Enterprise Sales Representative
hace 14 horas
Albany
Enterprise Sales Representative (Uncapped Commission) Sell for the agency behind growth programs at American Express, Sonos, Sears and NYU Langone, and keep 20% of every retainer you close for the life of the contract. Each deal adds to your monthly income instead of resetting at the end of the quarter. Hit year-one targets and you are on pace for about $350,000 USD, with a book that keeps paying as it grows. Why reps join Skyward • Recurring, uncapped income: 20% on every client, every month, for as long as they stay., • A paid ramp: a three-month stipend to cover your first quarter of pipeline building., • Founders in your deals: leadership builds proposals, joins pitches and helps you close., • An offer that sells: proposals built on the prospect's own data, backed by results for 40+ brands. Role snapshot • Title: Enterprise Sales Representative, • Company: Skyward, • Engagement type: Independent contractor (1099); uncapped commission plus a three-month ramp stipend, • Location: Remote, US-based, • Hours: Self-directed; full-time effort expected to hit targets, • Target customers: Mid-market and enterprise multi-location companies, typically 100+ employees or 20M+ USD revenue, • Reports to: Co-Founder About Skyward Skyward (Goskyward.io) is a performance marketing agency that builds search-driven revenue engines for B2B companies and multi-location service brands. Skyward does not sell stand-alone services. It brings paid search, SEO, AI search visibility, conversion optimization and LinkedIn account-based marketing together into one acquisition system measured on pipeline and revenue, not clicks. What Skyward sells • SEO and AI search visibility (AEO/GEO): product and competitor comparison pages, programmatic location and coverage pages at scale, enterprise problem-solution content, and tracking of how often ChatGPT, Gemini and Perplexity recommend the client., • Lead-generation systems for local and franchise businesses: custom funnels, appointment booking, email and SMS nurture, CRM setup, local SEO, review automation and live performance dashboards., • Paid media management: Google Ads and paid social strategy, account restructuring, smart bidding, ad creative refresh, A/B testing, landing page CRO, and weekly reporting and strategy calls., • Account-based marketing programs: AI-authored, human-edited 1:1 outreach to micro-segmented buyer groups, synced to the client's CRM. How Skyward wins deals • Discovery-led proposals. Every pitch starts with the prospect's own data: audience intelligence, an audit of their ad account and landing pages, and a test of who AI tools recommend in their category., • AI at scale, with humans in charge. Skyward's content pipeline built 25,000+ pages for enterprise clients at a ~95% quality pass rate, and no page publishes without editorial sign-off., • Low-friction commercial terms. Transparent tiered pricing, month-to-month agreements, and quick wins shipped in the first two weeks. Clients Skyward is trusted by 40+ brands, including American Express, Sonos, David Yurman, Revlon, Sears, NYU Langone, Universal Standard, Kitchen Guard, Manhattan Eye, Global Charter Services and Transport Network AU. Clients range from local franchise operators to enterprise data companies with eight-figure ARR. Role overview You own the full enterprise sales cycle, from first outreach to signed contract. This role suits a hunter who has sold marketing services or SaaS, has an existing network of marketing and revenue leaders, and wants uncapped, recurring earnings. You will work complex deals with multiple stakeholders, typically CMOs, VPs of Marketing, Heads of Growth, RevOps and procurement. Expect sales cycles of 30 to 120 days and deal sizes of roughly 25K–150K USD in first-year contract value. Key responsibilities Pipeline generation • Build and work a target account list of mid-market and enterprise prospects., • Run multi-channel outbound: email, phone, LinkedIn, referrals and events., • Use your existing network of marketing and growth leaders to open doors quickly. Sales execution • Run discovery to uncover business goals, current marketing performance and tech-stack gaps., • Deliver tailored presentations and demos, with significant support from leadership and the delivery team, who expect to be involved in creating, presenting and closing deals., • Build ROI cases, proposals and statements of work that tie spend to measurable outcomes., • Navigate buying committees, procurement, security reviews and legal redlines., • Negotiate pricing and terms within approved guidelines and close. Account handoff and growth • Hand closed accounts to onboarding and account management with clear documentation., • Stay