Enterprise Sales Representative

Skyward is a performance marketing agency that builds search-driven revenue programs for B2B companies and multi-location service brands. The Enterprise Sales Representative owns the full sales cycle, from prospecting and discovery through proposals, negotiation and close, and supports strategic account renewals and expansion.

Responsibilities:

• 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
• 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
• Hand closed accounts to onboarding and account management with clear documentation
• Stay involved on strategic accounts to drive renewals, upsells and expansion
• 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

Requirements:

• 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
• 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)