Remote Sales Representative jobs Jobs in North Chicago, Illinois | Remote Work From Home

Remote Sales Representative (Remote)Location: Remote — flexible hours around North Chicago, Illinois * Why we need you today:* We just closed a $12 M Series B round and launched two new SaaS products aimed at mid‑market tech firms in North Chicago, Illinois. The influx of inbound interest means we must turn qualified leads into paying customers faster than ever. --- ##The Reality ofThis Role We’re a ten‑person revenue team that grew from three to ten people in the last eight months. The surge has created a gap: we have more demos booked than we have reps to close them.You’ll join a squad that includes a senior account executive, a product‑focused solutions engineer, and a sales operations analyst who lives two weeks away in North Chicago, Illinois. Our manager, Maya, runs a short, three‑minute daily stand‑up that lives in a shared bolthires Calendar invite—no video required, just a quick “what’s on your plate?” ping. The work is not a parade of endless cold calls. We already have a warm pipeline of 420 qualified opportunities, but we need someone who can slice through the noise, nurture relationships, and hit a quarterly quota of $350 k ARR.You’ll be the voice that turns a curious prospect in North Chicago into a paying customer, while also handling the inevitable moments when a deal stalls and you have to rally internal stakeholders. Expect to juggle three priorities at once: prospecting, demo coordination, and deal‑closing paperwork. Our culture rewards those who can stay organized while still being personable—think “sales‑craft meets relationship‑building” in the heart of Illinois. --- ## What You’ll Actually Do - Own the full sales cycle for our Mid‑Market SaaS line, from first outreach to contract signature, targeting 120 new accounts per quarter.- Prospect daily using LinkedIn Sales Navigator and ZoomInfo, generating at least 25 qualified leads each week. - Qualify inbound leads in HubSpot, scoring them with our custom BANT model and assigning to the right AE within 24 hours. - Run discovery calls on Zoom (average 30 minutes) and log insights into Salesforce, keeping activity logs up to 95 % completeness. - Deliver product demos using our native demo environment, hitting a 30 % conversion from demo to proposal. - Negotiate contract terms, collaborating with the legal ops lead in North Chicago to accelerate approval times to under three business days.- Partner with the solutions engineer to build custom ROI calculations that boost average deal size by 12 %. - Track daily activity in Outreach.io, maintaining a minimum of 50 touches (calls + emails) per day. - Analyze win‑loss data in Gong.io, presenting a weekly “what worked” snapshot to the team and adjusting scripts accordingly. - Mentor newer SDRs on prospecting cadence, sharing templates through our internal Slack channel. All of this happens on a mix of tools: Salesforce for pipeline, HubSpot for inbound, Outreach.io for cadence, ZoomInfo for data, LinkedIn Sales Navigator for research, Gong.io for conversation intelligence, bolthires Teams for internal syncs, Slack for quick chats, and bolthires Workspace for documentation.--- ## Skills That Truly Matter Must‑haves - Proven track record of meeting or exceeding quota (average 110 % attainment) in a B2B SaaS environment. - Mastery of Salesforce, HubSpot, and Outreach.io—ability to build and refine reports without asking for help. - Strong written and verbal communication; you can craft a concise email that lands a meeting in 48 hours. - Comfortable navigating LinkedIn Sales Navigator and ZoomInfo to uncover decision‑makers in the tech sector of North Chicago and beyond.- Ability to interpret data from Gong.io and translate it into actionable script tweaks. Nice‑to‑haves - Experience with inside‑sales models or account‑based selling (ABM). - Familiarity with Pipedrive or other CRM platforms. - Background in selling to finance or healthcare verticals within Illinois. - A side project that shows you can generate revenue on your own – maybe a freelance consulting gig. - Knowledge of contract negotiation basics or a certification like Certified SalesProfessional (CSP).--- ## Standout Extras - Authored a “Modern Cold‑Email Playbook” that has been downloaded over 4,200 times by sales teams worldwide. - Mentored three junior SDRs who each achieved 130 % of their quarterly quota within six months. - Built a personal Salesforce dashboard that reduced reporting time from 4 hours to 30 minutes per week. - Participated in a startup accelerator in North Chicago where you pitched a SaaS idea and raised a seed round of $250k. - Regular speaker at the “Mid‑Market Sales Forum” in Illinois, sharing techniques for shortening sales cycles.--- ##Compensation & Benefits - Base salary: $78,000 – $92,000 USD, depending on experience and proven results. - Commission: Uncapped, with an average OTE of $150k when you hit 100 % of quota. - Home‑office stipend: $1,200 per year to keep your desk ergonomic. - Learning budget: $2,500 annually for courses, certifications, or conferences (including the annual sales summit in North Chicago). - 401(k) match: 4 % of your salary, vested after one year. - Health & dental: 85 % coverage for employee, 70 % for dependents.- Paid time off: 18 days per year, plus 8 paid holidays – you can roll over up to 5 days. All figures are transparent; we want you to know exactly what you’ll earn and what we invest in you. --- ## Growth & Culture We’re a fully remote team spread across four time zones, but the core of our collaboration rolls around the Pacific Time window of 8 am–12 pm, which syncs nicely with most of North Chicago’s workday. Our async culture means you’ll find recorded stand‑bolthires, Loom walkthroughs, and a well‑organized Notion hub that houses every playbook, metric, and celebration.Career path: In the first 12 months, you’ll be expected to consistently hit 120 % of quota, positioning you for promotion toSenior Account Executive or a Pivot to Sales Enablement. By year two, many of our newly minted senior reps are leading a small “focus group” of three SDRs, shaping the next wave of prospecting cadence. By year three, the roadmap includes a possible move into a Regional Sales Manager role, overseeing a team of 6–8 reps covering the entire Illinois market. We’re honest about the challenges.Deal cycles can stretch to 45 days, and during the quarterly close you may log 60+ touches a day. But we balance that with a culture that celebrates small wins—daily “shout‑outs” in Slack, a quarterly “Sales Wins” virtual happy hour, and a monthly “Ask Me Anything” with the CEO who lives just an hour away in North Chicago. --- ## Interview Process 1. Screening call (15 min) with our recruiting coordinator – we’ll confirm logistics, answer your questions about the role, and get a quick sense of your sales story.2. Phone interview (30 min) with Maya, the Sales Manager – you’ll walk us through a recent win, discuss your typical pipeline, and we’ll share the quarterly quota structure. 3. Live role‑play (45 min) with a senior Account Executive – you’ll conduct a mock discovery call using a prospect from our actual pipeline (we’ll send the brief 24 hours before). 4. Final conversation (30 min) with the Head of Revenue – we’ll dive into culture fit, discuss career aspirations, and outline next steps. Timeline: We aim to move from first call to offer within two weeks.If you’re not a perfect match on paper, we still want to hear from you – the right attitude can outweigh a missing certification. --- ## Closing We are an equal‑opportunity employer. North Chicago and Illinois talent from all backgrounds are encouraged to apply. If this sounds like you, we’d love to hear your story. Send us your resume, a one‑page summary of your biggest sales achievement, and a brief note about why you’re excited to sell from wherever you call home. --- *“When I first joined, I thought a quota was a number on a spreadsheet.After three months, I realized it’s the heartbeat of a team that cares about each other’s success. That’s why I’m proud to welcome new teammates who want to make that pulse stronger.”* – Maya, Sales Manager, North Chicago, Illinois. Apply tot his job