U.S. geography and expert-level skill using Google Maps for complex route planning and timing
  • Calm, decisive thinker who thrives under pressure and solves logistical challenges in real time
  • Proven ability to manage multiple high-stakes deals and live events simultaneously
  • Competitive, high-energy self-starter with a track record of hitting volume, response-time, and revenue targets
  • Bonus:
    Previous experience in group transportation, charter, or event logistics
Tools You’ll Use
  • Hub Spot CRM
  • GPS Tracking
  • Internal Dispatch Systems
  • Slack
  • Texting & Phone via VoIP
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