Account Executive (AiSDR)

Flyer One Ventures

Toronto, Canada (Remote) · Remote

<p>AiSDR is the AI sales agent that thinks before it acts. We are the AI SDR platform 300+ paying B2B SMBs across SaaS, professional services, and e-commerce already use to book qualified meetings on autopilot. 1,000+ meetings booked per month across our customer base. 30+ months in production. SOC 2 Type II certified. Profitable on a cash basis. Not raising.</p><p>We sell direct AND through partners. The AI SDR is the SDR, so most of your demos come from AiSDR-generated outreach, partner referrals, and inbound. We are looking for a full-cycle Account Executive. This is a hunter role with a clean inbound flow on top.</p><p><strong>About you:</strong></p><p><strong>Required:</strong></p><ul><li>3-5 years as a full-cycle Account Executive at a B2B SaaS company. Linear career progression preferred.</li><li>Product-company background. You have sold software, not services. No agency-only careers.</li><li>US Eastern Time Zone work hours. Time-zone overlap on 9am-6pm ET is non-negotiable.</li><li>Professional English fluency. Every demo, email, proposal, and Slack message in English.</li><li>Hunger. You measure yourself by closed-won, not activity metrics.</li><li>Pirate operator mode. You are the kind of AE who DMs a prospect on LinkedIn after the demo with one specific question, not the kind who waits for “next steps.”</li><li>Public output is a plus. LinkedIn posts, deal-debrief content, podcast appearances, substack — operators leave a trail.</li></ul><p><strong>Strongly preferred:</strong></p><ul><li>You were an early AE at a Series A or B sales-tech company (Apollo, Outreach, Salesloft, Gong, Lemlist, Clay, Reply.io, Cognism, HubSpot, ZoomInfo).</li><li>You have run cold outbound campaigns yourself, not just received SDR-generated leads.</li><li>You have used AiSDR or an AI SDR competitor as a buyer. You know what is real and what is theater in this category.</li><li>Professional sports or competitive-hobby background (triathlon, rowing, climbing, martial arts, esports at a serious level). We hire for discipline; sport correlates strongly.</li><li>You can name 3 specific objections you have heard about AI SDR products and the rebuttal you would use today.</li><li>HubSpot Solutions Partner ecosystem experience.</li></ul><p><strong>What will you do:</strong></p><p><em>Days 1-30 (ramp)</em></p><ul><li>Internalize the AiSDR sales playbook by shadowing 20+ recorded customer calls.</li><li>Run 15 first calls under co-pilot mode. Every call gets a 24-hour review.</li><li>Close 3-5 deals on the Explore plan ($900/month) or Grow plan ($2,500/month).</li><li>Build a working knowledge of HubSpot, Fathom, AiSDR (the product), Slack, and our quarterly-billing motion.</li></ul><p><em>Days 31-60 (own the book)</em></p><ul><li>Run 30-40 discovery calls per month. Maintain 3x pipeline coverage against your quota.</li><li>Hold 25%+ inbound-to-paid conversion. (Industry baseline 12-15%, our team average 22%.)</li><li>Average deal size: $2,700 to $7,500 quarterly billing.</li><li>Live in HubSpot. Every call has a Fathom recording linked, every note is searchable, every next step has a date.</li><li>Run AiSDR campaigns on your own seat. Yes, we dogfood. Your outbound is part of the inbound flywheel.</li></ul><p><em>Days 61-90 (compound)</em></p><ul><li>Close 12-18 deals in the quarter at minimum.</li><li>Source 3-5 named customer references for case studies.</li><li>Contribute weekly customer-feedback loops to product and marketing.</li><li>Identify and close one strategic enterprise deal (&gt;$30K ACV) per quarter.</li></ul><p><em>Standing responsibilities</em></p><ul><li>Full-cycle close: discovery, demo, proposal, negotiation, contract, hand-off.</li><li>Pricing negotiations: own them yourself. AiSDR rule on price: “I can’t do anything on the price. I can do it on the volumes.”</li><li>Clean hand-off of every closed-won deal to Customer Success within 24 hours of contract signature, with full conversation context.</li><li>Same-day response to every inbound demo request landing in your assigned territory.</li><li>Weekly pipeline review with the CEO and a monthly 1:1.</li><li>Quarterly retrospective on closed-won and closed-lost deals.</li><li>Industry presence: 2-3 LinkedIn posts per week on what you are seeing in the market.</li><li>Customer-led content: co-author one case study or customer-story post per quarter.</li><li>Product feedback: surface 5+ feature requests per quarter back to engineering, scored by deal impact.</li><li>Conference / event attendance: 2-3 per year (SaaStr, Pavilion, Inbound, or vertical-specific).</li></ul><p> <em>Tools you will use daily</em></p><ul><li>HubSpot CRM (deepest integration on the market, our system of record).</li><li>AiSDR (you will use the product to prospect for the product).</li><li>Fathom (every call recorded, summarized, searchable).</li><li>Slack (team communication, customer notifications).</li><li>Google Workspace (Calendar, Drive, Gmail).</li><li>LinkedIn Sales Navigator (or comparable).</li><li>Stripe (billing, you will share the buy links).</li><li>DocuSign (contract signing).</li><li>Loom (async demos, follow-up videos, custom walkthroughs).</li></ul><p><strong>We offer:</strong></p><ul><li>Commission: uncapped. Top performers on our team run materially above OTE.</li><li>Equity: quarterly grant, 4-year vest, 1-year cliff.</li><li>Remote. US Eastern Time Zone.</li><li>Annual offsite in Lviv or Warsaw (your choice).</li><li>Health: Healthcare stipend (you choose the plan, we cover the premium).</li><li>Time off: 25 days paid, plus federal holidays.</li></ul><p><strong>Join us!</strong></p>

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