Account Executive

JumpSeat • Chicago, IL

2d • Remote

About The Position

JumpSeat exists to eliminate random acts of sales and marketing. JumpSeat is a hybrid creative agency + advisory organization. We work alongside B2B marketing and revenue-generating teams in the US to drive financial growth and success for our clients across various business focus areas including creative, demand generation, sales, business development, and operations. Our team has an immediate opening for an Account Executive to drive new business development and revenue growth as we scale by 35-40% in 2026. The Opportunity We're looking for a hunter mentality with agency DNA. As our Account Executive, you'll be responsible for bringing in new revenue while helping us expand our footprint across B2B industries including SaaS, manufacturing, transportation, and beyond. This isn't a transactional sales role—you'll be consultative, strategic, and deeply embedded in understanding how creative and demand generation services drive measurable business outcomes for mid-market and enterprise clients.

Requirements

• Has 5+ years of B2B sales experience, with at least 3-5 years selling SaaS solutions or agency services (creative, demand generation, or marketing technology preferred)
• Proven track record of meeting or exceeding quota ($400K+ in annual new business)
• Experience selling solutions with deal cycles of 30-90 days
• Startup or high-growth agency experience strongly preferred—you're comfortable wearing multiple hats and building processes from scratch
• Bachelor's degree in business, marketing, or related field
• Exceptional communication skills: You can articulate value, tell compelling stories, and tailor your message to different audiences (CMOs, VPs of Sales, Operations leaders)
• Consultative selling approach: You lead with curiosity, ask great questions, and position solutions around business outcomes—not features
• Strategic thinking: You understand how creative and demand generation services drive pipeline, revenue, and brand equity
• Resourcefulness and initiative: You don't wait for leads to come to you—you create opportunities through hustle, creativity, and persistence
• Tech-savvy: Proficiency with CRM platforms (HubSpot, Salesforce), sales engagement and prospecting tools (Apollo, Outreach, Clay, LinkedIn Sales Navigator) and AI.
• Data-driven: You track metrics, optimize your approach, and forecast accurately
• Self-motivated: Whether full-time or fractional, you operate with autonomy and take ownership of your results

Nice To Haves

• Existing network or relationships within SaaS, manufacturing, or B2B service industries
• Experience selling to marketing and revenue operations leaders
• Familiarity with demand generation tactics (paid media, ABM, content marketing, sales enablement)

Responsibilities

• New Business Development (70-75%)
• Prospecting & Pipeline Generation
• Build and manage a robust pipeline of qualified opportunities within target industries (SaaS, manufacturing, B2B services, transportation)
• Conduct outbound prospecting through strategic outreach, leveraging LinkedIn, email campaigns, referrals, and industry events
• Identify and engage decision-makers at director level and above in marketing, revenue operations, and business development
• Qualify leads based on budget, authority, need, and timeline (BANT methodology)
• Consultative Sales Process
• Lead discovery conversations to uncover client pain points across creative, demand generation, sales enablement, and operational challenges
• Craft compelling, customized proposals that position JumpSeat's hybrid agency + advisory model as the solution to client business objectives
• Deliver persuasive presentations (virtual and in-person) that communicate value and ROI clearly
• Navigate complex B2B buying processes with multiple stakeholders
• Negotiate contract terms and close deals ranging from $70K to $1,000,000 annually
• Strategic Partnerships
• Build relationships with complementary service providers, technology platforms, and industry networks to generate referral business
• Represent JumpSeat at industry events, conferences, and networking opportunities
• Develop case studies and success stories in collaboration with account management teams to fuel future sales efforts
• Account Transition & Client Success (25-30%)
• Seamless Handoffs
• Partner with Strategic Account Managers to ensure smooth client onboarding and transition from sales to delivery
• Maintain relationships with key clients post-sale to identify expansion and upsell opportunities
• Support account teams in quarterly business reviews when strategic upsells are on the table
• Internal Collaboration
• Work closely with leadership to refine positioning, pricing, and packaging based on market feedback
• Provide insights on competitive landscape, buyer objections, and emerging opportunities
• Collaborate with marketing to develop sales enablement materials, case studies, and thought leadership content

Benefits

• Fully Remote, Flexible Team: We're a distributed team across the US, Italy and Latin America.
• Growth Trajectory: You're joining at an inflection point as we scale by 35-40%. Your success directly contributes to our ability to scale, add capabilities, and expand into new markets.
• Diverse, High-Impact Clients: You'll work with ambitious B2B companies across SaaS, manufacturing, transportation, and more. Every deal is a chance to solve real business challenges with creative and strategic solutions.
• Culture of Collaboration: We act as an extension of our clients' teams, and we extend that same philosophy internally. You'll have the full support of our strategy, creative, and account management teams.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level