involved on strategic accounts to drive renewals, upsells and expansion. Reporting • Keep all activity, opportunities and forecasts current in the CRM., • Share weekly pipeline and forecast updates with leadership., • Feed market and competitor insights back to marketing and delivery teams. Required qualifications • 5+ years of B2B closing experience, with at least 3 years in enterprise or mid-market sales., • Proven record selling marketing services (agency retainers, SEO, content, paid media or demand generation) or SaaS (annual or multi-year subscriptions, ideally martech, adtech or sales tech)., • Documented quota attainment, for example 100%+ of quota in at least two of the last three years., • Experience closing deals of 100K+ USD in annual contract value with multi-stakeholder buying committees., • Comfort talking with CMOs and marketing leaders about funnel metrics: CAC, LTV, pipeline, ROAS, organic traffic and conversion., • Full-cycle ownership: prospecting, discovery, demo, proposal, negotiation and close., • Strong written and verbal communication, including executive-ready proposals., • Daily use of a CRM and sales engagement tools., • Self-direction and discipline to work independently on a commission-based plan. Preferred qualifications • An active book of business or network of marketing decision-makers you can reach now., • Experience selling a services-plus-software bundle., • Industry depth in Skyward's core verticals: B2B SaaS and data, financial services and insurance, healthcare, retail and consumer brands, franchise and home services, and transportation., • Familiarity with a formal sales methodology such as MEDDICC, Challenger, SPIN or Sandler., • Prior success in a commission-based sales role., • Working knowledge of SEO, analytics and marketing automation tools (GA4, Semrush, HubSpot, Marketo). Traits we look for • Hunter mindset: you create pipeline, not wait for leads., • Consultative: you diagnose before you prescribe., • Resilient and accountable for your own numbers., • Honest with prospects about fit, which earns referrals and renewals. Compensation Uncapped commission plus a three-month ramp stipend. You earn a flat 20% of every client's monthly retainer for the life of the contract. • Ramp stipend: [X USD] per month for your first three months, to support pipeline building while your first deals close., • Rate: 20% on all deals, enterprise and growth alike, for as long as the client stays., • What that means: an enterprise retainer (about 20,000 USD per month) pays you about 4,000 USD per month, or 48,000 USD a year. A growth retainer (5,000–10,000 USD per month) pays 1,000–2,000 USD per month., • Targets: 10 enterprise and 10 growth retainers in year 1., • Estimated earnings: about 350,000 USD in year 1 if targets are hit, plus the stipend, with income continuing to grow as your book grows. Payout terms • Commissions are paid monthly for client payments received the prior month., • Commission is earned on collected revenue; refunds or chargebacks within [90] days are clawed back., • Excludes setup fees, pass-through ad spend and taxes unless stated otherwise., • Post-termination: commissions on deals signed during the engagement continue for 6 months of collected revenue., • All terms will be set out in a written commission agreement signed before work begins. What we provide • A three-month ramp stipend while you build pipeline., • Onboarding, pricing, ideal customer profile and competitive positioning., • Sales collateral: case studies, pitch decks, ROI calculators and proposal templates., • CRM access and sales tool coverage., • Pre-sales and delivery experts to join discovery calls, demos and technical reviews., • Inbound and referral leads when available., • Fast approvals on pricing and contracts, and direct access to leadership., • Flexible schedule and fully remote work. What success looks like • First 30 days: Complete onboarding, build a target list of 100+ accounts, and book your first [10] discovery meetings., • First 90 days: Build 3x pipeline coverage against your quarterly target and close your first 1–2 deals., • First 6 months: Close 5 new retainers. How to apply 1. Your resume or LinkedIn profile., 2. A short summary of your quota attainment for the last three years., 3. Two or three deals you closed in marketing services or SaaS: deal size, buyer, cycle length and your role., 4. A note on the industries and contacts in your current network. Shortlisted candidates will have an intro call, a mock discovery call, and a final conversation with leadership. Equal opportunity Skyward welcomes applicants of every background and does not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status or any other protected characteristic.