Fractional Account Executive [B2B, SaaS, Consulting]

JumpSeat•Chicago, IL

2d•Remote

About The Position

JumpSeat is a B2B growth agency and advisory focused on identifying non-obvious growth opportunities for go-to-market teams. They help clients turn these opportunities into highly relevant outreach that gets a response, acting as an antidote to generic automated outbound messages. Their Signal Intelligence methodology combines prioritized accounts, custom signal libraries, AI-assisted research, and personalized messaging based on real-time account activity. The company is now applying this methodology to its own growth and is seeking an AI-native Account Executive to work directly with the CEO on new business development. This is a hands-on selling role where approximately 90% of the time will be dedicated to prospecting activities such as cold calling, leaving voicemails, manual email outreach, and LinkedIn engagement. The company provides accounts, intelligence, messaging, and high-value offers, freeing the Account Executive to focus on working the accounts, converting signals into outreach, recognizing engagement, following up intelligently, and ultimately converting conversations into qualified opportunities. The ideal candidate will leverage AI for heavy lifting while applying their own judgment, creativity, commercial instinct, and human follow-through to achieve results.

Requirements

AI-native: Must already use AI for real work, including research, synthesis, messaging, and problem-solving, and know how to push it beyond generic output.
Commercially sharp: Ability to understand a business, recognize why a signal matters, and develop an angle a buyer might care about.
Good with people: Natural communication skills, ability to build rapport, and turn email exchanges into credible business conversations.
Hands-on: Comfortable researching accounts, editing emails, following up, recording Looms, and doing the actual work.
Reliable: Ability to work a set of accounts and follow through without constant direction.
Comfortable experimenting: Willingness to test angles, learn from prospects, and improve the playbook.
Formal sales experience is valuable, but commercial instinct, curiosity, communication skills, and follow-through matter more.

Nice To Haves

Experience generating B2B pipeline or selling consultatively.
Familiarity with outbound platforms such as SmartReach, HubSpot, Apollo, Outreach, or similar.
Experience with intent data, buying signals, ABM, account intelligence, or signal-based selling.
Exposure to logistics, transportation, manufacturing, B2B technology, or professional services.

Responsibilities

Work prioritized target accounts from signal to conversation.
Activate timely, highly relevant Signal Intelligence outreach across cold calls, voicemails, manual email, and LinkedIn.
Use AI to research accounts, sharpen angles, and create outreach that's difficult to ignore.
Follow up thoughtfully with engaged prospects rather than relying solely on automation.
Create lightweight proof, such as Looms, screenshots, observations, or mini-audits, when it can help break through.
Spot buying windows across replies, engagement, intent, and account activity.
Hold credible early sales conversations and turn engagement into qualified opportunities.
Feed learnings back into our signals, messaging, targeting, and sequences.